Valentine’s Day in Boston, Massachusetts

Boston offers a variety of romantic and enjoyable activities for Valentine’s Day. These ideas would also make for a great winter date even when it isn’t Valentine’s Day.

Here are some ideas:

Enjoy a Romantic Dinner:

Explore one of Boston’s many romantic restaurants for a special Valentine’s Day dinner. Some popular options include Parker’s at the Omni Parker House Hotel, where JFK proposed to Jackie Bouvier, or you can enjoy a view of the city skyline with some igloo dining at the Lookout Rooftop or Woodshill Pier 4.

Take a Cruise on the Charles River:

Take a romantic dinner cruise on the Charles River, enjoying stunning views of the city skyline and bridges. Dinner cruises offer a unique and romantic dining experience as you enjoy a meal on a boat while taking in scenic views of the city and its waterfront.

Boston, Massachusetts waterfront

To enhance the experience, many dinner cruises provide entertainment options such as live music, DJs, or even dancing. Some cruises may have themed events or special performances.

Visit a Museum:

Visit the Museum of Fine Arts or the Isabella Stewart Gardner Museum for a cultural and artistic experience. Museums often have quiet and intimate spaces that allow for more personal conversations. You can take your time exploring without the hustle and bustle of crowded places.

Visiting a museum for Valentine’s Day breaks away from the conventional and adds an element of novelty to your Valentine’s Day celebration.

Enjoy a Chocolate Tasting:

Indulge in a chocolate tasting at one of Boston’s renowned chocolatiers. L.A. Burdick and Beacon Hill Chocolates are excellent choices.

Chocolate tastings are often hosted in charming and romantic settings, creating a cozy and intimate atmosphere. This makes for a memorable and special Valentine’s Day experience.

Catch a Live Music or Theater Show:

Check out the local events calendar for live music performances or theater shows happening on Valentine’s Day.

The atmosphere at live performances is often romantic, with dimmed lights and a focus on the stage. It sets the scene for a romantic evening out.

Go Ice Skating at the Frog Pond:

If the weather permits, go ice skating at the Boston Common’s Frog Pond for a fun and romantic activity. The Boston Common, with its historic charm and the beautiful Frog Pond, provides a picturesque setting for a romantic date. The surroundings create a magical atmosphere, especially if the pond is lit in the evening.

Skating hand-in-hand with your partner creates a sense of connection and intimacy. Ice skating is a fun and playful activity, perfect for couples looking to enjoy a lighthearted and enjoyable date. You can laugh, share playful moments, and enjoy each other’s company on the ice.

Visit a Historical Site:

Explore historical sites like the Freedom Trail or visit the USS Constitution Museum for a touch of history. Many historical sites in Boston have picturesque settings, whether it’s cobblestone streets, historic buildings, or charming gardens. The romantic ambiance of these sites can enhance your Valentine’s Day celebration.

Boston has a variety of historical sites to choose from, ranging from the Freedom Trail to historical houses and museums like the Paul Revere House or the Old State House. You can tailor the experience to your interests and preferences.

Attend the Salem’s So Sweet Festival:

The Salem’s So Sweet Chocolate and Ice Sculpture Festival is a winter festival held in nearby Salem, Massachusetts, usually around Valentine’s Day.

The festival is centered around the celebration of chocolate. Participating businesses, shops, and restaurants in Salem often create special chocolate-themed treats, desserts, and beverages for the occasion. Visitors have the opportunity to indulge in chocolate tastings and samplings at various locations throughout Salem.

Alongside the chocolate festivities, the festival also features impressive ice sculpture displays. Talented ice sculptors create intricate and beautiful sculptures that are placed throughout the city for visitors to admire.

If you want to learn about the origins of Valentine’s Day, check out this article on the history of Valentine’s Day.

Colby, Celina and Valerie Li Stack, and Rachel Leah Blumenthal. “The 14 Most Romantic Restaurants Around Boston.” Boston Eater, 17 Jan. 2024,
Gale, Natalie. “How to celebrate Valentine’s Day in and around Boston.”, 10 Jan. 2024,
Gale, Natalie. “Comedy, Chocolate, and Seven More Things to Do North of Boston in January and February.” North Shore 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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