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If you’re a fan of the show Cheers, the Boston Red Sox, or even baked beans, a Boston vacation gives you the chance to go right to the source. But after having a beer at the bar and attending a baseball game, there are still plenty of things to do in Boston, aka Beantown.

Boston is a highly-walkable city, and each neighborhood has its own personality, like the “secret garden” vibe with row houses in Bay Village, or Charlestown, with its Irish roots. Plus, there are wonderful historical sites, museums, and gardens to explore, as well as great food of all kinds.

Here, you’ll learn about some of the top not-to-be-missed attractions, as well as ways to make sure your trip is as enjoyable and affordable as possible.

Best Times to Go to Boston

If you’re planning your Boston trip, you’re probably wondering when to go. June until October offers great weather, though summer travel can be more crowded. Aim for late September or October to catch the fall leaves and cooler weather.

If you want to plan your Boston vacation around major events, here are a few to consider:

•   January/February: Chinese New Year

•   March: Saint Patrick’s Day Parade

•   April: Boston Marathon

•   June: Dragon Boat Festival

•   August: Saint Anthony’s Feast

•   September: Oktoberfest

•   December: First Night.

If you are planning on traveling during in-demand and potentially pricier times, consider using credit card miles vs. cash back that you may have earned on your rewards card.

Bad Times to Go to Boston

Depending on how much you plan to be outside on your Boston vacation, you might avoid visiting in the winter months, when you may have to battle cold weather and snow. (And if you’re traveling with pets to this incredibly pet-friendly city, those icy months may not be a good time for your four-legged friend either.).

Average Cost of a Boston Vacation

As you build your budget for your Boston trip, it can help to know how much you’ll spend on airfare, hotel, food, and renting a car (though public transportation can get you around town well).

For a couple, the average price for one week in Boston is $4,255. Hotels can cost $131 to $484 a night, and vacation rentals run $280 to $610 per night.

Even if you don’t have four grand lying around right now, there are options for book now pay later travel that allow you to pay for your travels over time.

And remember: using a credit card that lets you earn points when you book travel gives you credit card rewards you can redeem for other travel expenses.

10 Fun Must-Dos in Boston

You’ll be spoiled for choice when it comes to fun things to do in Boston. No matter if you’re a sports fan, a foodie, a shopaholic, or history lover, there’s something for everyone. Here are the best things to do in Boston, based on top ratings online as well as recommendations from people who’ve been there and done that in Boston..

1. Catch a game at Fenway Park

If you’re a Red Sox fan, this is already on your list of must-dos. Fenway Park has been hosting baseball lovers since 1912. You can catch a game in-season (don’t forget to cover the price of tickets when growing your travel fund), or take a ballpark tour to learn about the unique history of this landmark. mlb.com/redsox/ballpark

2. Follow the Freedom Trail

This 2.5-mile stretch tells the story of early America, with museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers to explore. You can walk the trail yourself or take a guided tour. thefreedomtrail.org/

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3. Stroll Through the Boston Common and the Public Garden

Enjoy a beautiful day by strolling through these two Boston icons. The Boston Common was created in 1634, and was America’s first public park. The Public Garden was the first botanical garden in the country, founded in 1839. Choose your spot for a picnic and people-watching (a great free thing to do in Boston), or take a swan boat on the pond.
boston.gov/parks/public-garden

4. Get Educated About Harvard University

You don’t have to go to Harvard to go to Harvard! You can take a tour while you’re on your Boston vacation of this nearly 400-year-old institute of higher learning. There are several different tours, including those on the history of the university, a tour of the campus’ art galleries, a tour of Arnold Arboretum, and more. harvard.edu/visit/tours/

5. Tour the Boston Opera House

For a beautiful slice of Boston history, as well as the chance to watch a theatrical production, plan to visit the Boston Opera House. Additionally, you can take a tour of this nearly 100-year-old landmark and discover the intricate details of the opulent architecture, but you also can go behind the scenes of a modern production. bostonoperahouse.com/

6. Dine out in the North End (Little Italy)

If a trip to Italy isn’t in your near future, you can pretend you’re there in Boston’s North End neighborhood. Italian immigrants arrived in this quarter in the 1860s, and since then, Italian restaurants and businesses have sprung up, bringing European vibes to the city.

Save room for a cappuccino and something sweet, or plan to have lunch or dinner to enjoy authentic pizza or pasta at one of the many Italian eateries. (If you swipe a travel credit card as you dine, you can rack up more points to use on when on a trip.) meetboston.com/plan/boston-neighborhoods/north-end/

7. Have a Pint at a Boston Brewery

While the Samuel Adams Boston Brewery (samadamsbostonbrewery.com/) is the most well-known brewery in the city (and worth a visit), it’s far from the only one. Plan your day to include beer hotspots like Aeronaut Brewing Company, Harpoon Brewery, and Cambridge Brewing Company.

8. Visit the Boston Tea Party Ships & Museum

It’s hard to get far in Boston without running into a little history. The Boston Tea Party is an interactive experience that puts you in the middle of one of the most famous events in American history. It can be a fun thing to do in Boston with kids.

And after exploring the museum you can, of course, enjoy a cup of tea to commemorate the occasion! Tickets typically start at $25 for kids, $36 for adults. Looking online for coupons can be a way that families can afford to travel.
bostonteapartyship.com/

9. Enjoy the Art and Ambience at the Isabella Stewart Gardner Museum

Called a “millionaire Bohemienne,” Isabella Stewart Gardner made a name for herself in Boston’s elite and intellectual circles, and she opened an art museum at the turn of the 20th century. Heavily influenced by her travels to Venice, the museum now houses Isabella’s private collection, as well as modern additions. The museum is typically open daily except Wednesdays, and adult admission is usually $20. Also, there is a $10 million reward if you have any information about 13 works of art that were stolen 30 years ago! gardnermuseum.org/

10. Sign up for a Secret Food Tour

Want to know where the locals eat in Boston? Take a Secret Food Tour to find out. Accompanied by a Boston guide, you’ll discover hidden gems that are off the tourist path. You’ll get to try clam chowder, lobster rolls, and cannoli, among other delicacies. After all, let’s be honest: one of the top things to do in Boston is eat! The price of the tours will vary, but a three-plus hour eat-a-thon might cost $89 per person. secretfoodtours.com/boston/

The Takeaway

Boston is a vibrant city that was fundamental in the building of America. With history around every corner (not to mention something tasty to eat), you’ll find plenty to love about this city.

Whether you want to travel more or get a better ROI for your travel dollar, SoFi can help. SoFi Travel is a new service exclusively for SoFi members that lets you budget, plan, and book your next trip in a convenient one-stop shop. SoFi takes the guessing game out of how much you can afford for that honeymoon, family vacation, or quick getaway — and we help you save too.

FAQ

What should I eat in Boston?

Boston is known for several unique dishes, including baked beans, lobster rolls, Boston cream pie, and clam chowder.

What historical things should I see in Boston?

Founded in 1630, Boston has been the home to major historical events like the Boston Tea Party, which has its own interactive experience and museum. Also not to miss are the Freedom Trail, Paul Revere House, Harvard University, and Boston Public Library.

How many days should I spend in Boston?

Depending on how many sights you want to see on your Boston vacation, three to five days is the ideal amount of time.

Photo credit: iStock/Sean Pavone

¹See Rewards Details at SoFi.com/card/rewards.


SoFi Credit Cards are issued by SoFi Bank, N.A. pursuant to license by Mastercard® International Incorporated and can be used everywhere Mastercard is accepted. Mastercard is a registered trademark, and the circles design is a trademark of Mastercard International Incorporated.

Financial Tips & Strategies: The tips provided on this website are of a general nature and do not take into account your specific objectives, financial situation, and needs. You should always consider their appropriateness given your own circumstances.

Third-Party Brand Mentions: No brands, products, or companies mentioned are affiliated with SoFi, nor do they endorse or sponsor this article. Third-party trademarks referenced herein are property of their respective owners.

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Nestled within a chain of islands bordering both the Atlantic Ocean and the Caribbean Sea, Puerto Rico is a popular vacation spot. Plus, U.S. citizens don’t even need a passport when visiting although it can feel as if you’ve been transported to the ultimate far-flung tropical beach vacation.

Yes, sand and sea are a big part of the allure. But if you’re wondering what are some cool things to do in Puerto Rico, you’ll likely be happy to know that parks, museums, shopping, and historical sites are all waiting.

Read on to learn about top spots and attractions across the island, plus the best times of the year to go and other important details. With this advice, you’ll be ready to have an amazing getaway when visiting Puerto Rico.

Best Times to Go to Puerto Rico

If you’re looking for warm weather without the threat of hurricanes, plan your Puerto Rico trip for the winter or spring months. Temperatures average in the 80s all year long, but you’re more likely to avoid crowded beaches and other tourist spots if you focus on these milder months during the school year.

In fact, ending your holiday season with a trip to Puerto Rico lets you take advantage of festivals held throughout the island marking the epiphany in early January. Larger street parades are held in San Juan, but you can also find charming events in smaller towns as well.

Bad Times to Go to Puerto Rico

There are a couple of times of year that are less than ideal for a Puerto Rican vacation. Because a large portion of the local population is Catholic, crowds tend to swell around Easter. That could mean more lines and higher prices.

Another relatively bad time to visit: Hurricane season, which technically lasts from June through November. The most severe weather activity occurs between the middle of August through the middle of October. If you do travel to Puerto Rico during these months, consider purchasing travel insurance through an insurance provider or accessing credit card travel insurance.

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Average Cost of a Puerto Rico Vacation

Before you figure out where to keep your travel fund, calculate how much it will likely cost you. Flight costs vary depending on where you live and what time of year you plan to go.

Once you’re on the island, here are some estimated costs: Food costs can total $39 a day, and local transportation to be about $18. The average nightly hotel cost is $277 for a couple and $139 per person, though there are certainly ways to save money on hotels.

You’ll likely have other incidental costs as well, but here’s how much a week-long Puerto Rico vacation could cost once you’re there.

•   One Person Total: $1,524

•   Couple Total: $3,048

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10 Fun Must-Dos in Puerto Rico

No matter where you plan to stay, there are fun things to do in Puerto Rico across the entire island. The list you find here gathered intel from top-rated attractions on online review sites. In addition, travelers who have explored the island shared their knowledge. As a result, you’ll find a diverse range of activities for people of all ages and all types of groups, whether you’re going on a friends trip, a romantic getaway, or a family adventure.

1. Explore Old San Juan

When visiting Puerto Rico, a must-see is Old San Juan, the historic district of Puerto Rico’s capital city. The streets are lined with colorful buildings featuring Spanish colonial facades. You can take a guided walking tour if you’d love to know all the best historical facts and stories, or you can stroll on your own at no cost.

Be sure to include Fortaleza Street on your itinerary of things to see in San Juan, Puerto Rico. It has beautiful buildings as well as frequent modern art installations. There are plenty of shops and restaurants to try out in the neighborhood, as well as attractions like La Casa Blanca — the former home of Spanish explorer Ponce de Leon. nps.gov/nr/travel/american_latino_heritage/old_san_juan.html

2. Trek Through El Yunque National Forest

The only tropical national forest in the U.S., El Yunque is packed with natural excursions just outside of San Juan. It’s considered one of the top things to do in Puerto Rico. There are plenty of hiking trails, ponds, and a lagoon (complete with a rope swing so you can tap into your inner child).

There are more than 28,000 acres in El Yunque, and trails span 25 miles. You can create a plan for any level of exertion. If you’re staying in the San Juan area, definitely put this on your list of unique things to do in Puerto Rico. Admission is only $2, but make sure you have an advance reservation before you go. Bonus: If you are traveling with a pet, the trails are dog-friendly, though only service animals are allowed inside buildings. recreation.gov/ticket/facility/300017

3. Immerse Yourself in Art

Back in the city, get a dose of world-class art at the Museo de Arte de Puerto Rico. Open Thursdays through Sundays, this museum features permanent collections displaying the work of Puerto Rican artists dating from the 17th century to today.

Explore over 1,000 pieces that include paintings, prints, sculptures, photographs, and more. The museum, which is typically closed on Mondays and Tuesdays, is located in the Santurce neighborhood, which is about a 10-minute drive from Old San Juan. Tickets are $6 (not including taxes) per exhibition for adults; $3 for children. mapr.org/en

4. Get Glowing

One of the best things to do in Puerto Rico is to explore one of three bioluminescent bays, which have an otherworldly glow, thanks to microscopic organisms that light up. Seeing these bodies of water can be an amazing and memorable experience.

Mosquito Bay in Vieques is considered the world’s brightest bioluminescent bay. However, you’ll need to take a short flight or boat ride from San Juan to get there.

Alternatively, you can explore Laguna Grande in Fajardo (which is the closest option to San Juan) or La Parguera in Lajas, which is closer to Rincón. La Perguera is also the only place where you can swim rather than take a boat tour or kayak. The best time to go for any bioluminescent bay tour is December through April when there isn’t a lot of rainfall to cloud the water.

Tours can range from about $50 to $75 per person. This can be a good time to swipe with plastic when paying to earn credit card rewards.

5. Tour a Grand Historical Home

Museo Castilla Serrallés is a great thing to do in Puerto Rico if you love history and architecture. It’s the former home of the Serrallés family (of DonQ Rum), who built the extravagant tile-roofed Spanish Revival castle in the 1930s. It takes just under an hour and a half to drive from San Juan to Ponce where the property is, so you may want to think about getting a rental car.

Today, you can explore the home’s interior, as well as beautiful gardens outside. Learn about the history of rum through immersive exhibits, then stroll through the butterfly garden and Japanese gardens. The property is typically open from Wednesday through Sunday, and tickets cost $15 for adults. museocastilloserralles.com/

6. Get Wet

Located on the northwest corner of Puerto Rico, Aguadilla is about a two-hour drive from San Juan. It’s home to the pristine Crash Boat Beach, which is a great place to indulge in almost any kind of water activity you like, including swimming, snorkeling, and surfing (which is ideal during the summer travel season).

Crash Boat Beach is public, so add it to your list of free things to do in Puerto Rico. It definitely has a lively atmosphere, full of music and food to enjoy when you’re not in the water.

7. Stroll Through El Parterre Park

When you need a break from the beach, check out El Parterre in downtown Aguadilla. This beautifully landscaped park offers the perfect spot to casually stroll under mature trees, and there are plenty of benches for resting, reading, or picnicking, just like a local would. It’s also a good sunset watching spot.

El Parterre contains a natural water spring that has quite a bit of historical significance throughout the centuries. It was used as a water source by explorer Sir Francis Drake in the late 16th century and also by Spanish soldiers in later years.

8. Wander Into River Caves

Just an hour west of San Juan, Arecibo is a coastal location with diverse natural wonders to explore. One of the best things to do in Puerto Rico’s Arecibo area is to visit the Camuy River Cave Park. It’s one of the largest cave networks in the entire world.

Recently reopened in early 2023, you’ll walk through immense caverns that are estimated to be over 45 million years old. One of the most breathtaking spots is a sinkhole that shines in sunlight from hundreds of feet above. Tickets are $18 for adults, $13 for kids ages 4 to 12, with younger children admitted for free (which can help families afford to travel).

9. Surf at Domes Beach

Is surfing on your list of fun things to do in Puerto Rico? If so, check out Domes Beach in Rincón, located on the West Coast of the island (a little south from Aguadillo). Even if you don’t surf, you might enjoy catching a professional surfing competition throughout the year.

Domes Beach is also a great place to enjoy a sunset over the water. If you need a break from the waves, check out the Punta Higuero Lighthouse, a historic landmark originally built in 1892.

10. Venture to Vieques Beaches

A smaller island just to the east of the main Puerto Rican island, Vieques can only be reached by a short flight or ferry ride. Because of this, however, the beaches in Vieques are extremely tranquil and secluded. If you want a beach experience without large crowds or noise, this is an incredible option.

Plus, you can take one of the world’s best bioluminescent bay tours while you’re there.

The Takeaway

It’s easy to find dozens of things to do in Puerto Rico, whether San Juan or elsewhere. The hardest part is simply narrowing down your list of options to fit your time there. Whether you want a relaxed beach or an outdoor adventure, a historical home or a top-notch museum, you’ll find it all in Puerto Rico.

FAQ

Is Puerto Rico cheap for tourists?

It depends on your point of comparison. You’ll probably find it cheaper than large coastal cities on the U.S. mainland, but it also tends to be more expensive than other Caribbean island destinations.

What food is Puerto Rico known for?

Exploring traditional Puerto Rican cuisine is one of the best parts of visiting. Definitely check out mofongo, a mashed fried plantain side dish, as well as pasteles — similar to tamales but made with green banana masa and many options for fillings.

What can’t you bring back from Puerto Rico?

You can’t bring back fresh fruits or vegetables from Puerto Rico to the U.S. mainland. Cactus and citrus plants are also prohibited.

Photo credit: iStock/benedek
SoFi Credit Cards are issued by SoFi Bank, N.A. pursuant to license by Mastercard® International Incorporated and can be used everywhere Mastercard is accepted. Mastercard is a registered trademark, and the circles design is a trademark of Mastercard International Incorporated.

¹See Rewards Details at SoFi.com/card/rewards.

Financial Tips & Strategies: The tips provided on this website are of a general nature and do not take into account your specific objectives, financial situation, and needs. You should always consider their appropriateness given your own circumstances.

Third-Party Brand Mentions: No brands, products, or companies mentioned are affiliated with SoFi, nor do they endorse or sponsor this article. Third-party trademarks referenced herein are property of their respective owners.

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America’s coasts tend to steal the limelight from the rest of the country, with travelers setting their sights on New York and Los Angeles. But those cities can be pricey. And perhaps you’re looking for a trip not featured on every third Instagram account.

For me, Chicago checks all the boxes. Nestled against Lake Michigan, Chicago feels like a coastal city even if that isn’t technically true. Plus, you could visit every weekend for a year and not run out of things to do. Here are the must-sees and must-dos for your first visit to Chicago and beyond.

Best Times to Go to Chicago

The best time to visit Chicago is in the summer, as that is when most of the city’s biggest events happen. That includes the Chicago Air and Water Show (Aug 19-20, 2023), the Taste of Chicago (Sept 8-10, 2023; see below), and the Lollapalooza music festival (Aug 3-6, 2023; Lollapalooza.com). Visiting in summer means you’ll also be able to spend time at Chicago’s numerous beaches and catch a Cubs game at Wrigley Field or the White Sox at Guaranteed Rate Field.

Another great time to visit Chicago is in the winter. If you don’t often see snow, downtown Chicago will be especially beautiful at this time. You can shop at the Christkindlmarket or go ice skating in Millennium Park. And the Chicago Auto Show takes place every February.

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Bad Times to Go to Chicago

There are no bad times to visit Chicago, but the city isn’t as lively during the cold-weather months outside the holiday season. And when the weather is cold, but not quite cold enough for snow and ice, the city will be even less appealing because ice skating may not be an option.

Generally, January and February can be relatively uneventful in Chicago, especially if the Chicago Auto Show doesn’t interest you. If that is the case, you’re better off visiting either during the holiday season or when the weather is a little warmer.

Average Cost of a Chicago Vacation

The average cost of a Chicago vacation can vary significantly depending on the length of your stay and your accommodations. But suppose you plan to stay for one week in a nice hotel and fully immerse yourself in the culture during your trip. In this case, you can expect to spend about $1,260 for a single person and about $1,684 for a couple. It can be more expensive when traveling with a family.

Remember that these are only estimates, and you may be able to stay in Chicago for less. For example, a single person traveling on a budget could take a one-week vacation to Chicago for less than $1,000. Again, it depends on where you stay and how much you spend at local attractions, bars, and restaurants.

10 Fun Must-Dos in Chicago

Chicago is known for its music scene, great food, and world-class museums, among other things. There is so much to do in Chicago that choosing just 10 attractions isn’t easy. My picks let you experience the city for what it really is — gritty but determined and altogether incredible.

If you plan to do everything on this list, consider purchasing a Chicago CityPASS (CityPass.com/chicago). While these passes aren’t cheap ($134 adults; $104 children), they include entry to several of Chicago’s most popular attractions and will save you money overall. Also consider buying a weekly or monthly pass for CTA, Chicago’s mass transit system. Renting a car is another option, although it isn’t always the cheapest.

As far as where to stay, you can’t go wrong with areas like West Loop, South Loop, and River North. Or if you want to live more like a local, consider neighborhoods like Lake View, Logan Square, and Old Town. Of course, hotels can be expensive, so you’ll want to save money on accommodations whenever possible. From these areas, you can access most of the spots on this list via the CTA system.

1. Millennium Park

Have you even visited Chicago if you don’t see Millennium Park? The park features iconic art installations such as Cloud Gate (known colloquially as “The Bean”) and the Frank Gehry-designed Jay Pritzker Pavilion, an amphitheater that hosts live music. There’s also Crown Fountain, incorporating a water fountain and oversized LED screen projecting images of faces. Other highlights include Maggie Daley Park, where you’ll find an ice skating ribbon and an outdoor rock-climbing wall. 201 E. Randolph St.

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2. Willis Tower Skydeck

Formerly the tallest building in the world, Willis Tower stands 1,451 feet tall. Naturally, the Willis Tower Skydeck is the best way to view the city. Chances are, you’ve already seen photos of people visiting the Skydeck, with its clear-glass area simply called The Ledge. Adults $41, youth $33. TheSkydeck.com

3. Original Rainbow Cone

If you find yourself in Chicago during the searing summer months, you’ll need a way to cool down. Fortunately, Chicago has plenty of ways to do that, and one of the best is to visit the original Rainbow Cone in the Beverly neighborhood. The ice cream shop has been around for over 95 years and is famous for its original flavors: orange sherbet, pistachio, Palmer House, chocolate, and strawberry. 9233 S. Western Ave. RainbowCone.com

4. Art Institute of Chicago

Founded in 1879, the Art Institute is one of the oldest and largest art museums in the world. Featuring countless masterpieces, it has one of the best collections of Post-Impressionist paintings outside France. Look for classics like “A Sunday Afternoon on the Island of La Grande Jatte” and Picasso’s “The Old Guitarist.” The Art Institute’s permanent collection features nearly 300,000 works of art. 111 S. Michigan Ave. Adults $32, seniors and students $26, children under 14 free. Artic.edu

5. Taste of Chicago

Chicagoans know that Taste of Chicago is a unique opportunity to try the city’s many flavors all in one place. Sure, the food tends to be overpriced, but there’s no other way to experience so many Chicago dishes in so little time. (And the cost of food is a great excuse to earn credit card rewards.) Years ago, I saw a Counting Crows concert at the Taste, which is completely free to attend. Of course, events vary each year, but it’s worth the investment if you’ll be in town while the Taste is happening. Sept 8-10, 2023, in Grant Park.

6. Celebrate the Irish Spirit

People from all over the world have made Chicago their home since the start of the Industrial Revolution, but the Irish are some of Chicago’s loudest and proudest. As a result, Chicago is home to countless Irish festivals and parades. The St. Patrick’s Day parade downtown (ChicagoStPatricksdayparade.org) and the South Side Irish Parade (SouthSideIrishParade.org), also in March, are two of the best ways to experience Chicago’s Irish culture. And if you’re in Chicago for the downtown parade, be sure to check out the dyeing of the Chicago River. 2024 dates TBD.

7. Museum of Science and Industry

If you nerd out over science stuff, you can’t miss the Museum of Science and Industry (MSI). Touted as the largest science center in the western hemisphere, MSI was founded in 1893. Its marquee exhibits include the German U-505 submarine captured during World War II (admission is $18 for adults on top of museum entry fee), a full-size replica coal mine, and the command module from Apollo 8. If you buy a membership to the museum ($95 per year for individuals), you get unlimited entry at no extra cost. 5700 S. DuSable Lake Shore Dr. Adults $25.95, children 3-11 $14.95. MSIChicago.org/

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8. Shedd Aquarium

The Shedd Aquarium opened in 1930, and for a time its 5 million-gallon capacity was the largest in the world. It is home to 32,000 animals today, including fish, marine mammals, birds, snakes, amphibians, and insects. Some of its most popular species are penguins, sharks, sea otters, and turtles. The CityPASS program includes unlimited entries to the Shedd. 1200 S. DuSable Lake Shore Drive. Adults $40, children $30. SheddAquarium.org

9. Vito & Nick’s Pizza

If you think Chicago is all about deep-dish pizza, think again. I grew up just blocks from Vito & Nick’s, which has been featured in countless articles and TV shows over the years. Despite being a hole in the wall, the pizzeria draws people far and wide for arguably the best thin-crust pizza in Chicago. Located in Chicago’s Scottsdale neighborhood (or Ashburn, depending on who you ask), Vito & Nick’s is an escape from downtown, but it’s worth the trip. 8433 S. Pulaski Rd. VitoandNicks.com

10. Schubas Tavern

Located in the heart of the Lake View neighborhood, Schubas Tavern is housed in an old Schlitz brewery. The venue has a wide selection of drinks and food, and features an even wider range of live music, from indie to jazz. Perhaps the best part about seeing a show here is the intimate setting, which gives you an up-close-and-personal look at some great artists. 3159 N. Southport Ave. LH-St.com

The Takeaway

Chicago is a one-of-a-kind city with some of the best food, entertainment, and architecture in the world. Although it can sometimes be overshadowed by cities like London and New York, you can have an equally good time in Chicago — and likely for less money. If you’re looking for fun for the whole family, you are sure to find it here.

SoFi Travel is a new service offered exclusively to SoFi members. Earn 2x rewards when booking with your SoFi Mastercard or debit card. Then apply those rewards to your next trip when you book through our travel portal. SoFi makes planning a getaway fast, easy, and convenient — perfect for people on the move.

FAQ

What are the most popular things to do in Chicago with kids?

The most popular things to do in Chicago include trips to Millennium Park, the Shedd Aquarium, and the Skydeck at the Willis Tower.

What are the best outdoor activities in Chicago?

The best outdoor activities in Chicago include visiting Millennium Park, Navy Pier, and North Avenue Beach.

What are 5 things that Chicago is known for?

It’s tough to narrow it down to five, but we’ll go with the Magnificent Mile, Second City, Millennium Park, Chicago Riverwalk, and Skydeck Chicago.

Photo credit: iStock/tunart

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The hardest part is knowing where to start. We’ll walk you through planning timelines, money-saving tips, and ideas for when, where, and how long your reunion trip should be.

Benefits of a Family Reunion Trip

The benefits of a family reunion trip are many: It’s a rare chance to reconnect, strengthen relationships, and make new memories. Sure, you’ll see one another at the next wedding, graduation, or funeral, but a dedicated family reunion is an opportunity for multiple generations to simply be together, without the pressure of pre-scheduled events.

Family reunions are especially important for the oldest and youngest family members. Grandparents and great grandparents won’t be around forever. Little ones may not immediately appreciate the time they spend with older relatives, but they will be sure to appreciate these memories — and group photos! — years down the line.

How to Plan a Family Reunion Trip

Organization is crucial when it comes to destination family reunion planning. After all, you’re planning a vacation for potentially dozens of people of varying ages and interests. Maybe you’re a spreadsheet and travel aficionado, in which case, bon voyage! If not, read on for everything you need to consider when planning a family reunion trip, then divide and conquer.

Where, When, and How Long: Guidelines

Every family has diverging interests. Maybe the younger generation love long hikes, but Uncle Mike prefers antiquing, your grandmother could splash in the pool all day, and your brother is practically a vampire. A well-planned destination family reunion vacation will offer something for everyone.

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How Long Should A Family Reunion Trip Be?

Is your family thinking of a week-long vacation or a weekend getaway? Keep in mind that not everyone has the same vacation time from work, and some people may have other obligations they must allocate vacation days to. It’s also important to find out which families may be traveling with pets.

The length of a reunion is often determined by budget. Whoever the lead organizer is should simply ask the group (more on how to do that below) what everyone’s maximum budget is and go from there.

When and Where to Take a Family Reunion Trip

Agreeing on a time of year for your reunion may be easier than you think. First, take into account how many attendees have school-aged kids. For them, winter and summer breaks will be the most convenient times to travel, but also the most expensive. Instead, consider using a shoulder-season school holiday, like Indigenous Peoples’ Day in October or Memorial Day in May, and taking a long weekend trip. Bonus: The weather in many destinations will be pleasant, but prices won’t yet be sky-high.

When evaluating destinations, contemplate: How many people are coming? Will you fly or drive? Is it easier to stay somewhere walkable, or does the group prefer renting cars? Ask select family members for their top (realistic) destination ideas.

Recommended: How to Balance the Urge to Travel and the Need to Save

How to Save On A Family Reunion Trip

Accommodations tend to take a big bite out of travel funds. For most groups, sharing one or more houses or apartments will be much more affordable than booking hotel rooms. In Montana, for example, you may well find two nearby houses that can hold a dozen people each. In Fort Lauderdale, you’re more likely to find three- to four-bedroom condos.

Sharing accommodations can also make it easier to prorate costs, allowing those on a tight budget to select a smaller room or pull-out couch. (Also keep in mind credit card rewards, which are sometimes applicable to vacation home sites.)

Other advantages of a rental house are space to spread out, doors that can be closed when kids are sleeping but adults are up late talking, and the ability to prepare meals — another huge cost saver.

Family Reunion Planning Timeline

Your planning timeline will vary depending on your destination. If the gang is flying to Hawaii from across the country, you’ll want to book flights many months in advance and keep your eye on hotel prices. If everyone is driving, you can book accommodations a few months out and then wait to plan activities.

6–12 months out: Use a free online poll tool or the poll feature in messaging apps like Whatsapp and Telegram to vote on when and where to go. The group chat can be your best friend and worst enemy (btw, you may want to mute it), but it is useful for soliciting opinions. It’s important to confirm budgets and expectations now.

4–5 months out: Once a destination is decided, pull a few accommodation options to fit the group’s needs, whether that’s a block of hotel rooms, a few condos, or a rental house. Reconfirm everyone’s budget, as financial circumstances can change.

If your family reunion trip requires flights, compare the price of a ticket in miles vs. cash so you can decide whether to use a credit card that gives credit card miles vs. cash back.

2 months out: Keep the momentum going by booking any activities, whether you need lift tickets, plan to take tours, or want to go snorkeling. With major logistics out of the way, this is the fun part.

1 month out: Everything that needs to be booked in advance is done, and the countdown is on. Now is the time to look into nearby grocery stores, where people might eat if they arrive late, whether strollers and carseats can be rented or should be packed, etc.

Do’s and Don’ts for a Fun, Memorable Reunion

•   Don’t overschedule your family reunion trip: Try booking only one major activity per day for those who want to participate, whether that’s a beach excursion, a museum, or a walking tour.

•   Do respect peoples’ natural rhythms: Aunt Sue may be ready for 5am bird-watching, but your college-age cousins are more likely to roll out of bed several hours later. Everyone is more cheerful when they get enough sleep, so don’t wake people at the crack of dawn with a megaphone.

•   Don’t feel compelled to capture every moment. The pressure to take a million perfect photos is very real, but try to live in the moment. You may not see some of these people again for several years.

•   Bring an instant camera: These tangible memories are the perfect family reunion souvenir, and instant camera film colors are universally flattering.

•   Pack games: Uno, travel Scrabble, Code Names, even simple packs of cards provide entertainment after dinner and on rainy afternoons.

•   Make videos: Film older relatives talking about their lives. Prompt them with questions about their childhood, who their friends were, what they ate, what they dreamed their adult lives would be. This is a wonderful way to memorialize older generations.

After the Event

•   Create a place for everyone to share photos, like Google Drive or Dropbox.

•   Print a few of the best photos and mail them to your family with a short note; it’s a treat to get snail mail.

•   If people have suggestions for the next family reunion trip, note them.

•   Use an expense tracker to organize who owes whom for shared costs.

The Takeaway

A family reunion is a unique chance for relatives across generations to meet for the first time or reconnect. Summer is generally the easiest time for families with young kids to travel, but it’s also the most expensive. If your family reunion trip works for a long weekend within driving distance, this is the most budget-friendly option. While it takes some coordination — and maybe a little stress — be assured that it is worth the trouble.

Photo credit: iStock/ferrantraite

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If Cincinnati isn’t on top of your list of places to visit, reconsider! This is a vibrant, bustling city along the banks of the Ohio River with an abundance of attractions to enjoy. There are festivals, parks, museums, and historical sites to explore. Plus, you will definitely eat and drink well (Cincy is also well known for its eighty-plus breweries).

Whether you have just a weekend or a longer stay in mind, the city will have plenty to keep you busy. Here, you’ll learn the details on 10 cool things to do in Cincinnati, as well as tips to make planning and paying for your trip that much easier.

Ready to explore the best things to do in Cincinnati? Read on.

Best Times to Go to Cincinnati

Cincinnati has warm summers that typically don’t get scorchingly hot, as well as reasonably temperate spring and fall seasons. Those can be the prime seasons to visit.

Located in the southwest corner of Ohio, winters can be warmer than Ohio towns and cities further north, but they can get quite cold, snowy, and icy. In general, April through October is the best time, weather-wise, to plan a trip.

If you enjoy attending festivals, Cincinnati has plenty in the summer and early fall. So, choose ones of interest and plan accordingly. Some of the more popular festivals include:

•   Oktoberfest oktoberfestzinzinnati.com/

•   Cincinnati Music Festival www.cincymusicfestival.com/

•   Bunbury Music Festival bunburyfestival.com/

•   BLINK, a light and art festival in October blinkcincinnati.com/

If sports games are more your thing, check the schedules of the Cincinnati Reds MLB team and the Bengals NFL teams — or one of the many played by students at the University of Cincinnati.

If these fun things to do in Cincinnati have captured your attention, you may want to decide where to keep a travel fund and start saving.

Bad Times to Go to Cincinnati

You’ve already read that winters can be, well, wintery and perhaps not the best time to visit. If you’d like to walk around and enjoy the sights, you may be put off by the low temperatures and how roads can be snow clogged and slippery during that season.

Also, Cincinnati can experience traffic congestion, especially downtown. Hectic times can include opening days for the sports teams or when a big game is about to be played — or during an in-demand festival. So if you’re not planning to attend any of these events, consider avoiding those dates when downtown is likely to be especially crowded.

Also investigate the status of the bridge over the Ohio River that connects Cincinnati, Ohio to Kentucky. When there is bridge construction or people are traveling to Kentucky in higher numbers, traffic can get backed up into downtown Cincinnati.

Average Cost on a Cincinnati Vacation

On average, a trip to Cincinnati costs a solo traveler $146 a day or $1,025 weekly. Plenty of factors impact the price, however. If driving, gas prices play a role. If flying, knowing how to get cheap flights can reduce your costs.

Hotels range from budget inns to luxurious lodging with in-demand amenities and luxury add-ons, and restaurants can be quick bites at a fast food establishment or an indulgent meal at a steakhouse.

What you choose will of course affect the prices. To help with financial planning, consider your credit card rewards and how you can leverage them to splurge.

If some of things to do in Cincinnati, Ohio for couples catch your eye, know that an average Cincy hotel price for two is $163. Knowing how to save money on hotels can help to cut back the average weekly cost of $2,050 for two.

10 Fun and Affordable Must-Dos in Cincinnati

Cincinnati is an intriguing city with highly enthusiastic sports fans alongside those who have a passion for art and culture (and those who love both!). Not surprisingly, then, the things to do in Cincinnati, Ohio are quite diverse: art, nature, and history venues as well as dining, shopping — and even world-class amusement park experiences.

Here, you’ll find a list of 10 fun things to do in Cincinnati, gathered from top-ranking online reviews as well as city-smart travelers.

1. Visit the Cincinnati Zoo & Botanical Garden

Founded in 1873, this highly rated zoo is the second-oldest one in the United States. Although the initial collection of animals was quite small (including a talking crow), today’s zoo will introduce you to gibbons, gorillas, lemurs, manatees, hippos, and more. An international leader in wildlife conservation, this zoo is now one of the country’s largest and can be a terrific place to spend some time while in Cincinnati. cincinnatizoo.org/

2. Tour a Massive Museum

The Cincinnati Art Museum is one of the oldest in the country — and quite large with more than 67,000 pieces of art that span 6,000 years of creativity. The collection ranges from African and East Asian art to contemporary American works, European sculptures, musical instruments, and so much more. cincinnatiartmuseum.org/

3. Take a Walk in the Park

After touring the art museum, step outside! You’ll find yourself in Eden Park with the Hinkle Magnolia Garden, Mirror Lake, walking paths, eye-catching sculptures, playgrounds, and more. The grounds are also home to the Cincinnati Playhouse in the Park, the Krohn Conservatory, outdoor concerts — and an incredible view of the Ohio River with Kentucky located just on the other side. This can be a great place to spend a couple of hours if you’re traveling with a pet, plus it’s a free thing to do in Cincinnati. cincinnati-oh.gov/cincyparks/visit-a-park/find-a-parkfacility/eden-park/

4. Appreciate More Art

The Taft Art Museum is a terrific journey back in time. Housed in an 1820 National Historic Landmark that’s a treat to visit, the art collection includes French Renaissance enamels, Chinese porcelain, European and American paintings, and more. You’ll view works by Rembrandt, Goya, Whistler, and other prominent artists. taftmuseum.org/

5. Go for a Ride

When looking for fun things to do in Cincinnati, put Kings Island on the list! There are big-time roller-coaster adventures plus three dozen water slides. If you’re traveling with children, there are thrills for the smaller set, such as the Planet Snoopy kiddie rides. Plus, you’ll find plenty of mouthwatering in-park dining options along with quality live entertainment to applaud.

Look for coupons online or check with your hotel’s concierge; discounts can be a way for families to afford to travel. visitkingsisland.com/

6. Immerse Yourself in History

Located near the banks of the Ohio River — a geographic feature that once divided states where slavery was legal from those where it wasn’t — the National Underground Railroad Freedom Center contains permanent and traveling exhibits. Visitors will learn about this challenging time in history and the heroes of the Underground Railroad. freedomcenter.org

Across the street, there’s a sign spelling “Cincinnati” in script with plenty of people taking selfies there before they go.

7. Watch a Baseball Game

Also located by the Ohio River, this is the stadium for America’s first professional baseball franchise, the Cincinnati Reds. So, if in town on a game day, buy tickets! You’ll walk by a statue of the Hall of Fame baseball catcher, Johnny Bench, and can visit the Reds Hall of Fame and Museum to celebrate the glory days of the Big Red Machine and more. Plenty of exhibits exist, including interactive ones, and players sometimes schedule personal appearances. mlb.com/reds/ballpark

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8. Stroll Around an Arboretum

Although cemeteries aren’t typically on a vacation list, Spring Grove Cemetery and Arboretum is one of only two historic cemeteries to achieve Level III arboretum standards. Its stunning gardens focus on Midwest natives along with non-indigenous species with a focus on demonstrating the “vital relationship that exists between plants and people.” springgrove.org/arboretum/

9. Get Acquainted with an Aquarium

From white alligators to stingrays to penguins, the award-winning Newport Aquarium offers unique views of thousands of types of exotic aquatic life, along with amazing interactive adventures. Cross the world’s first rope bridge above a tank full of sharks, explore a sunken ship at “Shipwreck: Realm of the Eels,” and much more. newportaquarium.com/

10. Eat Well (Really Well)

If you are looking for delicious things to do in Cincinnati, Ohio, for couples or a family, stop by the Findlay Market. This is the state’s oldest surviving municipal market house. A huge range of good eats are available; if one of you is vegan and the other isn’t, no problem! There is something for everyone here: pho, arepas, BBQ, and more. Maybe take one of the market’s walking tours so you don’t miss anything. findlaymarket.org/

A Note About Getting Around

Although it’s not totally true that all of Cincinnati attractions are located downtown, many of them are. So, keep that in mind while engineering your itinerary for each day and when seeking convenient lodging.

•   If you want to avoid highly trafficked places to stay, spread out from the downtown area when looking for options, perhaps into Kentucky.

•   Although most attractions are open year round, check to ensure the ones you want stay open through the winter.

•   Consider the streetcar with its eighteen downtown stops if you’d like to see key places without having to drive.

•   If the attractions you want to see are quite far apart, you might look into renting a car to make sure you hit all the highlights.

Recommended: Credit Card Miles vs. Cash Back

The Takeaway

Fun things to do in Cincinnati take place throughout the year, depending upon your interests. Plenty of options exist for people who love art, nature, sports, music, food, and much more. Most festivals take place in summer and early fall, while football fun extends the fun of visiting further into the year. Whether you are traveling solo, with friends, or with family, you are likely to have more top things to do in Cincinnati than you can pack into a single trip.

Whether you want to travel more or get a better ROI for your travel dollar, SoFi can help. SoFi Travel is a new service exclusively for SoFi members that lets you budget, plan, and book your next trip in a convenient one-stop shop. SoFi takes the guessing game out of how much you can afford for that honeymoon, family vacation, or quick getaway — and we help you save too.

FAQ

What foods is Cincinnati famous for?

Chili! A Greek family brought its special recipes to the United States in 1949, and its been loved by Cincinnati residents and visitors ever since. This is also the city for beer lovers with its eighty-plus breweries and nightlife spots. Need a third one? Ice cream!

Is Cincinnati in two states?

Although you may hear portions of Kentucky and Indiana referred to as part of the greater Cincinnati metro area, the actual city lies within the geographical boundaries of just one state: Ohio.

Can you walk in downtown Cincinnati?

Yes! Cincy is a walkable city, and it isn’t unusual to see significant numbers of people strolling by on the sidewalks as well as in parks and other venues.

Photo credit: iStock/pawel.gaul

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