Massachusetts
Romantic Activities for Couples

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Our most recommended Massachusetts Romantic Activities for Couples

Boston: Harbor Champagne Sunset Sail from Rowes Wharf

1. Boston: Harbor Champagne Sunset Sail from Rowes Wharf

Embark on a sightseeing sunset cruise on Boston harbor and soak up the views of the famous skyline. Admire city highlights, including the Inner Harbor Islands and the Boston Fish Pier.    Board an elegant sailing yacht, the ' Adirondack III.' Travel in style on a classic 80 foot pilot schooner that is comfortable and spacious. Glide smoothly over the water and have the option of purchasing a refreshing drink at the onboard bar. Admire views of the historic scenery of Boston Harbor as you pass by the Boston Fish Pier and the Moakley Federal Courthouse at Fan Pier. Capture pictures of Castle Island and the Donald McKay monument. Cruise through the Inner Harbor Islands. Step back in time as you cruise by the historic Charleston Navy Yard. Go by the lush greenery of the Waterfront Park and take in the modern architecture of buildings like the New England Aquarium. Take a selfie in front of the Boston skyline. Have your questions about the sights and history of Boston Harbor and its surrounding areas answered by the attentive crew. Hear facinating facts and old-time legends about the maritime world of Boston. Return to your meeting point at the end of the tour.

Boston: Downtown Harbor Sailing Cruise

2. Boston: Downtown Harbor Sailing Cruise

Experience Boston like never before onboard the 80-foot pilot schooner Adirondack III. Enjoy a round-trip of smooth sailing, with some invigorating speed to boot. Within minutes of leaving dock, you’ll forget the distractions of life on land as you experience the joy of a sailing adventure. Cruise past landmark attractions, such as the Boston Fish Pier, Moakley Federal Courthouse at Fan Pier, and Castle Island. Drift past the Inner Harbor Islands and see the historic Charleston Navy Yard. Look out for the green oasis of Waterfront Park and the home to hundreds of marine critters, including sharks and sea turtles, at New England Aquarium. Your knowledgeable captain and crew will be on hand to answer questions about the sights and history of Boston Harbor and its surrounds, from interesting facts to old-time legends. Wines and local micro beers are available to purchase onboard, while complimentary soda and water will keep you hydrated along the way.

Downtown Boston Harbor Weekend Cruise with Brunch

3. Downtown Boston Harbor Weekend Cruise with Brunch

Weekends are a time for relaxing and getting your days started the right way. Join a Mimosa and Bloody Mary Cruise aboard the elegant Northern Lights to jump start your relaxation mode. While aboard, choose from a variety of mimosas and bloody Mary's. Enjoy the gourmet brunch buffet and select a cozy seat aboard the Northern Lights as you cruise around Boston Harbor to capture panoramic views of Boston. This is the perfect event for groups looking to entertain guests from out of town. You can see the sites without giving up a relaxing weekend. Small bridal parties can be accommodated and next day wedding parties. The Brunch Cruise offers the perfect event for individuals or a group looking to celebrate and relax. Also, see historic sites along the harbor such as: the harbor islands (Castle Island, Deer Island, Spectacle Island, Long Island, Lovells Island, Georges Island) Independence Fort, Bunker Hill Monument, USS Cassin Young, USS Constitution, Old North Church, Boston’s Seaport District with historic Fishing Markets and Boston’s incredible skyline.  The brunch menu includes pastries, granola, yoghurt, smoked salmon, bagels, fruit, scrambled eggs, potato hash, bacon, ham, salad, and dessert.

From Boston: Newport Mansions Full-Day Trip

4. From Boston: Newport Mansions Full-Day Trip

Enjoy Newport on this van tour from Boston. See how the wealthiest families lived during the gilded age with a visit to the Vanderbilt summer home and the Elms Mansion. Along the way, enjoy some complimentary snacks and bottled water while reading over a provided Newport guide book. Begin with hotel pickup in a luxury minibus, where the approximately 2-hour journey to Newport starts. The first stop is the Breakers, the Vanderbilt family's summer home. Take a self-guided audio-tour and explore the 70-room summer cottage. Here, you can also spend some time exploring the cliffs on a scenic cliff walk. Next, it's back to the mini-coach for a bus tour of Newport, which passes St Mary's Parish, where John F. Kennedy and Jacqueline Bouvier were married in 1953. After the bus tour, visit America's oldest existing synagogue, the Touro Synagogue. With your free time, you can do some shopping or have lunch on the waterfront. If you're a sports fan, you can enjoy discount admission to the International Tennis Hall of Fame. Finally, visit the Elms Mansion, where you can take a 90-minute self-guided audio tour. After the tour, return to the minibus, sit back, and relax as you enjoy the ride back to Boston.

From NYC: Exclusive Spanish-Language Day Trip to Boston

5. From NYC: Exclusive Spanish-Language Day Trip to Boston

Your trip to Boston begins in Midtown Manhattan at the entrance of your preferred pickup hotel: Millennium Broadway, Pennsylvania, or Manhattan at Times Square. Once you have been picked up, head north to the capital city of Massachusetts. There will be a stop halfway, where you will have time to have breakfast and use the services. Once you arrive in Boston, the first stop is Copley Square, where you can appreciate the architectural contrasts of the city. See iconic sites such as the first public library in the United States, the Hancock Tower, the Church of the Holy Trinity, and the Fairmont Copley Plaza Hotel. Within Copley Square, discover the monument to the Hare and the Turtle, which commemorates the cemetery of the Boston Marathon.  The next stop will be in the Church of Christ Scientist. Following, head through Massachusetts Avenue where you will see the Back Bay neighborhood, famous for its Victorian houses. Pass by Berkeley College, the largest private music school in the world. Then, marvel at the monument to Domingo Faustino Sarmiento and get up close to the Baseball Stadium Fenway Park, home of the Red Sox. Continue towards Cambridge where the MIT Massachusetts Institute of Technology and the prestigious Harvard University are located. Walk through the Harvard University Campus and past the famous monument of the three lies, after which you will have time to buy souvenirs. After this experience, back in Boston, walk one of the most attractive and expensive neighborhoods in the city "Beacon Hill." Leaving the neighborhood, pass by the bar made famous by the TV show "Cheers" and through the first public park in the USA. Cross through the Massachusetts Governorate, part of the Freedom Trail and the Financial Center, and the place of the Boston Massacre of 1770. The last stop will be at Quincy Market. At its inception in 1826, it was used as a center of production, purchase, and exchange of food products and is now the city's cultural center. In the market, you will have free time for lunch. Your guide will advise you as to where the best clam chowder and lobster sandwiches are sold, two of Boston's most famous local dishes. Finally, after lunch, head back to NYC and get dropped off where you were picked up.

Boston Harbor: Winter Holiday Weekend Brunch Cruise

6. Boston Harbor: Winter Holiday Weekend Brunch Cruise

Take a relaxing 2-hour morning cruise through the Boston Harbor during the holiday season in the warm, cozy, and festively decorated interior of your boat. While aboard, warm up with a cup of hot cocoa from a hot chocolate bar and enjoy the harbor sites. Enjoy a hot and freshly prepared three-course brunch as you soak in the panoramic views of Boston Harbor.  First course Pastries, Scones and Croissants, Fresh fruit and berries Yogurt Cranberry granola Bagels and lox Second course Scrambled eggs with herbs and cheese Roasted potato hash Bacon and smoked ham Winter salad Third course Peppermint bark chocolate squares and pumpkin bread pudding

Boston: Historical City Center Exploration Game

7. Boston: Historical City Center Exploration Game

Imagine you’re a professional record-setter who aims to be the first in everything you do, but how do you become the first at everything? Simple. You race to be the first person to visit every "first" in a country, a feat you can only accomplish in one place - Boston. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. Up for a fun challenge? Start at Boston’s Public Library. The game will take you around 1.5 hours to complete and you can also explore at your own pace: pause the game and resume anytime from the location where you paused it. You will finish at the Union Oyster House. After your booking, you will receive an email on how to download the game to your phone. You can play on your own, in a large group or in several smaller groups that compete against each other and meet at the final stop of the game. For larger groups, one person can purchase access for the entire group by selecting the number of people in the group. All group members will be able to download and play the city game on their phone. Alternatively, each person can make their own purchase.

Boston: Walking the Freedom Trail Exploration Game

8. Boston: Walking the Freedom Trail Exploration Game

Trace the steps of the Founding Fathers of the United States with a self-guided city exploration game on your phone. Discover buildings and landmarks related to the American War of Independence as you explore Boston at your own pace. Start the game at Massachusetts State House and explore at your own pace. As you solve challenges, the story unfolds and exact directions on your phone will guide you to the next location. See the Old City Hall, the Boston Massacre Sites well as many other local landmarks within the city related to the Founding Fathers. Park. Pause the game at any time to explore points of interest further on a fully self-guided adventure. Resume your tour from any location where you paused it. Finally, finish up your exploration of Boston at the statue of Samuel Adams.

East Boston: Self-Guided Bicycle Ride with Picnic Lunch

9. East Boston: Self-Guided Bicycle Ride with Picnic Lunch

Embark on an outing for two with a romantic picnic lunch and bicycle rental in East Boston. Grab everything you'll need for your picnic and set out on the back of a bike to seek out the perfect outdoor spot. Choose between a tandem bicycle and a Surrey cycle, a 4-wheel bike with a single bench that is ideal for some one-on-one time with your significant other. Take your pre-packed lunch with you and set out on your bicycle tour. Start in Bremen Park and glide down the East Boston Greenway. Stop anytime, at any place of your choosing for a picnic. Your picnic kit includes a blanket and a picnic basket complete with plates, napkins and utensils, a craving box of chips, fruit snacks, and cookies; bottled water, and sparkling cider.

Frequently asked questions about Massachusetts Romantic Activities for Couples

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Other Sightseeing Options in Massachusetts

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What people are saying about Massachusetts

Overall rating

4.3 / 5

based on 114 reviews

Such a fun experience. Staff was friendly and the boat was nice. We took public transportation because we did not want to have to find parking. Short walk from the station.

Great Cruise of Boston Harbor and the outer islands. Brunch was great, good selection! Crew & Staff were awesome! Highly Recommend!

Very good value for the cost. Crew was pleasant and helpful. Boat was clean and easy on and easy off

Fantastic experience! Crew was excellent! They were all friendly, informative and accommodating!

Staff are fabulous. Some rude passengers but that can't be helped.