Cruises & Sailing

(34 activities)
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    Dinner Cruise

    As you are boarding, the ship's photographer records the moment for your entire party. The Captain and crew greet you as you step onto the ship. Step inside your deck, the hostess will greet you and escort you to your private table where your wait staff will introduce themselves and give you the opportunity to decide for yourself how to pace your service. Serving begins. From each of her three climate-controlled dining decks to the Observation deck, Boston Dinner Cruise offers a singularly unique setting that begs to be explored. Understated art-deco accents. Enticing dance floors. And a distinctive atmosphere reminiscent of the classic ocean liners. Be sure to visit the Captain's bridge, open to all passengers throughout most of the cruise. Enjoy live entertainment for boarding and food service paired with an entertaining DJ that will get you up and dancing after their meal. Return, hours later. Relaxed. Refreshed. As you depart, you'll find your Souvenir photo ready for purchase. Classic Dinner Menu (subject to change) FRESH SALADS Organic Mixed Field Green Salad Organic Spinach and Kale Salad Mediterranean Couscous and Chickpea Salad MAIN COURSE Roast Salmon & Tilapia Chicken Parmesan Meatballs Twice Cooked Beef Short Ribs Baked Ziti Roast Broccoli DESSERTS Mini Pastries Cookies Brownies Seasonal Fruit
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    Lunch Cruise

    After you board your lunch cruise, have a little time to explore the boat as it pulls away from the dock. The lunch buffet will soon begin, and you can take as little or as much as you'd like from the all-you-can-eat buffet! For an extra special lunch, upgrade to the lobster option (seasonal). While you dine, enjoy a narrated look at Boston's breathtaking skyline from the panoramic windows.After you eat, head to the top deck - the largest outdoor patio deck in town - to catch a breath of fresh air and an amazing view. Or, rock 'til you dock while the DJ plays a variety of music, from line dances to Top 40 hits.During your cruise, pass by the World Trade Center, the financial hub of Boston. See where the Boston Tea Party took place in 1773, when rebels disguised as Indians dumped tea into the harbor to protest British taxes. Pass by the location of the Boston Massacre, which is now a simple circle of cobblestones that marks the site where five American colonists were killed by British soldiers in 1770. The brutality of this incident helped spark the anti-British rage that ultimately led to the American Revolution.See the USS Constitution, also known as Old Ironsides, a nickname earned because of her invincibility in battle. Old Ironsides was launched in 1797 and is the oldest, fully commissioned naval vessel in the world. You'll also see the World War II naval destroyer, the USS Casin Young.Then see the Tobin Memorial Bridge, erected in 1948-49 and opened to traffic in 1950. It connects the Charlestown section of Boston with Chelsea. Additionally, see Fort Independence and Castle Island. Fort Independence is located at the entrance to Boston Inner Harbor. First settled in 1634, the island features the nation's oldest fully maintained fort.
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    Boston City Lights Sail

    Liberty Fleet of Tall Ships
    Step on board a tallship for a night cruise through Boston. If you're wondering what the heck a tallship is, we'll give you a hint: Pirates of the Caribbean. Yes, you'll be sailing past the scenic city lights on a traditionally-rigged ship with huge, billowing sails and towering masts. Although the boat itself is beautiful, you'll also have breathtaking views of Boston and its historical points of interest. Help yourself to a cocktail or two and enjoy the view of the stars and skyline with a scenic tour on an even more splendid sailing craft.
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    Day Sail

    Classic Harbor Line
    The maritime world of Boston has many great stories to offer, and on this classic afternoon sail through the Boston Harbor, you'll get to see and hear it all. Experience the sights of the Boston Fish Pier, The Moakley Federal Courthouse at Fan Pier, Castle Island, the Donald McKay monument, the Charleston Navy Yard, and much more, on a sail aboard the Adirondack III, a classic 80 foot pilot schooner. Experience Boston like never before, on a schooner, a drink in hand, and a knowledgeable captain and crew to ask about all the stories behind some of Boston's most unforgettable sights.
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    BYOB Spectacle Island Picnic

    Boston Harbor Mini Tours and Shuttle LLC
    Set sail from Fan Pier for an adventure that includes dramatic views of Boston, time to explore the hills and beaches of Spectacle Island, and whimsical visits from the ghost of John Adams clad in fishing gear. You'll spend approximately 1 hour on the water, with 2 hours in between to hike the island, fly kites, check out the small museum, or even swim, weather-dependent. It's a fun getaway for kids, groups, dates and entertaining out-of-town visitors. Hop aboard a speed boat for a unique way to take in the sights of the city!
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    Boston Tea Party Sail

    Liberty Fleet of Tall Ships
    Come aboard Liberty Clipper (named after John Hancock's ship) to discover the Boston Tea Party and sail through the Boston Harbor. You'll be welcomed aboard by a professional reenactor dressed in period attire as you prepare to hoist sail. On this Boston Tea Party experience, expect to host a town hall meeting, fire the ship's cannon, and toss the tea into the sea! You will also have the opportunity to help set the sails and even take a turn at the helm with the ship's captain!
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    City Lights Sail

    Classic Harbor Line
    The maritime world of Boston has many great stories to offer, and on this classic sail through the Boston Harbor, with an evening sea breeze and all of Boston at your back, you'll get to see and hear it all. Experience the sights of the Boston Fish Pier, The Moakley Federal Courthouse at Fan Pier, Castle Island, and the Donald McKay monument, the Charleston Navy Yard, and much more, on a sail aboard the Adirondack III, a classic 80 foot pilot schooner. Experience Boston like never before, on a schooner, a drink in hand, and a knowledgeable captain and crew to ask about all the stories behind some of Boston's most unforgettable sights.
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    Boston Harbor Sail (Liberty Clipper)

    Liberty Fleet of Tall Ships
    Set sail for the Boston Harbor on Liberty Clipper, a magnificent schooner! On your Boston sail, you'll see the sights in Boston Harbor and everything the ship has to offer. The crew will invite you to help hoist the sails and even to take a turn at the helm. There will also be a bar stocked with soda, water, Sam Adams on draft, mixed drinks, wine, and snacks. Take the wheel, set the sails, or just sit back and enjoy the sights and beauty of the Boston Harbor and her islands! The choice is yours!
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    Brunch Cruise

    Classic Harbor Line
    Wake up and embark on an exciting sea voyage with a satisfying drink in hand! Start your day on the open water as you sail around the Boston Harbor while observing the fascinating and historic scenery. See the USS Constitution,Bunker Hill Monument, USS Cassin Young, and many more sights, firsthand! This cruise features a freshly prepared gourmet buffet brunch included with each ticket. Drinks are available for purchase on-board by credit card only. You will be so refreshed, even the morning people will want to channel your energy!
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    Sunset Sail (Liberty Clipper)

    Liberty Fleet of Tall Ships
    Enjoy a Sunset sail aboard Boston's tall ship known as the Liberty Clipper. On your sunset sail, you'll view Boston and the Harbor Islands while enjoying the majestic experience of sailing through this beautiful area. There will also be a bar stocked with soda, water, Sam Adams on draft, mixed drinks, wine, and snacks. It will be a relaxing end to the day where you can look at onto the water and enjoy the natural beauty of the area. Expect a great experience on this peaceful sail with a gorgeous view.
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