I've been reading about Florida issues like these for years, and signed a few petitions supporting anchoring, even though I never sail there. I have little interest in that.
My suggestion? Do what I do. I live in
New England. I sail to
Bermuda, and follow I 65 South to St Thomas. Or you might want to pick a point farther east so you can then sail downwind through the islands. Lots of places to anchor, and on return you can island hop, skirt
Cuba and
draft permitting, hit the Bahamas and then time it with the
weather for a fast return with a
Gulf Stream 4
knot assist. Or you can return straight north via
Bermuda which is what I do.
Some people are too timid to go
offshore. If you are, try
crewing a few times first. I crewed a few times and then skippered myself more times than I could count. A four man crew makes for easy watch keeping--three 2 hour watches 4.5 days to Bermuda, 5.5 to St Thomas. I aim for the west side Jost as the water is deep and free of
reefs.
ICW? Never done it. Don't want to have to be alert for every buoy. Yuck! Instead of a month to move north and south--motoring all day, you can be sailing
offshore can be done in eleven days, easy lovely sailing. Stop for a Cuban cigar in Bermuda at the smoke shop. Leave New
England on a north
wind if heading south in November and you have three days of cold instead of two, but a nicer
passage.
To provision in the islands. Walmart in Fajardo in
Puerto Rico is a good location. Pay for a slip at the marina for a day and Uber over to Walmart with an empty ice chest. Ask the driver to wait and offer to pay him cash directly. Fill up with the maximum provisions on ice, and
head back. My only caution would be to not trust anyone there. Ive been scammed a few times.
Provisioning elsewhere in the Caribbean is a nightmare, or super expensive IMO.
There are many places in the Northern Caribbean that will do your
laundry if you need that. Or you can do it yourself if you like.
After re-provisioning at Walmart, sailing upwind from PR to the USVI when finished will take a bit longer, but it is lovely sailing. I love Vieques, I could hang there for the whole
winter. Don't trust the free moorings in Esperanza, and the grassy bottom is poor holding--Ensenada Sun Bay is one of my favorite spots. It is a lovely Mateus bottle shaped harbor with 14-21'
depth and a shelf around the edge that quickly drops below 7'. One of the nicest harbors anywhere--and no one uses it. You can walk into town and at night listen to the horses running free.
I find that if I do anchor there people follow me in. Timid folk follow the leaders. Most people want to be close to the town. Not my style. I avoid those places yet everyone else seems to want to have the closest
mooring to shore. The free moorings in Esperanza are pathetic and the grassy bottom makes anchoring there a literal drag. Locals will try to scam you for
fees claiming to own them. If you do grab one for an hour while people go ashore, leave someone behind and definitely don't trust those moorings unless you dive on it. If it's empty and close to shore--it probably the worst one there.
You can leisurely sail east along the south shore and overnight at the last harbor,
Bahia Salina del Sur--I call it Unexploded Ordinance Bay, its' the best departure point heading east. Or you can hit
Culebra once you clear the eastern point. Spend a
day sailing up to St Thomas and then on to St John on the weekends for live
music. I could easily spend the whole winter in that area. The water is clear and you can see down 60' most places east of Esperanza. The few buoys are often missing. Do your approaches in daylight.
Coral Harbor at St John is a bit crowded but that is where you find some great live
music. Lots of whales near there in February.
No one tells you where you can or can't anchor. Every place in the USVI and SVI is better than Florida.
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