Massachusetts
Sailing Trips & Tours

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Our most recommended Massachusetts 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: Buffet Lunch or Dinner Cruise on Boston Harbor

3. 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.

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

4. 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

5. 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: New England Harbor Cruise

6. 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.

Boston: Sunset Tall Ship Harbor Cruise

7. 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.

Boston: Harbor Codzilla High Speed Thrill Boat

8. 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: Downtown Harbor Sailing Cruise

9. 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.

Boston: Sunset Cruise

10. 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.

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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!

Best weather of the year! Had a great waiter! Food was good and plentiful! Higgins was extremely attentive to our needs going above and beyond! Planning on returning next year!

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.