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

    Take to the open sea for a fully narrated 90-minute tour around Boston Harbor, bringing your history book to life. Immerse yourself in Boston's history as you 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. From the hero tales of the Revolutionary War to the local legends of the sea, you’ll be entertained and enthralled. Other highlights you’ll see include the nation’s oldest continuously manned lighthouse, the Harbor Islands National Park Area, Boston’s working port and examples of extravagant waterfront living.

    The sightseeing cruise was nice but there was no 11 am cruise. The company gave us seats on the noon cruise without a problem but we wasted an hour by getting to the dock for a cruise that didn’t exist. Don’t use Get Your Guide for booking. Try to go directly to the provider.

  • Boston Harbor Codzilla High Speed Thrill Boat

    2. 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 ...

    So much fun!! Crew was awesome and also had some interesting historical facts about the Haaaba

  • Boston Harbor Champagne Sunset Sail from Rowes Wharf

    3. 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 cap...

    We thoroughly enjoyed this sunset cruise. The Captain and the crew were knowledgeable, professional, and friendly. The view was amazing….. not only did we experience a beautiful sunset, but we saw about 8 planes coming into Boston Logan Airport with several fluting right over us. The boat was comfortable and the drinks were great. Would highly recommend.

  • Boston Harbor: Fall Foliage Luncheon Cruise

    4. Boston Harbor: Fall Foliage Luncheon Cruise

    Step aboard your yacht and settle into a seat in the climate-controlled observation cabin or on the open top deck. Once your captain has lifted the anchor, you are welcome to move around the boat and get your hands on a beverage from the bar.  As part of your ticket, enjoy a gourmet buffet-style lunch. Freshly-made seasonal items such as an assortment of sandwiches, fruit, chips, and desserts will be served directly to you. This cruise is excellent for families, friends exploring Boston and surrounding areas, and visitors or locals looking for a unique and relaxing afternoon adventure. Join the people that are drawn to New England every year thanks to its vibrant foliage. Capture the unique colors of fall on the Boston Harbor Islands while hearing stories about pirates and ghosts that haunt the islands. Find out how the islands have played an integral role in fortifying Boston in ever...

  • Boston Harbor Fall Foliage Weekend Brunch Cruise

    5. Boston Harbor Fall Foliage Weekend Brunch Cruise

    Capture the unique colors of fall on the Boston Harbor Islands while hearing stories about pirates and ghosts that haunt the islands. Find out how the islands have played an integral role in fortifying Boston in every war from the Revolutionary War until World War II.  Enjoy panoramic views of Boston Harbor with the decorative colors of fall and see historic sites along the harbor. Keep an eye out for harbor seals in early spring and fall, cormorants, ospreys, egrets, blue herons, oystercatchers, and other wildlife. Enjoy a 3-course brunch freshly made by the chef onboard. Menu items include: First Course: • Assorted muffins, scones, and tarts • Belgian waffles with maple syrup and roasted apples • New York bagels with herbed cream cheese • Yogurt and banana nut granola • Selection of sliced fruit Second Course: • Bourbon smoked bacon • Chicken apple...

  • Boston: Downtown Harbor Sailing Cruise

    6. 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 compliment...

    Overall a pleasant experience. It would be even better if the staff are more interactive with the passengers and provide commentary on things like how sail boats work, history of that boat, history of boston harbor, what buildings are on the skyline. I think that’s a great opportunity to further improve customer experience.

  • Boston Harbor: Full Moon Cruise

    7. 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.

  • Boston Harbor: Winter Holiday Weekend Brunch Cruise

    8. Boston Harbor: Winter Holiday Weekend Brunch Cruise

    Take a relaxing 2-hour morning cruise through the Boston Harbor during the holiday season in the warm, cozy, and festively decorated interior of your boat. While aboard, warm up with a cup of hot cocoa from a hot chocolate bar and enjoy the harbor sites. Enjoy a hot and freshly prepared three-course brunch as you soak in the panoramic views of Boston Harbor.  First course Pastries, Scones and Croissants, Fresh fruit and berries Yogurt Cranberry granola Bagels and lox Second course Scrambled eggs with herbs and cheese Roasted potato hash Bacon and smoked ham Winter salad Third course Peppermint bark chocolate squares and pumpkin bread pudding

    A wonderful, entertaining and relaxing experience. The atmosphere of the boat and Boston Harbor, the food, as well as a running commentary of Boston's sites made for a great experience. The food was delicious and the crew provided a great experience.

  • Boston: Champagne City Lights Cruise 1920s Commuter Yacht

    9. 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 interi...

    My experience with Boston Harbor Campaign cruise was wonderful. It was a great night with my family visiting from NYC. They were truly surprised by my thoughtfulness. They were also happy with their experience in Boston. Heartfelt thanks! Annette

  • Boston: Irish Christmas Carol Holiday Cruise Northern Lights

    10. Boston: Irish Christmas Carol Holiday Cruise Northern Lights

    Take to the water and get into the holiday spirit by singing some holiday ballads the way the Irish do, with a beer in hand and a whiskey or two. It’s the holidays and in this 1920s-styled motor yacht, Northern Lights, decked out with festive décor and the sound of the holidays in the air, this unique tour is sure to put you in a merry spirit. Get stunning panoramic views of the Boston skyline and iconic waterfront sites such as Bunker Hill Monument, USS Constitution and the Marriott Custom House Tower. Snuggle up on the lounge furniture with a hot cup of cocoa or grab a seat at one of the four tops. Snacks and tasty holiday adult beverages are also available on this Irish Christmas Carol Cruise. Take a cruise with friends to celebrate the season or as a fun way for two people to start the night together. Enjoy song in climate-controlled cabins (heating and air-conditioning). This crui...

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What people are saying about Boston Waterfront

Overall rating

4.6 / 5

based on 164 reviews

I've lived around Boston for 40 years but I still learned some real Pearl's from the narrator. Fabulous trip. It didn't hurt that it was a picture perfect day.

Great boat ride around the harbor. Lots of historical information we had not heard before even though we live here. Highly recommend.

So much fun!! Crew was awesome and also had some interesting historical facts about the Haaaba

Narrator was very detailed she spoke clearly Very interesting cruise

Great tour of the Harbor. Our guide was wonderful!