Great sailboat rentals near Annapolis, Maryland.

Sailing Reviews in Annapolis

1. AP

   Andrea

   38-ft Hunter 376 Sailing Adventure in Annapolis

   This was our crew’s second trip with Capt Alberto and was a second great experience. Capt Alberto shares his passion for sailing and teaching sailing! Capt and Grace are incredibly kind and make a great day spent out on the bay!

2. 

   Lisa

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Thank you so much Captain Alberto & Grace. We had a fabulous time and enjoyed learning about sailing. Thanks for trusting us to help steer and tack the boat. We had so much fun. You are a great teacher. We wish we could have stayed out longer.

3. JS

   Jen

   STARZ -Lagoon 42 Catamaran in Chesapeake Bay

   I highly recommend Chronic Sailing! We did a 4 hour charter out of Annapolis as a bachelorette party. Captain Steve and Sarah were so accommodating and made our time so memorable. We are so appreciative. They made everything so easy- from booking to sailing and making memories with us. The STARZ catamaran boat was incredible! It fit our big group comfortably and gave us a little bit of luxury as we lounged and enjoyed on the bay. Again, this was a great experience for all of us and I would love to use them again!

4. 

   Kasie

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Wonderful Captain and wonderful boat! Plenty of shade above and below deck if the August heat becomes too much. We did the three hour tour, and it was a great half day length. We received a tour of downtown Annapolis and then Captain Alberto opened up the sails and we went on a beautiful ride down the river. It was fun and unique - even for those who have motor boat experience. Sailing is quintessential Annapolis and Captain Alberto was a great host.

5. 

   Bobby

   38-ft Hunter 376 Sailing Adventure in Annapolis

   We went out for an afternoon sail with Capt Alberto and had an amazing time. We were blessed with a beautiful sunny day with perfect wind. Capt Alberto shared interesting stories and taught us a good bit about sailing along the way. Highly recommend!

6. ES

   Emil

   Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

   Capt. Joe gave us a wonderful afternoon! He is friendly, knowledgable, and fun! The boat is perfect for cruising around the Bay. Lots of space to lay out and clean facilities downstairs. An excellent value!