1 855 208 7566 (Toll-free)

The magic of
Annapolis sailing

From Havre de Grace to Hampton Roads and every place in between, sailing the Chesapeake Bay offers a unique feast of sights, sounds, food and culture.

Start making memories of a lifetime House Food
Bareboat Charters • Skippered Charters • Corporate Regattas • Yacht Sales and Management

The Chesapeake Bay is well-known as an outstanding waterway for sailboat cruising

Protected waters, great anchorages...

…gorgeous natural scenery, unique towns and villages, and a forgiving bottom make the Chesapeake an excellent choice for sailors, novice and expert alike. Historic Annapolis, the crown jewel of the Mid-Atlantic, is the best sailing destination on the East Coast, and is the perfect place for you to begin your exploration of the Chesapeake Bay.

At Annapolis Bay Charters, we are more than your everyday boat rental operation. We combine an impressive fleet of well-maintained sailboats and powerboats, a service-oriented staff with over thirty years’ experience, and a yacht charter location that makes it easy to visit some of the Chesapeake Bay’s hidden gems. Our friendly staff will help you select just the right boat for your next cruising vacation. To make your voyage as enjoyable as possible, we offer many extras, such as itinerary planning, Annapolis sailing instruction with our new NauticEd Sailing School, provisioning, captain and crew services.


Need help planning your cruise itinerary? We’ve got you covered. Follow the link above to find marinas and book online – or contact snag-a-slip directly at- hello@snagaslip.com

Latest news

Read all

Dream Yacht Management