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Chesapeake Bay Sailing Charter Directory & Reviews
You have found the right place to plan your next sailing charter in the Chesapeake Bay region. Identify the charter company best suited for your needs based on updated contact information and reviews from fellow sailors. We provide comprehensive listings, full contact information, and helpful advice to help make your next trip your best ever.
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Top 3 Rated Charter Companies in the Chesapeake Bay Region
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Blue Crab Chesapeake Charters - Rating:
10.0 -
Chesapeake Yacht Charters - Rating:
8.5 -
Let's Go Cruising - Rating:
8.0
Charter Company Map
Chesapeake Bay Sailing Charter Listings
Total of 14 charter companies
Is one missing? Add a listing!
Is one missing? Add a listing!
United States
Rating: 5.0
Annapolis Bay Charters (Annapolis)
BaySail School and Yacht Charters (Havre de Grace)
Rating: 10.0
Blue Crab Chesapeake Charters (Rock Hall)
C and C Charters (Grasonville)
Chesapeake Sailing School (Annapolis)
Rating: 8.5
Chesapeake Yacht Charters (Edgewater)
East Coast Yacht Management (Deltaville)
Fair Wind Sailing School (Chestertown)
Gratitude Yachting Center (Deltaville)
Haven Charters (Rock Hall)
Let's Go Cruising (Solomons)
Rating: 8.0
Let's Go Cruising (Annapolis)
Sail Solomons (Dowell)
Tred Avon Yacht Sales (Oxford)
Recent Chesapeake Bay Charter Reviews
Let's Go Cruising (Annapolis)
Rating
8
Submission date:
3/3/07 | Charter
date: September 2005
Submitted by: Garret | From: United States
Type of sailor: Novice skipper (0-1 years) | Age: 31 - 40
Submitted by: Garret | From: United States
Type of sailor: Novice skipper (0-1 years) | Age: 31 - 40
Great place in Annapolis
The boats are very new and come in all sizes - you can day sail or take a larger boat for a couple of weeks. They specialize in Jeanneau and Fountaine Pajot cats.
The best time to go is in September, when there is plenty of wind and the crowds are much smaller. August is weak and July is dead calm.
As far as where to go: If it is sailing, anchoring out, getting away from it all, the southern bay is great. If you are looking for a bit more activity / places to see, check out the northern bay. Annapolis, St. Mike's (with the Maritime Museum) will give you the he 'destination/ shopping/ dining' elements, while sailing into the Choptank river and/or mid-bay to Solomon's will provide good sailing.
The best time to go is in September, when there is plenty of wind and the crowds are much smaller. August is weak and July is dead calm.
As far as where to go: If it is sailing, anchoring out, getting away from it all, the southern bay is great. If you are looking for a bit more activity / places to see, check out the northern bay. Annapolis, St. Mike's (with the Maritime Museum) will give you the he 'destination/ shopping/ dining' elements, while sailing into the Choptank river and/or mid-bay to Solomon's will provide good sailing.
Annapolis Bay Charters (Annapolis)
Rating
5
Submission date:
6/28/10 | Charter
date: June 2010
Submitted by: Rebecca | From: United States
Type of sailor: Ancient Mariner (5+ years) | Age: 41 - 50
Submitted by: Rebecca | From: United States
Type of sailor: Ancient Mariner (5+ years) | Age: 41 - 50
Bad service, good boat
We chartered a 39 ft monohull which was in good condition. Comfortable boat--the electronics were flukey--maybe a short in the system that hadn't been diagnosed. All manageable. Our only complaint was the service. When we picked up the boat we were told the dinghy had a new engine and just-filled, half-tank. We checked--it was empty. Items that were supposed to be on board (coffee pot) weren't and we were scorned by staff for not finding it. It wasn't there. They brought a new one. Our calls to the emergency contact numbers went unreturned when the systems alarm went off in the early morning hours. A filing box with carefully labelled file for electronics, battery, etc. were largely empty. For the most part, the owner and his second in command were surly and glib. Not the kind of attitudes expected. We liked the boat but will surely use another charter company.
Chesapeake Yacht Charters (Edgewater)
Rating
7
Submission date:
11/21/08 | Charter
date: July 2008
Submitted by: Suzie | From: United States
Type of sailor: Experienced skipper (1-5 years) | Age: 41 - 50
Submitted by: Suzie | From: United States
Type of sailor: Experienced skipper (1-5 years) | Age: 41 - 50
needs a little work
boat was not prepped and as clean as could be - looked like we were not the first on board
Chesapeake Yacht Charters (Edgewater)
Rating
10
Submission date:
6/17/08 | Charter
date: May 2008
Submitted by: Jim | From: United States
Type of sailor: Ancient Mariner (5+ years) | Age: 51 - 60
Submitted by: Jim | From: United States
Type of sailor: Ancient Mariner (5+ years) | Age: 51 - 60
Chesapeake Bay Yacht charter
I rented this 50 foot power boat with 3 staterooms, enough for our entire family, from Chesapeake Bay Yacht Charter dealt with a guy named Griff Bell who runs the place they are located in Annapolis Maryland area.
Boat was awsome could not have been better had lots of room and all the comforts including air conditioning.
Bell was a pleasure to deal with and treated us wonderfully. We plan to use them in the future.
Boat was awsome could not have been better had lots of room and all the comforts including air conditioning.
Bell was a pleasure to deal with and treated us wonderfully. We plan to use them in the future.