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.
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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.
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.
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/
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.
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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
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