Build sailing confidence with a lesson tailored to your experience and goals
4 hrs
Up to 6 people
Sailing instruction, bottled water
Learn alongside an experienced instructor aboard a 42-foot ocean-going sailboat. Tailor the session to your first sail, beginner or intermediate skills, or a refresher.
Receive a full refund when you cancel at least 7 days before departure. Cancellations less than 7 days before departure, no-shows, and late arrivals are charged in full. Receive a full refund if the operator cancels due to weather, insufficient bookings, or unforeseen circumstances.
Product ID: 5VMW52
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.
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.
Relax in a floating Scandinavian wood-fired sauna on the Kennebunk River
Trace Portland's ghost stories and history on a private lantern-lit walk
Pedal Maine’s coast past lighthouses, forts, and harbor views
Sample Portland craft beer with a guide at three curated brewery stops
Taste global flavors on a 3-hour Old Port walk with a local guide and enough bites to make a full meal
Enjoy a private sail aboard Endurance with views of Casco Bay’s islands and lighthouses