Hillsmere Shores, Maryland Boat Rentals

Hillsmere Shores Reviews

1. 

   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.

2. 

   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!

3. LP

   Laura

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Captain Alberto and his wife are absolute jewels! We sailed with them a couple of years ago and were excited to have this time with them today. They are friendly, professional and just such a joy to be around. Will be seeing them again soon, for sure!

4. JS

   Jen

   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!

5. DC

   Donte

   New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

   From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!

6. 

   Danylle

   Yamaha SX210 Bowider w/Swim Platform 6 Passengers w/Captain

   Mike and Holly were great hosts! Very nice, knowledgeable of the water and the areas, showed us some great spots, allowed us to be completely relaxed and comfortable. Not to mention, took tons of fun pics of our group! Thank you so much, Mike and Holly. Don’t think, just book! …but not on a date that I want.. lol We will be booking again!! Thank you!