Best results for
Sailing in Annapolis, MD
Showing 1-14 of 14 results
Chesapeake Bay Day Sail on a 1935 Ketch in St. Michaels
Sail a Historic 1935 Ketch on the Miles River
5.0 • 1.4K reviews
38' Sailing Catamaran Charter in Essex
Sail the Middle River and Chesapeake aboard a private luxury catamaran
4.9 • 145 reviews
Private Sailing Catamaran Charter in St. Michaels
Sail the Miles River with room to relax aboard Epiphany
5.0 • 1.4K reviews
Chesapeake Bay Sunset Champagne Sail in St. Michaels
Sail Chesapeake Bay at sunset with champagne and light bites
5.0 • 1.4K reviews
Bachelorette & Bachelor Party Cruise in St. Michaels
Celebrate the bride or groom aboard a historic private sailboat
5.0 • 1.4K reviews
Private Half-Day Sail on a 1935 Ketch in St. Michaels
Sail the Miles River aboard a historic 1935 ketch
5.0 • 1.4K reviews
Sunset Champagne Cruise in St. Michaels
Sail a historic ketch at sunset with champagne and Chesapeake Bay views
5.0 • 1.4K reviews
Full-Day Private Sailing Charter in St. Michaels
Private catamaran sailing with harbor views and Miles River breezes
5.0 • 1.4K reviews
2-Hour Chesapeake Bay Sailing Cruise
Sail the Miles River aboard a spacious catamaran
5.0 • 1.4K reviews
Private Half-Day Sailing Charter in St. Michaels
Harbor views and wind-powered sailing on the Miles River
5.0 • 1.4K reviews
2-Hour Beer Tasting Cruise in St. Michaels
Savor rotating craft beer tastings aboard the historic Lady Patty
5.0 • 1.4K reviews
2-Hour Sailing Lesson in St. Michaels
Build Practical Sailing Skills With Private, Hands-On Instruction
5.0 • 1.4K reviews
Historic Ketch Sailing Lesson in St. Michaels
Take the Helm and Learn Hands-On Sailing Skills
5.0 • 1.4K reviews
Full-Day Private Sailing Charter in St. Michaels
Private Chesapeake Bay sailing aboard a 1935 ketch
5.0 • 1.4K reviews