Private sailing charters to see the Maine coast aboard a classic Wooden Boat.

Sail the Maine Coast aboard a classic wooden boat, captained with experience and charm, offering private charters with complete versatility, care and a lifetime of skill and adventure.

Adventure with experience.

Captain's log:
​ May 12, 2021

Ahoy there!  Welcome aboard in these interesting times. I'm heading into my tenth year offering socially distant sailing & island visiting possibilities. Next year will mark a decade of five stars reviews.  Come see why Bufflehead, myself and my kids have been the top rated activity in Rockland for years now. See the Maine coast as it should be seen, from the water under sail. 

I'll be starting operations for 2021 on May 28th, once I'm fully vaccinated.
​  
   Please enjoy the information here on my site about us and the area.
The pictures are all ours, of us and what we do.
More of my pictures are on my Instagram   
You can look at the nine years of five star reviews, on Trip Advisor
​
    Come sail with me to catch our local sights on the quickest, quietest, prettiest of them.  We've been top rated for the last nine years, come see why.

​     There's much more info on this site for you About Rockland+ and Before and After pages, as well as -

Check the calendar page to check availability or make a booking for 2021.

Check the Charter Options page for prices and trip descriptions. 

Come see how great it is!   My kids and I welcome you.  
​                                                     ​- Capt Daniel Bennett

Lifetime Memories Made Fresh Daily

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

 Daysails, Custom Trips, Lobsterbakes & Picnics;
from Rockland Maine, we sail Penobscot Bay.​

 Tour with us to see the Camden Hills, the islands, lighthouses, seals and schooners, lobster boats, eagles, and rocky spruce-clad shores, from the largest protected harbor in New England.

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. 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.

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 best of what the day offers
​and suits you most.
​
​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.
TripAdvisor Certificates of Excellence
​2013, 2014, 2015, 2016, 2017, 2018, 2019
​
Hall of Fame Certificate
2018, 2019
Picture
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.

9 Years of 5 Stars*

*​ Ok, one 4 star review, because that sail was only "Fantastic."​ 
​Read any of our 180+ reviews, on ​
Trip Advisor, Yelp and Google
because they will get you excited to sail with us!

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
​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 in the fridge and room in there for your stuff too.
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 2020.