Free Concierge Service
    Text or call 1-877-GREET-WELL
    Ask AIAI
    Ask AIAI
    1. Local experiences
    2. /Things to do in St. Michaels…
    3. /Water Activities
    4. /Sailing
    5. /2-Hour Chesapeake Bay Sail From St. Michaels
    Why travelers choose Greetwell

    Curated by our team

    Every experience is hand selected and approved by Greetwell.

    Personal concierge

    Real humans available to help before, during, and after your booking.

    Intimate & authentic

    Including unique in-home experiences you won't find anywhere else.

    Easy booking & cancellation

    Reserve in minutes with free cancellation on most experiences.

    Greetwell

    Experiences that stay with you long after the trip

    Greetwell curates authentic local experiences and provides personal concierge support in over 500 destinations, helping you explore confidently wherever you go.

    About

    • Our Story
    • For Experience Providers
    • For Hospitality Partners
    • For Developers

    Resources

    • Travel Guides
    • Help Center
    [email protected]1-877-GREET-WELL

    Safe & Secure Payments

    © 2026 Greetwell, Inc. All rights reserved.
    Privacy PolicyTerms
    Product image 1
    Product image 2
    Product image 3
    Product image 4
    Product image 5
    Product image 6
    Product image 7
    Gallery image
    Gallery image 1
    Gallery image 2
    Gallery image 3
    Gallery image 5

    2-Hour Chesapeake Bay Sail From St. Michaels

    Sail a Historic 1935 Ketch on the Miles River

    5.0 stars• 1.4K reviews
    From$159/ personincl. taxes and fees

    Duration

    2 hours

    Ideal For

    Up to 13 people

    Includes

    Bottled water, rain jackets

    Highlights

    Step aboard the historic Lady Patty for a relaxed sail through the harbor, Miles River, and Chesapeake Bay. Add a beer and wine tasting for $20 per person if you’re 21 or older.

    • Explore the harbor, Miles River, and Chesapeake Bay under sail
    • Look for osprey, bald eagles, and occasional dolphins
    • Join the working crew or relax on deck
    • Purchase soda, beer, wine, and champagne onboard

    What's Included

    • Bottled water
    • Binoculars
    • Rain jackets
    • Free parking

    Important details

    • All ages welcome
    • Children under 13 must wear a life preserver while aboard
    • A minimum of 2 people is required for the experience to take place
    • Amusement tax and crew gratuity are added to the listed price; amounts are not specified

    Cancellation Policy

    Per-person reservations: full refund up to 24 hours before departure. Private 2-hour charters: full refund more than 7 days before; 50% refund from 72 hours to 7 days before; no refund within 72 hours. Full refund if the operator cancels due to weather or unforeseen circumstances. No-shows are charged full price.

    FAQs

    Arrive 15 minutes before departure.

    Wear comfortable shoes that are easy to remove. Barefoot is welcome, but high heels are not permitted.

    Restrooms are available inside the hotel. A head (toilet) is also available onboard, but you are encouraged to use the hotel facilities before boarding.

    Meeting details

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

    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 #BGAEZT

    Passenger

    $159.16

    All ages welcome!

    0

    Private Charter

    $1,792.28

    Up to 13 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

    Nearby activities

    2-Hour Wine Tasting Cruise in St. Michaels
    Wine Tasting

    2-Hour Wine Tasting Cruise in St. Michaels

    Sample Six Curated Wines While Sailing Chesapeake Bay

    Sample Six Curated Wines While Sailing Chesapeake Bay
    5.0 • 1.4K reviews
    $298/ person
    Private Sailing Catamaran Charter in St. Michaels
    Sailing

    Private Sailing Catamaran Charter in St. Michaels

    Sail the Miles River with room to relax aboard Epiphany

    Sail the Miles River with room to relax aboard Epiphany
    5.0 • 1.4K reviews
    $1,237& up
    St. Michaels Marriage Proposal Cruise
    Engagement Packages

    St. Michaels Marriage Proposal Cruise

    Propose aboard a private yacht with champagne and a harbor sail

    Propose aboard a private yacht with champagne and a harbor sail
    5.0 • 1.4K reviews
    $1,377
    Bachelorette & Bachelor Party Cruise in St. Michaels
    Yacht Charters

    Bachelorette & Bachelor Party Cruise in St. Michaels

    Celebrate aboard a private 44-foot catamaran with champagne

    Celebrate aboard a private 44-foot catamaran with champagne
    5.0 • 1.4K reviews
    $1,377
    Chesapeake Bay Wine Tasting Cruise From St. Michaels
    Wine Tasting

    Chesapeake Bay Wine Tasting Cruise From St. Michaels

    Sip six curated wines while sailing St. Michaels’ waterfront

    Sip six curated wines while sailing St. Michaels’ waterfront
    5.0 • 1.4K reviews
    $187/ person
    Sunset Champagne Cruise in St. Michaels
    Sailing

    Sunset Champagne Cruise in St. Michaels

    Sail Chesapeake Bay at sunset with champagne and light bites

    Sail Chesapeake Bay at sunset with champagne and light bites
    5.0 • 1.4K reviews
    $298/ person