53+ Things to Do in Boston for Vacations

Boston is a city where history, culture and charm all in one place. Between walking the Freedom Trail and visiting world-class museums, to noshing on fresh seafood in the North End and catching a game at Fenway Park, there truly is a bit of something for everyone. Nature lovers can unwind in the Boston Common or hop a ferry to the Harbor Islands, and shoppers and foodies will adore Newbury Street and Quincy Market. From its colonial landmarks to its colorful neighborhoods and one-of-a-kind experiences, Boston will keep you busy! Here, then, is your ultimate guide to everything interesting, fun, and even iconic for visitors to do in Boston once you’re 55 or older.

Things to Do in Boston

1. Explore Boston’s Historic Landmarks

There’s a reason Boston is known as the “Cradle of Liberty” — it’s where the rebellion that became the American Revolution first caught fire. Strolling through the city is like returning to another era.

1. Freedom Trail – A 2.5-mile (4km) trail linking 16 historical sites such as Paul Revere’s House and Old North Church.
2. Boston Common – The first public playfield in America, established in 1634.
3. Massachusetts State House – A notable golden-domed building, which you can see from Boston Common.
4. Faneuil Hall – Referred to as “the Cradle of Liberty,” this is where revolutionary meetings were held.
5. Old South Meeting House – Best known as the site where the rally was first held that later led to the Boston Tea Party.
6. USS Constitution Museum– Hear about “Old Ironsides,” the oldest commissioned warship in the world.
7. Bunker Hill Monument – A giant obelisk to the war in which Tall Joe became a hero.
8. Granary Burying Ground-Burial site of Samuel Adams, John Hancock, and Paul Revere.
9. King’s Chapel & King’s Chapel Burying Ground – Colonial buildings combining history and architecture.
10. Old State House – Don’t miss and the reading of the Declaration of Independence to Bostonians.

2. Discover Boston’s Museums & Cultural Attractions

Some of the best museums and art collections in the country are in Boston. Regardless of whether you’re into science, fine art, or all-things quirky, the city won’t let you down.

1. Museum of Fine Arts – 500k+ works from the ancient to contemporary.
2. Isabella Stewart Gardner Museum – Venetian palace with an incredible number of art objects.
3. Boston Children’s Museum – Fantastic for kids, loads of hands-on learning displays.
4. Museum of Science – With a planetarium and IMAX theatre as well as hands-on science stand.
5. Boston Tea Party Ships & Museum – Step back in time and experience the rallying cry that sparked a revolution.
6. John F. Kennedy Presidential Library and Museum – Honors the memory of the 35th President of the United States.
7. Institute of Contemporary Art (ICA) – Streamlined waterfront museum featuring modern art.
8. Harvard Museum of Natural History – Features interesting displays such as the world-renowned Glass Flowers.
9. MIT Museum – Exhibits on robotics, artificial intelligence, and emerging technologies.
10. Gibson House Museum – Reflects the lifestyle of a 19th century Boston Family.

3. Outdoor Activities & Parks in Boston

If you love the outdoors, Boston has amazing parks, harborside strolls and green spaces to recharge your batteries.

1. Boston Public Garden – Known for swan boats and vibrant flowers.
2. Charles River Esplanade – Great for bike riding, running or kayaking.
3. Greenway – A contemporary park in the city with fountains, art, and seasonal markets.
4. Boston Harbor Islands — Perfect for a day of hiking, picnicking, and exploring old forts.
5. Arnold Arboretum — A 281-acre expanse of rare plants and trees.
6. Castle Island – Scenic walk and historic Fort Independence (outside food is allowed).
7. Blue Hills Reservation — Not too far from Boston, perfect for hiking and wide open views.
8. Back Bay Fens – A Frederick Law Olmsted park that nature lovers will appreciate.
9. Mount Auburn Cemetery – Serene location with beautiful gardens and history.
10. Spectacle Island – Known for trails and beautiful city skyline views.

4. Sports & Entertainment Experience in Boston

Boston is a sports-crazy city and also offers plenty of fun entertainment options.

1. Fenway Park – Watch the Red Sox play at the oldest Major League Baseball stadium in America.
2. TD Garden – Host to the Boston Celtics and Bruins.
3. Harvard Stadium – Watch college football at this historic stadium.
4. Head of the Charles Regatta – See the world’s largest 2-day rowing race in October.
5. Boston Marathon – The oldest annual marathon in the world, run in April.
6. House of Blues  – Top live acts and events.
7. Wilbur Theatre – Offers comedy acts, live acts and more.
8. Boston Symphony Orchestra: Famous for its performances of classical music.
9. Opera House – Gorgeous building combined with Broadway shows.
10. Blue Man Group – Silly and different and great for all ages.

5. Food & Shopping

Visit to Boston is not complete without tasting its legendary seafood and shopping in its renowned neighborhoods.

1. Quincy Market – A lively food court featuring clam chowder, lobster rolls, and more.
2. Union Oyster House – America’s oldest restaurant: serving fresh oysters since 1826.
3. North End (Little Italy) – Renowned for authentic Italian cusine and pastries e.g. cannoli.
4. Legal Sea Foods – A Boston seafood classic.
5. Boston Public Market – The place for fresh, local food and locally-made products.
6. Time Out Market – A hipster food court of all different foods.
7. Copley Place – High-end shopping with luxury boutiques.
8. Newbury Street – Home to boutiques, restaurants, and art galleries.
9. Prudential Center — Shopping, food, and Skywalk Observatory.
10. Harvard Square — A bustling center of activity with stores, bookshops and street performers.

6. Quirky Day Trips From Boston

In addition to its traditional tourist draws, Boston is also home to offbeat and unusual sights and activities.

1. Samuel Adams Brewery Tour – The Samuel Adams Brewery, learn about craft beer and sample some.
2. Boston Duck Tours – Amphibious vehicles of land and shining sea.
3. Ghosts & Gravestones Tour – A night-time, fright-filled foray to Beantown’s most haunted places.
4. Whale Watching Cruise — See humpback and finback whales on the coast.
5. Harvard University Tour – Tour America’s first university with a student tour guide.
6. MIT Campus Tour – Tour one of the world’s best tech universities.
7. Day trip to Cape Cod – Great for beaches and seafood.
8. Day trip to Lexington & Concord – See Revolutionary War battlefields.
9. New England Aquarium – A family friendly aquarium with penguins, sea turtles and massive ocean tanks.