20 Things To Do in Boston for a Wicked Good Vacation

Boston is a city with something for everyone. Whether you're looking for free and fun things to do in Boston or unique experiences at varying price points, these ideas are great for adults, families, or groups. Known as both The Walking City and a destination with extensive public transportation exploring all the city offers isn't complicated in Boston.

Things To Do in Boston for Adults, Kids or Both

There's a wide range of activities to do in Boston, MA, for every age. So whether you're looking for historical sights, hoping to catch a baseball game, or taking a tour, explore everything it offers and then some!

1. Boston Tea Ships and Museum

If you're searching for things to do in Boston for adults and kids alike, The Tea Party Ships and Museum is an experience you don't want to miss. The tickets are roughly $30 for adults and $22 for kids aged 5-12. Watch actors dressed up in costumes from that time period as they reenact the famous event off these ships around Boston Harbor!

2. Look for the Boston Red Sox Schedule at Fenway

What comes to mind when you think of iconic ballparks all over the United States? For me, it's Fenway Park. Outside of catching a game, this historic site serves as an attraction where tourists can take interesting photos with entertainers on stilts, jugglers, and different displays such as a lego statue of David Ortiz. Touring the stadium any time of year is a great bucket list thing to do in Boston.

3. Duck Boat Tour

The Duck Boat Tour is a must-do activity if you need a break from walking! Besides the fact that it's super fun, it's one of the unique things to do in Boston that's great for all ages. Listen to the tour guide explain historical tidbits of different landmarks while riding through Bean Town in a boat on wheels before making its way to float along the Charles River.

4. Swan Boats

If you've always wanted to ride the swan boats in Boston, take a peek at the schedule in Mid-March at SwanBoats.com to see when opening day is for the year. Hop a ride on a swan boat from April/May to Labor Day, located in the Boston Common. It is a quick, inexpensive ride (under 5 dollars per ticket) that is another fun activity for all ages.

5. Trolley Rides

Wait for a trolley at one of the many stops around Boston. Various companies offer a guided tour for a complete joy ride around town. Knowledgeable drivers will tell you stories and interesting tidbits that include history from long ago and recent happenings.

This is another way to explore the city while giving your feet a break from so much walking. If you do not want to sit the whole way through, or you want to break up your ride, be sure to find one of the many trolleys that allow you to hop on and off to see particular areas up close.

Things To Do in Boston for Free

Bust out your most comfortable shoes and take in history on foot. Walk all over the city while learning about days long past. The trails are a popular spot for those who like to be outside and informally take in bits and pieces of history. Each path unlocks the significant details of days past.

6. Freedom Trail

The Freedom Trail connects the historical dots by including sixteen locations that span 2.5 miles. To peek at a map and get more details about the route and where the Freedom Trail starts, go to TheFreedomTrail.org for more information.

7. The Black Heritage Trail

You can also find the Black Heritage Trail and The Irish Heritage Trail. If you are wondering, “How long is the Black Heritage Trail?” According to NPS.gov, it's 1.6 miles.

Make your way through the Beacon Hill neighborhood to follow the trail. Learn about what life was like for the Black Community surrounding the American Civil War time period. If you want to peek at the path, there is a virtual tour online at nps.gov.

8. The Irish Heritage Trail

Recount history through the experience of the Irish. Though there is some overlap on this trail with the Freedom Trail,  For example, The U.S.S. Constitution is on both paths and is a worthwhile activity. This trail is more spread out and is roughly 3 miles.

9. Harborwalk

If you are not tired of walking after exploring the many trails mentioned above and need other things to do in Boston this weekend or longer, take a leisurely walk along the Harborwalk. The salty air and lively scene will be perfect for a day outside.

BostonPreservation.org explains, “The Boston Harborwalk is a nearly 40-mile public waterfront walkway that winds through Boston's waterfront neighborhoods, stretching from Chelsea Creek to the Neponset River, through East Boston, Charlestown, North End, Downtown, Fort Point, South Boston, and Dorchester.”

10. U.S.S. Constitution

Learn about wars and battles fought and the commanders and crews on the voyages of two historical ships in the Charlestown Navy Yard. Sightseers can catch the museum as part of the Freedom Trail. Or, if you opt to take a trolley ride during your trip, the route also passes by there. Passengers can hop off to see the museum and get back on another trolley once finished. You can always make your way on your own too.

11. Boston Public Garden

So what's so special about the Boston Public Garden? According to Boston.gov, it was “the first public botanical garden in America. It was decorative and flowery from its inception, featuring meandering pathways for strolling.” It is a free attraction and a perfect low-key activity if you need some downtime from the business of this big city.

12. Museums

If you have flexibility in your itinerary while visiting, you can see many museums in Boston for free. Some of them have an allotted block of time on a specific day for no-charge admission. With a bit of research and planning, visit one of the many museums in Boston without paying a penny. There are also places such as the Children's Museum that offer admission at a reduced rate of $1 on Fridays. It is one of the exciting things to do in Boston with kids, especially if they need to get their energy out.

13. The Lawn on D

What is there to do at The Lawn on D? If you are near the Convention Center in May or other warm weather months, stop by this popular park. The Lawn on D is free, and both adults and kids alike will enjoy the circular swings, art, and music there. There are also outdoor yard games to play, such as Cornhole, Jenga, Ping pong, and more.

Things To Do in Boston: Places To Eat

14. The Bull and Finch Pub

Though the Cheers restaurant in Faneuil Hall recently closed, the Bull and Finch Pub still remains on 84 Beacon Street across from the Public Garden. Yes, this is where the real Cheers bar is located. This location inspired the popular, long-running T.V. series from the 1980s. It opens daily at 11 AM, and children are allowed until 10 PM. After that, it's the 21 and over crowd only. Cheers!

15. Cask -N- Flagon

If you visit Fenway Park or you happen to be close by, consider visiting Cask -N- Flagon. Their website (and sign above the restaurant) touts how this iconic restaurant was named the Top Baseball Bar by ESPN. Dana Van Fleet owns the restaurant and sports bar established in 1969. It offers tasty sandwiches for lunch and appetizers, soups, salads, entrees, and more.

16. Eataly

If you are near the Prudential Center, head inside to the first level. A cannoli stand awaits you at the top-notch Italian food market entrance. Find groceries as well as multiple restaurants housed within. Sit down for a fancy meal or opt for a quick bite. You can even grab some groceries on your way out.

17. Quincy Market

If you are wondering what the famous market in Boston is called, it is Quincy Market! In my opinion, if you have never been before, it is one of those things everyone should experience at least once. Located within the Faneuil Hall Market Place, it houses many places to eat.

It is the perfect place to stop if every person in your party is in the mood for something different. There are a wide variety of options, including food Boston is famous for, such as baked beans, clam chowder, lobster rolls, and other types of seafood. You can also find international fares such as Asian, Greek, Mexican, Italian, and Middle Eastern dishes. Stopping here is the perfect way to keep everyone happy and well-fed.

18. Boloco

Though I enjoy eating at fancy sit-down places, I do not want every meal to take up so much time when I am traveling. If you're looking for some quick, cheap eats, Boloco has your back with modern Mexican food. You can not go wrong with this less formal atmosphere, reasonable prices, and great counter service. Their tasty food will have you wanting more!

19. Tatte Bakery & Cafe

Tatte is the perfect location for those who want to sit for a bit or grab something to go. Whether you order a meal, baked item, or just coffee, it's a pleasant experience for breakfast, lunch, or dinner. Check out one of the many locations in Boston. According to their site, each has its own unique style, but they “all stay true to the original spirit.” No matter which one you try, the common denominator is great tasting food

20. Jaho

If you have been walking all day during warm weather months or want a treat after lunchtime, give your feet a rest while enjoying some Japanese-style ice cream. I visited the one on 665 Washington Street and loved the texture and flavor of this treat. If you go during cooler months, check out their coffee bar, food creations, and baked items, or if you are into day drinking, have a boozy bubble tea, craft beer, or other alcoholic beverages.

More Articles by Wealth of Geeks

Disney Just Got More Expensive. Here are 8 Reasons Locals Prefer Universal

Best Time to Visit Hawaii: How to Plan an Epic Vacation

This article was produced and syndicated by Wealth of Geeks.

Featured Image Credit: Wealth of Geeks.


As a busy working parent, Karen Cordaway struggled to find free time & money for herself. Once she discovered how to reclaim both, she infused more fun into everyday life.

She has written for US News Money, Huff Post & Clark Howard & now combines her money know-how with bucket list topics.

As the author of The Everyday Bucket List Book, she shows her step-by-step process to turn dreams into reality.