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    1. Local experiences/
    2. Things to do in Kennebunkport…/
    3. Water Activities/
    4. Sailing/
    5. 1.5-Hour Morning Sailing Cruise in Kennebunkport
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    1.5-Hour Morning Sailing Cruise in Kennebunkport

    Sail Kennebunkport with options to relax or take the helm

    4.9 stars• 252 reviews
    From$89/ personincl. taxes and fees

    Duration

    1.5 Hour Sail

    Ideal For

    Up to 12 people

    Includes

    Soda & water

    Highlights

    See Kennebunkport from the water on a 1.5-hour sail with a local captain and crew. Sit back and relax or get hands-on as you enjoy sun and salt air.

    • Ride out on a 1.5-hour morning sail
    • Learn local points of interest from the captain and crew
    • Help haul line, set sail, or take a turn at the helm
    • Choose a public sail or book a private charter
    • Bring snacks and your favorite beverage

    What's Included

    • Complimentary soda
    • Water

    Things to know

    Ages 5+ only. Gratuity is not required; typical charter boat gratuity is around 20% of the trip total.

    Cancellation Policy

    Per person bookings: full refund if you cancel 3+ days before departure. Private charters: full refund with 5 days notice. If Pineapple Ketch cancels due to severe weather, mechanical failure, or safety issues, reschedule or get a full refund. No-shows are non-refundable.

    FAQs

    Arrive to the boat 10–15 minutes before your scheduled departure time. The sail departs the dock promptly at the scheduled time.

    Park at the Nonantum Resort; free parking is extended to all guests of the Pineapple.

    Pack something to eat along with your favorite beverage. Soda and water are provided.

    Experience provided by Pineapple Ketch
    Experience provided by Pineapple Ketch

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Report an issue

    Reference #JMZ7SM

    Guest

    $89.04

    AGES 5+

    0

    Private Charter

    $1,068.48

    Up to 12 People

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.9
    Excellent
    252 reviews•Google Maps

    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.

    What people are saying

    Review 1 of 4
    5/5

    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!

    Photo of ewan Bennett

    ewan Bennett

    December 21, 2025

    Review 1 of 1
    5/5

    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!

    Photo of ewan Bennett

    ewan Bennett

    December 21, 2025

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