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Chesapeake Sailing Tours

1050 Deep Creek Ave, Arnold, MD 21012-1731
+1 410-349-4360
Review Highlights
Plebe PPW vacation

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

Reviewed August 10, 2017
Seaside, California
via mobile
Highly Recommend!

Our family of 4 recently sailed with Captain Dan, and we had a great time! We sailed up the river... read more

Reviewed July 21, 2017
Jennifer T
Woodbridge, Virginia
Read all 14 reviews
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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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Travelers talk about
“captain dan” (13 reviews)
“hour sail” (2 reviews)
1050 Deep Creek Ave, Arnold, MD 21012-1731
+1 410-349-4360
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Reviews (14)
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1 - 10 of 14 reviews

Reviewed August 10, 2017 via mobile

We had time to tour and relax before the scheduled events of USNA Plebe PPW. The two hours were so relaxing. A beautiful day with family and friends. Thank you Capt Dan for a much needed relaxing afternoon.

Thank dmkoenig4
Daniel T, Owner at Chesapeake Sailing Tours, responded to this reviewResponded August 12, 2017

Donna, Thanks for the kind words, and please come back and see us again when you are back in town!

Reviewed July 21, 2017

Our family of 4 recently sailed with Captain Dan, and we had a great time! We sailed up the river and into the Chesapeake Bay on a 2-hour sail. The boat is clean and well-maintained. Captain Dan was great about letting us do as much...More

Thank Jennifer T
Reviewed September 18, 2016

My son and girlfriend came for a visit and this was a perfect addition to our day in Annapolis. Comfortable boat and just the right amount of time out on the water. My husband got to help out with the sailing and we all really...More

Thank BarbT0m
Reviewed July 11, 2016

Had a great 3 hours of sailing with Captain Dan. Afternoon wind picked up and we were able to head out to the Chesapeake.....lots of fun!!! Highly recommended.

Thank gd2Bhr
Reviewed July 9, 2016

My niece was coming to visit from Kansas and we wanted to show her something different. We booked a trip with Captain Dan and his trimaran, Dragonfly. We had a wonderful time. The weather was great and he was very informative. We were very comfortable...More

Thank drohlwing
Reviewed June 13, 2016

My friends were coming into town for the weekend and I wanted to take them sailing. I called Chesapeake Sailing Tours the morning of and I spoke with Captain Dan and he was able to accommodate my friends and I later that day for a...More

Thank lmac228
Reviewed June 2, 2016

We had Captain Dan take us out for a couple hours during Navy Graduation week. It was a very relaxing and fun trip, weather was great, winds were good, waters were relatively calm. It is a 27-28 foot Dragonfly sailboat. You, and up to 3...More

Thank mcchuck2014
Reviewed August 9, 2015

Captain Dan made the outing most enjoyable. Trimaran was very comfortable and the trip was a lot of fun. Perfect size sailboat for a relaxing time with friends.

Thank andrea g
Reviewed June 9, 2014

We spent 2 hours on the dragonfly sailboat in the Chesapeake, but would have liked to done much more. Captain Dan is a very good sailor and made us comfortable on his boat. It was just my travel companion and myself on the boat, but...More

1  Thank turfclan
Reviewed July 27, 2013

Captain Dan and his Dragonfly sailboat made for a perfect Saturday afternoon in July on the Chesapeake! All-in-all, we could not have asked for a better trip for 3 hours less than an hour from Washington DC and Baltimore. Capt. Dan made it comfortable and...More

1  Thank Keeaden
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