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Classic Sail Charters

Closed Now: 8:30 AM - 8:30 PM
Open today: 8:30 AM - 8:30 PM

Classic Sail Charters
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“crackers”(6 reviews)
“yummy snacks”(2 reviews)
About
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.
Closed Now
Hours Today: 8:30 AM - 8:30 PM
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Contact
1 Walton Ln, Annapolis, MD 21403-2410
Website
+1 571-331-6241
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Reviews (98)
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All reviews crackers yummy snacks incredible job beautiful experience beautiful boat great captain amazing afternoon great outing chesapeake bay great pictures weather was perfect in great shape hour tour naval academy suzy engagement helm
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1 - 10 of 98 reviews
Reviewed October 24, 2018

My friends and I are from North Carolina and Florida and Texas! We were so happy with the whole experience of sailing. Captain Clay was incredibly wise and also very entertaining! If we could we would’ve rented it for hours and hours! Definitely will go...More

Review collected in partnership with this attraction
Date of experience: October 2018
Thank Alyssaeramo
Reviewed October 16, 2018

Captain Rook took my husband, our 3 adult sons, and me out for an afternoon sail on a perfect September day. He explained just the right amount, encouraged us to sail the boat to the extent we wanted to, shared a lot of info about...More

Review collected in partnership with this attraction
Date of experience: September 2018
Thank C V
Reviewed October 14, 2018 via mobile

We highly recommend sailing with Captain Tony ! We have booked many trips with him, including a family reunion sailing day this past summer . Our friends and family are always thrilled to be on the boat and are always so impressed by Tony’s hospitality...More

Date of experience: October 2018
Thank Chimme
Tony I, Owner at Classic Sail Charters, responded to this reviewResponded October 23, 2018

You are always welcome! Capt. Tony

Reviewed September 17, 2018

We were looking for a sailing option during our visit and found this to be reasonable cost and the ability to be just our family. It was fabulous and we thoroughly enjoyed ourselves and highly recommend to anyone looking for this kind of outing!

Review collected in partnership with this attraction
Date of experience: September 2018
Thank sodear
Reviewed September 7, 2018

Captain Tony did a great job. The booking was easy, and we received clear instructions. We went as a wedding gift from my father, and a Bay Sail was the perfect relaxing way to spend a 1/2 day of honeymoon! The Licentia was clean, well...More

Review collected in partnership with this attraction
Date of experience: September 2018
Thank radio-c6aqq
Tony I, Owner at Classic Sail Charters, responded to this reviewResponded September 9, 2018

Very happy you you enjoyed your first day of marriage. We wish you a long and happy life together!

Reviewed August 28, 2018

Fabulous time with friends on the Chesapeake Bay The sailboat was beautiful, clean and well maintained. Captain Tony and his First Mate Grace were very congenial and provided a lot of interesting information about sailing and the area. Very interactive. A great way to spend...More

Review collected in partnership with this attraction
Date of experience: August 2018
Thank anitalynnbode
Tony I, Owner at Classic Sail Charters, responded to this reviewResponded August 29, 2018

Thanks Lynn - see you again next year!

Reviewed August 26, 2018

A lovely three hour sail around Chesapeake Bay. I went with my sister and her husband who had done this trip with Tony before and wanted to do another one as they had enjoyed the first time so much. Captain Tony and first officer Grace...More

Date of experience: August 2018
Thank Joannie707
Reviewed August 6, 2018 via mobile

Booked an afternoon tour while visiting D.C. to visit family. 2 adults and 1 teenage boy. Took a 3 hour tour sailing in the Chesapeake Bay. We asked a lot of newbie questions and got lots of great answers. My son drove the boat for...More

Date of experience: August 2018
1  Thank ilct1972
Reviewed August 5, 2018 via mobile

We had a great time out on the water with captain Tony. Such a super fun thing to do!!!! Beautiful boat, great crew-all around great time

Date of experience: August 2018
Thank okijen
Reviewed July 30, 2018 via mobile

Decided to visit Annapolis for our anniversary. We used to own a sailboat until we moved last year, so we decided to book a sailboat. Many choices on the web, but upon further review decided this was our best bet. We were not disappointed with...More

Date of experience: July 2018
Thank Gary S
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Questions & Answers
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Snoozan
August 10, 2018|
AnswerShow all 2 answers
Response from Merle D | Reviewed this property |
I imagine the cost would be the same if you wanted to sit back and relax! As far as weather I imagine it would be nice . We plan on sailing in the Long Island sound in sept and I am told the wind is even better than on aug... More
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Gosto69
July 5, 2018|
AnswerShow all 2 answers
Response from Tony I | Property representative |
Good morning - we are limited to 6 passengers, not including crew, by USCG regulation. Cheers and Fair Winds, Capt. Tony
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