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    Bufflehead Sailing Charters

    4.8 (18 reviews)
    Open 9:00 am - 9:00 pm

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    Response time

    4 hours

    Response rate

    100%

    Services - Bufflehead Sailing Charters

    Boat charters

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    Saw a lighthouse from afar! Cape Dan told us it was slightly haunted...

    Had a wonderful time sailing with Captain Dan on the boat with a group of five. Got to sit and trade stories, and even sit at the very front of the boat and watch the waves up close. We brought snacks and drinks for our 3hr ride, and had a great time. It can get slightly cold with all the wind, so I'd suggest bring a windbreaker! Overall very fun and relaxing experience.

    The family relaxing with Captain Dan
    David B.

    I took my family of six out for a sail on a morning in August. It is a beautiful boat. The bay and surrounding waters are just gorgeous. Daniel is a very knowledgeable sailor and captain. It was fun to watch him sail the boat all my himself. He seemed to know every person working in the area and every ship. Daniel is extremely well-versed in sailing and the surrounding area, but also in many other things :-). We loved his quirky personality and especially his love for sailing, old boats, the environment and his hometown of Rockland. This was exactly the beautiful sailing experience that my family and I wished for and I would highly recommend this to any others

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    Review Highlights - Bufflehead Sailing Charters

    Our last sail was up in the air due to weather until the last minute and Dan was totally cool about playing it by ear.

    Mentioned in 10 reviews

    Read more highlights

    Schooner Heritage

    Schooner Heritage

    (10 reviews)

    Had a glorious time onboard with my daughter. Captains Ben and Shawn are experienced and always…read morewilling to explain things onboard. The crew are young and hilarious, albeit rookies at the craft. The ship is beautiful and a joy to be aboard. The food is excellent and plentiful. The trip was everything I was hoping for and more.

    We have been sailing with the Schooner since it was launched in 1983, initially with Skippers Doug…read moreand Linda Lee. The Heritage, being designed from the keel on up by the Lees for the more contemporary application of transporting people around Penobscot Bay for pleasure instead of transporting things like pig iron and coal from Maine to New York, Is therefore far more comfortable than the older restored/rehabbed neighboring boats, with a spacious common area for eating and reading and broader decks for sitting and taking in the scenery. Yet its historically accurate design and on-board equipment, such as a wood-burning stove and an old gas-powered one-cylinder "donkey" engine from the 1920's, harkens to the seafaring tradition of the old commercial off-shore coastal schooner. To quote JFK, "The torch has now been passed to a new generation," and Ben and Sean are now the proud Co-captains of this marvelous ship. In addition to touring the magnificent coastal scenery of the state of Maine, they bring on-board their own unique talents. Ben is notable for his precision when commanding the vessel and Sean, as executive chef, brings out wonderfully savory meals. Fear not, there is no wanting for food on this vessel - if you are a Hobbit used to 8 meals a day, this boat is for you. Both Sean and Ben are accomplished guitarists and they will entertain you onboard in the evening with an absolutely professional level of vocal and instrument harmony. I have a high bar for musical entertainment, and will walk away (or swim away, in this case) from second rate performances, but these two will sweep you away with their talent. Finally, the famous Wednesday "Lobster Island" lobster boils are not to be missed. The mixture of live lobster freshly boiled with Maine seaweed gives the lobster a sweetness that just cannot be replicated in any restaurant (or home, for that matter). There's more I could say but why drone on? Take a look at the photos that decorate their web site and imagine you are there. Time to book another rez for next year.

    Bufflehead Sailing Charters - boatcharters - Updated July 2026

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