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Boston

Sailing Trips & Tours

Our most recommended Boston Sailing Trips & Tours

Boston Duck Tour: The Original and World-Famous

1. Boston Duck Tour: The Original and World-Famous

Make a splash on an 80-minute “Duck” tour of Boston and see the city from the land and water on one non-stop journey. Climb aboard your World War II-style amphibious landing vehicle at the Museum of Science or Prudential Center, and set off to discover unique neighborhoods. You will be welcomed on board by one of the legendary “ConDUCKtors®” who will narrate your tour and tell you about Boston as the birthplace of freedom and place of “firsts.” Travel by the golden-domed State House to Bunker Hill, and continue to Boston Common and Copley Square. Hear about the “Big Dig,” and marvel at fashionable Newbury Street. Go to historic Quincy Market, and more. As the best of Boston unfolds, your “ConDUCKtor®” will give you lots of little-known facts and interesting insights into the heritage of the city. Then, just when you think you've seen it all, it's time for a splash into the Charles River. Enjoy views of Boston and Cambridge that you won't get anywhere else. All tours feature a fun, informative local guide. In addition, foreign language tours depart every half hour from the Museum of Science location. These tours utilize cutting-edge GPS technology to offer tours in Spanish, German, French, Mandarin, Japanese, Italian, Portuguese (Brazilian dialect), Cantonese and Korean, at no additional cost to you. If you require this multilingual commentary, be sure to choose the option from the Museum of Science.

Boston: Historical Sightseeing Cruise

2. Boston: Historical Sightseeing Cruise

Experience breathtaking views, refreshing sea breezes, and vividly told stories of Boston past and present, aboard this one-hour tour around Boston Harbor. Depart from Long Wharf, then Cruise past the USS Constitution, the oldest commissioned US Navy war ship afloat today, marvel at the Bunker Hill Monument, and catch a glimpse of the fabled Old North End Church steeple. From expert narrators, you’ll hear heroic tales and local legends from the Revolutionary War, and learn how the harbor was transformed into one of the cleanest waterways in the country. The boat is equipped to give you the best view no matter the weather, with spacious outdoor viewing decks when the weather is fine, and indoor spaces with large windows if you want to be indoors. Onboard refreshments and snacks are also available for purchase.

Boston: Harbor Codzilla High Speed Thrill Boat

3. Boston: Harbor Codzilla High Speed Thrill Boat

Spark your adrenaline on a high-speed boat ride around Boston Harbor. Ride at break-neck speeds and enjoy the lively atmosphere on board with loud music and crew interaction. 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. 

Boston: Buffet Lunch or Dinner Cruise on Boston Harbor

4. Boston: Buffet Lunch or Dinner Cruise on Boston Harbor

Admire the sights of Boston with a 2-hour lunch or 3-hour dinner cruise on Boston Harbor. Savor an extensive buffet aboard the Spirit of Boston, and visit any of the 3 climate-controlled decks to watch the city glide by. Upon arrival, receive a personal greeting and have your photo taken by the ship's photographer to capture the memory. After being seated at your private table, feast on your lunch or dinner buffet consisting of creative meals prepared fresh daily. While you eat, listen to tunes from an onboard DJ. After your meal, go out on deck for panoramic city views. SAMPLE BUFFET MENU Salads Caesar Salad Romaine Lettuce | Aged Reggiano Parmesan Cheese | Herb Croutons Bow Tie Pasta Salad Scallions | English Cucumbers | Roma Tomatoes | Dill & Mustard Vinaigrette Vegetables, Potatoes, and Pasta Roasted Broccoli Florets, Creamed Corn and Cheddar Cheese Casserole, Mashed Potatoes Entrees Baked Ziti Pasta, Oven-Baked Atlantic Flounder, Filet Honey, and Sesame Chicken, Italian Beef Meatballs, Braised Beef Short Ribs Desserts Seasonal Spirit Dessert Display Please note that menu items are subject to change.

Boston: Afternoon Sailing Trip Around Boston Harbor

5. Boston: Afternoon Sailing Trip Around Boston Harbor

Embark on a scenic sailing trip on board an authentic tall ship in Boston Harbor. Sailing offers a great family-friendly way to see Boston from a new viewpoint. Choose between a 1.5-hour sail on the Liberty Star or a 2-hour sail on the Liberty Clipper. Hop on board and be transported back to the time when the tall ships would come in from the Old World. You can help set the sails, take the wheel, or sit back and enjoy the passing scenery of the Boston Harbor and the surrounding islands with the city skyline as a backdrop. The Liberty Clipper is a 125-foot gaff-rigged schooner designed after early American privateers. There is a cash-only bar on the ship with beer, wine, mixed drinks, sodas, bottled water, and snacks available. The Liberty Star is another gaff-rigged schooner modeled after 19th-century vessels that were once known for their speed and agility. The vessel offers a similar taste of what it was like to sail the magnificent ships that were once a common sight in every port. 

Boston: Sunset Cruise

6. 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: New England Harbor Cruise

7. Boston: New England Harbor Cruise

Boston Harbor is home to 34 islands and nearly every island has a story to tell. From its fortifications and hauntings to lighthouses and wildlife sanctuaries, the harbor is full of rich and unique history that will keep your attention throughout the trip.  Notable things to see include the Old North Church, Bunker Hill Monument, USS Cassin Young, the USS Constitution, Fort Independence, Boston's Seaport District, and Spectacle Island. The motor yacht's design was inspired by classic New England 1920s style steamships. She is one of the most comfortable and versatile cruise vessels in the Boston Harbor. She is 115-feet in length, features six bathrooms and provides ample seating throughout the ship. She is built for taking groups of people on spectacular sightseeing adventures. Thus, she is excellent for taking out groups of friends and family to see the harbor. Sit back and relax in the climate-controlled cabin or enjoy the sea breeze on the open top deck. During your harbor cruise, the captain will provide narration and the crew will be around to assist in making your trip more comfortable. Be sure to visit the fully stocked bar on the main deck to purchase refreshments.

Cape Cod Fast Ferry from Boston: One-Way or Round Trip

8. Cape Cod Fast Ferry from Boston: One-Way or Round Trip

This summer, forget about Cape traffic and parking hassles when you set sail aboard Boston's first, fastest, and most luxurious ferry to Provincetown and Cape Cod. Enjoy historic and scenic sites on the Provincetown ferry, while relaxing in the refreshing sea breeze as we whisk you away to the restaurants, beaches, shopping, and nightlife unique to Provincetown and the Outer Cape. And with cushioned airline and booth style seating, air-conditioning, free onboard WiFi, an audiovisual system with satellite TV, full cash bar, and food, getting there is half the fun.

Boston: Harbor Sunset Yacht Cruise

9. 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: Sunset Tall Ship Harbor Cruise

10. Boston: Sunset Tall Ship Harbor Cruise

Set sail onboard a genuine tall ship such as the 125' Schooner Liberty Clipper or the 67' Liberty Star and be transported back in time. See the Boston skyline, its harbor, and the different neighborhoods from the water during this sunset cruise. While breezes keep you cool you are welcome to help the crew hoist the sails the old-fashioned way (use those muscles) or just relax, enjoy a drink, and watch as others haul sails. Take a turn at the helm (steering wheel). Both ships offer both alcoholic and non-alcoholic beverages for sale. Do you think you might get hungry while you are onboard? Bring your favorite take-out and make it a picnic (sorry, no coolers or BYOB permitted). Choose between a 1.5-hour cruise on the 67" Liberty Star or a 2-hour cruise on the 125" Liberty Clipper.

Frequently asked questions about Boston Sailing Trips & Tours

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Other Sightseeing Options in Boston

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What people are saying about Boston

Overall rating

4.2 / 5

based on 228 reviews

This sunset cruise around the harbor was very enjoyable and well worth the price. The boat and seating options are nice, as are the route and landmarks that you can see along the way. Heads up, drinks from the bar are a tad bit expensive. I would definitely recommend this sunset harbor cruise!

My family and I loved this Duck Tour. Very informative and also fun for the whole family. Our guide was fantastic, and he really made the tour very enjoyable. Definitely recommend for anyone visiting Boston!

Great tour, came in April and it was great so when we came back in August for our son’s wedding, we took the family from AK with us.

Really fun way to spend some time on the harbor and learn a bit about Boston.

Excellent cruise. Unintrusive commentary and really relaxing.