Things to do in Boston

Insider Tips: Planning a trip to Boston

Matthew Kepnes runs the award winning budget travel site, NomadicMatt.com. His writings and advice have been featured in The New York Times, CNN, The Guardian, Budget Travel, BBC, Time, The Wall Street Journal, and countless other publications. When not traveling the world, he lives in New York City.

What should I do on my first trip to Boston?

If it's your first trip to Boston, make sure you walk the Freedom Trail. It's a 2.5-mile trail that takes you around the city's most important historical sites, including the State House and Bunker Hill (the site of an important battle during the Revolutionary War). After, spend some time relaxing in Boston Common, the country's oldest city park.

What are some hidden gems to see in Boston?

The Coit Observatory offers free stargazing on Wednesdays throughout the year (pending clear skies). Space is limited so you need to book your free tickets in advance but it's a fun and interesting activity a lot of people don't know about. Just make sure to check the weather as you'll be outside so you'll need to dress appropriately.

How much time should I spend in Boston?

Boston makes for a great weekend destination, so 3 days is perfect if you want to see the main sights. That gives you time to walk the Freedom Trail, visit some museums, and maybe even catch a came at Fenway Park. If you're a huge history buff and want to really dive deep into US history, 3-5 days would be best.

What food is Boston known for?

Seafood has played an important part in the city's history, so you'll want to make sure you have some while you're here. Be sure to try a lobster roll or clam chowder. They're local favorites! Some other favorite places to eat include Zaftigs (the best brunch) and FuGaKyu (the best sushi).

What is the best way to get around Boston?

While much of the city is walkable, the easiest and cheapest way to get around is public transportation. The bus can get you anywhere you need to go and there's a day-pass option available if you're going to be using it a lot. The city also has a bike sharing program if you'd prefer to bike around.

What are the best months to visit Boston?

While the summer (June-August) is when most people visit, personally I think the shoulder season is best (April/May or September/October). The weather is still nice but there will be fewer crowds. Prices will be a little lower too. Just pack a sweater for the cool evenings and mornings.

What are the best neighborhoods to visit in Boston?

My favorite neighborhood is Back Bay/Copley. It’s got a little bit of everything, it’s centrally located, and there are a lot of great restaurants in the area. If you'e a budget traveler, stay in Brighton/Allston. It has lots of cheap food and nightlife options and is where a lot of young people live.

What's are 4 best tips for a person traveling to Boston?

1) Enjoy free concerts – During the summer, there are a lot of free concerts. Check with Visit Boston to see what’s happening during your visit.

2) Get the Boston City Pass – This pass provides up to 50% off at a number of attractions. If you plan on seeing and doing a lot, it will likely save you money.

3) Eat at Quincy Market – The Quincy Market in Faneuil Hall offers a wide range of food stalls at low prices. It’s a hugely popular place to eat, especially during lunch.

4) Enjoy the free parks – You can experience nature for free at the Arnold Arboretum. There are over 260 acres of free public space here, open from sunrise to sunset. There are running trails, gardens, open lawns, and lots of flowers from all over the world. It’s super relaxing!

What should people avoid doing in Boston?

Boston has an iconic accent — don't try to imitate it while you're here. While most people probably won't care, they won't really like it either. Also, avoid wearing Yankees clothing. There's a huge baseball rivalry between Boston and NYC and Red Sox fans here hate the Yankees. Don't stir the pot!

What are your top 5 favourite GetYourGuide experiences in Boston?

1) Boston: Guided Walking Tour of the Freedom Trail

2) Boston: Whale Watching Catamaran Cruise

3) Boston: 1.5-Hour Ghosts and Gravestones Tour

4) Boston Fenway Park: Guided Ballpark Tour with Options

5) Boston: Boston Tea Party Ships and Museum Interactive Tour

What is one thing that surprised you about Boston?

I grew up here so nothing surprises me about the city aside from the fact that so many people visit the US each year but only a small fraction of them visit Boston. The city has a lot to offer (specially if you love history or sports) so I think it deserves much more attention!

What is the best family-friendly thing to do in Boston?

If you're visiting with kids, be sure to stop by the Museum of Science. It's one of the best museums in the country in my opinion, and while it's mostly designed for kids, adults will have fun too. Their permanent exhibits showcase dinosaurs, energy conservation, cartography, wind and weather, nanotechnology, and, of course, space. There's a planetarium too.