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Set sail from Kennebunkport with Pineapple Ketch for a 1.5-hour mid-day cruise. Whether you want to take the helm or relax with refreshments, this trip offers an easy and authentic taste of Maine’s rugged coastline.
Set sail from Kennebunkport with Pineapple Ketch for a 1.5-hour mid-day cruise. Whether you want to take the helm or relax with refreshments, this trip offers an easy and authentic taste of Maine’s rugged coastline.
Book with Pineapple Ketch
Verified experiences and guided adventures in the surrounding area.
Operated by Pineapple Ketch · Kennebunkport, Maine
Kennebunkport, Maine, sits on a rugged coastline where granite meets the Atlantic, offering sweeping ocean views and a vibrant maritime heritage. At 95 Ocean Ave, Pineapple Ketch invites adventurers and leisure seekers alike to experience the coast from a fresh vantage on their Mid-Day Sail. This 1.5-hour sailing trip balances hands-on engagement and restful cruising, making it accessible to everyone from novices to seasoned sailors.
Aboard the Pineapple Ketch, a classic wooden vessel, a knowledgeable captain and crew guide you through the rhythms of the sea. Whether you want to try your hand at trimming the sails or simply lean back with the sea breeze on your face, the trip adapts to your mood. Along the way, you’ll spot iconic coastal features—lobster boats hauling traps, granite outcrops dusted with pine, and perhaps a curious harbor seal or two.
The experience highlights the distinct maritime landscape of southern Maine, where tides carve the shore and seabirds wheel overhead. Historic landmarks appear on the horizon, including scenic harbors and quaint waterfront homes that reflect centuries of fishing and sailing traditions. Complimentary refreshments make it easy to soak in the salty air and coastal sun comfortably.
Pineapple Ketch has built a reputation as a cornerstone of Kennebunkport’s outdoor offerings by combining genuine local knowledge with high-quality service. The company’s approachable style welcomes families, solo travelers, and groups who want a taste of Maine’s sailing lifestyle without needing prior experience. This makes their Mid-Day Sail a standout among outdoor activities in the area—offering both the thrill of open water and serene coastal beauty within easy reach of Portland and Boston.
Whether you’re chasing a peaceful break or an engaging nautical lesson, Pineapple Ketch’s Mid-Day Sail delivers a memorable connection to Maine’s sea-bound spirit.
easy.
1.5 hours.
Suitable for all fitness levels, including families with children age 5 and up.
No prior experience is necessary. The crew welcomes all skill levels and can provide basic sailing instruction if you want to participate.
Yes, complimentary water and soda are served during the trip, but you are welcome to bring your own snacks and beverages.
The trip is family-friendly, suitable for children ages 5 and up.
Layered clothing, a windbreaker, and non-slip shoes are recommended to stay comfortable and safe.
Absolutely. Guests are invited to help haul lines, trim sails, or take the helm under crew supervision.
Trips may be rescheduled or canceled in the event of unsafe weather conditions to ensure guest safety.
Kennebunkport’s maritime history dates back to the 1700s, with a strong tradition of shipbuilding and fishing shaping the local culture.
Pineapple Ketch promotes eco-friendly practices on board, including waste reduction and awareness of local marine habitats to minimize environmental impact.
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