We use cookies to improve your browsing experience.
And dolphins make us happy. Find out more about our cookies policy here.
Page 1 of 1 • 24 listings
Noelle
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
My group and I had an amazing time! If you’re looking to have a great experience make sure to book with Captain McCoy. The boat was very clean. Getting on board was simple and finding the dock was easy. Also enjoyed stopping in the middle of our trip to just enjoy the weather and laying out on the front of the boat. I’d definitely book again!
RH
Roger
Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!
Great vessel. Well maintained. Up to date equipment. Very relaxed.
LW
Lianna
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Captain McCoy was wonderful! Very accommodating and communicative. Our group had a great time!
KC
Kevin
41' Lagoon Catamaran in Maryland
Captain Jess was fantastic! Great experience!
George
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Great value! Excellent sailing gear!! If you are an experienced sailor with at least one other person, you won't find a better value for day or overnight sailing near Annapolis. I will definitely be renting this boat again either with my family for the day or some buddies overnight. Took Icarus on a two night late-October trip from Rock Hall, overnight in Annapolis then St. Michaels with a couple buddies. James made the process VERY easy - very communicative and willing to go the extra mile for our convenience. This Hunter 34 sails really well (especially upwind.) It is set up that one experienced sailor and one other person can easily manage it. Comfort-wise it is probably better dockside on shore power in order to be able to utilize the cabin climate control system and power outlets for charging your phones (bring portable chargers if you won't be on shore power.) Returning the boat into the slip was a little tricky and James offered to be there to "coach us" in but we managed it on our own. The diesel was very reliable and fuel efficient - recommend you listen very carefully to James when he explains how to start it because can be a little tricky (as of Oct 2023.) Recommend you bring a handheld (or phone) GPS because as of Oct 23 the GPS is in the cabin. Bottom line - this is a great value - don't hesitate to book!!
Janessa
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
We had a wonderful experience chartering Jim’s sailboat over Labor Day weekend. Jim was very accommodating, walking through the boat with us and making sure everything was in great shape before we began our charter. We sailed from Rock Hall to Annapolis and back, spending two nights aboard Icarus. His upgrades to the boat really helped make it easier to sail and more comfortable to relax in, and Jim was always readily available if we had any questions. Could not recommend this more highly, and we don’t think there’s a better charter out there for the price in the Chesapeake.