Annapolis, Maryland Boat Rentals & Yacht Charters

Annapolis Reviews

1. 

   Sarah

   $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!

2. 

   Geoffrey

   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.

3. JC

   Janna

   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.

4. AV

   Ariel

   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!

5. DC

   David

   Charter 44' Orana Cruising Catamaran In Deale, Maryland

   Our group of seven spent a fabulous half day with Captain Rob and Mate Dianna. Couldn't have been happier with the whole experience. Communication was quick and easy. On board, they were super friendly and engaging. The vessel itself was spotless and super comfortable as we hung out on the front "trampoline" area, sailing around the Bay. Thanks for such a fun adventure. We are already talking about a future engagement!

6. RD

   Ryan

   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.