Sail the Chesapeake on a 1935 ketch with the option to join the crew
2 hours
Up to 13 people
Bottled water, binoculars
Enjoy a relaxed two-hour sail aboard the historic Lady Patty, departing from St. Michaels. Cruise through the harbor and out on the Miles River for shoreline views and possible wildlife sightings.
Maximum 13 people. Amusement tax and crew gratuity are added on—confirm the amount with Greetwell before booking. Beer and wine tasting is available as an add-on for an additional $20 per person (21 and older).
Per-person: full refund if you cancel 24+ hrs before departure. Private charter: full refund if you cancel 7+ days before; 50% refund if less than 7 days and more than 72 hrs; no refunds within 72 hrs. No-shows charged full price. Full refund if operator cancels due to weather.
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.
Harbour Inn, 101 N. Harbor Rd, St. Michaels, MD 21663
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!
Beth Berquist
October 16, 2025
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!
Beth Berquist
October 16, 2025