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    1. Local experiences/
    2. Things to do in Kennebunkport…/
    3. Water Activities/
    4. Sailing/
    5. Midday Sailing Cruise in Kennebunkport
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    Midday Sailing Cruise in Kennebunkport

    Sail Kennebunkport at midday with a local captain, public or private

    4.9 stars• 252 reviews
    From$112/ 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 midday sail with a local captain and crew. Relax in the sun and salt air, or get involved with sailing as you go.
    • Choose a public sail or book a private charter
    • Listen as the captain and crew point out local sights
    • Help haul line, set sail, or take a turn at the helm
    • Bring your own food and favorite beverage
    • Plan to arrive 10–15 minutes before departure

    What's Included

    • Soda
    • Water

    Things to know

    Ages 5+.

    Gratuity is appreciated but not required; typical charter boat gratuity is around 20% of the trip total.

    Cancellation Policy

    Per person bookings: cancel 3+ days prior for a full refund. Private charters: 5 days’ notice for a full refund. Operator may cancel due to severe weather, mechanical failure, or other safety-related circumstances; reschedule or full refund offered. No-shows are non-refundable.

    FAQs

    Yes. Pack something to eat and bring your favorite beverage. Soda and water are provided.

    Yes. You can help haul line, set sail, or take a turn at the helm if you’d like, or you can sit back and relax.

    Yes. Park at the Nonantum Resort; they extend free parking to guests of the Pineapple.

    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 #TGYWD3

    Guest

    $112.78

    AGES 5+

    0

    Private Charter

    $1,304.73

    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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