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Page 1 of 1 • 24 listings
53
Annapolis
Maryland
7
Selby-on-the-Bay
Maryland
51
Baltimore
Maryland
116
Washington
District of Columbia
8
Oxon Hill
Maryland
30
Arlington
Virginia
14
Fort Washington
Maryland
165
Potomac River
United States
9
Cape May
New Jersey
9
Wildwood
New Jersey
8
Lake Anna
Virginia
209
Chesapeake Bay
United States
8
Long Beach Island
New Jersey
18
Toms River
New Jersey
7
Richmond
Virginia
12
Brick
New Jersey
18
Brielle
New Jersey
9
Belmar
New Jersey
SN
Sarah
Quick Private Annapolis Harbor Boat Ride - Oceanus 12 VST Inflatable
Stephen is the type of guy who makes the whole experience of boating on the water a once-in-a-lifetime feat. From his warm demeanor to his approach to helping each guest he takes on, to his allowance of people driving his own boat, his guidance along the way makes each and every guest wanting to come back for more. As soon as he met me outside the marina, he steered us on his boat into the waters of Annapolis Harbor, and did not hesitate to explain the landmarks we would be seeing alongside how boating actually works. For a newbie, he guided me on the logistics of how to drive his boat, which is something I thought was very warm and interesting. Stephen is an extremely friendly guy and is willing to do anything it takes to make his guests feel respected, relaxed and willing to know all about “the way of the water”. I learned a lot from him, and was left feeling fulfilled by my visit. I highly recommend Stephen to anyone who wants to do boating on the waters of Annapolis because he is a very knowledgeable and friendly person who always goes the extra mile.

Sarah
$1100 2hrs| 39ft Regal | 12 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!

Lauren
Charter 42' Lagoon Catamaran in Annapolis, MD
We had an amazing day on the bay with Captain Adam! He was super communicative leading up to the trip, providing amazing instruction to make it as easy as possible to get aboard. While on board the vessel was very clean and comfortable and he and his team were knowledgeable about the area. Highly recommend! They’re lovely!
RK
Richard
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Our group of four had a great three days onboard the Icarus. The boat was easy to sail and operate. No problems motoring around in the marinas, steers easy in reverse too. Jim was a great host, very responsive and knowledgeable. Highly recommend his boat to sail the Chesapeake!