If you are anything like me, you will love traveling south on the ICW. Everyday is different, the scenery changes constantly, and you'll always be close to "civilization" if you need it. Anchorages abound and you'll occasionally run across free dockage (Elizabeth City, Southport, Myrtle Beach). This will also be a great shakedown cruise for you and your vessel.
Like me, being a 60 year-old singlehander offers its own set of challenges. I've been singlehanding my Hunter 30 off and on for the last 7 years and two things most concern me while singlehanding.
Anchoring. I've been anchoring out almost forever and I've got a pretty good routine established. What I don't like is having to go out on deck to manually raise the anchor in rough conditions. I would love to have a windlass to help do the heavy lifting, quickly. Repeated trips to and from the cockpit to move the boat forward, is not the best situation.
Deck work. Anytime you leave the safety of the cockpit, you put yourself at risk. Whether it's falling over the side or taking a nasty fall, singlehanding requires much more concentration on your part. For this reason, when I'm alone I always wear my inflatable life jacket and clip my harness to the boat, even in the cockpit.
Another thing, assume for a minute its a nice quiet day, you've got the anchorage all to yourself, and you fall overboard. With your stern ladder tied in place and your dinghy still strapped to the deck, how do you climb back aboard? For this reason I secure my stern ladder with bungee cord so I can pull it down if necessary. The point I'm trying to make is that without a partner, you have to stay focused. As you think about scenarios like this, you will develop a series of behaviors that will help keep you safe.
Finally, crossing to the Bahamas is no big deal, provided the weather conditions are right and you invest in good charts and a gps unit. For me, this was actually my first real overnight sail out of the sight of land. As a singlehander you will give repeated thanks to your autopilot. I suggest you buy an egg timer so you can catnap for 10 minute intervals during your crossing. I was surprised by how many things there are to run into in the middle of the Gulf Stream, especially when you fall asleep.
My last advice is to take your time, wait for the right weather windows, and leave your schedule book at home.
You're going to have a blast!!
P.S. I can only hope that your Admiral enjoys the cruising life more than mine (now ex-Admiral) did. Cruising alone wears thin after a while.