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Address: 1 Walton Ln, Annapolis, MD 21403-2410
Phone Number: +1 571-331-6241
Website
Today
8:30 am - 8:30 pm
Open now
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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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TripAdvisor Reviewer Highlights

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Not to be missed

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... read more

5 of 5 starsReviewed 1 week ago
V R
,
Bluffton, South Carolina
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49 Reviews from our TripAdvisor Community

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Showing 49: English reviews
Bluffton, South Carolina
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 1 week ago

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 

Helpful?
Thank V R
Montclair, New Jersey
1 review
5 of 5 stars Reviewed 3 weeks ago

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.

Helpful?
Thank marks752016
Dover, New Jersey
Level Contributor
3 reviews
5 of 5 stars Reviewed August 22, 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:)

Helpful?
Thank busymom998
Fairfax, Virginia
Level Contributor
38 reviews
7 attraction reviews
common_n_attraction_reviews_1bd8 15 helpful votes
5 of 5 stars Reviewed August 21, 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 

Helpful?
Thank too-err-ist
2 reviews
5 of 5 stars Reviewed August 9, 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!

Helpful?
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!

Helpful?
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.

Helpful?
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 

Helpful?
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!

Helpful?
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 

Helpful?
Thank Craig M

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Questions & Answers

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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?