St. Michaels Sailing Charters

06/17/2026

Looking to become an ASA certified sailor? ⛵ Earn your ASA 114 Cruising Catamaran certification aboard Epiphany on the Chesapeake Bay with hands-on, small-group instruction from our ASA-certified crew!

📅 ASA 114 dates: July 22-23 & October 5-6

Swipe to learn more, then book at stmichaelssailingcharters.com 🌊

06/17/2026

06/15/2026

Your bach trip deserves more than a bar crawl. ⛵️ Meet Epiphany.. our luxury catamaran and your new favorite party venue on the Chesapeake!
Bring your sashes! Sails and stemless wine glasses included in this celebration🥂⚓️

06/13/2026

Set sail this Father’s Day! ⛵️

Give Dad an experience he’ll never forget with a sailing adventure on the Chesapeake Bay. Book your charter today and make some memories on the water. 🌊

📍 St. Michaels Sailing Charters

🔗 stmichaelssailingcharters.com

06/12/2026

What people are saying about Lady Patty⛵️

Book your charter today!
[link in bio]

www.stmichaelssailingcharters.com

06/10/2026

Flag Day on the water 🇺🇸⛵ Join us this Sunday, June 14th for the St. Michaels Flag Day Boat Parade! One of the most festive days on the Bay! 🌊
Spots are limited and 25% off right now! Don’t miss it → Link in bio

06/08/2026

⛵ The 2026 St. Michaels Log Canoe Race season is HERE and it’s one of those Chesapeake Bay traditions you truly have to see to believe! 🌊

Log canoes are some of the oldest racing sailboats in the United States built from hollowed logs in the 1800s. It’s part sport, part history, and 100% Eastern Shore magic! ✨

Want a front-row seat? We recommend a half-day private charter for the full race experience! 360 views, no crowds and memories for life!

Book your charter through the link in bio! 🔗

06/03/2026

Some nights, the Chesapeake puts on a show.
We’ll always save you a seat. 🌅

06/01/2026

This past weekend, Lady Patty was dressed for the most special occasion! ⚓️

This beautiful couple chose to say “I do” right here on the water, and honestly? We couldn’t have dreamed up a more perfect day if we tried. The water, the light, the love in the air..

Watching two people start their forever surrounded by the Chesapeake made our whole crew beam with joy. 🥂

To the newlyweds, thank you for choosing Lady Patty as the backdrop for the most important “yes” of your lives. We are so honored to have been part of your story. Wishing you endless adventure together!💍🤍