Chester, Maryland Boat Rentals

Chester Reviews

1. 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!

2. ET

   Eris

   Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

   This is everything you could want. Great boat and captain. McCoy has everything you need for a great trip. Plenty of space onboard for all your food and drink and all the toys you could want for a fun day on the water. We count thank him enough fro a such great experience and a great price! We will be booking again for sure!

3. 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!

4. GA

   Giselle

   38-ft Hunter 376 Sailing Adventure in Annapolis

   Capt. Alberto and Graciela, the best! We had a great time and enjoyed learning about sailing with them. Everything was as described and much better. You’ll have a great time too! ⛵️☀️🩵

5. QT

   Quang

   Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

   been through a few yacht but Joe is the best host. He makes sure you will have a wonderful trip. And his boat is gorgeous, clean and spacious!

6. WW

   Walter

   Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

   Overall, we had a good experience. We ran into some mechanical issues with the boat and had to cut our trip short. Captain McCoy offered to give me a partial refund and was very apologetic. Things happen sometimes, and we were not upset. We will come back.