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    1. Local experiences
    2. /Things to do in St. Michaels…
    3. /Water Activities
    4. /Sailing
    5. /7-Hour Sailing Charter in St. Michaels
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    7-Hour Sailing Charter in St. Michaels

    Private catamaran sailing with harbor views and Miles River breezes

    5.0 stars• 1.3K reviews
    From$3,453incl. taxes and fees

    Duration

    7 hours

    Ideal For

    Up to 6 people

    Includes

    Private boat, bottled water

    Highlights

    Set sail aboard Epiphany for a private Chesapeake Bay outing from St. Michaels. Begin with waterfront views on a harbor cruise, then raise the sails on the Miles River.
    • Explore St. Michaels waterfront on a brief harbor cruise
    • Raise the sails and follow the wind across the Miles River
    • Customize your outing with pre-ordered food from local businesses
    • Add a champagne sunset cruise or beer and wine tasting
    • Use onboard binoculars to take in the shoreline views

    What's Included

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

    Know before you go

    • Children under 13 must wear a life preserver aboard under U.S. Coast Guard regulations
    • Beer and wine tasting is for ages 21+ and costs an additional $20 per person
    • A champagne sunset cruise is available for an additional $255
    • Amusement tax and crew gratuity are added to the listed price

    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, or go barefoot. Do not wear high heels.

    Bring your own food aboard. Do not bring outside alcoholic beverages; beer, wine, champagne, soda, and sparkling water are available for purchase onboard.

    All ages are welcome. Children under 13 must wear a life preserver aboard, and 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 #89URMK

    Private Charter

    $3,453.08

    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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