I've been looking at the NOAA ENC charts. And it looks like anything around Deltaville has shallow water to deal with. I will have the wing keel at a depth of something like 4'3" So as long as I can stay in the channels it looks like I should be ok.
I've talked to StingRay point and from there website it sounds like a good place. I was talking about FishingBay Marina as I didn't realize it was separate from the FBYC. I think until I really figure out if I'm in the right spot I'm going to avoid expensive yacht clubs. I saw that StingRay Point has a Yacht Club onsite so it might be fun to join that.
I've been sailing for some time now. Most of our sailing has been on a flood control lake in Iowa. But we've also chartered in the BVi and the Greek Isles. I think that I could make it back from Annapolis to Deltaville but due to relocation and such we've been off boats for a couple years and it's that local that I'm afraid I just don't have.
Stingray Harbour Yacht Club is the largest club in Deltaville outside FBYC as far as I'm aware, but they're a marina based club with no facilities of their own. We were members during our time down there and met a lot of great folks. I definitely understand your point on the commitment to a yacht club. That's why I never joined but you should know about them if you're going to be in the area, especially if you intend to race you will want to get to know some folks over there. SHYC, is not a racing club.
As far as D'ville having shallow water, from what I've seen, it's no worse than anywhere else on the Chesapeake and it has a plethora of qualities that endeared the area to my heart. 1. If it's blowing stink on the bay, you can turn left and go up the Rappahannock from Broad Creek, or right to sail in the Piankatank rivers. 2. There are so many good anchorages within a few hours you almost always have the option of being alone or at least not feel crowded. 3. There are very few power boats in the area, most are work boats, and they all seem far more courteous than powerboaters in my current area, even the SeaRay's. 4. Deltaville is about at the widest spot on the bay and crossing over to Onancock, you'll be out of site of land while still in relatively safe protected water.
Here's a short list of places you'll want to visit:
Off the Rappahannock River
-Corratoman River - We loved the West Branch but the East Branch has its attractons also
-Urbanna - Don't miss the Oyster Festival
North of Windmill Point
Great Wicomico - The anchorage behind Sandy Point is one of those post card places
-Fishing Bay - One of those Must see anchorages on the Chesapeake
BTW, with your level of experience I think you could easily handle the delivery and it would give you a bit of that local experience over the most popular sections of the bay. A trip down south from Deltaville and you,d be comfortable taking your boat just about anywhere on the bay since you'd have at least been by most places before.