Romantic Things to Do in Boston

Known for fantastic food, walkable neighborhoods, and easy proximity to other New England attractions, Boston is an ideal destination for an adventure with your sweetheart. Here are some ways to get romantic in the waterfront city.

Sail on Boston Harbor

Nothing says romance quite like a sailing excursion on Boston Harbor. Hop on a clipper ship, sails and all, or opt for a pilot schooner to savor views of top sights such as the Boston Harbor Hotel, New England Aquarium, and Mystic Tobin Bridge. 

Taste Food, Wine, and Chocolate

It’s been said that the way to the heart is through the stomach, so take your significant other on a gastronomic adventure around Boston. If you have a sweet tooth, join a chocolate tour; for a more elevated culinary option, consider a food and wine tasting in the lovely Back Bay neighborhood. 

Take a Sunset Dinner Cruise

For skyline views and a romantic evening on Boston Harbor, book a cocktail or sunset dinner cruise. Tours typically offer a buffet, a live DJ, and drinks, so dine in style and dance all night with your special someone.

Enjoy the New England Foliage

New England is known for its colorful autumn leaves, so don’t miss the chance to take your partner along on a fall foliage journey along the winding roads of the White Mountains. Tours usually leave from Boston, and include hotel drop-off.

Spend a Day in Martha’s Vineyard

A short ride from Boston, you’ll find the quaint island paradise of Martha’s Vineyard, a scenic stretch of coastline just south of Cape Cod. Stroll through the island’s charming villages, check out the pastel-colored cottages, and explore the waterfront. If you’re there in summer, hang out on the beach and take a quick dip in the Atlantic.