Chesapeake Bay Sailing Trips in St. Michaels, MD

Want to relax? Join our friendly crew and learn about St. Michaels while cruising in comfortable well-maintained historic and modern sailboats on the Chesapeake Bay. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy outdoor scenery on your personalized sailing boat tour!

Experience a breathtaking Chesapeake Bay sunset while savoring a glass of champagne or handcrafted beer or wine on this romantic St. Michaels, MD sunset cruise. Book now to embark on an unforgettable journey that’s perfect for couples looking for a unique and romantic date night activity.

During this 2-hour voyage, savor the rich aromas and flavors of three red and three white wines, thoughtfully selected from around the world. Our curated wine list changes regularly, offering a fresh and personalized tasting journey each time.

Looking for a fun and refreshing way to quench your thirst with a cold beer while exploring the St Michaels area? Sit back and enjoy some great Maryland Craft breweries aboard St. Michaels Sailing Charters.

Imagine saying your vows surrounded by the calm waters of the Chesapeake Bay as the sails fill with wind and the sun reflects across the Miles River. Our nautical wedding packages offer a relaxed, intimate alternative to traditional venues, creating a truly unforgettable celebration on the water.

Step aboard St. Michaels Sailing Charter sailing yachts and begin your journey with an enchanting tour of historic St. Michaels harbor. As the sails catch the breeze, feel the excitement of setting off on a 4 1/2 hour day sail up the stunning Miles River.

Join us for a full 7 hour day of sailing on this boat tour that includes a mini-tour of the St. Michaels harbor before cruising along the Miles River and discovering its hidden coves enjoying the views and wildlife of Chesapeake Bay.

Embark on an unforgettable sailing adventure with our seasoned team aboard one of our sailing yachts. Experience the freedom and exhilaration of sailing while learning new skills and building confidence on the water. This introduction to the basics that will transform the way you connect with mother nature.

Ready to get engaged? Surprise your fiancé with a one-of-a-kind proposal aboard a private sailing yacht. If you’re dreaming of a creative and meaningful way to pop the question, this Engagement Package delivers an unforgettable experience.

Looking for a unique and unforgettable way to celebrate a bachelorette or bachelor party in St. Michaels, Maryland? Set sail aboard our historic 1935 ketch Lady Patty or our spacious, modern 44-foot catamaran for a one-of-a-kind celebration on the water!

Celebrate Independence Day in style! Watch the stunning St. Michaels 4th of July fireworks reflected over the serene Miles River. Enjoy an open bar of cold beer, wine or champagne, and be pampered on this exclusive 6-13 guest experience. Book now to avoid disappointment – we sell out fast!

Have more than 6 people in your group? Click here to book a sail for up to 13 people!