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.
Sail by Owls Head Light, Maine
Most trips get us by at least two lighthouses! Here, Bufflehead turns the homeward corner by Owls Head light.
      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.
Sailing through the Maine Windjammer Fleet Rockland Maine
Sailing Amidst the Maine Windjammers. Local historic working sail, gone from dirty work to the passenger trade. Here, they're anchored in Rockland after an annual race, Bufflehead gliding along on the faint breeze like magic.
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.}

 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.  
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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
​Read any of our 200+ reviews, on ​
Trip Advisor, Yelp and Google
because they will get you excited to sail with us!

Explore the Possibilities

1 min video

Sea the Sights

Touring Maine from the sea is a great way to experience its rugged beauty. 
5 min video

Explore the Islands

Sail to local islands, hike the sights, and have a picnic. 
1 min video

Sail Among the Tall Ships

The 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 tours 

Choose 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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click image to watch 1min video
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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Bufflehead sails the area so much that people often recognize us & call out with greetings from the shore.
​We tour Penobscot Bay from Rockland's historic working harbor to see islands, lighthouses, lobstering, wildlife and our local fleet of historic, working sailboats.

Imagine sailing along the rugged scenery of Maine's coast aboard Bufflehead: inhaling the tasty light spice of salt in the clean ocean air, hearing the bow splash as we smoothly cruise along the glistening water, waving to passing schooners, spotting wildlife, seeing lighthouses and exploring islands.

Every day is different and the light is always changing. Don't miss out on this authentic Maine sailing experience. Come sail and share the beauty and interest as we explore among the islands of Maine.

Family Business!
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Occasionally we sail for pleasure. Off on a family jaunt here, Raya is trying her new wetsuit while we're anchored.
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.

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
​in Mid Coast Maine
- Your Guide 
​to Everything Kid Friendly
​in Maine
We are fully equipped to safely ensure an enjoyable day of fun.
  • lifeline netting along deck
  • child, youth and infant PFDs​
  • Extensive safety gear includes radios, multiple hand and electric pumps, signal flares, fire extinguishers, tools, spares, and an extensive first aid kit.
  • We also have coloring paper and crayons, usually some toys as well as a stereo and USB charging outlets!
  • We have a large tank of drinking water, as well as some bottles in the fridge and room in there for your stuff too.
  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.