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Are you a seasoned sailboat captain with a passion for the open water? We’re looking for an enthusiastic, flexible individual to lead custom sailing adventures aboard our beautiful vessel, exploring the stunning Caribbean. This is a unique liveaboard opportunity where you’ll guide private groups on bespoke itineraries.

Custom Itinerary Planning: Collaborate with guests to design personalized Caribbean adventures.

Professional Tour Services: Provide exceptional, safe, and memorable experiences for all guests.

Sailboat Management: Oversee vessel maintenance, safety, and operational readiness.

Logistics & Navigation: Plan port of entry procedures, customs, and mooring strategies.

Social Media Assistance: Contribute content to showcase our trips and the Caribbean’s beauty.

We are looking for a Captain for a Princess Y78 for long term , will be based in Japan.
Please contact me via email.

Need a captain from 6-8pm on July 3rd. Please suggest an hourly rate

Looking for a captain for our 2008 Sea Ray Sundancer 260 for the 4th of July to watch the fire works with a few family and friends.

Looking for a captain for our 24 ft jet boat to take family and friends out for a day Barnegat bay.

Captain the vessel for day trips, overnights, and multi-day New England excursions
Oversee all vessel readiness, including mechanical upkeep and cleanliness

maintaining comfort, safety, and a high level of hospitality

coordinate, and manage third-party vendors

Trips and Itinerary (Examples)

Day trips: 9/10am to 8pm around Norwalk Islands, with family or friends (40–50s age range, sometimes with our 3 kids: 12, 10, and 6)

Multi-day runs: 2–5 day cruises to destinations like Nantucket, Newport, Sag Harbor, Montauk, and Block Island

Vibe may range from laid-back family boating to more festive days on the water with couples

Compensation

Monthly stipend

if needed accommodations in Norwalk

Term: Seasonal potential for offer for the 2026 season (May 1- Oct 1)

Take my boat from Liberty Landing on or around 7/1/2025 to Hampton Bays rented slip, then pick it up on July 14th or 15 and return it to Libery Landing tto my slip

Looking for stew to accommodate owner and charters in Hamptons for summer, boat will go back to florida after the fall

My husband and I are looking for help on our 2022 LEEN 72 (LOA 76′) power trimaran that was built for us in France. The yacht is currently on Cape Breton in Nova Scotia, Canada and we plan to cruise to Newfoundland leaving in about 3 weeks. Then we will bring the boat down the East Coast of Canada and the US to Maine and then potentially to the Caribbean in the winter.

Pictures of our boat are on the LEEN website: https://leen-trimarans.com/range/leen-72/
And a video tour of the boat: https://www.youtube.com/watch?v=e3afuFJe2jU

My husband and I are looking for help on our 2022 LEEN 72 (LOA 76′) power trimaran that was built for us in France. The yacht is currently on Cape Breton in Nova Scotia, Canada and we plan to cruise to Newfoundland leaving in about 3 weeks. Then we will bring the boat down the East Coast of Canada and the US to Maine and then potentially to the Caribbean in the winter.

Pictures of our boat are on the LEEN website: https://leen-trimarans.com/range/leen-72/
And a video tour of the boat: https://www.youtube.com/watch?v=e3afuFJe2jU