St Michaels Sailing Charters

Ahoy from the crew! Delivering the most personalized and enjoyable boat tours on the Eastern Shore of the Chesapeake Bay is always the top priority.

The owners, GM and Laura, both grew up sailing and bring a lifetime of experience to every trip. GM has been on the water since childhood and previously taught sailing in St. Michaels, Maryland. His adventures have taken him across the Mediterranean, Mexico, Hawaii, California, the U.S. East Coast, the Delaware River, the Bahamas, and throughout the Chesapeake Bay. He has held a U.S. Coast Guard captain’s license since 2014. Laura also grew up sailing on monohull sailboats with her family and now has years of experience along the East Coast and in the Bahamas. She is also a professional photographer with a passion for capturing life on the water.

GM spent several summers serving as first mate aboard a historic Chesapeake vessel, gaining valuable experience that helped shape the style of tours offered today. After several successful seasons operating on Broad Creek, the operation will move across the harbor for the 2026 season and...