Massachusetts
Romance & Special Occasions

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Our most recommended Massachusetts Romance & Special Occasions

Boston: Harbor Sunset Yacht Cruise

1. Boston: Harbor Sunset Yacht Cruise

Embark on a sunset yacht tour of Boston Harbor. Step aboard the classic Northern Lights yacht, a coast guard certified vessel with a captain and crew. The motor yacht Northern Lights is stylized after the classic New England 1920s-style steamships. Sit back and relax in a climate-controlled (with heating and air-conditioning) cabin, or enjoy the sea breeze on the open-top deck. Be sure to visit a fully stocked bar on the main deck to purchase refreshments by credit card, to sip refreshing drinks as you cruise along the harbor. The Northern Lights yacht is one of the most comfortable and versatile cruise vessels in Boston Harbor, at 115 feet in length it features six bathrooms and provides ample seating throughout the ship for up to 149 passengers. Built for taking groups of people on spectacular sightseeing adventures, she is the perfect vessel for taking groups of friends and family out to see the harbor.

Boston: Harbor Champagne Sunset Sail from Rowes Wharf

2. 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: Sunset Cruise

3. Boston: Sunset Cruise

Meet at Rowes Wharf and set off on a guided boat tour. This sunset cruise will give you unparalleled views of Boston's famous landmarks. Escape the heat and admire Boston’s beautiful skyline and the historic USS Constitution as the sun sets behind the city. Your expert guide will be able to tell you about some of the city's landmarks and history. As evening sets in, the sunset cruise will highlight popular and famous scenes set at Boston Harbor from both past and present. Snacks and cold beverages including water, juice and soda; as well as a full bar, are available on every boat.

Boston: Summer Nights Sunset Trolley Tour

4. Boston: Summer Nights Sunset Trolley Tour

Discover Boston’s illustrious story aboard Old Town Trolley on this exciting new sunset tour. Watch the city skyline fade into the night over the Charles River. See the moonlight light up Boston’s cobblestone streets and colonial architecture as guides show you the city’s most iconic locations. Take in all the picturesque scenery as you pass by iconic locations such as the North End, Boston Harbor, the Boston Commons, the Massachusetts State House, Boston Public Library, the Bunker Hill Bridge, TD Garden, the Museum of Science, Trinity Church, John Hancock Tower, and Cambridge. Discover the rich history of America’s Cradle of Liberty on this 90-minute tour. Witness history come to life as soft music and lively narration set the stage for a beautiful sunset over the Charles River.

Provincetown + National Seashore : Private Pedicab Tour

5. Provincetown + National Seashore : Private Pedicab Tour

Enjoy an open-air private pedicab tour. Discover all the highlights of the town as your driver provides light narration. Start and stop anytime you wish, for photo opportunities or other points of interest. Ride down the famous Commercial Street, stop by MacMillan Wharf, and swing by Pilgrim Monument. See the Scenic and Historical Cape Cod National Seashore and Herring Cove Beach the way it was meant to be seen; in the wide open-air. Receive a free Polaroid souvenir photo as a memento of your visit to Provincetown.

East Boston: Self-Guided Bicycle Ride with Picnic Lunch

6. 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.

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Other Sightseeing Options in Massachusetts

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What people are saying about Massachusetts

The sunset cruise was a beautiful way to see the Boston skyline. There’s a lot of space and seating. The cruise also makes sure to stop and let passangers see the USS Constitution shoot it’s evening cannon. Great experience for the price!

Our cruise was fabulous! The boat exceeded our expectations- no metal benches!- the interior was gorgeous!! Even though it was rainy, we had a lovely time. Service and atmosphere were spectacular! 10/10 recommend!

It was a pleasant experience, the staff was very helpful, and made it very easy when boarding the yacht. I would definitely book one again and recommend it to my friends!

It was absolutely lovely. Very chilled out. Lots of space on upper deck. Great bar. Lovely vibe. LOVED EVERY MOMENT.

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