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Boat Rental in Chesapeake Bay

Bareboat, Crewed & Luxury Yacht Charters
Port Annapolis Marina on Back Creek

Only a handful of waterways in the world can match the Chesapeake Bay for sheer sailing pleasure. At about 200 miles long, it’s the largest estuary in the United States with thousands of miles of shoreline to explore. It offers sailors protected waters, great anchorages, a forgiving bottom, gorgeous natural scenery, and unique towns and villages steeped in history. Rent a boat in Chesapeake Bay, it’s perfect for novices just learning to sail, yet challenging enough to keep experts captivated for a lifetime. Please note that Tropical Yachts has a Best Price Policy (Click for more info.)



Our exceptional selection of monohulls and catamarans for charter out of Annapolis are available in the following classes:

CHESAPEAKE BAY BAREBOAT CHARTERS - The ultimate in privacy & freedom, bareboat rentals are for groups having their own qualified skipper. Hiring a captain and or hostess/cook always remains an option. For a list of our available Bareboat yachts, please Click Here.


Port Annapolis Marina: Our base is at Port Annapolis Marina on Back Creek in historic Annapolis. A sailing Mecca if ever there was one, Annapolis lies at 38 degrees 58 minutes north latitude and 76 degrees 29 minutes west longitude. Maryland’s capital city is the perfect starting point for your Chesapeake Bay exploration.

Before embarking, however, seeing the sights of Annapolis is a must. You can stroll down to “Ego Alley” at Annapolis Harbor, and then grab a sandwich at Chick and Ruth’s Delly on Main Street. A couple of streets over, you can visit the Maryland State House, historically distinctive because it’s the oldest state capitol in continuous legislative use, topped by the largest wooden dome in the nation. Annapolis is also home to the U.S. Naval Academy.


Annapolis Marina, North: 7 Day Itinerary
Before embarking, seeing the sights of Annapolis is a must. Stroll down to “Ego Alley” at Annapolis Harbor, and then grab a sandwich at Chick & Ruth’s Delly on Main Street. Visit the Maryland State House – the oldest state capitol in continuous legislative use topped by the largest wooden dome in the nation. The Chesapeake Bay takes its name from a Powhatan word, “Chesepioc,” or “Great Shellfish Bay.” The French founded Annapolis as a settlement called Port Royal in 1605, and Captain John Smith became the first European to explore and thoroughly map the Chesapeake Bay in 1609, writing in his journal that “heaven and earth have never agreed better to frame a place for man’s habitation.” With so many delightful creeks, coves, rivers, towns and villages to visit, Annapolis makes for a dream sailing vacation.

Annapolis Marina, South: 7 Day Itinerary
Begin by sailing to Herrington Harbour, a very popular place. We recommend Mango’s Bar & Grill for beautiful waterfront dining in a classy but laid-back atmosphere. Sail to Oxford, a quiet, small town where townspeople make visitors feel like old friends. Sail to Cambridge, about 13 miles from the mouth of the Choptank River, then to St Leonard Creek, considered one of the most beautiful areas on the Patuxent River. Visit Solomon’s Island, a picturesque island town nestled in the joining of the Patuxent River and the Chesapeake Bay, Visist St Michael's Village, the site of the Chesapeake Bay Maritime Museum.

Annapolis Marina, South: 14 Day Itinerary Only a handful of waterways in the world can match the Chesapeake Bay for sheer sailing pleasure and Annapolis is right in the heart of this sailing paradise, as the perfect departure point for your sailing vacation. In this itinerary you can visit Solomon's Island, Dozier's Regata in Deltaville,The Ocean Marine Yacht Center just 0.5 miles south of mile marker zero on the Intracoastal Waterway in Portsmouth, Bay Creek with it's perfect blend of elegant homes great dining and word class golf resorts; and plenty more!


Below you will find a link to additional information we are certain you will find useful pertaining to your yacht charter vacation.

Frequently Asked Questions about
Chesapeake Bay

Frequently Asked Questions about your yacht charter

Tropical Yachts
4906 N Travelers Palm Lane. Tamarac, FL 33319
Tel: 1 (305) 735-3460

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