A little advance recon at an unhurried pace and with a clear head can pay big dividends, my friend. This is definitely the voice of experience talking.
My most recent advance recon was a 200 mile round trip ride with wife for company to check out the ramps off Clearwater and Dunedin, FL for the 2014 Florida Get Together. Found Seminole Ramps much to my liking and got familiar with the route there and back through dense urban traffic.
In truth, there was an outstanding Quilt Shop near one of the ramps which interested my wife. Went up on a weekday and wouldn't you know it the darn thing was closed! But she enjoyed the ride and quality time together anyway. I'll have to make another trip up there soon when the Quilt shop is OPEN.
High speed travel to the upper Chesapeake and launch there sounds like a great idea. It will provide more time to cruise and explore the Chesapeake, my cruising grounds for 20 years with 4 sailboats (progressively larger) and finally a liveaboard trawler. Truly, one of the best cruising grounds in all of North America!
Oh well, time to get back to my 17' trailerable Sun Cat, trailerable homemade 12' Selway-Fisher Highlander 12, and trailerable 17' Bayliner Bow Rider w/90HP. Always something to do.