First off, congrats on your excellent taste in boats, the Bristol 32 has always been a favorite of mine, incredibly sweet boats...
Vega and others have nailed it, modestly and simplicity are the greatest virtues if you want to go soon... Luxury and complexity while cruising only apply to those with unlimited budgets... I know many people don't want to hear or accept that, but chances are those are the ones who will get out there later as opposed to sooner, and likely stay out there for a shorter duration, as opposed to a more extended period...
If you've never seen it, you might have a look at John Atkisson's website of his Atlantic Circle on his Bristol 32 KESTREL... I had the great pleasure of meeting John in Beaufort, NC during his return trip, he was a wonderful gentleman. Sadly, he passed away a few years ago, a sober reminder of the value of getting out there sooner, as opposed to later...
S/V Kestrel
The key for me has been to configure my boat for energy self-sufficiency, and living life off the grid indefinitely - it's always a surprise to me how many cruisers out there haven't done that, being either dependent on a regular dose of marina umbilical cords, or lots of engine run time to keep all their systems "charged"... In a place like the islands, a combination of articulating solar and wind should be all you ever need, your boat is too laden with electrical demands if you need more, IMHO... Configure a reliable rainwater collection arrangement, it will pay off in spades...
Couple of excellent reads, THE CRUISING LIFE by Jim Trefethen offers some very good advice, financial and otherwise, for bringing the dream to life... And, Don Casey's SENSIBLE CRUISING: THE THOREAU APPROACH is in my estimation one of the best books EVER written about cruising, at least for people of relatively "ordinary" means...
Yours is a sweet sailing boat, but a good light-air sail inventory that will keep a typically overweight boat laden for cruising moving through the lighter stuff is one of the best investments a cruiser can make.. .For all the focus on storm sails that most people will go years without using, a sail like a Code O will usually pay for itself over time by so often making the difference between sailing, and motoring... Heading south outside can save a ton of money, it's amazing how much some people are blowing by motoring down the Ditch, and then succumbing to the lure of nights in marinas, and dinners ashore... There's always a time and place for that, of course, but one of the things I often hear from first-time Snowbirds by the time they make it to south Florida, is that the trip down wound up costing significantly more than they had budgeted for...
My last few trips south for the winter, I've wound up
saving money over what it would have cost me to simply sit at home, and play on the internet (grin) By turning off the water, heat, internet/cable TV, letting my car insurance expire, and all that other crap that it costs simply to live day to day, I come out ahead by hanging out off the grid for the winter, availing myself of all that "free" energy from the wind and sun... (grin)
Good luck, you've certainly got the boat for it, she would be an awesome boat for the Bahamas, for example...