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.
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Difficulty
easy
Duration
1.5 hours
Fitness Level
No special fitness required; guests should be able to embark and disembark a sailboat safely.
Wildlife
History
Kennebunkport has a rich maritime history rooted in fishing, shipbuilding, and lobster trade dating back to the 18th century.
Conservation
Efforts by local organizations promote marine habitat preservation, ensuring wildlife and water quality are protected amid increasing tourist activity.
Pineapple Ketch
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.
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.
Dress for Coastal Weather
Layered clothing is key as temperatures can shift quickly on the water, especially during evening sails.
Arrive Early for Boarding
Plan to arrive 10-15 minutes before your departure to settle in and receive a safety briefing.
Limited Guest Capacity
Tours accommodate up to 10 guests, so book in advance to secure your spot on this intimate sail.
Bring ID for Age Verification
This experience is for guests aged 21+, so carry valid identification for boarding.
Windbreaker Jacket
Protects against coastal breezes and variable spring weather during the sail.
spring
Comfortable Non-Slip Shoes
Ensures safety and stability on the deck during boarding and sailing.
Sunglasses
Shields eyes from glare reflecting off the water on sunny summer afternoons.
summer
Warm Hat
Adds warmth during cooler fall evenings on the water.
fall