Daysail Charters from Rockland, Maine

Unique Maine Coast Sailing Experience

​Islands, lighthouses, sea-life, lobstering and real sailing on world famous Penobscot Bay, aboard a classic wooden sailboat.

She sails like a cross between a magic carpet and a Cadillac.

Safe, swift, seaworthy and sweet.

​1 hr to all day, up to six people.
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Custom scheduling, personal service.


13 Years of Great Reviews
​200+ reviews:
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Trip Advisor
Yelp
Google

Island Lobsterbakes

Explore the Possibilities

1 min video

Sea the Sights

The best way to see Maine is from the water.
5 min video

Explore the Islands

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.
1 min video

Sail Among the Tall Ships

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 popular options. 
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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!
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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. 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
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​and I claim all contents as Copyright 2025