Sip wine on a 90-minute Kennebunkport sail with a sommelier-led tasting
1.5 Hour
Up to 10 people
Wine tasting, Charcuterie cup
Step aboard the Pineapple Ketch for a 90-minute sail along the Kennebunkport coastline with a curated wine tasting. Enjoy an intimate, adults-only evening hosted by certified sommelier Betsy Ross.
Ages 21+ only. Gratuity is appreciated but not required; typical charter boat gratuity is around 20% of the trip total.
Per-person bookings: full refund if you cancel 3+ days before departure; private charters: 5 days. If Pineapple Ketch cancels due to severe weather, mechanical failure, or safety circumstances, you can reschedule or get a full refund. No-shows: no refund.
Arrive 10–15 minutes before your scheduled departure time. The boat departs promptly at the scheduled time.
If you miss the scheduled departure, it is treated as a no-show and no refund is issued.
Park at the Nonantum Resort; free parking is extended to Pineapple guests.
With an exceptional reputation among recent visitors, this Maine sailing operation clearly knows how to create memorable experiences on the water. Captain Justin, Josh, Charlie, and Jim get enthusiastic praise for being friendly, knowledgeable, and professional throughout trips. The crew shares fascinating local history and landmarks around Kennebunkport, adding educational value to the beautiful scenery. Guests appreciate that you can bring your own beverages and snacks while enjoying peaceful sunset sails or morning cruises along the coast. The boat itself earns consistent compliments for being clean, spacious, and well-maintained, with plenty of room even for larger groups. Multiple reviewers mention feeling safe and comfortable, even nervous first-timers who requested life jackets. The relaxed, personable approach from the crew keeps everyone laughing and learning throughout the journey. One interesting bonus: they also offer a floating sauna experience with cold plunging for those seeking something different. It's a genuinely excellent choice for getting out on the water around Kennebunk.
This was a fantastic experience. Water was brutally cold (10/21/2025) but the feeling of stepping back into the hot sauna is like no other. I have access to a commercial gym sauna for free and paying for this experience felt totally worth the money. If you live in New England or are visiting ME I think this is a must do! Justin was easy going and totally psyched to facilitate our experience, Enjoy!
ewan Bennett
December 21, 2025
This was a fantastic experience. Water was brutally cold (10/21/2025) but the feeling of stepping back into the hot sauna is like no other. I have access to a commercial gym sauna for free and paying for this experience felt totally worth the money. If you live in New England or are visiting ME I think this is a must do! Justin was easy going and totally psyched to facilitate our experience, Enjoy!
ewan Bennett
December 21, 2025