Learn to sail with a private instructor on a 42-foot boat
About 4 Hours
Up to 6 people
Instructor, sailing lesson, water
Build sailing skills in a private 4-hour lesson tailored to your experience level. Bring up to 6 people and choose whether to participate or relax onboard.
Gratuity is not included and is optional. An additional fee applies for the Biddeford pickup location; confirm the amount with Greetwell before booking.
Full refund if the operator cancels due to weather or other unforeseen circumstances. Cancel 7+ days prior to departure for a 100% refund. Cancellations made less than 7 days, no-shows, and late arrivals will be charged the full price.
Dress in layers (it can feel cooler and windier on the water) and wear soft-soled shoes. Bring sunscreen, a hat, sunglasses, and a raincoat if you want one.
Yes. You can bring your own drinks, food, and snacks. You can also store items in the onboard refrigerator to keep them cool.
You get cold bottled water at no charge. You can also choose from a selection of soda, iced tea, mixed drinks, beer, cider, and wine once aboard.
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