Trips Offered in Midcoast Maine, & Beyond

Please review the trip descriptions below, including the pricing, and then fill out the form with your questions or booking request.

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Sailing Trips

Enjoy the serenity of being moved by the wind alone. Sailing is a very unique and enjoyable experience that connects us to a deep inner knowing of an earlier era. Guest often marvel at the familiar nostalgic feeling they get when sailing for the first time; like they missed it, even thought they’ve never done it before. Choose an adventure that fits your interest, your budget, and your desired level of adventure. All sailing trips depart from Boothbay Harbor, ME.

Harbor Tour 2 Hours

  • Get a good taste of what sailing the Maine coast is all about. See seals, bald eagles, and other wildlife as we weave through the islands in & around Boothbay Harbor.

  • $100/person, max capacity 6 passengers. Ask about private tours and opportunities for you and your crew to sail the boat.

Half Day 4 Hours

  • This four hour sail is enough time to really start exploring around the islands & coast outside of Boothbay Harbor. See light houses, working lobster boats, seals, porpoise, puffin, and the best coastal scenery Maine has to offer.

  • $200/person, max capacity 6 passengers. Ask about private tours and opportunities for you and your crew to sail the boat.

Full Day Island Destination 8 Hours

  • Take a full day for an epic adventure, and enjoy one of our most popular cruises. We will be surrounded by the most stunning examples of classic Maine coast scenery as we sail out of Boothbay Harbor and onto the open ocean. We’ll secure the boat to a mooring at Damariscove or Seguin Island and go ashore for a step back into Maine’s rich history. Enjoy spectacular panaramic views of the Maine coast and the open Atlantic Ocean while enjoying a walk on the island before returning to the harbor. Snacks, picnic lunch, and non-alcoholic beverages are provided. $400/person, max 6 passengers.

  • $400/person, max capacity 6 passengers. Ask about private tours and opportunities for you and your crew to sail the boat.

Island Ferry Service

Enjoy a quick and safe passage to one of our spectacular island destinations. We’ll pick you up in Boothbay Harbor, Bath, Georgetown, Phippsburg, or other locations, and whisk you away to another world. Visiting an offshore island is like going back in time. Life moves at a much slower pace, and the whole experience is rejuvenating. You can’t beat the scenery, the feeling, and the adventure of these unique Maine island experiences. It is a very rare opportunity to get to experience a day of island life!

Damariscove Island

  • This island, just outside of Boothbay Harbor, is a spectacular destination and a relatively short trip. You’ll get dropped at the dock and enjoy a variety of well-marked trails with the most spectacular views.

  • $100/person round trip from Boothbay Harbor or Georgetown

    $125/person from Fort Popham, Phippsburg

    $150/person from Bath or Sebasco Harbor Resort

Monhegan Island

  • Monhegan is 10 miles off shore. This is an adventure for the most adventurous! We will cross miles of open water, and it can get rough, but the destination is worth the tirp.

    There has been European activity on this island since the early 1600’s. Today it boasts a vibrant arts community, spectacular hiking trails, decedent restaurants, and the distinctive culture of an offshore island. Count on this trip taking most of your day.

  • $ 250/person from Boothbay Harbor or Georgetown

    $ 300/person from Fort Popham, Phippsburg.

    $ 350/person from Bath or Sebasco Harbor Resort

    add gas fee ($150) for parties less than 3

Malaga Island

  • Malaga Island is a Maine State Historic Site. It was once the location of a thriving interracial community. Unfortunately, the state removed the residents, destroyed their homes, and sent many of the people to mental institutions in the early 1900’s. Hike to island trails and learn more about the history.

  • $150/person from Boothbay Harbor or Georgetown

    $175/person from Bath

    $100/person from Fort Popham or Sebasco Harbor Resort

    ($100 gas fee for parties of less than 3)

Sequin Island & Lighthouse Tour

  • Enjoy a scenic ride to Seguin Island, 2.5 miles off the coast near Popham Beach. We'll grab our mooring and transport you to shore (there's no dock, so plan on your feet getting wet when you get to the beach). Hike to the lighthouse, and enjoy stunning panoramic views of the Maine Coast and the open Atlantic Ocean. We'll come back to pick you up at the scheduled time.

  • $100/person round trip from Boothbay Harbor, Georgetown, or Fort Popham.

    $125/person from Sebasco Harbor Resort

    $150/person from Bath

    ($50 gas fee for parties of 3 or less)

Eagle Island

  • Eagle Island was the summer home of Admiral Robert Perry, believed to be the first explorer to make it to the North Pole. Explore the grounds, and visit the museum. This is a fascinating glimpse into history.

  • $250/person from Boothbay Harbor or Georgetown

    $275/person from Bath

    $200/person from Fort Popham or Sebasco Harbor Resort

    ($150 gas fee for parties less than 3)

Advanced RippleSmith Training

Advanced RippleSmith trainings are extended trips for people wanting a deep dive into purposeful work using sailing as a metaphor for life. Passengers will spend 2-7 days healing, growing, and developing the skills, knowledge, and awareness needed to live a more happy, fulfilling, and purpose-full life.

Voyage Toward the Sacred Masculine: Spring & Fall 2026

  • Spend three days learning to sail and spend two nights at anchor at an off-shore island, all while gaining the knowledge, skills, and confidence to become a better man. Max capacity 4 passengers.

  • $400/person

    Includes all food and beverages. Max capacity 4 passengers.

Voyage Toward the Sacred Masculine: Winter 2026/’27 USVI

  • Spend a week sailing the US Virgin Islands, while taking a deep dive into men’s work. Bluild confidence, skills, and knowledge in all aspects of wellness and manhood while sharing an epic tropical adventure with other growth-focused men.

  • $2,500/person, 6 days, 7 nights

    Includes all food and beverage, all boat expenses, snorkel gear, and daily activities, facilitation, and instruction for mastering manhood. Max capacity 10 passengers.

Songwriter’s Retreat

  • Enjoy a 2 day sailing adventure with other songwriters on the pristine waters of Midcoast Maine in the Spring or Fall of 2026, or a full week on the turquoise waters of the US Virgin Islands during the winter of 2026-’27. Be inspired by this immersion in the natural beauty of the ocean and coastline while collaborating with your peers.

  • Spring/Fall 2025, Casco Bay, Maine: $500/person for 2 days & an overnight. Max capacity 4 passengers.

    Winter 2025-’26, US Virgin Islands: $3,000/person for 6 days & nights. Max capacity 10 passengers.

    Price includes all food, non-alcoholic beverages, fuel, and boat fees.