Custom scheduled sailing charters aboard a classic wooden boat; an hour to all day, private and public, sightseeing and island trips.
BYO food/drink or we can cater for you, up to full Lobsterbakes.
I am away on a sailing trip with my son until Sunday (likely with limited cell coverage) and will be resuming operations Monday through the middle of October. Come see what’s so special about Maine and the way we share the coast with you.
Experience the Maine coast, aboard our classic, comfortable & beautiful wooden sailboat.
We offer unique experiences sharing our corner of paradise with you.
BYO food/drink or we can cater for you, up to full Lobsterbakes.
I am away on a sailing trip with my son until Sunday (likely with limited cell coverage) and will be resuming operations Monday through the middle of October. Come see what’s so special about Maine and the way we share the coast with you.
Experience the Maine coast, aboard our classic, comfortable & beautiful wooden sailboat.
We offer unique experiences sharing our corner of paradise with you.
We sail with small groups of up to six. You can choose length and time for either a private or open trip or join an existing open sail. I sail most every day May to October with a variety of custom scheduled daily/hourly trips, using flexibility to craft wonderful memorable experiences for my guests. Open space on my calendar is waiting for your custom adventure to sail to see lighthouses and lobstering, the Maine coast and islands in a very special way.
We sail Penobscot Bay from Rockland, Maine! See the sights aboard one of the sights! Bufflehead is the swiftest and sweetest boat around. We offer sightseeing, island visits, from short to all day, bring your own treats or have us cater for you, we even do island lobsterbakes! As of 2023, I've now sailed about 24,000 nautical miles doing just this, sailing folks around mostly within 40 miles of Rockland. We cover about 2,000 nm a year, We know how to find you the best of it! That's enough to have gone around the world! I used to sail long distance across oceans. There's a lot of wonder out there. Let us share with you some wonders in this magnificent sailing paradise, the Maine coast, our historic seaport harbor, sailing the calm protected waters of our unique corner of Penobscot Bay, amidst lighthouses, mountains, islands, wildlife, lobsterboats, the schooners of the Windjammer Fleet, and uninhabited islands crowned with nature's glory. While quietly dancing on the wind to be part of it all, with safety and serenity, speed and comfort, interest and intrigue. We melt stress and refill wonder tanks using time tested wind based transport to bring you the real taste of the Maine coast experience. You can't see it from the road. Come see why we come so highly recommended. |
A South African filmmaker, studying locally, made a short film in three days. Rudi Wild crafted a beautiful portrait of his sail and our story, with some lovely footage of my office (Penobscot Bay, Maine Coast and lighthouses), with drone and onboard photography! Thanks, Rudi. {Pardon the goofy beginning...and the score makes it sound so dramatic...kinda light wind, but a pretty film and decent introduction to my and Bufflehead's story in under four minutes.}
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Captain's log --- August 18th, 2024.
Sailing has been great. It'll keep being great. Today, it looks like there's a decent window this afternoon. I have four open seats, 2:30-4:30. Looks like rain the next few days, then some good weather. Check my calendar for details.
Ahoy there! Welcome. We have of bookings coming in, but lots of availabilty. We looking forward to getting you sailing and to a great thirteenth summer making memories sharing our world!
Come see our unique family operation, the experiences we offer, why Bufflehead, the crew (my kids), and I are so highly recommended. Experience the Maine coast as it should be, from the water and under sail, afloat on a sea of beauty, history and interest. We are excited to share our beautiful world, its intrigue, info and inspiration, from aboard the sweetest sail boat around.
Come sail with us to experience our local sights on the quickest, quietest, prettiest of them. We've been top rated for years, specializing in fabricating custom experiences, lifetime memories, be it an hour harbor cruise or an all day island adventure. Come explore our coast and see why Maine is different, and what makes sailing with us special.
Check the calendar page to check availability then contact me to make a booking directly.
Check the Charter Options page for prices and trip descriptions.
My kids and I welcome you to our website, aboard our boat and to our area.
- Capt Daniel Bennett
Come see our unique family operation, the experiences we offer, why Bufflehead, the crew (my kids), and I are so highly recommended. Experience the Maine coast as it should be, from the water and under sail, afloat on a sea of beauty, history and interest. We are excited to share our beautiful world, its intrigue, info and inspiration, from aboard the sweetest sail boat around.
Come sail with us to experience our local sights on the quickest, quietest, prettiest of them. We've been top rated for years, specializing in fabricating custom experiences, lifetime memories, be it an hour harbor cruise or an all day island adventure. Come explore our coast and see why Maine is different, and what makes sailing with us special.
Check the calendar page to check availability then contact me to make a booking directly.
Check the Charter Options page for prices and trip descriptions.
My kids and I welcome you to our website, aboard our boat and to our area.
- Capt Daniel Bennett
12 Years of Great Reviews
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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 |
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 13 of her 16 years, knowing navigation, she qualifies as first mate. Silas, my son, at 9 1/2, is our able deckhand and tour guide with six 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. I try to keep house, be a good 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 (lifejacket.)
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 origination help from the awesome, talented, wise and funny Quinton Donleavy,
and I claim all contents as Copyright 2024.
with origination help from the awesome, talented, wise and funny Quinton Donleavy,
and I claim all contents as Copyright 2024.