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

    Sail into the evening light along Kennebunkport’s rocky coast

    4.9 stars• 274 reviews
    From$148/ personincl. taxes and fees

    Duration

    1.5 Hours

    Ideal For

    Up to 12 people

    Includes

    Soda, water

    Highlights

    Step aboard The Pineapple Ketch for a 1.5-hour evening sail from Kennebunkport, cruising out the Kennebunk River and along the rocky shoreline. Enjoy the soft light near sunset, plus complimentary soda and water onboard.

    • Board at the Nonantum Resort docks in Kennebunkport
    • Sail out the mouth of the Kennebunk River and up the coast
    • Choose a public sail or book a private charter
    • Bring your own snacks or beverages to enjoy onboard
    • Plan to arrive 10–15 minutes before departure

    What's Included

    • Soda
    • Water

    Things to know

    Minimum age is 5+. Gratuity is optional; typical charter boat gratuity is around 20% of the trip total.

    Cancellation Policy

    Per person bookings: cancel 3+ days before departure 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 concerns; reschedule or full refund. No-shows are non-refundable.

    FAQs

    Arrive at 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; they extend free parking to all Pineapple guests.

    Soda and water are provided. You can also bring your own snacks or beverages to enjoy onboard.

    Meeting details

    95 Ocean Avenue Kennebunkport, Maine 04046

    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 1-877-GREET-WELL

    Report an issue

    Reference #6EQ7BU

    Guest

    $148.40

    AGES 5+

    0

    Private Charter

    $1,779.61

    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
    274 reviews•Google Maps
    240
    8
    2
    2
    2

    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 5
    5/5

    Great crew, great day, greal sail! Thank you.

    Photo of Christopher Gilbert

    Christopher Gilbert

    July 6, 2026

    Review 1 of 1
    5/5

    Great crew, great day, greal sail! Thank you.

    Photo of Christopher Gilbert

    Christopher Gilbert

    July 6, 2026

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