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2-hour sailing cruise on the scenic Chesapeake Bay
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Guided tasting of 6 curated wines (3 reds & 3 whites)
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Relaxing waterfront views of St. Michaels and surrounding waterways
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Intimate experience with professional crew aboard a classic sailboat
Wine Tasting Cruise On Lady Patty
About Tour
Indulge in a 2-hour wine tasting cruise aboard a classic sailboat on the stunning Chesapeake Bay. Sample a curated selection of 3 reds and 3 whites while enjoying gentle breezes, scenic waterfront views, and the relaxed charm of St. Michaels, Maryland. With expert crew, comfortable seating, and beautiful bay scenery, this experience blends the basics of wine tasting with the joy of sailing for a memorable outing on the water.
- Duration: 2 hours
- Group Size: 13
- Ages: 21 +
- Live Guide: English
Why travelers love this
(3 reviews)
5.0 out of 5 stars (based on 3 reviews)
(3 reviews)
4.9
Suitable for beginners
Professional local guide
Safety-First Experience
Highlights
What’s included in the Wine Tasting Cruise?
The 2-hour cruise includes a guided tasting of 3 red and 3 white wines from around the world while sailing on the historic Lady Patty. Bottled water is complimentary, and additional beverages like champagne, craft beers, and non-alcoholic drinks are available for purchase.
What should I bring and are there age or weather policies?
Guests must be 21+ to participate in wine tasting. It’s recommended to bring comfortable shoes, sun protection, and a light jacket because it’s about 10°F cooler on the water. The captain may cancel the cruise due to bad weather, and if it’s canceled, there’s no charge for that sail.
Laura & GM Bell
CEO / Founder
About the operator
St. Michaels Sailing Charters offers exceptional sailing experiences from the scenic waters of St. Michaels, Maryland, providing guests with a memorable blend of relaxation, adventure, and local maritime charm. Whether you’re seeking a romantic sunset cruise, a private charter for family and friends, or a customized sailing excursion on the Chesapeake Bay, their experienced crew delivers top-notch service and personalized attention from start to finish.
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Customer Photos
Reviews
5.0 out of 5 stars (based on 3 reviews)
A Must-Do in St. Michaels
February 24, 2026
If you’re visiting St. Michaels, don’t miss this wine tasting sail! The combination of smooth sailing, delicious wines, and friendly crew created the perfect evening. Everything was organized beautifully, and the atmosphere was both classy and comfortable. It’s a unique way to experience the Chesapeake Bay.
Relaxing, Elegant, and So Much Fun
February 24, 2026
This cruise exceeded our expectations! The boat is charming and comfortable, and the wine tasting was thoughtfully presented with great explanations for each pour. It felt intimate and relaxed — not rushed at all. The breeze on the water and scenic views made it such a memorable experience. We’ll definitely book again on our next visit.
Perfect Wine & Sunset Experience
February 24, 2026
The Wine Tasting Cruise on Lady Patty was absolutely magical! The selection of wines was well curated, and the host made the tasting both educational and fun. Sailing around St. Michaels while enjoying beautiful sunset views made it even more special. The crew was attentive and welcoming from start to finish. Highly recommend for a romantic evening or girls’ night out!
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