Chesapeake Bay, US Boat Rentals & Yacht Charters

Chesapeake Bay Reviews

1. hm

   hanna

   Cruise the Chesapeake on a Classic 46’ Deadrise – Up to 30 Guests

   Amazing communication and very fun boat. I recommend everyone to book with her!!

2. RP

   Rick

   34' Hunter Cruising Monohull In Rock Hall, Maryland United States

   Great boat and great value. She still sails beautifully and we had some great wind to prove it. A little aged around the edges, but everything that counted was great.

3. FC

   Francesco

   34' Hunter Cruising Monohull In Rock Hall, Maryland United States

   We simply loved our three days sailing excursion of the Chesapeake bay. The boat Icarus is very comfortable to maneuver and to live in for a family of four. The bay has numerous nice coves and spots were to stay for the night. Mr James help has been crucial for maximizing our time and energies on these limited days. Thank you Jiim!

4. MI

   Maria

   34' Hunter Cruising Monohull In Rock Hall, Maryland United States

   One of the best sailing weekends we have ever experienced! The boat is manageable and in great shape! James is a great host, he explained everything when we got there, suggested an amazing route and was there when we got back to make sure everything went well. 100% recommended, we’ll definitely rent it again!

5. 

   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!!

6. 

   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.