Testimonials

  Great way to experience Annapolis! – Captain Tony gave us a fantastic experience! He communicated well with us so we knew what to expect. He provided a brief but thorough safety overview, and then, we… read more five friends relaxed in the sun and took in the beautiful fresh air, sunshine, and sights around us. We don’t live far and will plan more excursions with Classic Sail Charters. What a great way to spend an afternoon!

  Perfect experience  – I wanted a day out on the water and so I made a few phone calls. Captain Tony was very responsive, followed up w me and we made the schedule… read more work. He was great at explaining things and just a nice, easy to get along with guy. The boat was very well maintained! Can’t wait to go back!

  11/10 Recommend!!!  – Had a great mid day charter (2-5 pm) with Captain Tony. He was an excellent tour guide and sails man. Made us feel comfortable and safe. We learned some facts… read more about sailing. Beautiful boat, weather, and views. Very relaxing. 11/10 recommend doing a charter with Captain Tony!

  Exciting Birthday Sail  – Under very challenging conditions, Capt. Tony delivered both an exciting yet safe adventure. He clearly has a mastery of sailing and was very personable as well. HIGHLY recommend using… read more Classic Sail Charters – we will again!

  Great Sail!  – A wonderful experience. Great sail had by all. Capt. Tony did a fantastic job of guiding us along the Chesapeake Bay and Bridge.

  Captain Tony Ireland is a great sailor, teacher, and host  – We were 4 adults sailing in the morning on the Chesapeake with Classic Sail Charters. Full range of partipants from novice to experienced sailors. Tony explains what he… read more is doing, shows you the key sights on shore, and makes everyone feel at home. The boat is a 42 foot Catalina– handles well, very clean, and plenty of snacks on hand. Tony and his assistant are quite professional, but low-key and friendly. I highly recommend this experience.