Chesapeake Flotillas offers guided flotilla cruises for the northern portion of the Chesapeake Bay. Custom cruise planning is also available. Call us for more information at 908.672.3609.
A guided flotilla cruise is simply a fleet of chartered cruising yachts sailing to a common destination each day. The flotilla is supported by trip leaders who will sail on their own boat. In some cases, it may be possible to put experienced crew aboard your yacht to assist with sailing the vessel. Participants get the benefits of a bareboat chartering experience and experienced guides to help you find and enter lesser known anchorages and towns in the cruising area.
The cost of each trip generally includes:
Chesapeake Flotillas can create flotilla cruises which can start from Annapolis, Rock Hall, or Havre de Grace, MD. Ocassionally there are boats available in places like Solomons, MD and Deltaville, VA. Two-day trips run Saturday through Sunday with boarding Friday evening. Three- and four-day trips start on Friday. Reserve a whole boat and assemble your own crew or sign up to possibly join an existing crew. Sailors signing on as Skippers for a flotilla will be required to submit a sailing resume at the time of reservation. Chesapeake Flotillas reserves the right to determine whether one is qualified to skipper.
Our 2009 trip schedule is now available. We are offering several flotilla cruises on the Chesapeake Bay in 2009. Our loyal customers are being invited on a private cruise designed with their input. We will be offering a three-day weekend in conjunction with an event being sponsored in part by the Universal Sailing Club. We hope to draw participants from the Black Boaters Summit as well. Lastly you will find a link to our French West Indies Adventure scheduled for the spring. Click the links below for more details on these trips.
| Trip | Dates | Cost |
| French West Indies Adventure | Completed | |
| Private Birthday Cruise | August 15-16 | |
| Private Cruise | Sept 18-20 | |
| BBS & Universal Sailing Club Event | No longer available | $480.00 |
| Four-Day October Flotilla | October 16-19, 2009 | $475.00 |
Do you need some help with your boathandling technique? Or perhaps all you need is a little refresher course to start your season off. Check out the training opportunities.
Do you have an idea for a special or themed cruise you might like to take? We will create an experience for you as if it were our very own! Contact us at 908.672.3609. The journey begins with YOU.
Send us an email now to find out how to create your sailing vacation. You may also call Chesapeake Flotillas at 908.672.3609.
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