Fun Things to Do in Boston for Adults: Activities in Boston for Retirees

The Boston skyline along the harbor, reflecting the fun things to do in Boston for adults
The Boston skyline along the harbor, reflecting the fun things to do in Boston for adults

From historical monuments to sunset cruises, there are plenty of things to do in Boston for adults. Whether you’re a long-time resident or showing visitors around, playing tourist in this city can make for a fun and memorable weekend! 


Summary:

  • Fun Things to Do in Boston for Adults, Overall

  • Indoor Activities in Boston for Adults

  • Fun Things to Do in Boston for Adults at Night

  • Best Things to Do in Boston for Seniors

  • Conclusion


Fun Things to Do in Boston for Adults, Overall

For fun adult activities, Boston offers endless options. To help jump-start your residential tourist experience, these are some of the must-see and most popular Boston, MA, attractions for adults:


  • Freedom Trail: Leading from downtown Boston to the North End and Charlestown, the Freedom Trail is one of the best things to do in Boston for active adults. This 2.5-mile pathway weaves its way around 16 historic locations and is a great starting place for new residents to learn more about the city. Even if you’re not a history buff, learning about Boston’s past can be a fun way to pass the time.


  • Faneuil Hall Marketplace: Since 1742, Faneuil Hall has been a shopping center and space for debate, renowned speeches, and famous speakers. The first level now has more than 40 local vendors selling gifts, clothing, accessories, and trinkets. The second level is available for touring every 30 minutes. You can also enjoy daily performances from local musicians.


  • Quincy Market: Located inside the Faneuil Hall Marketplace, Quincy Market is the oldest and largest dining hall in the country. While you’re out exploring or enjoying fun Boston activities for adults, stop here for a bite to eat. You’ll find everything from salads and sandwiches to coffee and desserts. 

 

  • Boston Common: America’s oldest park, Boston Common is a 50-acre green space in the downtown area and is also home to the Boston Public Garden, the country’s first botanical garden. Spend an afternoon wandering the trails, taking in the historic monuments sprinkled throughout, and immersing yourself in the beautiful gardens.
A statute in Boston Common park, one of the best Boston attractions for adults
A statute in Boston Common park, one of the best Boston attractions for adults

Indoor Activities in Boston for Adults 

Given Boston’s remarkable past—the city was officially named and founded in 1630—you’ll find a plethora of museums to visit. On days when it may be raining or too hot or cold to spend a lot of time outside, check out these Boston attractions for adults that will keep you out of the elements and entertained:


  • USS Constitution Museum: Launched in 1797, the USS Constitution is the world’s oldest commissioned naval warship. Not only do visitors have the opportunity to explore the Charlestown Navy Yard and the ship’s museum, but you can also climb aboard this impressive vessel to learn more about its role in the War of 1812 and the sailors who commanded the ship in its prime. In addition to being one of our favorite spots, this museum has over 3,000 reviews on Tripadvisor® and a 4.5-star rating as of December 2024. It’s one of the best things to do in Boston for adults.  


  • Isabella Stewart Gardner Museum: The Isabella Stewart Gardner Museum offers contemporary art galleries, lush gardens, and a history museum all in one place. Roam the gardens, check out the rotating exhibits, or spend time with the museum’s permanent art collection. This museum is a local gem, and Tripadvisor reviewers agree, rewarding it with a 4.5-star rating as of December 2024. 


  • Boston Tea Party Ships & Museum: Another floating museum and one of the fun activities in Boston for adults is the Boston Tea Party Ships & Museum. Visitors can travel back in time and experience the famous Boston Tea Party event aboard the full-scale replica of a sailing vessel, complete with live actors and interactive exhibits.


  • Historic house tours: For a different kind of museum experience, you can buy tickets to a variety of tours and explore famous homes around the city. Boston has several old house museums you can visit, such as the Nichols House, the Otis House, and the Gibson House.


Fun Things to Do in Boston for Adults at Night

When the sun goes down, there are even more fun things for adults to do in Boston. Spend an evening enjoying one of these fun adult activities in Boston: 


  • Catch a baseball game at Fenway Park: For baseball fans in Boston, a game at Fenway Park is almost a rite of passage. Known as “America’s Most Beloved Ballpark,” in addition to watching the Red Sox play, you can also tour this beloved baseball field. 


  • Enjoy a harbor sunset cruise: Boston has several companies that provide sunset cruises around the harbor. For example, Massachusetts Bay Lines, outfitted with snacks and a full bar, offers a senior discount for their 90-minute tour and has a 4.4-star rating on Google as of September 2024.


  • Get dinner: Depending on what you crave, you can head to the harbor for fresh seafood or the North End for authentic Italian food. Check out this restaurant list from Boston Magazine when you’re looking for some of the city’s top dining spots on your next date night. 


  • Relax to jazz at Wally’s Café: Founded in 1947, Wally’s Café is still a family-owned and operated jazz club. This venue is where musicians-in-training can perfect their craft, with many musicians coming from local schools and universities, and you can listen to jazz any night of the week. 
An older couple out golfing in a golf cart, one of the best things to do in Boston for seniors
An older couple out golfing in a golf cart, one of the best things to do in Boston for seniors

Best Things to Do in Boston for Seniors

For other fun things to do around Boston, especially for active adults enjoying retirement, consider adding these activities to your list: 


  • Go golfing: There are both public and private golf courses in Boston. The Westborough Golf Course is about three miles from the Del Webb® 55+ community of Chauncy Lake. If you’re seeking a private club, the award-winning course designed by Arnold Palmer at TPC Boston is legendary.


  • Play tourist in Worcester: Just 12 miles away from Chauncy Lake is the city of Worcester, Massachusetts. This city has an art museum, an interactive science and nature museum, a historic mansion, and local shops and restaurants.  


  • Hit the beach: As a waterfront city, Boston has several lovely beaches. Residents of Martin’s Landing, a Pulte® active adult community in Boston, are less than 20 miles from Red Rock Park and Lynn Shore & Nahant Beach.


  • Visit Boston Harbor Islands National and State Park: Thirty-four islands and peninsulas surround the Boston harbor, and they’ve been designated as national and state parks. You can catch a ferry from downtown and spend the day exploring forts, beaches, historical sites, and parks.

Conclusion

Use this handy guide anytime for some of the best Boston activities for active adults. You can plan a romantic night out, a fun day exploring historic sites with family and friends, or a relaxing day at the beach. Whether you enjoy museums, sports, or the great outdoors, when it comes to fun things to do in Boston for adults, there’s something for everyone.


Explore active adult communities in Boston, MA, today or browse more Del Webb blogs. 



Written By: Alexandra Shimalla, Freelance Journalist

Last Updated: 4/10/25