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Classic Sail Charters

7040 Bembe Beach Road, Annapolis, MD 21403
571-331-6241
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Ranked #5 of 26 activities in Annapolis
Type: Boat Tours
Owner description: 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... more » Owner description: 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. « less
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23 reviews from our community

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English first
Seattle, Washington
Contributor
16 reviews 16 reviews
3 attraction reviews
15 helpful votes 15 helpful votes
5 of 5 stars Reviewed June 27, 2014

While attending a wedding at the Naval Academy, we chartered Captain Tony's 42' Catalina for an afternoon and sailed into the Bay. Wonderful host, fine Captain skills. Watching him maneuver the lines, sails and the cranks was a show in itself. A sudden storm appeared and effortlessly, he sailed us safely back to the dock. We celebrated with a lovely... More

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Richmond, Virginia
Reviewer
4 reviews 4 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed June 12, 2014 via mobile

I booked a sunset tour with Tony to celebrate by sweetheart's birthday last weekend. When I mentioned that I was traveling in from out of town, Tony suggested the bed and boat option. For an additional $150 we could sleep on the boat and enjoy the beautiful water view and quaint neighborhood of the Marina. This was such a great... More

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Miami, Florida
1 review
5 of 5 stars Reviewed October 8, 2013

There is nothing like a relaxing day aboard Capitan Tony Ireland’s world class 42’Catalina. It could not have been nicer and he spares no effort to insure everyone enjoys the outing. The day was just the right mix of real sailing combined with comfort on board. Don’t miss this opportunity to experience the sailing capital of the eastern seaboard off... More

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Lancaster, Pennsylvania
Senior Contributor
25 reviews 25 reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed October 6, 2013 via mobile

Captain Tony showed us a spectacular day sailing. We booked a full day to include lunch at a wonderful marina stop. Let this captian and his 42' Catalina take your stress away.

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Washington DC, District of Columbia
Reviewer
3 reviews 3 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed September 3, 2013

If you're looking for a great way to decompress and experience the Chesapeake up close, book a sail with Captain Tony Ireland. Our family's Labor Day sail with him felt like three days away from the busy-ness of DC - a perfect end-of-summer mini vacation. Tony was a gracious host, putting out snacks and drinks throughout the day, answering our... More

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Holbrook PA
Reviewer
4 reviews 4 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed August 10, 2013

We booked a weekend sail as a family vacation for adult family and spouses. It was an excellent experience with something for everyone in our party, from just relaxing on deck to taking the helm to learning something of the history of the Chesapeake...even wifi aboard for the teenager in our party. Captain Tony also helped us choose a destination... More

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1 review
5 of 5 stars Reviewed August 7, 2013

I booked the sunset sail as a surprise for our 24th Anniversary. My husband wants to learn to sail and it was a fun way to see what its all about. Tony let us help him sail as much as we wanted and taught us a lot. It was a fun, relaxing, beautiful evening. The wind and weather were perfect... More

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Bel Air, Maryland
1 review
5 of 5 stars Reviewed August 5, 2013 via mobile

I took my girlfriend out with Captain Tony for a sunset sail. We had enough wind to sail for about at hour then we had to go motor back to the harbor. I popped the question at sunset right outside downtown Annapolis at sunset. The experience couldn't have been any better. The crew brought is champagne to celebrate and took... More

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Charlottesville, Virginia, United States
1 review
5 of 5 stars Reviewed July 22, 2013

A friend and I recently booked an afternoon sail with Capt. Tony and first mate Susie. We had SUCH a wonderful time. The sail itself was relaxing and lovely, and it was a real treat to see Annapolis from the water for the first time. Tony and Susie were a pleasure to sail with... they left us alone to the... More

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Senior Contributor
33 reviews 33 reviews
10 attraction reviews
35 helpful votes 35 helpful votes
5 of 5 stars Reviewed July 7, 2013

Tony did an awesome job catering the cruise to our ability levels. I had sailed before, and my two other friends had minimal experience he let us sail the boat, haul and rig the sails. His rate includes adult refreshments and a great mix of Jimmy, Classic Rock and Cool Tunes, or you can plug in your own iphone/ipod. He... More

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