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 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 continuing maintaining traditional lifestyles. In the northern part of the Bay, you can stop in Baltimore, Annapolis, Georgetown and Chestertown. The sailing is all “line of sight” with the breeziest times of 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.

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Jeanneau 43DS (3cabins) - Annapolis Berths: 4 Cabins: 3 Crew: Bareboat Type: Sail Year: 2006 Enquire for prices Add to “My Yachts”
Bavaria 37 - (2 Cabin) - Annapolis, USA Berths: 5 Cabins: 2 Crew: Bareboat Type: Sail Year: 2001 Enquire for prices Add to “My Yachts”
Catalina 360 MkII - 2 Cabins - Annapolis, USA Berths: 4 Cabins: 2 Crew: Bareboat Type: Sail Year: 1999 From $ 2240 per week Add to “My Yachts”
Jeanneau SO 35 - 2 Cabins - Annapolis, USA Berths: 4 Cabins: 2 Crew: Bareboat Type: Sail Year: 2006 From $ 2240 per week Add to “My Yachts”
Jeanneau 36i - 2 Cabins - Annapolis Berths: 4 Cabins: 2 Crew: Bareboat Type: Motor Year: 2007 From $ 2300 per week Add to “My Yachts”
Jeanneau 39i - 2 Cabins - A/C - Annapolis Berths: 4 Cabins: 2 Crew: Bareboat Type: Catamaran Year: 2007 From $ 2400 per week Add to “My Yachts”
Jeanneau 40.3 - (3 Cabins) - A/C - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Sail Year: 2003 From $ 2400 per week Add to “My Yachts”
Delphia 37 - 2 Cabins - Annapolis, USA Berths: 6 Cabins: 2 Crew: Bareboat Type: Sail Year: 2006 From $ 2436 per week Add to “My Yachts”
Jeanneau 37 - 2 Cabins - Annapolis, USA Berths: 4 Cabins: 2 Crew: Bareboat Type: Sail Year: 2004 From $ 2436 per week Add to “My Yachts”
Beneteau 393 - 2 Cabins - Annapolis Berths: 4 Cabins: 2 Crew: Bareboat Type: Sail Year: 2003 From $ 2471 per week Add to “My Yachts”
Jeanneau 39DS - (2 Cabins) - A/C - Annapolis Berths: 4 Cabins: 2 Crew: Bareboat Type: Sail Year: 2007 From $ 2500 per week Add to “My Yachts”
Beneteau Oceanis 393 - 3 Cabins - Annapolis USA Berths: 6 Cabins: 3 Crew: Bareboat Type: Sail Year: 2003 From $ 2765 per week Add to “My Yachts”
Jeanneau SO 40.3 - 3 Cabins - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Sail Year: 2005 From $ 2765 per week Add to “My Yachts”
Sun Odyssey 40.3 - 3 Cabins - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Sail Year: 2005 From $ 2765 per week Add to “My Yachts”
Delphia 40 - 3 Cabins - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Sail Year: 2006 From $ 2800 per week Add to “My Yachts”
Mahe 36 - (2 Cabins) - A/C - Annapolis Berths: 4 Cabins: 2 Crew: Bareboat Type: Catamaran Year: 2007 From $ 2900 per week Add to “My Yachts”
Jeanneau 43 DS - (3 Cabins) - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Sail Year: 2005 From $ 3200 per week Add to “My Yachts”
Jeanneau 42DS - (2 Cabins) - A/C - Annapolis Berths: 4 Cabins: 2 Crew: Bareboat Type: Sail Year: 2007 From $ 3400 per week Add to “My Yachts”
Jeanneau 42i - 3 Cabins - A/C - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Sail Year: 2007 From $ 3400 per week Add to “My Yachts”
Jeanneau 43 DS - (4 Cabins) - A/C - Annapolis Berths: 8 Cabins: 4 Crew: Bareboat Type: Sail Year: 2004 From $ 3400 per week Add to “My Yachts”
Jeanneau 42DS - (2 Cabins) - A/C - Annapolis Berths: 4 Cabins: 2 Crew: Bareboat Type: Sail Year: 2006 From $ 3500 per week Add to “My Yachts”
Jeanneau 42 DS- (2 Cabins) - A/C - Annapolis Berths: 4 Cabins: 2 Crew: Bareboat Type: Sail Year: 2007 From $ 3750 per week Add to “My Yachts”
Lagoon 38 - 3 Cabins - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Catamaran Year: 2001 From $ 3850 per week Add to “My Yachts”
Lavezzi 40 - (3 Cabins) - A/C - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Catamaran Year: 2005 From $ 4220 per week Add to “My Yachts”
Jeanneau 49DS (3 Cabins) - A/C - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Sail Year: 2005 From $ 4800 per week Add to “My Yachts”
Jeanneau 49DS - (3 Cabins) - A/C - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Sail Year: 2005 From $ 5100 per week Add to “My Yachts”
Jeanneau 49DS - (3 Cabins) - A/C - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Sail Year: 2007 From $ 5200 per week Add to “My Yachts”
Jeanneau 49DS - (3 Cabins) - A/C - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Sail Year: 2006 From $ 5200 per week Add to “My Yachts”
Jeanneau 49DS - (3 Cabins) - A/C - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Sail Year: 2007 From $ 5300 per week Add to “My Yachts”
Orana 44 - (3 Cabins) - A/C - Annapolis Berths: 6 Cabins: 3 Crew: Bareboat Type: Catamaran Year: 2008 From $ 5450 per week Add to “My Yachts”

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