Boston Waterfront
Sightseeing Tours

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Our most recommended Boston Waterfront Sightseeing 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: Full Moon Cruise

4. 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 Citywalks: Private Personalized Walking Tour

5. Boston Citywalks: Private Personalized Walking Tour

Boston Citywalks will personalize a 2-hour tour of the city that offers you just the right mix of history, architecture and culture, bringing Boston alive and making you feel a part of the city. We’ll share our love for this special place with facts, stories and humor that reflect Boston’s quirky nature. Our customized walking tours are created in line with your interests, highlighting what you’d like to see. We’ll meet you at your hotel and take you on a unique excursion around Boston and show you what makes this city so special. We may visit Beacon Hill and Back Bay and walk along the Freedom Trail. We may choose to visit Chinatown and the North End – or head to the Waterfront and maybe Charlestown. If you prefer, we can even take an excursion to Cambridge and visit Harvard Square. Whatever you choose to see, our aim is for you to experience the warmth, timeless beauty and unique historic charm of Boston that will make this tour memorable. If you are not familiar with Boston or prefer to leave all that up to us, just let us know. We can give you a Boston Highlights Walking tour or design one just for you based on your focus. For example: history, architecture, culture, shopping - or a mix of all.

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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 91 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.