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:
October 14th, 2021

Ahoy there!  Welcome aboard in these interesting times.

We have finished sailing for the year in these glorious fall days of our tenth season.   I will be hauling the boat out for the winter Monday after downrigging.
​
   This was my tenth year offering custom (naturally socially distant) sailing & island visiting possibilities, with a decade of five star reviews. 

   Come see why Bufflehead, myself and my crew 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.   Fall sailing is here, with some colors along the shores, and crisper days and evenings with wonderful sailing.
 
Please, please, look at my calendar to see when in the future I am already booked and the open times available to customize around your plans.
​
​Please note: With school, on Wednesday, Thursday and Friday I need to get my kids to school and pick up my crew for the afternoon when they get done. On those days, I am available between 10-2 or after 4.  But not after 4 on Thursdays due to my daughter's cello lesson. I'm running solo on the boat in the morning those days and the rest of the week, and have my awesome first mate (my 13 year old daughter) and great deckhand (my almost 7 year old son) on Wed-Fri sunset sails, and on Saturday.
I'm a single dad, and I am wide open and kidless Sunday, Monday, Tuesday.


​
   Please enjoy the information here on my site about us and the area.
The pictures are all ours, of us and what we do.

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

More pictures of what we do are on my Instagram   
You can look at the nine years of five star reviews, on Trip Advisor
​
    Come sail with me to experience our local sights on the quickest, quietest, prettiest of them.  We've been top rated for the last nine years, come explore our coast and see why.

Check the calendar page to check availability then contact me to make a booking.

Check the Charter Options page for prices and trip descriptions. 

Contact me by email, phone, text or the contact form on the website, and I can put your booking on my calendar!

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

10 Years of 5 Star Reviews*

*​ Ok, one 4 star review, because that sail was "Fantastic, Wish I'd gone longer."​ 
​Read any of our 190+ 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

 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.

#1
​Activity & Boat Tour
In Rockland
Picture
Also 2018, 2019 & 2020. 10 Years of only five star reviews. (Except for a four star "Fantastic.") (And one two star from folks with illegal requests...)
​Rockland's Chosen
​Sailing Adventure
 #1
​Best Day Sailing Trip
​on the Maine Coast.

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.
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.
Picture
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!
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.

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 2021.