Boston Waterfront
Sailing Trips & Tours

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Our most recommended Boston Waterfront Sailing Trips & Tours

Boston: 90-Minute Historical Sightseeing Cruise

1. Boston: 90-Minute Historical Sightseeing Cruise

Bring history to life as you take to the open sea for a fully narrated 90-minute tour around Boston Harbor. Cruise past the oldest commissioned ship in the US Navy, the USS Constitution, marvel at the Tea Party ships, and catch a glimpse of the Old North End Church. Listen to heroic tales and local legends from the Revolutionary War, and learn about the oldest continuously manned lighthouse in the nation, the Boston Light. Cruise past Boston's working port and marvel at examples of extravagant waterfront living.

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Boston Harbor Champagne Sunset Sail from Rowes Wharf

2. Boston Harbor Champagne Sunset Sail from Rowes Wharf

A perfect way to wind down after work or begin a night of romance...    Experience a beautiful Boston harbor sunset on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. You will be aboard the most elegant sailing yacht in town, Adirondack III - a classic 80 foot pilot schooner.     She is a smooth, gentle sailing vessel with some speediness to boot, the Adirondack III offers a comfortable ride for you and your loved ones.  Within minutes of leaving the dock, you'll forget the distractions of life on land, as you experience the ambiance of a sunset sailing cruise aboard a stellar vessel.  Enjoy the historic scenery of Boston Harbor:  The Boston Fish Pier The Moakley Federal Courthouse at Fan Pier Castle Island and the Donald McKay monument Inner Harbor Islands Charleston Navy Yard Waterfront Park The New England Aquarium Your knowledgeable captain and crew are always ready to answer your questions about the sights and history of Boston Harbor and its surrounding areas. From interesting facts to old-time legends, the maritime world of Boston has many great stories to offer. Ask them anything you'd like to know. Come enjoy the ride, see the sights and have a drink with us!

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Boston: Downtown Harbor Sailing Cruise

3. Boston: Downtown Harbor Sailing Cruise

Experience Boston like never before on board the 80-foot pilot schooner Adirondack III, and enjoy a 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 on board, while complimentary soda and water will keep you hydrated along the way.

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Boston Harbor Codzilla High Speed Thrill Boat

4. Boston Harbor Codzilla High Speed Thrill Boat

Hold on to your hats. It's Codzilla! This is no ordinary boat ride. True to its name, Codzilla is monstrously fun, a thrill a minute as you scream across the water at up to 40 mph, with a few hairpin turns and 360-degree spins thrown in for evil measure. Take a cruise on the wild side as you scream for more after riding Codzilla. The wind roars, the music blares and the waves will splash during a wet and wild 40-minute ride at full blast. The ride features an original soundtrack and a show scripted by Hollywood screenwriters. Sit back and relax? Not on this cruise. The boat, Codzilla, is 70 feet of marine aluminium and bad attitude, prowling the ocean with 2 turbo-charged diesel engines, state-of-the-art water jets and 2,800 horsepower. Its unique hull design makes it capable of thrilling 360-degree turns and spinning on a dime. So be sure to secure all hats, scarves, eyewear and bad hairpieces. 

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Boston Harbor: Full Moon Cruise

5. Boston Harbor: Full Moon Cruise

The cruise will start from Rowes Wharf and head out towards the fish pier and logan airport. Boarding begins 30 minutes prior to departure. During the cruise, you will be right under the flight path of Boston Logan Airport and hear the engines roar as the planes land and take off. We will head towards the Boston Harbor Islands and then back to the dock along the East Boston and Charlestown waterfronts. View the USS Constitution, the United States Navy's oldest commissioned ship, in all its splendor under the moonlight. There is a full service bar and light snacks available for sale during your cruise. You can also select an option to have a glass of prosecco included in your ticket.

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Boston: Champagne City Lights Cruise 1920s Commuter Yacht

6. Boston: Champagne City Lights Cruise 1920s Commuter Yacht

Sit back and relax with a loved one for a romantic cruise or enjoy the evening with a group of friends and experience the twinkling lights of downtown Boston. Cruise by the North End and catch a glimpse of the Old North Church made famous by the midnight ride of Paul Revere. Enjoy the buildings of downtown Boston such as the Custom House Tower, International Place, Independence Wharf and the New England Aquarium. Pass by the U.S.S. Constitution and hear how she got the nickname "Ironsides." View the Bunker Hill Monument, which sits behind the U.S.S Constitution. Marvel at the construction of the Leonard B. Zakim Bridge. Check out the colorful lights on the buildings in Boston’s Seaport District such as the new Vertex Building, World Trade Center and the Institute of Contemporary Art. The Northern Lights offers bench seating outside on the top deck as well as a climate controlled interior cabin. Adult beverages, soda, water and snacks are available for purchase by credit card only.

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Other Sightseeing Options in Boston Waterfront

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What people are saying about Boston Waterfront

Overall rating

4.6 / 5

based on 164 reviews

Great history and tour. Very informative. Parents did not control their children. They were screaming and running around and I could not hear the guide.

Easy to book. Cancellation policy generous. Tour was enjoyed by all even though we went out on a rainy December afternoon.

First time in Boston and this cruise was a perfect intro to the city! Definitely worth it!

Nothing it was great and you can sit upstairs or downstairs.

Wonderful tour, great guides and interesting facts.