Sail the Chesapeake Bay on a 2-hour sunset cruise aboard the historic Lady Patty. Enjoy champagne, scenic river views, and a relaxing, romantic atmosphere guided by knowledgeable crew.
2 Hour Relaxing Chesapeake Day Sail on Lady Patty
About Tour
Join this peaceful 2-hour sailing adventure aboard the historic Lady Patty on the stunning Chesapeake Bay. Glide through the scenic Miles River and harbor waters from St. Michaels, Maryland, with sweeping views, possible wildlife sightings, and gentle breezes. Whether you help raise the sails or simply relax on deck, you’ll enjoy expert crew, picturesque waterways, and the charm of America’s Eastern Shore on this unforgettable day sail.
Duration: 2 Hours
Group Size: 13
Ages: All ages
Live guide: English
Why travelers love this
(3 reviews)
5.0 out of 5 stars (based on 3 reviews)
Suitable for beginners
Professional local guide
Safety-First Experience
Highlights
What’s included on the 2-Hour Relaxing Chesapeake Day Sail?
This 2-hour sail aboard the historic Lady Patty includes a peaceful cruise on the Chesapeake Bay with stunning views of St. Michaels Harbor and the Miles River. You’ll be accompanied by an experienced crew who share stories about the area and sailing. Bottled water is complimentary, and you can purchase beer, wine, or soda on board. You’re welcome to participate in sailing or simply relax and enjoy the scenery.
What should I know about booking, cancellation, and weather?
Check-in is recommended 15 minutes before departure. Per-person bookings can be canceled up to 24 hours before the sail for a full refund, while private charters have their own refund policy. If the captain cancels due to bad weather, you’ll receive a full refund. It’s wise to bring sun protection, comfortable shoes, and a light jacket as it can be cooler on the water.
Laura Bell
CEO / Founder
About the operator
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Customer Photos
Reviews
5.0 out of 5 stars (based on 3 reviews)
Beautiful and Relaxing Adventure
February 24, 2026
Absolutely loved this relaxing sail on Lady Patty! The historic boat has so much character, and the crew made the trip both fun and educational. It was just what we needed to escape and enjoy the bay breeze. Would do it again!
Great Experience for Families and Friends
February 24, 2026
We took the day sail with our kids and everyone had a great time. The staff made us feel welcome, and the sailing was smooth. We even saw some wildlife along the way! Fantastic way to see St. Michaels from the water.
Peaceful and Scenic Bay Cruise
February 24, 2026
This 2-hour sail was the highlight of our trip to Maryland! The crew was friendly and informative, and the views of the Chesapeake were breathtaking. It was relaxing without feeling rushed — perfect for anyone looking to unwind on the water. Highly recommended!
From: $95.00
- Free cancellation up to 24 hours before the scheduled start time.
- Reserve now, pay later and keep your travel plans flexible.
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