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“If you really want to feel like you've experienced Annapolis, this is it!” 5 of 5 stars
Review of Classic Sail Charters

Classic Sail Charters
7040 Bembe Beach Road, Annapolis, MD 21403
571-331-6241
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Ranked #4 of 38 Activities in Annapolis
Type: Boat Tours, Adventure
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Owner description: Enjoy your private sail charter with captain (up to 6 people) for a half day, full day, or sunset cruise in the Chesapeake Bay. Sail under the Bay Bridge, tour the light houses, or sip wine with a special someone as the sun sets over Annapolis.
Senior Contributor
33 reviews 33 reviews
10 attraction reviews
Reviews in 16 cities Reviews in 16 cities
36 helpful votes 36 helpful votes
“If you really want to feel like you've experienced Annapolis, this is it!”
5 of 5 stars Reviewed July 7, 2013

Tony did an awesome job catering the cruise to our ability levels. I had sailed before, and my two other friends had minimal experience he let us sail the boat, haul and rig the sails. His rate includes adult refreshments and a great mix of Jimmy, Classic Rock and Cool Tunes, or you can plug in your own iphone/ipod. He was friendly and allowed us to experience sailing on our own terms. Would definitelyl rebook or book an all-day or even overnight in the future. This is a bit more pricey and keeps away the "Woodwind" tourists.

Visited July 2013
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28 reviews from our community

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  • English first
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English first
1 review
“Amazing Anniversary Experience”
5 of 5 stars Reviewed May 14, 2013

My husband and I recently decided to treat ourselves to a sailing trip for our 1st Anniversary. Not having any experience sailing, we were both a bit nervous going onto the boat but were quickly relieved of worries seeing the large clean ship and an assuring captain. It was great to have the boat all to ourselves and leave the work up to Tony and his crew member. Definitely a romantic experience at sunset.
After our tour ended, both my husband decided we need to come back again, perhaps with friends.

Visited May 2013
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New Bern, North Carolina
1 review
“BVI rocks with Classic Sail Charters”
5 of 5 stars Reviewed April 8, 2013

Classic Sail Charters helped me explore the British Virgin Islands. What an adventure! Captain Tony showed me all the sights to be seen. . . Jost Van Dyke, Tortola, St John, St Thomas. A vacation I will never forget. I highly recommend Classic Sail Charters for your next excursion.

Visited January 2013
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Christiansted, St. Croix
1 review
“Experiencing the Caribbean like a local”
5 of 5 stars Reviewed April 4, 2013

The best part of my Caribbean vacation in the U.S. Virgin Islands was sailing aboard Licentia with Tony! The captain led me to a quiet anchorage at St. John where we went ashore via dinghy to explore. I found coconuts near the towering palm trees, snorkeled in the clear blue water, and sunbathed on the white sandy beach. It was paradise!! I especially enjoyed that their weren't any other tourists around in our spot; I wanted to feel a unique experience. After a satisfying immersion into the tropical scenery, we headed back to have lunch and rum drinks on the sailboat. What a perfect day! The photos I have to share with my family and friends can't fully explain how much I appreciated the reality of it all. I will absolutely sail again with Classic Sail Charters and highly recommend this adventure.

Visited January 2013
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Washington DC, District of Columbia
2 reviews
“Could not have asked for a better proposal....”
5 of 5 stars Reviewed September 8, 2012

Gentleman, if you are planning on proposing and being outside of "the box" I recommend letting Classic Sail Charters set the stage. My boyfriend (now fiance) planned a sunset sail for his proposal and I could not of asked for a more romantic and scenic setting.
We were immediately greeted by Captain Tony's deck-hand Steve as we approached the dock. We boarded the Licentia and were guided into the cabin where feta stuffed olives, fresh creamy brie with crackers and grapes and a chilled bottle of the most delightful Pinot Grigio were waiting for our arrival.
Captain Tony gauged his conversation and entertainment perfectly. I never would have thought that anyone else was on the Licentia but my boyfriend and I. The boat was something to write home about with its beauty. Captain Tony navigated the waters with such grace.

When it was time for the 'proposal' Captain Tony laid the foundation by playing a song at the request of my boyfriend which they orchestrated a cue behind the scenes when the sail was planned. Captain Tony never lead on that a proposal was in tow. He did an incredible job mapping out the placement of the boat and they were sure to allow the proposal to be a private one. Following the successful proposal, Captain Tony was Johnny on the spot (that was obviously my fiance's adjective) with two glasses of wine and a camera to capture the memory of those moments.

I HIGHLY recommend Classic Sail Charters....it truly was the perfect setting.

Visited August 2012
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