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Step aboard the Pineapple Ketch for a coastal wine sail along Kennebunkport’s shores, guided by an expert sommelier and paired with artisanal charcuterie. Discover a unique 90-minute journey blending seafaring beauty with wine education.
Step aboard the Pineapple Ketch for a coastal wine sail along Kennebunkport’s shores, guided by an expert sommelier and paired with artisanal charcuterie. Discover a unique 90-minute journey blending seafaring beauty with wine education.
Book with Pineapple Ketch
Verified experiences and guided adventures in the surrounding area.
Operated by Pineapple Ketch · Kennebunkport, Maine
Kennebunkport’s rugged coastline is a draw for sailors and sightseers alike, but Pineapple Ketch elevates this seaside escape by blending maritime charm with refined wine appreciation. Their Sip & Sail Wine Sail offers a 90-minute journey along Maine’s storied shoreline aboard a classic ketch, a graceful sailing vessel designed for both comfort and adventure. This is more than a boat ride—it’s an intimate gathering capped at 10 guests, where the natural drama of crashing waves and rocky outcrops pairs seamlessly with a handpicked selection of wines and artisanal charcuterie.
Guided by Betsy Ross, a Certified Sommelier whose twenty-year career spans Michelin-starred restaurants and vineyard floors from California to France, the experience invites guests to engage with wine on a personal level, demystifying varietals and tasting notes against the backdrop of the Atlantic. The coastal views unfold slowly: jagged granite ledges, seaweed-draped rocks, and the occasional harbor seal break the surface with curious eyes. Kennebunkport itself, rich in maritime history and shipbuilding tradition, sets the stage for this sensory adventure.
This tour uniquely anchors luxury and learning in an outdoor setting rarely paired with such sophistication. Winter storms and summer sails alike offer their own moods, but every trip finds magic in Maine’s shifting sky and sea. Whether it’s a first date, a special occasion, or a casual evening with friends, Pineapple Ketch’s Wine Sail crafts a memorable dialogue between land, sea, and cellar.
Perfect for visitors looking to combine coastal exploration with a refined palate, this charcuterie and wine pairing sail stands out as a signature adventure in Kennebunkport’s outdoor offerings, blending local culture and natural beauty seamlessly.
easy.
1.5 hours.
No special fitness required; guests should be able to embark and disembark a sailboat safely.
Absolutely. The tour is designed to be engaging and accessible, with Betsy Ross guiding guests to enjoy wine without jargon or pressure.
Tours may be canceled or rescheduled due to unsafe weather conditions; guests will be notified in advance.
This experience is 21+ only due to the alcohol served on board.
Yes, each guest receives a curated artisanal charcuterie cup paired with the wine selections.
The departure point is in Kennebunkport, Maine, at 95 Ocean Ave.
Yes, private bookings can be arranged for groups up to 10 guests for a more personalized experience.
Kennebunkport has a rich maritime history rooted in fishing, shipbuilding, and lobster trade dating back to the 18th century.
Efforts by local organizations promote marine habitat preservation, ensuring wildlife and water quality are protected amid increasing tourist activity.
Pineapple Ketch is a boutique maritime operator located in Kennebunkport, Maine. The business offers four distinct water-based experiences designed to showcase the local coastline and provide relaxed, intimate outings for individuals and small groups. Offerings include a luxury Floating Sauna on the Kennebunk River featuring a traditional Scandinavian wood-fired sauna and cedar aroma; a Mid-Day Sail with a knowledgeable captain and crew that allows guests to participate in sailing or simply relax with complimentary refreshments; a 90-minute Sip & Sail Wine Sail led by Certified Sommelier Betsy Ross for up to 10 guests, pairing curated wines with artisanal charcuterie; and a 90-minute Evening Sail that highlights sunset views along the rocky Kennebunkport coast and invites guests to bring personal snacks and drinks to toast the day. Safety and guest enjoyment are supported through attentive crew service and clear pre-departure information. The Floating Sauna emphasizes a restorative, nature-connected experience combining heat and cedar scent with river scenery. Mid-day and evening sails offer scenic coastal views and comfortable cruise options for those seeking relaxation or light sailing engagement. The Sip & Sail experience adds guided wine appreciation led by a certified sommelier. Booking information, availability, and specific operational details are provided directly by Pineapple Ketch via its reservation channels for those planning visits to Kennebunkport.
Book with Pineapple Ketch