Boston is a city that offers “best of both worlds,” as far as size – meaning it’s large enough to offer endless things to do (especially for people in their 20s and 30s) and it’s small enough to not feel overwhelming.  It’s an extremely walkable place, filled with outdoor venues, and activities for recent grads, and young professionals to enjoy. So, if you are looking for ideas about things to do in Boston, we've compiled some of our favorites spots for you here:

Photo by daniela de gol on Unsplash

1. Discover the Rose Kennedy Greenway

The 17-acre green ribbon of the Rose Fitzgerald Kennedy Greenway is a true treasure to the city of Boston.  

Along the Greenway, you'll find wide open green spaces with bright red adirondack chairs, beautifully manicured gardens, a rotation of quirky, interactive art, a contemplative peace labyrinth, ,and other well-known features such as the Greenway carousel, swinging benches, and several spray fountains that are a most welcome places to splash and cool off, or watch others do the same. 

Mingle at Trillium Beer Garden

Outdoor beer gardens have taken the city by storm lately, and Trillium Beer Garden on the Rose Kennedy Greenway is a super cool place to mingle with other young professionals in the city.  Happy hours here quite popular and people line up and are very willing to wait awhile to get inside the fences. Food Trucks line up right nearby so you can grab a quick bite while you wait. 

Photo by Trillium Brewing

2. Tour the city in a unique, new way

  • In addition to being a terrific walking city, guests and locals alike can select from many different ways to tour the city.  Popular options include Boston Segway Tours, where you'll get to see the city up-close and personal in a short amount of time – while learning Boston's history while riding your own personal Segway! 
  • Duckboat Tours feature a ride around Boston in an authentic, renovated World War II amphibious landing vehicle.  The ‘Duck’ tours the city by both land and water, and splashdown into the Charles River is quite a thrill, providing views of the Boston skyline from the water..  
Photo by Boston Duck Tours
  • Step back into time on a Freedom Trail Walking Tour, where a Colonial guide dressed in old fashioned garb takes you on a 90-minute walking tour of The Freedom Trail, from Boston Common to Faneuil Hall/Quincy Market

3. Experience the Boston Waterfront

Boston sits along Boston Harbor and offers tourists and locals alike the chance to experience . Along the waterfront are lots of options for those looking to head out on the water. There are also plenty of activities on land within view of the sea.

Take a Boston Harbor Cruise and visit an old fort

A great day trip might include taking a ferry ride out to visit one of the scenic Boston Harbor Islands. Ferries depart from Atlantic Wharf with destinations of Spectacle Island or Georges Island and Historic Fort Warren.

Photo by Boston Harbor Islands

Visit a historic fort, (Fort Independence at Castle Island). Castle Island is actually accessible by car, and features a beautiful walkway (a 2.16 mile loop), big grassy areas for running and playing, BBQ pits,lots of parking, and a small beach area. Carson Beach is just down the road offering more space to stretch out on.

Fort Warren is only accessible by boat, so you can take a Boston Harbor Ferry out for a visit. Ferry rides are about 50 minutes so it's a terrific day trip. Tours of Fort Warren are available, and if you are daring, you may opt to take the “Lady in Black” tour, and hear the tale of Fort Warren's infamous ghost!

Experience Codzilla, Boston's high speed boat ride

Codzilla is Boston's first and only high-speed thrill boat ride featuring two turbo-charged diesel engines generating 2,800 horsepower and speeds of approximately 40 miles an hour. Get ready for some thrills, laughs and more speed than you ever imagined as you zip across the ocean at up to 40 miles per hour with the wind roaring and the music blaring through a state of the art sound system.

Photo by Boston Harbor Cruises

Boston Harbor Hotel Summer Events

The Boston Harbor Hotel hosts a variety of free entertainment along the water every summer. This includes Classic Movies by Moonlight and concerts featuring a variety of different types of music.  There is a large bar/restaurant there that provides ample seating and views. And for the dancing souls, the barge is open for people to get up and dance along to the music.

4. Take a tour or watch a baseball game at Fenway Park

No visit to Boston would be complete without a trip to Fenway Park!  Catch a baseball game, or take a tour at the home of the Boston Red Sox, including the press box, dugout, field, and more. Tours run daily and leave from the Souvenir Store across Jersey (Yawkey) Way.  It’s always exciting to be at or near Fenway on game day.

Photo by Taylor Rooney on Unsplash

5. Third Thursdays at the Isabelle Stewart Gardner Museum

Soak up the enchanting atmosphere of the Isabella Stewart Gardner Museum at night at Third Thursday celebrations.  These lively, social evenings features music, creative collaborators, a cash bar, playful gallery activities, and hands-on art making, not to mention just being in the museum at night, as if you were one of Isabella's guests from long ago.

Photo by Isabelle Stewart Gardner Museum

6. Open Newbury Street days

Shopping and dining on Newbury Street is a fun way to spend an afternoon no matter what, however, over the course of 3 summer Sundays, Newbury Street becomes a pedestrian-only walkway, closing to vehicles allowing people the opportunity to use the full width of the street.    Some restaurants even put tables outside and visitors can dine al fresco so you can fully enjoy the beautiful summer weather.

7. Climb the Bunker Hill Monument

Bunker Hill Monument is located over the Charlestown bridge (just about a mile from TD Garden, with a pretty walk over the bridge to Charlestown).  Take the challenge and make the walk. Then, see if you can climb all 294 steps to the top.  

The obelisk was built to commemorate the famous Battle of Bunker Hill, and there is only one way up and one way down. The views (and bragging rights) are worth the climb. Be prepared for a cardiovascular workout.

Photo by the National Park Service

After your visit, you can  reward yourself with a quick visit to see Old Ironsides, the oldest commissioned warship afloat in the world. Tours are free, and it’s a pretty cool experience.  Just down the pier, you can opt take a scenic ferry ride back downtown from Charlestown pier. It's about an 18 minute ride that affords splendid views of the Boston skyline as well as a refreshing breeze.

8. The North End

Boston's ‘Little Italy' is known as The North End.   It's a neighborhood filled with character, charm and terrific restaurants.  You can't go wrong finding a great place to eat here, just walk around and peruse the menus, or follow the delicious aromas, and you are sure to find a winning meal. 

Hanover Street is the main artery, but you can find hidden gems on side streets, back alleys and on Ipswich Street.  No visit to the North End would be complete without stopping at either Mike's Pastry or Modern Pastry for a cannoli. Try them both to see which one is your favorite. 

Photo by Mark Boss on Unsplash

The North End abuts a beautiful park along the Rose Kennedy Greenway that features swinging benches, a wide open lawn & garden, and gentle spray fountains where kids can frolic.   It's a popular place to stroll after dinner or to sit and enjoy your box of pastries.   

It's also a short walk to the Christopher Columbus Park, a beautiful waterfront venue with benches and restaurants as well as Faneuil Hall and Quincy Market.   You could spend an entire day just walking along the Boston Harborwalk and the Greenway, discovering all sorts of fun things to do along the way.

9. Community Boating & Sailing

Community Boating is a non-profit organization dedicated to providing sailing and boating opportunities to anyone interested in learning to sail. Visitors can also rent sea kayaks, stand-up paddleboards, and windsurfers for a daily fee.  This is a terrific way to spend a summer afternoon on the Charles River.

Photo by Community Boating, Inc

10. Enjoy the views from the Envoy Hotel's rooftop bar

There are few public spaces that boast a view like the Envoy Hotel’s Rooftop Bar. Located along the Fort Point Channel, the large patio space is a great place to be seen among the young professional crowd, catching refreshing breezes from the harbor and enjoying views of the city and many boats, yachts and other waterway activity.  

During the winter, the patio replaces it’s summer seating and shade umbrellas with super cool LED igloos, so patrons can still enjoy a beverage with friends inside these cozy domes.  

Photo by Kelly Sikkema on Unsplash

In short, Boston is a terrific walking city that features lots of things to do for all ages.  Proximity to large waterfront affords entertainment both on and off shore; plus, the four seasons provide different environments for each activity.  

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