We recently chartered from Sunsail in Annapolis. It was a great experience. The base is excellent, well-equipped and very well-managed by Matthias a delightful French guy. We chartered a 37′ Hunter with built-in AC, a critical feature for cruising the Chesapeake in August. The boat was 10 years old but well-maintained and kitted out with everything you could possibly need including a bloody electric waffle iron and a microwave!
The only problem we had was the engine played-up. Matthias graciously waived the gas fees to make up for it.
That said I give this place 4 out 5.
If you haven’t sailed Chesapeake Bay, I strongly recommend it. It is a beautiful wide bay banked by green countryside. We sailed to St Michael’s for an overnight and stayed at the St Michael’s Marina. St Mike’s has Revolutionary War charm, a some great places to eat and an excellent open-air maritime museum that gives Mystic Seaport a run for its money. St Mike’s Marina is well-run operation but jam-packed full of motor boats ands very expensive.
It’s too bad that the winds on the Chesapeake can be so fluky in the summertime.