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    1. Local experiences
    2. /Things to do in Kennebunkport…
    3. /Water Activities
    4. /Sailing
    5. /Sail Kennebunkport Coastline With Wine Tasting
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    Sail Kennebunkport Coastline With Wine Tasting

    Sip wine on a 90-minute Kennebunkport sail with a sommelier-led tasting

    4.9 stars• 312 reviews

    Duration

    1.5 Hour

    Ideal For

    Up to 10 people

    Includes

    Wine tasting, Charcuterie cup

    Highlights

    Step aboard the Pineapple Ketch for a 90-minute sail along the Kennebunkport coastline with a curated wine tasting. Enjoy an intimate, adults-only evening hosted by certified sommelier Betsy Ross.

    • Board the Pineapple Ketch for a 90-minute coastal sail
    • Taste a curated selection of wines with sommelier Betsy Ross
    • Enjoy an artisanal charcuterie cup during your sail
    • Choose a public sail or book a private option
    • Join a small group experience with up to 10 guests

    What's Included

    • Curated selection of wines
    • Artisanal charcuterie cup

    Things to know

    Ages 21+ only. Gratuity is appreciated but 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: 5 days. If Pineapple Ketch cancels due to severe weather, mechanical failure, or safety circumstances, you can reschedule or get a full refund. No-shows: no refund.

    Product ID: C9RS42

    FAQs

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

    If you miss the scheduled departure, it is treated as a no-show and no refund is issued.

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

    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

    Guest

    $178.08

    AGES 5+

    0

    Private Charter

    $2,136.96

    Up to 12 People

    0

    Why book through Greetwell?

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      No booking or service fees, ever

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      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
    312 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

    Such a wonderful experience. We had a great sail and as a bonus we got to see some white sided dolphins. Such an amazing experience. My husband and I did this for our anniversary. So much fun and it was a great relaxing first time sailing.

    Photo of Dina Kreutzer

    Dina Kreutzer

    August 31, 2026

    Review 1 of 1
    5/5

    Such a wonderful experience. We had a great sail and as a bonus we got to see some white sided dolphins. Such an amazing experience. My husband and I did this for our anniversary. So much fun and it was a great relaxing first time sailing.

    Photo of Dina Kreutzer

    Dina Kreutzer

    August 31, 2026

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