Captain's Message: 

    Ahoy! Welcome!
July Sailing Perfection. Lots of last minute arrangements this year in July. Try me. See why folks love Bufflehead and what I do with her.

The bay has warmed up and the sailing is great. We offer authentically shared experience of the Maine Coast, aboard a small classic wooden sailboat, as it's meant to be seen, aboard wood woven to hold weight, water and wind so we can wander and wonder, amidst history and beauty, lighthouses and lobstering. Perfect for families, kids, and couples, small groups, you can sail or steer, relax in comfort or be involved, go places or just sightsee. We do lobsterbakes, on islands with all the trimmings or can simply cook you a couple fresh lobsters after your sail to eat by the wharf.

We offer a unique way to truly experience the Maine Coast, sailing. Come, see what sets what we do with Bufflehead apart. 2026 is my fifteenth summer sharing this wonderful part of the world with our dear lovely sailboat. She's just right to ride like a Cadillac crossed with a magic carpet, with comfort, safety and ease.

One hour to all day trips up to six passengers, catered or BYO, private or open to joiners, aboard a lovely classic gaff sloop.

We don't just seat you like cargo, like many 2 hour "head boats."  You are welcome, guest, we treat you like family, even better, because ours works on the boat! (You know we love it.) You can do what you want, swim, climb around, learn something or do nothing but enjoy the seabreeze.

Big comfort, small boat real feel, safety, speed and beauty, with personal service by me, your host and Captain, with thirty seven of my fifty years on boats. Let's get you out on the bay aboard my traditional classic wooden sailboat to ply the summer sea and find seals, scenery and more amidst the lighthouses, islands, beauty and history.

We can visit islands, swing by lighthouses, you can sail as much as you want to or just relax on our cushions.  We can take you to picnic, serve you lobster or simply sightsee and let the sea and wind work their magic through our marvelous boat.

You can relax anywhere aboard or steer Bufflehead yourself! We can go where you want, or we will take you to the best of it, chase wildlife, lighthouses, schooners and more.

At your service;  I, my boat and half the week, my able deckhand son (Wed-Sat) sometimes an occassional non kid deckhand.

 "Do What YOU want," is our motto.
 ("Within reason and ethical code" is what my kids have advised me to add.)

We have a cushioned bow seat, a comfy cockpit and the best sailing boat around!
A fridge, stove, board and plates etc, toilet and cozy cabin. It's all painted fresh and ready to go again this fifteenth year of offerring custom sailing experiences!

Be in touch to get on the calendar to see why so many people come year after year, why Bufflehead is so wonderfully unique and come truly see the coast under sail.  It's the best way to see it.

No Set Schedule
​Sail When You Want,
Seven days a week.

Last minute discounts!

I'll sail with two people for two hours for 200, open booking.
Half price private charter!

War Inflation Economy discount!
Mainer, Knoxian and Rocklander
15% (each) discounts!

Sails From 1 hr to All Day.
Harbor and lighthouse tours,
island trips, hiking and lobsterbakes.
Custom adventures. Memories.

Peaceful Comfort,
Vintage Style.
​1 hr to all day, up to six people.

​Islands, lighthouses, sea-life, lobstering and real sailing on world famous Penobscot Bay, aboard a classic wooden sailboat.
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She sails like a cross between a magic carpet and a Cadillac.
Safe, swift, seaworthy and sweet. ​
13 Years of Great Reviews
​
Trip Advisor
Yelp
Google

​​200+ reviews:

Island Lobsterbakes

Explore the Possibilities

1 min video

Sea the Sights
​1 & 2 hr Sails

The best way to see Maine is from the water.

Less crowds, more sightseeing. 
5 min video

Explore the Islands
5 & 6 hr Sails

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

​With five hours and longer, we can get to uninhabited islands  to hike, swim and picnic.

This is our most popular option!
1 min video

Sail Among the Tall Ships
July 4th: Great Schooner Race

The best way to see the tall ships that roam the bay, is from aboard Bufflehead. 
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​Photo: Rich Hansen

Maine Memories

Vacation Planning Made Easy

Choose your own Adventure
Our flexible scheduling makes planning easier.

You're welcome to bring whatever food and drinks you like, or we can cater your sail.

​Charters of up to six people.  Sunset sails, lobsterbakes, island picnics and night sails are great options. 
Picture
click image to watch 1min video
​We tour Penobscot Bay from Rockland's historic working harbor.

Every day is different and the light is always changing. Don't miss out on this authentic Maine sailing experience. 

Family Business!
Picture
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. Ive been sailing for thirty five years, worldwide on big boats and solo across oceans. Now we've sailed Bufflehead enough miles to have gone around, but within thirty miles of Rockland.

My daughter, Raya, crewed aboard for a decade, and now runs the sailing camp in town.  We try to find her on the water, when we can.

​Silas, my son, at 10 1/2, is our able deckhand, steward's asst, comedian and a keen professional helmsman and tour guide with six years in the business of sharing wonder, knowledge and humor.  He's aboard Wednesday through Saturday.

Together, my kids and I run a tight ship.  I try to keep house, be a great father and run this business which supports our family. 

We offer a really unique Maine coast experience.

We appreciate your patronage by sailing with us, telling folks how great we are in a review and sharing your pictures on social media. 
Welcome Aboard!

Kid Friendly Adventure
Vacation planning with children can be difficult, we make it easier.
​The scenery, sights, and the workings of a sailboat and  vessels 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 legos, as well as a stereo and USB charging outlets!
I, Captain Daniel Bennett, made, maintain and administer this website, with origination help from the awesome, talented, wise and funny Quinton Donleavy ​of PigPile Adworks
​
​and I claim all contents as Copyright 2025