New England
Sailing Trips & Tours

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

2. 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 Romain 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.

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Boston: Harbor Sunset Yacht Cruise

3. Boston: Harbor Sunset Yacht Cruise

Enjoy a 2-hour experience (15-minute pre-boarding) in Boston Harbor. Step aboard the classic Northern Lights yacht, a coast guard certified vessel with an extremely friendly and knowledgeable 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.

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Boston: Lunch or Dinner Cruise on the Odyssey

4. Boston: Lunch or Dinner Cruise on the Odyssey

Experience an elegant dining cruise on the Boston Harbor aboard the luxury cruising vessel, Odyssey. Your voyage begins with being welcomed aboard by the captain and crew. The ship's photographer will take a picture to capture the memory.  After being seated, enjoy your gourmet meal consisting of creative appetizers and entrees prepared fresh onboard daily by the executive chef. The wait staff will time your meal according to your preferences so you can savor every moment of your cruise.  The 3-course menu includes vegetarian, meat, and fish options. After your meal, listen to the live music or relax on one of three climate-controlled decks as you enjoy the scenery of the Boston skyline.

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Boston Harbor Champagne Sunset Sail from Rowes Wharf

5. 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: 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.

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Boston: Downtown Harbor Sailing Cruise

7. 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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Downtown Boston Harbor Weekend Cruise with Brunch

8. Downtown Boston Harbor Weekend Cruise with Brunch

Weekends are a time for relaxing and getting your days started the right way. Join a Mimosa and Bloody Mary Cruise aboard the elegant Northern Lights to jump start your relaxation mode. While aboard, choose from a variety of mimosas and bloody Mary's. Enjoy the gourmet brunch buffet and select a cozy seat aboard the Northern Lights as you cruise around Boston Harbor to capture panoramic views of Boston. This is the perfect event for groups looking to entertain guests from out of town. You can see the sites without giving up a relaxing weekend. Small bridal parties can be accommodated and next day wedding parties. The Brunch Cruise offers the perfect event for individuals or a group looking to celebrate and relax. Also, see historic sites along the harbor such as: the harbor islands (Castle Island, Deer Island, Spectacle Island, Long Island, Lovells Island, Georges Island) Independence Fort, Bunker Hill Monument, USS Cassin Young, USS Constitution, Old North Church, Boston’s Seaport District with historic Fishing Markets and Boston’s incredible skyline.  The brunch menu includes pastries, granola, yoghurt, smoked salmon, bagels, fruit, scrambled eggs, potato hash, bacon, ham, salad, and dessert.

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Portland: Schooner Tall Ship Cruise on Casco Bay

9. Portland: Schooner Tall Ship Cruise on Casco Bay

Set sail on a two-hour cruise from Portland along the rugged coast of Casco Bay. Pack a meal and your favorite wine or beer, and sit back and relax as you slip through the peaceful waters of Maine. Enjoy views of lighthouses, seals, and other coastal wildlife aboard a famous schooner tall ship. Join the crew to hoist the sails or take a turn at the ship's wheel if you feel inspired. Whether you're nine years old or 99, sailing aboard a Maine schooner is a unique adventure. Learn more about the wooden windjammers which are all listed on the National Register of Historic Places and were built in Maine.

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Boston Harbor Codzilla High Speed Thrill Boat

10. 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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Other Sightseeing Options in New England

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What people are saying about New England

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!

nice experience to me and my family. food,drinks and music were very good.

Wonderful tour, great guides and interesting facts.