Summer Date Ideas in Boston, Massachusetts

Have a date in Boston this weekend and can’t think of anything to do? You’re in luck because we have a whole list of ideas for a fun summer date.

The following is a list of summer date ideas in Boston:

Grab a Drink at a Rooftop Bar:

A rooftop bar with a beautiful view of the Boston skyline is a very romantic place to have a date at a warm summer night.

There are many rooftop bars to choose from and they feature open air terraces, panoramic views of the city, stylish seating and great food and drinks.

Some popular rooftop bars in Boston include the Lookout Rooftop and Bar at the Envoy Hotel, the Rooftop at Revere, Deck12 at Yotel Boston and Six / West Rooftop Bar.

Get a Beer at a Beer Garden:

Enjoying a pint at a local outdoor beer garden is a nice way to enjoy a cold beer on a summer night. The many beer gardens in Boston have great food, a huge selection of beer on tap and spacious outdoor patios.

Some popular beer gardens in Boston include the Owl’s Nest Beer Garden, Trillium, Cambridge Brewing Company, Cisco Brewers Seaport, Dorchester Brewing Co and the Sam Adams Faneuil Hall Taproom.

Enjoy Some Outdoor Dining:

Outdoor dining became wildly popular during the pandemic and still is thanks to the city’s newly created outdoor dining program.

These restaurants feature outdoor patios, great food and drinks, comfortable seating and sometimes even views of the city skyline or harbor.

Some popular outdoor dining spots in Boston are Woods Pier 4, Alcove, Chickadee, B&G Oysters, Harvest, Oleana and the Barking Crab.

Attend a Summer Festival:

Many fun summer festivals take place in and near Boston during the summer months. These festivals include everything from art festivals, pride parades, cultural festivals, maritime festivals and numerous food festivals.

The festivals have free admission, live music, great food and some even have fireworks.

Some of the summer festival that place in or near Boston are the Boston Pizza Festival, the Boston Hong Kong Dragon Boat Festival, the Boston Jerk Fest, St. Anthony’s Feast and the Revere Beach Sand Castle Sculpting Festival.

Go on a Dinner Cruise in Boston Harbor:

Could anything be more romantic than a sunset dinner cruise with a view of the city? A dinner cruise is a great way to enjoy a beautiful summer night without all the crowds and noise.

The many dinner cruises available feature great food and drinks, live DJs, dancing and spacious observation decks to enjoy the view.

Some popular dinner cruises include the Boston Premiere Odyssey Dinner Cruise, the Boston Signature Dinner Cruise with Buffet, Classic Harbor Line Sunset Cruise and the Spirit of Boston Dinner Cruise.

Boston Summer Nights Tour:

Old Town Trolley offers a Boston Summer Nights Tour that would make for a great date experience.

The tour is 90-minutes long and begins at sundown so you can enjoy the beautiful sunset while taking a narrated trolley ride through historic Boston.

The tour is a journey through some of Boston’s most iconic locations, such as the North End, the Esplanade, the Prudential Center, Boston Common and the Boston Public Garden, while you learn about the city’s rich history from the tour guide.

Visit the IFC Museum After Hours:

The Institute of Contemporary Art is a great art museum in Boston that offers a number of after hours events on the first Friday of every month during the summer.

Some of these events include a Poolside Pride Party, a Vinyl Nights Party and a Caribbean Fashion Week Party.

These events feature dancing, DJ music and drinks on the IFC’s outdoor patio overlooking Boston Harbor.

Take a Ride on the Boston Common Frog Pond Carousel:

The Boston Common Frog Pond Carousel is a beautiful old-fashioned carousel ride that is open from mid-April until October every year.

The carousel was built in 1947 by the Chance Morgan Ride Company and features an oak floor, beveled glass mirrors, and a standard pie top with a lighted crown along with a variety of Bradley and Kaye horses, wildlife figures, and a chariot.

Afterwards, you can take a walk through the historic park, which is the oldest city park in America, before heading off to dinner or drinks at one of Boston’s rooftop bars or outdoor dining spots.

For more ideas on fun things to do in the summer, check out this article on summer attractions in Massachusetts.

10 Best Rooftop Bars in Boston.”,
Becker, Kayla. “23 best rooftop restaurants and bars in Boston.” Time Out Magazine, 23 Feb. 2023,
Osei, Zipporah and Emily Collins. “Here’s a running list of the best restaurants for outdoor dining in Greater Boston.”, 12 April. 2022,
Boston’s Best Outdoor Dining: 64 Amazing Patios, Roof Decks and More.” Boston Magazine,
Outdoor Dining Program.” City of Boston,
Grossman, Eric. “The Best Beer Gardens in Boston.” Time Out Magazine, 22 July. 2020,
Cain, Jacqueline and Scott Kearnan. “16 Best Beer Gardens to Visit This Summer.” Boston Magazine,

About William Briscoe

William Briscoe is a seasoned travel blogger and adventurer based in Massachusetts. With a passion for exploring hidden gems and sharing his travel experiences, Briscoe's website, "Mass Attractions," has become a go-to resource for those seeking seasonal attractions in Massachusetts. In addition to his website, William has contributed travel stories and articles to various travel publications, and his work has been featured in several magazines and online platforms. He also collaborates with tourism boards and travel companies to promote sustainable and responsible travel practices. William enjoys exploring the scenic beauty of New England, spending time with his family and two rescue dogs, and experimenting with classical New England recipes in his kitchen. He holds a degree in English Literature from Boston University, which he believes laid the foundation for his writing skills.

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