Romantic Things To Do in Boston on a Date

Boston Summer Nights Tour & Charles River Cruise

Seasonal tour • Runs from late May to early September

Embrace romance in Beantown with Old Town Trolley’s Boston Summer Nights Tour & Charles River Cruise! Imagine holding hands as your trolley travels the city’s historic streets and the sun dips below the horizon, casting a warm glow over everything it touches. Let the city lights guide your path as you explore iconic landmarks and hidden gems, all while creating cherished memories with your loved one. Then, set sail on the tranquil waters of the Charles River, where you can both marvel at the starlit sky above.

A Night at the Opera or Symphony

Enjoy a ballet, opera or other musical performance at the historic Boston Opera House. The Boston Symphony Orchestra is one of the most revered musical ensembles in the world. Symphony Hall is famous for its acoustical qualities. Dressing up in your evening finest accentuates the magic and is a great romantic thing to do in Boston.

Take in a Show at the Wang Theater

This romantic Boston landmark has afforded a stylish setting for Broadway quality plays since 1925. Statuesque columns made from imported marble and crystal chandeliers enhance the elegant setting. A private box offers an even more intimate experience.

Visit the Public Garden

Take a stroll through the oldest botanical garden in the country. Enjoy the view from the historic footbridge or sit back and relax in one of the famous swan boats inspired by the romantic opera “Lohengrin.” Pack a picnic basket and then spread a blanket on the sprawling lawn where you can gaze at the colorful grounds and enjoy the fragrant aromas. The vibrant hues of the Public Garden afford many spectacular photo opportunities.

Stroll Through the Common

While the Public Garden is picturesque with its iconic footbridge and swan boats, Boston Common also has a romantic legacy. Stretching northward from the southeast corner at Boylston Street to Joy Street, the Long Path plays a role in Oliver Wendell Holmes’ story “The Autocrat of the Breakfast Table.” The titular character proposes to his beloved on the walkway by asking if she will take the Long Path with him. This request symbolizes the journey through life. Taking a walk through Boston Common is one of the most romantic things to do in Boston.

Kindle the Passion with Love from the Past

Visit the Boston Tea Party Ships & Museum and discover the passionate spirit of Colonial America as you explore interactive exhibits and authentically restored vessels. Afterwards, indulge in a delightful afternoon tea at Abigail’s Tea Room, where you can savor the ambiance of a bygone era and tranquil water views of Fort Point Channel.

Travel Back in Time

Take a ride in one of Boston’s delightful horse-drawn carriages to experience a classic romantic Boston night out. Enjoy a leisurely tour of downtown as well as other historic neighborhoods and sights, such as Copley Square, Newbury Street, the Public Garden and the Theatre District.

Experience Venice in Boston

Enjoy the view of the Esplanade as you float down the Charles River in an authentic gondola while being serenaded by musicians. These tours may include roses, Champagne, chocolate and more to evoke the romantic atmosphere of Venice. You can also stroll along the Esplanade enjoying the breathtaking views as the colors of nature change throughout the year. The colorful palette of seasons includes the budding green of spring, the vibrant hues of summer, the blaze of autumn glory and the winter wonderland during the holiday season. The picturesque scenery of the Charles River is the perfect romantic thing to do in Boston.

Gaze at the Stars

Stargazing is a perfect romantic Boston activity. You and your loved one can spend an evening with the “Astronomy After Hours” program hosted on the roof of the Museum of Science. Gaze into space during the seasonal event using high-tech telescopes that afford the opportunity to marvel at the night sky and heavenly wonders above.

The Art of Love

View works celebrating love and beauty by a variety of masters at the Isabella Gardner Museum, which also features romantic gardens and courtyards. Based on a Venetian palace, these colorful oases include the historic Jordan Garden and the picturesque Monk’s Garden. They are the perfect spot for a quiet conversation or popping the question.

Love and All that Jazz

Situated in the Doubletree Suites, live music in Scullers Jazz Club can provide the soundtrack for you and your sweetheart. The intimate venue attracts a variety of legendary performers who write the melody of love.

Skate Arm in Arm

During colder weather, enjoy skating on the Frog Pond. Located on the Common, it is easy to reach. You can also try the rink underneath the Boston Harbor Hotel’s signature archway on the waterfront.

Picnic with a View

A delicious basket of food, fresh air and an awesome view combine to set the stage for a perfect date. When the weather is nice, enjoy a quiet respite on one of the hills surrounding the city. While the Corey Hill Overlook affords romantic views of the Boston skyline, you can also opt for Piers Park if you want a quiet spot near the water.

A great Boston date night awaits you in this romantic destination. You can shower love and affection on that special someone whether they are an art and music lover, a nature enthusiast or literary aficionado as the Hub offers numerous romantic Boston things to do year-round.