Private sailing lesson for up to 6 with a customized focus
2 Hours
Up to 6 people
Instructor, Bottled water, Blankets
Sail with an experienced instructor on a private 2-hour lesson tailored to your level, from first-time to intermediate. Choose how hands-on you want to be while you build skills and confidence on the water.
Gratuity is not included and is optional. An additional fee applies for the Biddeford pickup location; confirm the amount with Greetwell before booking.
If the operator cancels due to weather or other unforeseen circumstances, you can reschedule or receive a 100% refund. Cancel 7+ days prior: reschedule or 100% refund. Less than 7 days, no-shows, or late arrivals after departure: charged full price.
Dress in layers and consider a windbreaker or warmer layer. Bring sunscreen, a sunhat, sunglasses, soft-soled shoes, and a raincoat. You can bring your own drinks, food, and snacks; an onboard refrigerator is available to keep items cool.
You get cold bottled water at no charge. You can also select drinks once aboard, and lobster roll dinner and other meal options are available.
Yes. Each person can choose how much they want to participate. Anyone who prefers can relax and watch while others sail.
Kennebunkport, Maine
Travelers consistently praise the intimate sailing experiences led by Captain Bob and his team, particularly highlighting crew members like Lucy, Chloe, Abby, and Nolan. The warmth and professionalism stand out across every review, with guests remarking on how welcomed and comfortable they felt throughout their cruises. The captains share fascinating local knowledge about Maine's coastline, wildlife, and working lobster boats, making the trips educational without feeling like a forced tour. The boats themselves are spotless and well-maintained, equipped with everything guests need for a comfortable outing. Sunset cruises appear especially popular, though midday sails get equally enthusiastic feedback. The husband-and-wife team running many of the trips creates a genuinely hospitable atmosphere, with thoughtful touches like blankets, drinks, and snacks. People appreciate the smooth booking process and describe the overall experience as relaxing yet engaging. It's clearly a family-run operation that takes pride in sharing their home waters with visitors.
Beautiful, intimate cruise with knowledgeable and kind captain and guide.
Bryce Ferguson
October 18, 2025
Beautiful, intimate cruise with knowledgeable and kind captain and guide.
Bryce Ferguson
October 18, 2025