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    Bufflehead Sailing Charters

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

    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

    Captain Dan is a wealth of knowledge about the area and it's evident he loves what he does.

    Mentioned in 6 reviews

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    Schooner Yacht Heron

    Schooner Yacht Heron

    (14 reviews)

    What a fabulous fun experience sailing out of Rockport, ME on The Heron. It was the highlight of…read moreour trip. Bonnie did a great job telling us some of the history of the ship and area. Love when the sails are lifted!!! Motor turned off, quiet, smooth ride! So relaxing. It is a beautiful ship. Lots of shinny teak. Delightful with great crew and just a few guests on board. Free parking right by dock. Thank you, Bonnie and Twig for making my sail special. Highly recommend!

    One of our favorite things to do when in Rockland is sailing aboard the Schooner Heron. We sailed…read more2x with them in 2020 and the first thing we did when we got back to Rockland this year was to look at the weather and book a trip with them. I picked an afternoon with an expected 14mph wind, so I knew we would sail smartly. I was surprised that Taylor was captaining the boat this trip instead of Twig, but his boat handling was conservative and flawless. Of coarse Bonnie was aboard to do her excellent narration regarding the history of Rockland's lime, timber, ice, shipbuilding and lobster industries and also tell us all about the lighthouse, islands, and seals we saw. Twig and Bonnie's personable adult daughter Rachel was also on board as crew. Bonnie and Rachel handled hoisting, trimming, reefing and tacking the sails as a well-oiled team. We started out conservatively with the fore mast and main mast sails both reefed, but were later able to shake out the reef on the fore mast sail for a little more speed without heeling the boat. We were able to sail near Robinson's Rock and saw that there were several seals sunning them selves there. We sailed midweek on a Thursday and there was lots of room for everybody on board. Taylor and Rachel cheerfully answered my many questions about the boat, the boat's offshore passages to and from the Caribbean each year and about local events. This was the first time sailing for the family seated across from us, but they had a good time. There was another group forward of us that pretty much kept to themselves so I didn't have a chance to chat with them, but they seemed to be enjoying themselves too. I did a bunch of small boat pleasure sailing and medium sized keelboat racing while I was at the University of Texas. I don't own a sailboat so the only sailing I have done since has been on Hobie Wave catamarans at all-inclusive resorts in Mexico and the Caribbean. I really enjoy chances to sail on bigger boats like the Schooner Heron. The Schooner Heron sails three trips daily from Rockport Harbor: Private morning sail, an afternoon Educational Eco Tour, and a Happy Hour Sunset Sail. Custom charters are also available on request. There is free parking in the harbor lot. Whether you have sailed before or just want to try it on vacation, I highly recommend sailing on the Schooner Heron as a solo, couple or family activity. You will have fun and be entirely comfortable with the ship and crew. They will treat you right. We're back in Rockland in a couple of weeks and will surely sail with them at least once more before heading back to Texas.

    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 May 2026

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