Day sailing the Chesapeak

May 4, 2013
4
Hunter 25.5 Nashville, TN
I am a relatively new sailor and am looking to try the Chesapeak Bay. Ideally would like a great place to use as a base for day sailing and a place the wife would enjoy as well. Any help would be great.
 
Dec 14, 2003
75
Hunter H37C, H23 Annapolis MD
Well the Annapolis area is good sailing with several charter companies. Suggest you pick up a copy of the Gunkholers Guide to the Cheaspeake and pick out one of the suggested trips that fits your schedual then go for it when the warm weather returns. Lots of downtown shopping for the wife in Nappytown as well (and a few good Bars for you to wait in while she shops). Enjoy
 
Feb 19, 2008
46
Catalina 320 Pasadena, MD
The Chessie is a great place to sail, if you're trailer sailing you might want to check out marinas and parks for a base. We used a state park on the Eastern Shore of Virginia called Kipopeke (check spelling) when we had our Hobie 16 although we had to pull it up onto the trailer every night...they really aren't too boat friendly but we made it work and had a great time. Personally we avoid Annapolis, it's too crowded for us but that's just a matter of taste and opinion.
 
Jan 19, 2010
12,565
Hobie 16 & Rhodes 22 Skeeter Charleston
I can second Kiptopeke State Park. I've sailed out of there also. There is a nice Day's Inn across the road from the park or you can tent camp. They let you park your boat on the trailer for a small fee and leave it at the park. The park has two WWI battle ships that have been sunk to make an artificial break water so the water just in front of the ramp is well protected. There are some strong currents just outside the breakwater so make sure your O.B. is working well.