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Classic Sail Charters

7040 Bembe Beach Road, Annapolis, MD 21403
571-331-6241
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Ranked #4 of 28 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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27 reviews from our community

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  • English first
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English first
Vienna, Virginia, United States
1 review
5 of 5 stars Reviewed August 12, 2014

Captain Tony made my engagement the most unforgettable night of my life!! He helped my fiance plan a sunset sailing trip, took pics of our entire proposal for us, and even got flowers and champagne for my fiance to give to me after the proposal! He is so friendly, easy going, and welcoming on his boat! I highly recommend his... More

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Northern VA
Senior Contributor
31 reviews 31 reviews
4 attraction reviews
30 helpful votes 30 helpful votes
5 of 5 stars Reviewed August 3, 2014

I booked a private charter with Tony about a week in advance. It was a ladies day out in Annapolis that ended with the sunset cruise for a friend's birthday. Tony was great! He had cheese, crackers, chips, pretzels, and drinks ready for us as soon as we arrived. He gave us the safety briefing, popped in my ipod, and... More

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Virginia
Reviewer
5 reviews 5 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed August 1, 2014

I chartered the sailboat for a 2.5 hour sunset cruise for my boyfriend's birthday. It was a wonderful evening. We felt so welcome on the boat. There was a nice spread of snacks and wine and beer available to us. We kicked off our shoes and sat back on chairs on bow and watched as our captains (we had a... More

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Washington DC, District of Columbia
1 review
5 of 5 stars Reviewed July 23, 2014

Four friends and I toured the Bay on a July afternoon, and we couldn't have been happier with the experience. Tony and Susie started on time, provided us with a nice lunch spread (cheese, crackers, fruit, some other options, wine and beer) and pointed out scenic spots/significant landmarks along the way. We were mostly there to catch up socially (rather... More

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Seattle, Washington
Contributor
17 reviews 17 reviews
4 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
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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
6 helpful votes 6 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
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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
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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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