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Sailing Chesapeake Bay

Listed under Sailing in Appalachian States, United States.

  • Photo of Sailing Chesapeake Bay
  • Photo of Sailing Chesapeake Bay
  • Photo of Sailing Chesapeake Bay
  • Photo of Sailing Chesapeake Bay
  • Photo of Sailing Chesapeake Bay
  • Photo of Sailing Chesapeake Bay
  • Photo of Sailing Chesapeake Bay
  • Photo of Sailing Chesapeake Bay
Photo of Sailing Chesapeake Bay
Photo by flickr user chriswsn
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For sheer scale and freedom, the Chesapeake Bay is one of the best sailing areas in the United States. The largest estuary in the US, it is 200 miles long, providing an expanse of shoreline to explore and a massive diversity of attractions from cosmopolitan cities to tiny islands and sleepy waterways. Soaked in American and naval history, offering incredible seafood feasts, landscapes and night life, Chesapeake Bay has enormous variety for sailing experiences.

Chesapeake Bay was formed 10,000 years ago when melting glaciers caused the Atlantic ocean levels to rise. Today, it is dotted with historical cities to which you can cruise and moor up to enjoy. In Baltimore, with its world renowned Inner Harbour, you can get right into the heart of the city. The harbour hosts dozens of great restaurants and fun night life. Look out for the USS Constellation, a civil war ship which is permanently docked in the harbour and open to the public year round.

Annapolis, known as the 'sailing capital of the world', will be a long anticipated stop for sailors. Maryland's capital city is home to its famous naval academy and the National Sailing Hall of Fame and Museum.

The Bay also provides countless quiet and beautiful destinations to get away from the city bustle. Islands such as Solomens and Tangier are home to small communities and have strong sailing roots and therefore decent facilities. When eating in the plentiful seafood restaurants try the oyster and crabs which have been traditionally caught here for hundreds of years. Off the Maryland coast, you can still see the traditional skipjack, the state boat used for catching oysters in an area where laws prevent the use of powerboats for oyster fishing.

Chesapeake Bay is famous for its fishing and there are plenty of companies which take guests out to the best spots. Due to strict fishing regulations it is best to have a guide or go on an organised trip. There are marinas and charter companies dotted up the bay which provide bare boat and skippered chartered as well as sailing courses and lessons.

Written by  Jane Ferguson.

Comments, reviews and questions by other travellers

Wow, I never knew that Balearic Island Charters. That's pretty interesting

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Rent a sail boat for a week early November in Chesapeake area - either just for my husband and myself or as part of a group or flotilla. Any ideas where I can find a company to book this through?

amazing scenery and fantastic fishing

The Chesapeake-or 'the bay' as locals refer to it as- is beautiful. Sail boats and motor boats are on the water all day long, and sometimes into the night doing some night fishing. the coastline stretches on the west side of you showing off gorgeous cliffs, trees and some fantastic looking sea-side houses. The eastern shoreline shows up after a semi-long ride but is worth it. The fishing is fantastic for rock fish and trout. A lot of people crab along the bay also, so while on the boat look out for the crab pots! Whereas a lot of pollution has gotten dumped into the bay, local communities are trying their best to clean the area.

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