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48
Annapolis
Maryland
119
Washington
District of Columbia
31
Arlington
Virginia
7
Oxon Hill
Maryland
13
Fort Washington
Maryland
165
Potomac River
United States
10
Cape May
New Jersey
10
Wildwood
New Jersey
8
Lake Anna
Virginia
209
Chesapeake Bay
United States
7
Richmond
Virginia
8
Long Beach Island
New Jersey
16
Toms River
New Jersey
11
Brick
New Jersey
17
Brielle
New Jersey
15
Keyport
New Jersey
8
Belmar
New Jersey
8
Middletown
New Jersey

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!

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.
LM
Liz
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!
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.
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!

Erika
38-ft Hunter 376 Sailing Adventure in Annapolis
We had such a great time! The boat was perfect and Alberto and his wife were great hosts. It’s a good sized boat, kid-friendly (they had kids life jackets), and the cabin was spacious with plenty of room to eat.