Sailing Sasa

Sailing expeditions around the globe. Sail Away Somewhere Amazing.

Summer 2026 Coastal Maine CHARTERS

Trips
Penobscot Bay Getaway
Aug 17
Penobscot Bay Getaway
A Taste of Maine: Coastal Sailing
Aug 21
A Taste of Maine: Coastal Sailing
The Downeast Passage: Belfast to Bar Harbor
Sep 2
The Downeast Passage: Belfast to Bar Harbor
View all trips

Sailing Offerings

Your dream sail, your way. Whether you want hands-on sailing training or total relaxation, we create unique and tailored itineraries that let you experience the magic of life on the water. Our signature sailboat charters throughout Maine and beyond include:

  • All about the action. Spend your days hiking, snorkeling, surfing, you name it—then unwind on deck with epic views. Perfect for ocean lovers who want a bit of extra adventure exploring vibrant marine life and hidden coves on the next level, all from the comfort of your own sailboat.

  • Combines hands-on sailing instruction with the adventure of a sailing vacation. This trip teaches all about blue water sailing while exploring beautiful Maine coastlines. You’ll live aboard the sailboat, participate in daily lessons, and gain real experience under the guidance of a professional skipper.

  • The ultimate bonding experience with the whole family. Swim, hike, explore island beaches, and learn a bit of sailing together. With a relaxed pace and a flexible itinerary, there’s something for everyone, from toddlers to teens. Create lifelong memories aboard your private floating home.

Captain Tyler standing on the bow of Sailing Sasa, adjusting the sails during a Sailboat Charter Trip in Maine. Sailboat in the foreground with a Coastal Maine sunset view from the water in the background.

Messages from our clients

“An absolute dream from start to finish. We hiked on islands you can only reach by boat, saw seals every morning, and learned so much about sailing along the way. It was the perfect mix of adventure and calm.”
— Riley T.
“We’ve traveled all over the world, but nothing compares to this. Waking up on the water, exploring hidden islands, swimming off the boat, and watching the sunset from the deck. This is the way to visit Maine!”
— Trevor & Shane
“Sailing on Sasa was hands-down the highlight of our trip. Watching the sunset from the deck with a drink in hand, surrounded by nothing but water was unreal. The crew made us feel right at home. We didn’t want to leave!”
— Sam H

Follow along on our SasAdventures

Stargazing on the deck of Sasa during a Sailboat Charter Trip in Maine. 2 people sitting on the deck of the sailboat looking up at the stars of Maine's night sky.
Beach exploration during a Maine Sailboat Charter. Family standing on the beach with the coast of Maine and the orange colors of the setting sun in the background.
Sunset from an Island in Maine during a Maine Sailboat Charter. The orange setting sun peaks through the silhouette of pine trees.
Family posing for a picture at Seal Bay in Maine while aboard S/V Sasa for a Sailboat Charter. Family and child are standing on the beach, surrounded by rocks, pine trees, and the water of the bay.