Classic Harbor Line

(11 activities)
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    Sunset Harbor Cruise

    Treat yourself and someone special to a relaxing, romantic sunset cruise. Take in Boston’s skyline as the sun slowly sets and turns brilliantly orange or red. As you cruise further throughout the Boston Harbor, you’ll pass by historical and cultural points of interest, such as Fort Independence, Tobin Bridge, the U.S.S. Constitution, the Old North Church, and North End. Enjoy views of Boston on the open back deck or in the shade at midship. The boat features wraparound seating and a crowd-free environment, so you’re ensured a great, comfortable view. On top of all that, you’ll be provided complimentary soft drinks, water and light music to set a relaxing mood -- but feel free to bring your own picnic on board and purchase drinks from the cash bar!
    Sunset Harbor Cruise

    60 Rowes Wharf, Boston

    • Enjoy a romantic sunset cruise on a classic 1920s style yacht
    • View Boston’s city skyline, Fort Independence and other historical points of interest
    • Experience the romantic side of Boston with a scenic and relaxing tour
    • Bring a picnic and enjoy complimentary soft drinks on board
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    25 positive reviews
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    Sunset Sail

    The maritime world of Boston has many great stories to offer, and on this classic sail through the Boston Harbor, as the Sun dips below the horizon, 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.
    Sunset Sail

    60 Rowes Wharf, Boston

    • Enjoy the historic scenery of the Boston Harbor aboard a classic 80 foot pilot schooner
    • Experience a beautiful Boston Harbor sunset on the water
    • Ask your knowledgeable staff and crew anything you’d like to know about the sights
    • Enjoy the ride, see the sights and have a drink onboard
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    25 positive reviews
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    Day Sail

    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.
    Day Sail

    60 Rowes Wharf, Boston

    • Enjoy the historic scenery of the Boston Harbor aboard a classic 80 foot pilot schooner
    • Ask your knowledgeable staff and crew anything you’d like to know about the sights
    • Experience the joy of a leisurely sailing cruise
    • Enjoy the ride, see the sights and have a drink onboard
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    25 positive reviews
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    City Lights Sail

    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.
    City Lights Sail

    60 Rowes Wharf, Boston

    • Enjoy the historic scenery of the Boston Harbor aboard a classic 80 foot pilot schooner
    • Experience the beautiful Boston Harbor at night
    • Ask your knowledgeable staff and crew anything you’d like to know about the sights
    • Enjoy the ride, see the sights and have a drink onboard
    BOOK NOW ← Back
    25 positive reviews
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    Harbor Islands Picnic Sail

    Hop aboard the smooth sailing and elegant Adirondack III for a tour of the Boston Harbor Islands. Escape from the city and enjoy the lush greenery of Spectacle Island, Long Island, Thompson Island, Gallops Island, Georges Island, and Lovells Island -- among many other fascinating sights! No need to pack a lunch on this three-hour tour as you’ll be provided with complimentary soft drinks and a meal (vegetarian options are available). One thing you won’t want to forget though is a camera; there will be excellent photo opportunities the whole trip. Sail past the mysterious sunken island known as Nixes Mate, enjoy a perfect photo opportunity in front of Long Island Head Light, and see America's oldest light house, Boston Light and Fort Warren. Your friendly captain and crew will provide you with top-notch customer service and background on anything you’d like to know, whether it’s historical background or sailing lore of the islands.
    Harbor Islands Picnic Sail

    60 Rowes Wharf, Boston

    • Enjoy a relaxing sail and picnic to the Boston Harbor Islands
    • Take advantage of numerous photo ops as you discover the lush greenery of the islands
    • Hear about sailing lore and historical background of the islands
    • Get away from the city and enjoy what the Boston Harbor Islands have to offer
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    25 positive reviews
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    City Lights Cruise

    Take in the sparkling city lights of the Boston skyline with this relaxing, romantic after-dinner cruise. Your smooth-sailing ship offers wraparound seating and a crowd-free environment, so you’re ensured a breathtaking view as you sail past historic points of interest. Sit back and relax as you take in sights such as North End and the church that inspired the Midnight Ride of Paul Revere, Old North Church, as well as iconic landmarks including the U.S.S. Constitution, the buildings of Downtown Boston and much more. On top of all that, you’ll be provided complimentary soft drinks, water and light music to set a relaxing mood -- but feel free to bring your own picnic on board and purchase drinks from the cash bar!
    City Lights Cruise

    60 Rowes Wharf, Boston

    • Enjoy a relaxing cruise on a classic 1920s style yacht at night
    • View Boston’s sparkling city skyline, Old North Church, and sail past other historical points of interest
    • Experience the intimate side of Boston with minimal commentary and scenic views
    • Bring a picnic and enjoy complimentary soft drinks on board
    BOOK NOW ← Back
    25 positive reviews
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    Harbor Islands Sail

    Hop aboard the smooth sailing and elegant Adirondack III for a tour of the Boston Harbor Islands. Escape from the city and enjoy the lush greenery of Spectacle Island, Long Island, Thompson Island, Gallops Island, Georges Island, and Lovells Island -- among many other, fascinating sights! One thing you won’t want to forget though is a camera; there will be excellent photo opportunities the whole trip. Sail past the mysterious sunken island known as Nixes Mate, enjoy a perfect photo opportunity in front of Long Island Head Light, and see America's oldest light house, Boston Light and Fort Warren. Your friendly captain and crew will provide you with top-notch customer service and background on anything you’d like to know, whether it’s historical background or sailing lore of the islands.
    Harbor Islands Sail

    60 Rowes Wharf, Boston

    • Enjoy a relaxing sail to the Boston Harbor Islands
    • Take advantage of numerous photo ops as you discover Spectacle Island and Long Island
    • Hear about sailing lore and the historical background of the islands from your friendly captain and crew
    • Get away from the city and enjoy what the Boston Harbor Islands have to offer
    BOOK NOW ← Back
    25 positive reviews
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    Morning Mimosa Sail

    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. Experience Boston like never before, on a pilot schooner with a knowledgeable captain and crew to ask about all the stories behind some of Boston’s most unforgettable sights. See the Boston Fish Pier, the Moakley Federal Courthouse at Fan Pier, and many more sights, firsthand! A variety of beverages will be available for your purchase to satisfy any refreshment you may desire. You will be so refreshed, even the morning people will want to channel your energy!
    Morning Mimosa Sail

    60 Rowes Wharf, Boston

    • Set out on an early and invigorating sail on the Boston Harbor
    • Experience the joy of a leisurely sailing cruise and the historic scenery of the Boston Harbor
    • Expect to forget the distractions of life on land within minutes of leaving the dock
    • Kick back, and enjoy seeing the historic sights of Boston with a drink in hand
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    25 positive reviews
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    Bridges and Locks Infrastructure Cruise

    All aboard the Beacon, a smooth sailing boat with wraparound seating and breathtaking views. Enjoy a relaxing, crowd-free professionally narrated cruise through the bridge and lock system of the Charles River. Sit back and take in historical sights, such as the Leonard B. Zakim Bridge, the Old North Church made famous by the Midnight Ride of Paul Revere, the U.S.S. Constitution, and the B & M Railroad Bridge -- among many other, fascinating landmarks and places. Experience the bridge and lock system, invented by the Chinese in the 10th century, all while taking in the sun on the open back deck or in the shade midship. Feel free to bring your own picnic or purchase alcoholic beverages on board for this excellent nautical adventure.
    Bridges and Locks Infrastructure Cruise

    60 Rowes Wharf, Boston

    • Enjoy a relaxing, informative cruise on the Charles River
    • Sail past Boston’s historical sights and landmarks like the Old North Church and U.S.S. Constitution
    • Gain insight into the area’s history with a professionally narrated tour
    • Experience Boston’s history with Boston’s skyline as your backdrop
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    25 positive reviews
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    Harbor Island Cruise

    Get away from the hustle and bustle of the city by exploring the Boston Harbor Islands on this relaxing and crowd-free boat tour. This two-hour cruise will take you past the lush islands and numerous points of interest of the Boston Harbor, such as Long Island, Nixes Mate, a mysterious sunken island, Long Island Head Light, the oldest lighthouse in America, Fort Warren on George’s Island, and Lovell’s Island -- among many other, fascinating sights. Commentary from local legends will be shared by your friendly and knowledgeable captain. Soak up the sun on the ship’s open deck or relax in the shade midship while you sit back and take in the sights. Complimentary soft drinks and water will be provided, but feel free to bring your own picnic or purchase alcoholic beverages on board for this excellent nautical adventure.
    Harbor Island Cruise

    60 Rowes Wharf, Boston

    • Enjoy a relaxing sail to the Boston Harbor Islands
    • Take advantage of numerous photo ops as you see Fort Independence and Spectacle Island
    • Cruise by Long Island and see Long Island Head Light
    • Hear about sailing lore and historical background of the islands
    BOOK NOW ← Back
    25 positive reviews
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    Sails & Ales

    What’s better than the salty breeze, a glittering sunset, and a local brew? Let us know if you ever find out! In the meantime, come aboard and relish the unique flavors of a local brewery’s finest ales for a full tasting experience on the open water. You will be given a guided tasting of five flagship or seasonal beers while learning about the sophisticated processes of brewing these bad boys. Snacks will be provided to help elevate your tasting experience to the fullest. Whether you’re looking to unwind after a stressful day or celebrate a special occasion, come and add some flare to your evening’s activities.
    Sails & Ales

    60 Rowes Wharf, Boston

    • Enjoy a dazzling sunset sail while tasting beers provided by a favorite local brewery
    • Learn the intricacies of the beer-making process from the experts aboard
    • Discuss and differentiate the different flavors of each unique drink
    • Hear the history and tales of the waterfront sites, such as Independence Fort, “Old Ironsides," and Spectacle Island
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    25 positive reviews

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