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Romantic Things To Do in Boston on a Date

swan ride unique things to do boston

The cobblestone streets, beautiful parks and historic buildings of the Cradle of Liberty set the perfect backdrop to celebrate a budding or long-term romantic relationship. Boston features a number of romantic things to do. Whether you are heading out to celebrate an anniversary, Valentine’s Day or just the perfect Boston date night, you can choose from simple pleasures or extravagant adventures. Locals as well as visitors can experience unforgettable outings with one of the following romantic things to do in Boston.

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  • Entertainment Entertainment

Boston Summer Nights Tour & Charles River Cruise

Boston Public Garden and Washington Statue at duskSeasonal 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.

boston symphony hallA 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.

boston public gardenVisit 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.

boston commonStroll 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.

Boston Tea PartyKindle the Passion with Love from the Past

Visit the Boston Tea Party Ships & Museum for a glimpse of love and romance in Colonial America. Hear passages from the hauntingly intimate love letters of John and Abigail Adams. The emotion-filled correspondence provides insight into the strength of their love that lasted 54 years in the face of personal tragedies, periods of separation and some of the most monumental events in the country’s history. The selection of letters reveals the undying love and respect that they had for each other.

boston copley squareTravel 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.

boston charles river esplanade during a romantic boston dateExperience 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.

Exterior of Boston Museum of Science during a romantic date in BostonGaze 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.

boston isabella stewart gardner museumThe 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.

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