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Page 1 of 1 • 24 listings
51
Annapolis
Maryland
7
Selby-on-the-Bay
Maryland
48
Baltimore
Maryland
124
Washington
District of Columbia
7
Oxon Hill
Maryland
33
Arlington
Virginia
13
Fort Washington
Maryland
165
Potomac River
United States
10
Cape May
New Jersey
9
Wildwood
New Jersey
8
Lake Anna
Virginia
209
Chesapeake Bay
United States
8
Long Beach Island
New Jersey
16
Toms River
New Jersey
7
Richmond
Virginia
10
Brick
New Jersey
16
Brielle
New Jersey
8
Belmar
New Jersey
KG
Kathleen
Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch
Highly highly recommend booking with Stephen! We had friends coming to visit from out of town and we had the most wonderful charter. Stephen was an excellent captain and very kind host. The boat itself is very cool, with plenty of room to hang on the bow (and a clean bathroom!). Can’t say enough about what a great time we had!!
RB
Richard
Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch
Not sure I can say enough about how absolutely incredible our experience was with Steve. Boat was perfect. Communication was perfect. But the experience was incredible! He took my wife, two sons and I out to the Wednesday night races in Annapolis, and we got to engage right into the races, feel the speed of the boats, see the tight turns, and it’s an experience my sons will not forget. Can’t recommend highly enough.
LF
Linda
Exclusive Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch
Stephen was wonderful! A few days before our sailing trip, the weather forecast looked questionable, but he stayed in touch the entire time, offering to start earlier or even reschedule for a different day if needed. He was incredibly flexible and genuinely wanted to make sure we had the best possible experience. Thanks to his communication and commitment, we had a fantastic trip. I highly recommend sailing with Stephen!
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
$1250 2hrs| 12 Guests | 39ft Regal
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.