Boston Sailing trips & boat tours

Our most recommended Boston Sailing trips & boat tours

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: Downtown Harbor Sailing Cruise

3. 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.

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What people are saying about Boston

Overall rating

4.2 / 5

based on 228 reviews

Turned up at the wharf to see a small group of people sitting waiting for the boat to turn up. Had 45 minutes until the tour so decided to explore around the wharf. When we got back, the line was huge. Convinced that this must be about three ships worth of people, we were shocked to learn that all of these people were going with us. That being said, once you got on the boat, there was plenty of room to pitch up at your preferred spot, either inside or out on deck. I would recommend taking a drink/flask with you as the line for the servers was very long at times. If you struggle to stand, you may want to arrive early to get the start of the line to secure a seat but that will hinder your view as they are not around the side rails and that’s where the majority of people stand to see the action.

Wonderful day, wonderful experience. For the time of the year we of course didn't get a sea-full of whales, but although the sea was quite rough, the captain and her crew did their utmost and manouvered the ship to get us close to the whales. Thumbs up.

saw the biggest pod of dolphins & 4 whales played by the boat forever!

Very relaxing. Good food. Great narration of the views!

Nice, pleasant afternoon around the Boston Harbor.