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Address: 1 Walton Lane, Annapolis, MD 21403
Phone Number: +1 571-331-6241
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8:30 am - 8:30 pm
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Hours:
Sun - Sat 8:30 am - 8:30 pm
Description: Enjoy your private sail charter with captain (up to 6 people) for a half...
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.
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Fabulous sail

I chose Classic Sail Charters for my silver jubilee wedding anniversary and captain Suzy and Tony made it a wonderful morning sail that lasted for hours. We did not even realize... read more

5 of 5 starsReviewed June 2, 2015
Sharath K
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31 Reviews from our TripAdvisor Community

Date | Rating
  • English first
  • Any
English first
1 review
5 of 5 stars Reviewed June 2, 2015 NEW

I chose Classic Sail Charters for my silver jubilee wedding anniversary and captain Suzy and Tony made it a wonderful morning sail that lasted for hours. We did not even realize that it was noon when we got back to shore. Captain Suzy and Tony are exceptional with abundance of knowledge about sailing. The boat was absolutely amazing, clean, spacious... More 

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Reviewer
3 reviews 3 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed May 28, 2015 NEW

Took my fiance out on her first sailboat and we had a wonderful time. The crew was very knowledgeable, friendly and helpful. We took the sunset tour, and it was very pleasant. Would recommend to anyone looking to spend time together or even for a family outing.

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Senior Contributor
37 reviews 37 reviews
12 attraction reviews
38 helpful votes 38 helpful votes
5 of 5 stars Reviewed May 25, 2015

We had amazing wind, perfect weather, great company! We go about once a year with Capt. Tony and Suzy. Everytime is a blast. If you want someone to do all the work they are there. If you like to sail they let you run the boat. Almost makes you not want to buy a boat of your own! Must do... More 

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1 review
5 of 5 stars Reviewed May 18, 2015

I hired Classic Sail Charters for a surprise sunset cruise as a memorable setting for a marriage proposal and couldn't have been happier with the experience. My girlfriend (now fiancée... the proposal went well) loved the experience, and Captain Tony was the perfect host for our few hours on the Bay. He supplied us with the necessary provisions of wine,... More 

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maryland
1 review
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed August 29, 2014

My wife and I recently had the great pleasure of spending a glorious afternoon with Captain Tony and Suzy aboard the Liicentia. From the moment that they welcomed my wife and I on board, we were treated as friends who had been invited to spend a day on the water sailing on a beautiful boat. The drinks and appetizers that... More 

Was this review helpful? Yes 2
Vienna, Virginia, United States
1 review
5 of 5 stars Reviewed August 12, 2014

Captain Tony made my engagement the most unforgettable night of my life!! He helped my fiance plan a sunset sailing trip, took pics of our entire proposal for us, and even got flowers and champagne for my fiance to give to me after the proposal! He is so friendly, easy going, and welcoming on his boat! I highly recommend his... More 

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Northern VA
Senior Contributor
43 reviews 43 reviews
7 attraction reviews
31 helpful votes 31 helpful votes
5 of 5 stars Reviewed August 3, 2014

I booked a private charter with Tony about a week in advance. It was a ladies day out in Annapolis that ended with the sunset cruise for a friend's birthday. Tony was great! He had cheese, crackers, chips, pretzels, and drinks ready for us as soon as we arrived. He gave us the safety briefing, popped in my ipod, and... More 

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Virginia
Contributor
13 reviews 13 reviews
11 helpful votes 11 helpful votes
5 of 5 stars Reviewed August 1, 2014

I chartered the sailboat for a 2.5 hour sunset cruise for my boyfriend's birthday. It was a wonderful evening. We felt so welcome on the boat. There was a nice spread of snacks and wine and beer available to us. We kicked off our shoes and sat back on chairs on bow and watched as our captains (we had a... More 

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Washington DC, District of Columbia
1 review
5 of 5 stars Reviewed July 23, 2014

Four friends and I toured the Bay on a July afternoon, and we couldn't have been happier with the experience. Tony and Susie started on time, provided us with a nice lunch spread (cheese, crackers, fruit, some other options, wine and beer) and pointed out scenic spots/significant landmarks along the way. We were mostly there to catch up socially (rather... More 

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Seattle, Washington
Contributor
19 reviews 19 reviews
4 attraction reviews
16 helpful votes 16 helpful votes
5 of 5 stars Reviewed June 27, 2014

While attending a wedding at the Naval Academy, we chartered Captain Tony's 42' Catalina for an afternoon and sailed into the Bay. Wonderful host, fine Captain skills. Watching him maneuver the lines, sails and the cranks was a show in itself. A sudden storm appeared and effortlessly, he sailed us safely back to the dock. We celebrated with a lovely... 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?