The Virgin Islands
, specifically the British Virgin Islands
would be a good choice as far as ease of sailing and availability of sailing classes
and possibly boats that could be used for liveaboard
purposes. Not sure you would want to "Dock" somewhere... that is rather a commercial
term. Plenty of slips available in marinas
for pleasure boats. Some offer live aboard and Mooring
fields or anchorages
for use. A slip in a marina is typically considered expensive, even using some of the mooring
balls can cost $25.00 a day.
You may find it less expensive and more private to consider St. Johns in the US Virgin Islands
. Both provide you with ease of access to what is considered some of the very best sailing conditions in the world which would allow you to develop your skills while still being within quick access to many services should you need them... such as ICE.
I would recommend you pick up a copy... best to order on line a copy of a Virgin Island Cruising Guide. Check Amazon or this link
A copy of the Anchorages
book with great photos is also helpful.
Get only those for sailboat/ motor
boat cruising not ship cruising. Avoid the cruising guided by Foror's and Formmer'r they are the wrong type. Those by Street,
Doyle are far superior and will give you detailed information on anchorages and marinas
in the area you select.
When your skills have improved, it is not difficult to move beyond the Virgins into the Leewards and Windwards. The US, British and even Spanish Virgin Islands may keep you busy for years. Not much better sailing anywhere in the world for someone starting the adventure.