The Top Charter Yachts in Annapolis and Chesapeake Bay

Cruising Chesapeake Bay

Boatbookings curated list of the best charter yachts to Explore Annapolis and the Chesapeake Bay

The Chesapeake Bay is an enormous inland waterway in the Mid-Atlantic States of Virginia and Maryland. It is a sailor’s paradise with over 5,000 miles of shoreline to explore.

You will enjoy delicious seafood (especially the famous Bay crabs!), gorgeous sandy beaches, inland rivers, and historic towns like Annapolis, home of the US Naval Academy, and the vibrant port city of Baltimore. In the Southern part of the Bay, you can see the famous wild horses on the islands of Chincoteague and Assateague.

Sailing northward into Maryland, you can stop in Soloman’s Island, visit St. Mary’s City, and sail up the Patuxent and St. Mary’s Rivers. You won’t want to miss Smith and Tangiers islands, written up in National Geographic for maintaining their traditional lifestyles. In the northern part of the Bay, you can stop in Baltimore, Annapolis, Georgetown, and Chestertown. The sailing around the Chesapeake Bay is all “line of sight” with the breeziest times of the year in the spring and the fall.

In the middle of the summer, the weather can be very hot and humid and less breezy (or even still) with afternoon thunderstorms that break the heat. The waters of the Bay are brackish (a mixture of salt and fresh) varying from very salty near the mouth of the Bay to almost fresh at the northern end. We have a fantastic selection of the best bareboat charter yachts from Annapolis or contact us if you would like us to find the right bareboat for you. 

Annapolis/Chesapeake Catamarans. If you're looking for a comfortable and relaxing catamaran, we have a great selection of Annapolis Catamarans here.

If you love sailing, you owe yourself the thrill of sailing up to the Naval Academy, as well as the experience of sailing to some of the prettiest areas on America's storied East Coast. Please see below our curated list of the best charter yachts out of Annapolis and please let us know which one best meets your needs for a Chesapeake Bay charter!

See our Chesapeake sailing itinerary