Interesting question and interesting trip. Have you thought about buying
one of those waterproof duffles like they sell for kayaking and river rafting? Then you could anchor
off a bed/breakfast or hotel
, swim ashore with your clothes, and spend the night.
Then the question becomes searching out the places you want to stay near the water
. I'd ask them seriously about the security
of the boat, though, if you're not aboard. You might HAVE to stay in marinas
for that reason.
A few possible stops along the way that come to mind: Iles des Saintes, Cul de Sac du Marin- Martinique
, Marigot Bay- St. Lucia, Palm Island- The Grenadines. Don't know if any of those really fit the bill, but they might be a good place to start looking.