Events Calendar

Step aboard and discover the timeless beauty of the Chesapeake Bay with St. Michaels Sailing Charters. Whether you’re seeking relaxation, romance, celebration, or adventure, our thoughtfully curated sailing experiences offer an unforgettable way to enjoy the water in charming St. Michaels, Maryland.

If you’re looking for a relaxing boat tour, hoping to unwind in nature, or searching for the best things to do in St. Michaels, our luxury sailing yachts — Lady Patty and Epiphany — provide the perfect escape. From historic elegance to modern comfort, every sail is designed to deliver peaceful, memorable moments on the Bay.

Choose between two exceptional vessels: Lady Patty, a beautifully restored 1935 Maryland-built ketch steeped in maritime history, or Epiphany, a spacious and contemporary 44-foot Leopard catamaran offering smooth, luxurious cruising. Each experience includes a two-hour (or longer) sail led by knowledgeable captains and a welcoming crew dedicated to creating a truly first-class outing.

Guests can enjoy classic daytime sails or select from a variety of specialty experiences, including sunset champagne cruises, wine and beer tastings, private sailing lessons, and custom charters for life’s most meaningful celebrations. From intimate proposals and nautical weddings to festive bachelorette parties and Fourth of July fireworks sails, there is a perfect voyage for every occasion.

Signature Experiences Include:
• 2-Hour Relaxing Chesapeake Day Sail
• Chesapeake Bay Sunset Champagne Sail
• Wine & Beer Tasting Cruises
• Nautical Wedding & Elopement Packages
• Half-Day & Full-Day Private Sails
• Private Sailing Lessons
• Marriage Proposal & Engagement Cruises
• Bachelor & Bachelorette Party Sails
• Fourth of July Fireworks Cruise
• Private Catamaran Charters

Set sail, slow down, and experience the Chesapeake the way it was meant to be enjoyed.