I bought my boat
in Charlotte Harbor
on the west coast
of FL, it's pretty nice over there. Came back through Okeechobee, then offshore
to Cape fear from Ft Pierce. Just depends on what you're looking for, but for sure you need some good connectivity. St Simons, GA or Fernandina Beach offer chances to hang out at Cumberland Island etc for your excursions. That's a hop, skip and a jump from you and requires less distance to get there, has warmer weather
and new cruising grounds.
You could spend a few weeks in different places and have your adventure getting to each new location that meets your needs for telecommuting. Charleston, Hilton Head
, St Simons/Bruswick/Jekyll, Fernandina, St Augustine, and on and on. Sounds like a blast. All these places offer all the resources you would need, things like Kettlewell suggested, and fun stuff to do and see along the way. Easy to have a visitor too, not always so in the Bahamas
5 with LTE is smokin -- like 15 MBPS sometimes -- which opens up some more quiet anchorages
. I don't know what you like, but I can be productive as hell out in a secluded anchorage surrounded by marsh with my 4G hotspot. That's where I go for retreat. Might still need a little heat sometimes, but if your lucky, you'll get plenty of days well into the 70's. Way less of a big deal than being across the stream, these destinations are easy to reach from the Chesapeake. I like to sail to SC/GA/FL for the winter then rent a car and come home to the farm. I get to sail there for a few weeks and weekends over the winter, but have to keep the farm going. Your opportunity sounds like a good one, and you should definitely point south somewhere in Oct/Nov. Best of luck, and stay warm, it is getting cold again.