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

    Sail the Miles River aboard a spacious catamaran

    5.0 stars• 1.3K reviews
    From$269/ personincl. taxes and fees

    Duration

    2 hours

    Ideal For

    Up to 6 people

    Includes

    Bottled water, rain jackets, hats

    Highlights

    Explore Chesapeake Bay aboard Epiphany, a 44-foot Leopard catamaran. Glide from the harbor into the Miles River for water and shoreline views.

    • Watch for osprey, bald eagles, and occasional dolphins
    • Choose a public sail or reserve a private charter
    • Relax on spacious deck space for socializing and casual refreshments
    • Enjoy Chesapeake Bay scenery from the water

    What's Included

    • Bottled water
    • Binoculars
    • Free parking

    Know before you go

    • A minimum of 2 people is required for the experience to take place
    • Children under 13 must wear a life preserver while aboard
    • Beer and wine tasting is available for an additional $20 per person for ages 21+
    • Amusement tax and crew gratuity are added and are not included in the listed price

    Cancellation Policy

    Per-person reservations: full refund up to 24 hours before departure. Private charters: full refund more than 7 days before, 50% refund 72 hours to 7 days before, and no refund within 72 hours. Full refund if the operator cancels due to weather or unforeseen circumstances. No refund for no-shows.

    FAQs

    Wear comfortable shoes that are easy to remove, or go barefoot. Do not wear high heels. Apply spray sunscreen before boarding.

    Bring your own food aboard. Outside alcoholic beverages are not permitted; bottled water is included, and beer, wine, champagne, soda, and sparkling water are available for purchase onboard.

    All ages are welcome. Children under 13 must wear a life preserver while 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

    Related locations

    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 #4VBKRG

    Passenger

    $269.88

    All ages welcome!

    0

    Private Charter

    $1,377.08

    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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