Sailing The Chesapeake Bay:
The Chesapeake Bay is the largest estuary in the United States. It is a complex ecosystem which covers over 4000 square miles being about 200 miles long and about 30 miles wide and incredibly with its tributaries has over 11,000 miles of shoreline - more than the entire west coast of the United States. So, a simple day sail will only touch the fringes of all the Chesapeake has to offer (see map), the beautiful water, the intricate shoreline, the fish and wildlife, the history. That is why we offer overnight cruises and multiple overnight cruises, to let you at least taste one of these fringes and wet your appetite for more.
The Chesapeake Bay played an important role in the history of the United States starting with Jamestown and Captain John Smith and is covered with historic seafaring towns like Baltimore and Annapolis. We can pick you up at the historic waterfront in Baltimore or Annapolis or at other small waterfront communities on the Bay. We can even arrange for pickup at one of the nearby airports or from Washington, D.C.. We can show you the Captain John Smith Chesapeake National Historic Trail, the nation's first all water National Historic Trail. Or, we can just find the best of Maryland's Famous Blue Crabs. Whether you like Crab Cakes, Steamed Crabs, Crab Soup, Soft Shell Crabs or a hamburger, we know where to take you.
Let Bread On The Water introduce you to what the Chesapeake Bay has to offer: great sailing, history, fishing, crabbing . . . the Chesapeake has something for everyone and every cruise on Bread On The Water is tailored to your tastes and interests to make your day(s) with us the best of your visit to the Chesapeake Bay.
We can also put together some fun packages to suit your needs:
- Weddings, Birthdays, Anniversaries, Proposals - Celebrate the special moments of your life enveloped in the magnificence of the Chesapeake Bay!
- Sailing to a Crabfeast - We sail to one of the many fine local crabhouses for a sumptuous seafood feast! Are you really a crab fan? How about a weekend Crabfeast with a different crabhouse for every meal?
- Cruising the Chesapeake - A two, three, or four day sail to the waterways of the Eastern Shore. Stay in a different secluded anchorage each night.
- Destination Cruises - Sail to Annapolis, Maryland's Eastern Shore or Baltimore's Inner Harbor for a memorable day of sailing, history, exploration and fun!
- Lighthouse Tours - The Chesapeake Bay has many different historic lighthouses, many just an easy sail away.
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Joan and Gary,
Thank you very much for the great sailing on the Chesapeake Bay this weekend. It was a wonderful, relaxing time for us. Thanks for the sailing instructions, delicious food and all the attention you have given our boys. They loved dinghy rides with Roxy and Alex was very proud he could motor by himself under Gary's watchful eye. Hope to see you soon!
Wishing you a great summer on Chesapeake,
Gosia, Chris, Alex & Nicholas (June 2009)
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We Offer the Following
Full Day Sail
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We pick you up in the morning in Annapolis, Baltimore or at any number of small towns along the coast of the Chesapeake Bay. We spend the day sailing the Chesapeake or sailing up some of the small rivers that feed the bay like the Magothy River or Broad Creek. We stop for lunch in some secluded anchorage or drop you off for lunch at some quaint bay side restaurant for some fresh Maryland seafood. In the afternoon we sail back to wherever we picked you up with you doing a much or as little of the sailing as you like.
$950 for up to six people.
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Overnight / Next Day Sail
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We pick you up in the afternoon in Annapolis, Baltimore or at any number of small towns along the coast of the Chesapeake Bay. We find a nice quiet anchorage like Dobbin's Island and you settle in for cocktails while watching the sunset. Joan will prepare you a wonderful dinner. After dinner you can lay out on deck and watch as the stars come out before heading down below to your private cabin to be lulled to sleep by the sound of the water lapping on the sides of the boat. After a wonderful night's sleep you wake up to the smell of breakfast cooking in the galley. Next, we set sail for any number of wonderful destinations along the Chesapeake with you doing a much or as little of the sailing as you like.
$1600 for up to four people.
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Two Day Sail with an Overnight
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We pick you up in the morning in Annapolis, Baltimore or at any number of small towns along the coast of the Chesapeake Bay. We spend the morning sailing the Chesapeake or sailing up some of the small rivers that feed the bay like the Chester River or the Patapsco River. We stop for lunch in some secluded anchorage or drop you off for lunch at some quaint bay side restaurant for some fresh Maryland seafood. In the afternoon we sail along the Chesapeake or to the Eastern Shore of Maryland with you doing a much or as little of the sailing as you like.
We find a nice quiet anchorage and you settle in for cocktails while watching the sunset. Joan will prepare you a wonderful dinner. After dinner you can lay out on deck and watch as the stars come out before heading down below to your private cabin to be lulled to sleep by the sound of the water lapping on the sides of the boat. After a wonderful night's sleep you wake up to the smell of breakfast cooking in the galley.
Next, we set sail for any number of wonderful destinations along the Chesapeake with you doing a much or as little of the sailing as you like and spend the whole day relaxing on the water.
$2100 for up to four people.
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Extra Overnight
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Add an extra night sleeping on board under the stars with the sound of the water lapping the hull to lull you to sleep.
$950 for up to four people.
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Examples of Possible Chesapeake Bay Trips
Example 1
Great Sailing
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We pick you up at the historic dock in center of Annapolis and set sail for the Eastern Shore of Maryland. After a scrupulous lunch of Maryland's Famous Blue Crabs. We spend the rest of the afternoon sailing back to Annapolis while you relax in the comfort of the cockpit or stand at the helm looking for other sailboats to "race".
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Example 2
One Overnight
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We pick you up in the afternoon and find a nice secluded anchorage on the Magothy River. We settle in with cocktails to watch the sunset before sitting down to one of Joan's delicious meals. After dinner you lay out on deck and watch as the stars come out before heading down below to your private cabin to be lulled to sleep by the sound of the water lapping on the sides of the boat. After a wonderful night's sleep you wake up to the smell of breakfast cooking in the galley. Next, we set sail for any number of wonderful destinations along the Chesapeake with you doing a much or as little of the sailing as you like. After lunch we head back to drop you off - unless you want to stay another night?
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Wake up to a Magothy morning. The Magothy River (see map) is a favorite among boaters for the popular anchorage behind Dobbins Island. Swim in the shadow of Dobbins Island, ogle the real estate on Gibson Island and duck into any of the Magothy's creeks for a beautiful slice of nature.
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We pick you up at the historic waterfront harbor in Annapolis in the afternoon and sail up the Corsica River until we find a quiet, secluded anchorage where we settle in for the evening. The next morning we finish our sail upstream to Chestertown and sail past the graceful old waterfront homes. Chestertown itself is a gorgeous, well preserved historic town where George Washington use to hang around. Now, the town is home to artists of all ilk - sculptors, painters, potters, poets. C-town is a walking town with beautiful gardens and a comfortable neighborhood feel. After spending the day exploring Chestertown, you return to the boat for a quiet cocktail to revisit all you've seen. After dreaming of Colonial times, you have a leisurly breakfast and prepare to sail back to Annapolis - unless you want to stay another night?
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Please contact us for availability and pricing or for more information about the many sailing options available in the beautiful waters around the USVI and the BVI or on the Chesapeake Bay.
443-604-3005 ~ 443-604-4600 ~ 340-513-9220
Email Us
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Bread on the Water accepts Visa and Mastercard
 
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