The Best Boat Rentals Near Rock Hall

$1100 2hrs| 39ft Regal | 13 Guests | Annapolis

An absolutely fantastic experience from start to finish! The captain was wonderful and the scenery was breathtaking, making for an unforgettable trip out on the water. The boat was spotless, the booking process was a breeze, and everything ran like clockwork — couldn’t recommend it more highly!

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

Icarus is a great boat and very well equipped. The sails and everything else on the vessel are in great shape and the fact it only draws 4' 6" is perfect for the Chesapeake. I spent a week on Icarus and everything worked well. The value of chartering Icarus is undeniable. I plan to charter Icarus again. Icarus has a lot of sail area, so if the winds are strong douse the headsail early.

Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

We had a wonderful time on Captain Bill's boat! We booked a 2-hour charter and it was the perfect quick escape for our family of 6. The crew was friendly and welcoming. The boat had plenty of space to relax. It was a smooth, stress-free experience ideal for families or friends needing a taste of the water.

Luxurious 51’ SeaRay Flybridge Yacht With Twin 600 Hp Cummins Engine

Mike and Norma were absolutely phenomenal! I booked a boat with them for my proposal, and they went above and beyond to make the entire experience unforgettable. From the planning process to the day itself, they were professional, accommodating, and genuinely invested in making everything perfect. Their attention to detail and hospitality helped create a memory that my fiancée and I will cherish forever. I highly recommend booking with them if you're looking for a special and stress-free experience on the water.

38-ft Hunter 376 Sailing Adventure in Annapolis

We had a lovely experience out on the bay. Captain Alberto let my husband steer the boat & put the kiddos to work as well. We were able to play & relax as well while out on the water. Very family credibly experience and lovely to get to know the captain & his wife! Overall 5 stars for a sailing experience on the bay!

Welcome Aboard Optimystic! Create a beautiful memory on the water.

Charles was an outstanding guide. Before the outing (which was a birthday gift for my fiancé) he even offered to pick up a cake so that it could be a surprise. He and his wife made us feel at home right away as if we were out just sailing with friends. It was a gorgeous late afternoon / sunset sail with the option of swimming and cooking on the boat. We didn't rush back. Riding on the bow was so relaxing. He took time explaining sailing tips to my fiancé and let him drive the boat for awhile. Communication was clear. We'd love to book again with Charles and Renee!