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Classic Sail Charters

Open Now: 8:30 AM - 8:30 PM
Open today: 8:30 AM - 8:30 PM
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Review Highlights
Great outing!

We were looking for a sailing option during our visit and found this to be reasonable cost and the... read more

Review collected in partnership with this attraction

Reviewed yesterday
sodear
,
Kansas City, Missouri
Relaxing and fun

Captain Tony did a great job. The booking was easy, and we received clear instructions. We went... read more

Review collected in partnership with this attraction

Reviewed 1 week ago
radio-c6aqq
,
Baltimore, Maryland
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“yummy snacks”(2 reviews)
“wine beer”(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.
Open 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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Reviewed yesterday

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
Thank sodear
Reviewed 1 week ago

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
Thank radio-c6aqq
Tony I, Owner at Classic Sail Charters, responded to this reviewResponded 1 week ago

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

Reviewed 3 weeks ago

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
Thank anitalynnbode
Tony I, Owner at Classic Sail Charters, responded to this reviewResponded 2 weeks ago

Thanks Lynn - see you again next year!

Reviewed 3 weeks ago

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

Thank Joannie707
Reviewed 7 August 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

1  Thank ilct1972
Reviewed 5 August 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

Thank okijen
Reviewed 30 July 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

Thank Gary S
Reviewed 30 July 2018

When I went searching for sail options in Annapolis I wasn't sure what I was looking for but from my first visit to the Classic Sail Charters website I knew I had found it. The pricing was easy to follow and the size of the...More

Review collected in partnership with this attraction
Thank brenthayhurst
Reviewed 28 July 2018

I booked this trip for my staff as an after-tax season treat. We had to cancel due to weather and finally went last night. Captain Tony had snacks waiting for us as well as wine, beer, and water. I had been sailing once and found...More

Thank Patty M
Reviewed 19 July 2018

Wonderful day from start to finish, easy to arrange, very knowledgable and easy going. A pod of dolphins seen north of the Bay Bridge was an added bonus. Will boo again and highly recommend

Thank Henryq
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Questions & Answers
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Snoozan
11 August 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
6 July 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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