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Address: 1 Walton Ln, Annapolis, MD 21403-2410
Phone Number:
+1 571-331-6241
08:30 - 20:30
Closed now
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Sun - Sat 08:30 - 20:30

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 54 reviews
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Bachlorete Party done right!

My lovely Bestie (the bride to be) and all 4 of us awesome bridesmaids sailed with Captain Tony and Captain (oh no please forgive me I am drawing a blank on the second Captains... read more

Reviewed 3 days ago
Silver Spring, Maryland
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54 Reviews from our TripAdvisor Community

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Showing 54: English reviews
Silver Spring, Maryland
1 review
Reviewed 3 days ago NEW

My lovely Bestie (the bride to be) and all 4 of us awesome bridesmaids sailed with Captain Tony and Captain (oh no please forgive me I am drawing a blank on the second Captains name). The Chesapeake was perfect that day. Great breeze and not too hot, not too cold. The boat was beautiful and the Hull was cozy and... More 

Thank skbailey2017
1 review
Reviewed 6 days ago NEW

We hired them for a nice day on the bay with our bride to be. The crew of 2 was professional yet down to earth. The boat was in tip top shape and clean. The price included snacks. We brought our own yet were very surprised at how high quality the food and drinks that were provided. High ended cheese,... More 

Thank Laura W
Level Contributor
4 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 9 April 2017 via mobile

A sail was tranquil and the sunset was breathtaking. See you next year! If you like to sail. Contact Classic Sail.

Thank Kenneth W
1 review
Reviewed 14 March 2017

This was a truly magical experience. Nothing beats going to an island using nothing but wind power, spend the night and see the stars all night, go for a swim in the morning with some coffee and then be surprised by the unexpected visit of a playful dolphin. Tony makes all of the above even better by sharing stories, explaining... More 

Thank Daniel R
Holland, Pennsylvania
1 review
Reviewed 19 January 2017

We decided to take a last minute excursion to Annapolis for Easter weekend 2015, which was in late March that year. And yes, my review says March 2016, that's how late I was in providing one. While looking for things to do I decided to lookup charters and came across Captain Tony. I arranged for a sunset charter for my... More 

Thank A_Sajeski
Bluffton, South Carolina
Level Contributor
6 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 18 September 2016

Let me begin by saying that I spend every birthday on the water. This year it was Annapolis with an afternoon celebration for me and a dear friend on a beautiful day midway between our two milestone days. It was a fabulous afternoon! For folks who like the particulars, this is a professional and friendly organization that goes out of... More 

Thank V R
Montclair, New Jersey
1 review
Reviewed 6 September 2016

Captain Tony was a great host and made sure out teen and tween had a great day. Fantastic weather & setting made this a real family adventure.

Thank marks752016
Dover, New Jersey
Level Contributor
3 reviews
Reviewed 22 August 2016

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
53 reviews
13 attraction reviews
common_n_attraction_reviews_1bd8 19 helpful votes
Reviewed 22 August 2016

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
1 review
Reviewed 9 August 2016

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

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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?