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Page 1 of 9 • 196 listings

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.

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!
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.
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.
AM
Aisha
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Captain McCoy did a great job with our charter! He was flexible with our plans as we were figuring out booking and made sure we had tons of toys when out on the water. Would definitely recommend him in Annapolis and beyond!
KK
Kara
We had a fantastic experience with 24 people across two boats! Coordinating a group this size could have easily been complicated, but the team made everything feel seamless. Captain Chip, Captain Todd and Muhammad were all friendly, helpful and easy to communicate with, and they did a great job coordinating both boats so our group could spend the day together on the water. The boats were clean, spacious, and comfortable, and there was plenty of room for everyone to relax and enjoy themselves.We had a beautiful day on the Potomac and would absolutely book with them again for a large group event. One thing I'd recommend for larger groups booking multiple boats is confirming pickup locations in advance. Our boats ended up boarding from two different marinas before meeting up, which wasn't a problem in the end, but it's helpful information to have ahead of time when coordinating a larger group. Overall, we had an amazing experience and would absolutely book again. Highly recommend.