Private sailing charters to see the Maine coast aboard a classic Wooden Boat.
Daysails, Custom Trips, Lobsterbakes & Picnics;
For small groups up to six people.
We sail Penobscot Bay from Rockland, Maine!
Captain's log:
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10 Years of 5 Star Reviews** Ok, one 4 star review, because that sail was "Fantastic, Wish I'd gone longer."
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Explore the Possibilities
Sea the SightsTouring Maine from the sea is a great way to experience its rugged beauty.
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Explore the IslandsSail to local islands, hike the sights, and have a picnic.
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Sail Among the Tall ShipsThe best way to see the tall ships that roam the bay, is from aboard ours.
Photo: Rich Hansen |
Tour with us to see Rockland's fascinating harbor, the Camden Hills, islands, lighthouses, seals and schooners, lobster boats, eagles, and rocky spruce-clad shores, from the largest protected harbor in New England aboard a beautiful classic wooden sailboat that rides like a cross between a magic carpet and a Cadillac.
Lifetime Memories Made Fresh Daily |
Flexible, custom sailing toursChoose your own Adventure |
Book a sail on Bufflehead because flexible scheduling allows us to offer a quick highlight to your trip, or a full day of sights, memories and meals. It also makes planning your vacation easier. We sail when you want, for how long you want, our motto is "Do What You Want." We are bound to see at least one lighthouse in our interesting harbor, and more in the sailing paradise beyond. You're welcome to bring anything you like, or we can cater you.
My mission is to see that, in the time and tides we share aboard, I'll find you the most of what the day offers and suits you best.
Our family offers Maine sailing charters of the beautiful coast aboard a classic wooden boat; custom daysail charters for up to six people on a safe and nimble 32' gaff sloop. Sunset sails, lobsterbakes, island picnics and night sails are also options. You can bring whatever food or drinks you like, or we can cater local delights to complete your Maine experience, and let us support or spoil you as we're known for doing. Special events are our specialty, as well as making the ordinary extraordinary. |
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I run my boat to create memorable custom experiences
for our guests, 1 - 6 people at a time, doing what YOU want. |
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Family Business!
I am Captain Daniel Bennett owner & operator. My daughter, Raya, has crewed aboard for 9 of her 12 years, knowing navigation, she qualifies as first mate. Silas, my son, at 6 1/2, is our able deckhand and tour guide with three years of experience already.
Together, my kids and I run a tight ship and its business, a bit of a homestead and a happy family. Silas's mom works in the food and wine industries, as well as making jewelry, and much else. Raya's mom is a teacher and a dancer. I try to keep house, be a good single dad and run this business which supports our family. We appreciate your patronage by sailing with us and your online support by sharing your enjoyment through taking the time to review and share your posts. |
Thank You and Welcome!
We look forward to hosting you on your unique experience.
We look forward to hosting you on your unique experience.
Kid Friendly Adventure |
We do provide and ask that, in accordance with State law, anyone under 11 wears a PFD.
Vacation planning with children can be difficult, we make it easier.
The constantly changing scenery and variety of sights, and the workings of a sailboat and the grand schooners and working boats around us are endlessly engaging for the antsy and curious. A Magical Family Sail |
We are fully equipped to safely ensure an enjoyable day of fun.
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I, Captain Daniel Bennett, made, maintain and administer this website,
with help from the awesome, talented and wise Quinton Donleavy,
and I claim all contents as Copyright 2021.
with help from the awesome, talented and wise Quinton Donleavy,
and I claim all contents as Copyright 2021.