Everybody is correct! Do more in the Virgins (US and BVI) to get yourself really comfortable sailing to islands and
anchorages away from the normal herd of
boats. But still revisit some of your favorites from last time as you will see new aspects of them as a "returnee." Then branch out to longer
sails - say to St. Croix, Viegues,
Culebra, and the
east coast of
Puerto Rico.
After several seasons getting "seasoned" to sailing and living onboard then do the islands from Antiqua to
Grenada. There are charter outfits in all these islands. Which ones you choose will be determined by the season you charter in. In the
winter months the northern islands are great. From Antiqua you can visit St Barths;
St Kitts;
Nevis; Montserrat and northern
Guadeloupe. From the French Islands you can visit all the islands from
Guadeloupe; Saintes;
Dominica; and Martinque. In the summer or
winter from St Vincent or Canouan (The Moorings) there are the Grenadines and
Grenada. From Grenada there is Grenada and the Grenadines.
That should keep you busy for 10 years or more. Then you will have experience in many different
boats and be able to know which
boat is best for you to buy and enter the world of "world cruisers" sometimes referred to as a "heavenly life" with maybe a little bit of "hell" occasionally mixed in.