I really feel sorry for people, that for various reasons have never
lived on a sailboat, gone island-hopping, lived with island tribes.
There are advantages and disadvantages of course, in a cruising sailboat
you have to have enough room to carry all your provisions, repair parts
and materials, workshop with you, which slows you down, but tends to get
you back home when things break down. The sea is unforgiving , bad
planners and the unlucky suffer at its hands.
But it is a largely tax-free existence, without the tax-paid amenities
we take for granted. I used to take along a ten-speed Kawasaki
motorcycle to get around on land, a lot of it roadless---found it to be
a lot better than walking or paddling a canoe along the shore.
It may have changed, but when I lived in the Bahamas, there were no fees
except at a marina for a transient boat, and you could import for
permanent use anything that floated (including my floating hex
houseboats pulled up in a land excavation) for the sum of $17.50---not
bad for a then $28,000 fully-equipped house.
Unfortunately the bigger and more comfortable the boat, the less it is
capable of detailed exploration of islands---for that you need a small
Proa, and following are a large number of Proa links, Sure, a seagoing
kayak will do the job, but there is no charge for the wind driving a
lazy-man's tiny sailboat either.
http://www.bijlard.demon.nl/page40.html
(tacking, Proa turns into wind, then reverses course, vs. trimaran and
single-hulls which turn into wind, around and away on the other tack.)
http://www.schachtdesign.com/proafile/
(more on Proa design, rigging---great for shallow waters, drag up on
beach instead of anchor. I would prefer (strength permitting) ratcheting
the structure supporting outriggers across the hull to provide greater
leverage from the leeward side of the boat.)