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    5. Take a Private 2-Hour Sailing Lesson in Maine
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    Take a Private 2-Hour Sailing Lesson in Maine

    Private sailing lesson for up to 6 with a customized focus

    5.0 stars• 376 reviews
    From$801incl. taxes and fees

    Duration

    2 Hours

    Ideal For

    Up to 6 people

    Includes

    Instructor, Bottled water, Blankets

    Highlights

    Sail with an experienced instructor on a private 2-hour lesson tailored to your level, from first-time to intermediate. Choose how hands-on you want to be while you build skills and confidence on the water.

    • Learn sailing basics or get a refresher at your own pace
    • Practice reading wind and weather and adjusting sails
    • Build confidence with safety procedures and handling changing conditions
    • Work on docking, mooring, navigation, and teamwork skills
    • Bring up to 6 people and decide who sails and who relaxes

    What's Included

    • Experienced instructor
    • Cold bottled water

    Things to know

    Gratuity is not included and is optional. An additional fee applies for the Biddeford pickup location; confirm the amount with Greetwell before booking.

    Cancellation Policy

    If the operator cancels due to weather or other unforeseen circumstances, you can reschedule or receive a 100% refund. Cancel 7+ days prior: reschedule or 100% refund. Less than 7 days, no-shows, or late arrivals after departure: charged full price.

    FAQs

    Dress in layers and consider a windbreaker or warmer layer. Bring sunscreen, a sunhat, sunglasses, soft-soled shoes, and a raincoat. You can bring your own drinks, food, and snacks; an onboard refrigerator is available to keep items cool.

    You get cold bottled water at no charge. You can also select drinks once aboard, and lobster roll dinner and other meal options are available.

    Yes. Each person can choose how much they want to participate. Anyone who prefers can relax and watch while others sail.

    Meeting details

    Kennebunkport, Maine

    Experience provided by Broad Reach Adventures
    Experience provided by Broad Reach Adventures

    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 #SHQ76H

    Private Charter

    $801.43

    Be our exclusive guests onboard ~ Up to 6 passengers per boat

    0

    VIP Private Charter

    $1,032.55

    Be our exclusive VIP guests! To see a description of the VIP benefits, select quantity of 1 & click below VIP info box.

    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

    5.0
    Excellent
    376 reviews•Google Maps

    Travelers consistently praise the intimate sailing experiences led by Captain Bob and his team, particularly highlighting crew members like Lucy, Chloe, Abby, and Nolan. The warmth and professionalism stand out across every review, with guests remarking on how welcomed and comfortable they felt throughout their cruises. The captains share fascinating local knowledge about Maine's coastline, wildlife, and working lobster boats, making the trips educational without feeling like a forced tour. The boats themselves are spotless and well-maintained, equipped with everything guests need for a comfortable outing. Sunset cruises appear especially popular, though midday sails get equally enthusiastic feedback. The husband-and-wife team running many of the trips creates a genuinely hospitable atmosphere, with thoughtful touches like blankets, drinks, and snacks. People appreciate the smooth booking process and describe the overall experience as relaxing yet engaging. It's clearly a family-run operation that takes pride in sharing their home waters with visitors.

    What people are saying

    Review 1 of 5
    5/5

    Beautiful, intimate cruise with knowledgeable and kind captain and guide.

    Photo of Bryce Ferguson

    Bryce Ferguson

    October 18, 2025

    Review 1 of 1
    5/5

    Beautiful, intimate cruise with knowledgeable and kind captain and guide.

    Photo of Bryce Ferguson

    Bryce Ferguson

    October 18, 2025

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