Set sail aboard the Pineapple Ketch for a mid-day journey across Kennebunkport Bay. This private charter offers intimate encounters with Maine’s rugged coastline and local wildlife, blending hands-on sailing with expert storytelling.
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; no strenuous physical effort required but comfortable standing and moving on the deck is needed.
Wildlife
History
Kennebunkport’s coastline has long been central to New England’s maritime trade and fishing industries, with colonial-era homes reflecting its storied past.
Conservation
Pineapple Ketch emphasizes responsible wildlife viewing and supports local efforts to keep Kennebunkport’s marine habitats clean and protected from boating impact.
Pineapple Ketch
Set sail aboard the Pineapple Ketch for a mid-day journey across Kennebunkport Bay. This private charter offers intimate encounters with Maine’s rugged coastline and local wildlife, blending hands-on sailing with expert storytelling.
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.
Tours Offered
4 Tours
Curated coastal experiences in Kennebunkport
Small Groups
Up to 10
Intimate and personal outings
Typical Duration
90 Minutes
Most sails run ninety minutes
Sommelier-Led
Certified Sommelier
Wine sail led by Betsy Ross
Select dates and book directly to secure a Mid-Day Sail, Sip & Sail, Floating Sauna, or Evening Sunset Sail.
Book Ahead for Preferred Time
Private charters fill quickly, especially during peak months—reserve your spot early for the best sailing window.
Dress in Layers
Coastal conditions can change quickly; bring layers to stay comfortable against changing winds and sun exposure.
Bring Binoculars
Binoculars help catch close-up views of seals, seabirds, and coastal features otherwise missed from the deck.
Respect Wildlife Viewing Guidelines
Maintain a respectful distance from seals and birds to avoid disturbing their natural behavior during your sail.
Windbreaker or Waterproof Jacket
Protects against wind and occasional spray, crucial for staying comfortable on open water.
spring|summer|fall
Non-Slip Deck Shoes
Ensures firm footing on wet, potentially slick surfaces aboard the ketch.
Sunglasses with UV Protection
Shields your eyes from reflective glare off the water during sunny sailing conditions.
spring|summer|fall
Binoculars
Enhances wildlife and coastal feature viewing from the boat.