Chesapeake Sailing Tours

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1050 Deep Creek Ave
Arnold, MD 21012
We are a charter sailing business in the Annapolis Md.and Chesapeake Bay area. We would love to take your group of up to four people out for a sail on the Chesapeake Bay! We have a very fast, fun, and stable trimaran called Dragonfly that we use to sail in the Annapolis area. Whether you want to go for a sunset sail, or a day charter, we will do our best to meet your needs!

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5.016 reviews
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Sunset sail!
6/2/2019

We booked a sunset cruise with Dan last minute and had a perfect evening. We had a quick bite to ea...

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Great Trip!
7/9/2018

Four friends had a 3 hour tour of the Bay. Dan is the perfect captain — friendly, knowledgeable but ...

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Plebe PPW vacation
8/10/2017

We had time to tour and relax before the scheduled events of USNA Plebe PPW. The two hours were s...

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