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Address: 1050 Deep Creek Ave, Arnold, MD 21012-1731
Phone Number:
+1 410-349-4360

We are a charter sailing business in the Annapolis Md.and Chesapeake Bay...

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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Wonderful sailing experience

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... read more

5 of 5 bubblesReviewed 18 September 2016
Sheboygan, Wisconsin
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12 Reviews from our TripAdvisor Community

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Showing 12: English reviews
Sheboygan, Wisconsin
Level Contributor
65 reviews
24 attraction reviews
common_n_attraction_reviews_1bd8 20 helpful votes
5 of 5 bubbles Reviewed 18 September 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 enjoyed our time on the boat. Thanks Captain Dan, you are a wonderful sailing host.

Thank BarbT0m
Baltimore, Maryland
1 review
5 of 5 bubbles Reviewed 11 July 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
Nottingham, Maryland
Level Contributor
24 reviews
12 attraction reviews
common_n_attraction_reviews_1bd8 5 helpful votes
5 of 5 bubbles Reviewed 9 July 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 and had a very pleasant trip. My son was able to help with the steering... More 

Thank drohlwing
Level Contributor
3 reviews
5 of 5 bubbles Reviewed 13 June 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 2 hour sail. We had a great time sailing on the Magothy River! He was... More 

Thank lmac228
Atlanta, Georgia
Level Contributor
126 reviews
29 attraction reviews
common_n_attraction_reviews_1bd8 82 helpful votes
5 of 5 bubbles Reviewed 2 June 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 others can sail with him. You can be active and sail the boat or just... More 

Thank mcchuck2014
Ellicott City, Maryland
1 review
5 of 5 bubbles Reviewed 9 August 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
Little Rock, Arkansas
Level Contributor
26 reviews
common_n_attraction_reviews_1bd8 23 helpful votes
5 of 5 bubbles Reviewed 9 June 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 he can take up to 4 comfortable. A very fast boat and I would recommend... More 

1 Thank turfclan
Arlington, Virginia
Level Contributor
65 reviews
19 attraction reviews
common_n_attraction_reviews_1bd8 17 helpful votes
5 of 5 bubbles Reviewed 27 July 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 fun. Best of all, it was just the three of us! My wife had never... More 

1 Thank Keeaden
Baltimore, Maryland
Level Contributor
4 reviews
5 of 5 bubbles Reviewed 14 September 2012

My friends and I had great time this week with Captain Dan on his Dragonfly. We tried other sailing tour before, however did not feel too much fun when with a large group of tourists. A small private group tour with a very experienced and friendly captain is so much better. This tour is tailored to our needs and requests.... More 

Silver Spring, Maryland, United States
1 review
5 of 5 bubbles Reviewed 30 July 2012

We had a great trip this weekend on Dragonfly with Captain Dan. He let us sail when we wanted, or just relax and enjoy the experience. We had a nice breeze which kept us cool, and powered the trimaran at a nice clip. We had fun overtaking every other sailboat that was out there! If you enjoy sailing already, or... More 

Thank Graham9001
Daniel T, Owner at Chesapeake Sailing Tours, responded to this review

Thanks Grahm for the great review! Thanks for posting on our "Chesapeake Sailing Tours" Facebook page as well! I hope you had a great birthday, and enjoyed the sail as much as I did. You have a great family, and I hope you guys come back to Annapolis for more sailing! More 

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?