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. 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!

5. 

   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!

6. 

   Megan

   Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

   Captain McCoy made us feel right at home from the start. He is incredibly friendly and welcoming, and he handled our large group of ladies very well! He is a host and a captain! The boat itself was even better than expected, and Captain McCoy helped us enjoy all the amazing amenities (the speaker, the mounted cameras for group pics, the giant beanbag chairs for lounging on the bow). We will book with him again!