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Address: 1 Walton Ln, Annapolis, MD 21403-2410
Phone Number: +1 571-331-6241
8:30 am - 8:30 pm
Closed now
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Sun - Sat 8:30 am - 8:30 pm

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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TripAdvisor Reviewer Highlights

Read all 47 reviews
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  • 47
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    Very good
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Professional, customized and FUN!

From booking to the pictures they sent at the end, we had a FANTASTIC time! Captain Suzy went above and beyond to make sure she knew what was important to us and to make it fun... read more

5 of 5 starsReviewed 3 days ago
Dover, New Jersey
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47 Reviews from our TripAdvisor Community

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Showing 47: English reviews
Dover, New Jersey
Level Contributor
3 reviews
5 of 5 stars Reviewed 3 days ago NEW

From booking to the pictures they sent at the end, we had a FANTASTIC time! Captain Suzy went above and beyond to make sure she knew what was important to us and to make it fun for our whole family! She was very patient and encouraging of our kids to even take the helm and steer the boat:)

Thank busymom998
Fairfax, Virginia
Level Contributor
38 reviews
7 attraction reviews
common_n_attraction_reviews_1bd8 15 helpful votes
5 of 5 stars Reviewed 4 days ago NEW

It helped that we had a strong breeze on a very hot day, but Classic Sail Charters did their part to make this an an absolutely wonderful afternoon to celebrate my wife's birthday with our four children. Capts. Tony and Suzy run a great operation. The 42 footer was in great shape and comfortable, with plenty of room for the... More 

Thank too-err-ist
2 reviews
5 of 5 stars Reviewed 2 weeks ago

My fiancé and I had a lovely time on the Sunset Sail with Classic Sail Charters. They were very friendly, professional, and safe. We highly recommend it!

Thank Rachel K
Cumberland, Maryland
1 review
5 of 5 stars Reviewed July 14, 2016

Perfect proposal/sailing experience. Tony and his crew were very safe and professional. Also, Tony did a great job putting his personal touch on our perfect evening. I would HIGHLY recommend his company, very safe and professional. Our experience will be one that we will never forget and we will be chartering with Captain Tony again in the near future!

Thank Sarah G
Level Contributor
14 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 10 helpful votes
5 of 5 stars Reviewed June 27, 2016

My husband surprised me for our 10th anniversary with a sail on the Chesapeake. Captain Tony and his able assistant Michael were wonderful hosts. Tony had provided wine, cheese and fruit, as well as pleasant conversation. The day was beautiful and it was so relaxing being on the water. I would highly recommend this special outing.

Thank Carrie G
1 review
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed June 23, 2016

Tony hosted me and my son and friend for 2 glorious days in May 2016, in celebration of my son's graduation. From the first time I contacted Tony on a clod call he was cordial, polite and accommodating. (I recommend reservations especially for special occasions like mine.) We departed on our first daylong trip, and even without the best winds... More 

1 Thank Jeff K
Cooper City, FL
Level Contributor
12 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed June 15, 2016 via mobile

Captain Tony and his mate, Michael, made sure our family of 5 had a great sail. Tony told us a lot about the area and was very friendly. We would definitely go again! Thanks, Tony, for a great time!

Thank Floridamom208
Timonium, Maryland
1 review
5 of 5 stars Reviewed September 1, 2015

August 28, 2015 - We had an absolutely beautiful night on the Chesapeake Bay celebrating my wife's 50th birthday with four of our closest friends. Capt. Rob and Carol were extremely accommodating, friendly, and very knowledgeable. Carol even took pictures which arrived through email a few days later at no charge. They allowed us to help raise the sails, steer... More 

Thank Craig M
London, United Kingdom
2 reviews
5 of 5 stars Reviewed August 24, 2015

We visited DC in August 2015 from London and wanted a day on Chesapeake Bay. Tony and Suzy were fantastic and showed the four of us (all non-sailors) how to sail. They were very attentive and looked after us extremely well - even down to demonstrating how to get the best out of a crab at a local crab shack... More 

Thank Robert M
London, United Kingdom
Level Contributor
11 reviews
common_n_attraction_reviews_1bd8 9 helpful votes
5 of 5 stars Reviewed August 24, 2015

We went out for a full day with our two teenage boys. It was quite simply one of the best things we have ever done on holiday. We were staying in Washington in August and it was lovely to be able to break up the trip by spending a day on the water. Tony and Suzy are wonderful hosts,really relaxed... More 

Thank Baedeckers

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Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Classic Sail Charters and other visitors
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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?