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    1. Local experiences
    2. /Things to do in St. Michaels…
    3. /Water Activities
    4. /Sailing
    5. /Private St. Michaels Sailing Charter
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    Private St. Michaels Sailing Charter

    Harbor views and wind-powered sailing on the Miles River

    5.0 stars• 1.3K reviews
    From$2,345incl. taxes and fees

    Duration

    4.5 hours

    Ideal For

    Up to 6 people

    Includes

    Private boat, bottled water, gear

    Highlights

    Explore St. Michaels from the water aboard Epiphany, beginning with waterfront views before sailing the Miles River. Let the wind shape your private outing and enhance it with optional food or tasting experiences.
    • Cruise past St. Michaels waterfront on a brief harbor tour
    • Sail the Miles River as the crew raises the sails
    • Customize your outing with pre-ordered food from local businesses
    • Add a sunset champagne cruise on afternoon sail times
    • Sample a beer and wine tasting add-on for ages 21+

    What's Included

    • Bottled water
    • Binoculars
    • Rain jackets
    • Hats
    • Blankets
    • Free parking

    Know before you go

    • Children under 13 must wear a life preserver while aboard
    • Beer and wine tasting is available for ages 21+ at an additional $20 per person, not included in the listed price
    • A sunset champagne cruise is available on afternoon sail times for an additional $200, not included in the listed price
    • Amusement tax and crew gratuity apply in addition to the listed price; amounts are not specified

    Cancellation Policy

    Full refund if the operator cancels due to weather or other unforeseen circumstances. No-shows are charged the full price.

    FAQs

    Wear comfortable shoes that are easy to remove. Bare feet are welcome; do not wear high heels.

    Bring your own food, or add optional pre-ordered food for your private sail.

    Children under 13 must wear a life preserver while aboard. Infant, toddler, and youth life jackets are available.

    Meeting details

    Dock behind Harbor Inn & Marina, 101 N Harbor Rd, St. Michaels, MD 21663

    Experience provided by St. Michaels Sailing Charters
    Experience provided by St. Michaels Sailing Charters

    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 #VT95R6

    Private Charter

    $2,345.88

    Up to 6 people | All ages welcome!

    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

    What people are saying

    Review 1 of 4
    5/5

    We had the most fabulous sunset cruise with the Selina II! Iris and her first mate, Matt, where the best. We were worried that our sail might be cancelled because of the hurricane winds and the rain, but the day ended up clearing and the sun came out for a breathtaking sunset. Even though we have lived in St. Michael's for 13 years, we learned so much that we never new about the area. It was truly a delight and would highly recommend to both locals and tourist!

    Photo of Beth Berquist

    Beth Berquist

    October 16, 2025

    Review 1 of 1
    5/5

    We had the most fabulous sunset cruise with the Selina II! Iris and her first mate, Matt, where the best. We were worried that our sail might be cancelled because of the hurricane winds and the rain, but the day ended up clearing and the sun came out for a breathtaking sunset. Even though we have lived in St. Michael's for 13 years, we learned so much that we never new about the area. It was truly a delight and would highly recommend to both locals and tourist!

    Photo of Beth Berquist

    Beth Berquist

    October 16, 2025

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