Amigo - As a stepping stone to open water passages and more remote cruising, I recommend the St John-St Croix-Spanish Virgin Islands (Vieques, Culebra, Culebrita) loop. Start from St Thomas then head to either St John or Culebra first depending on the 7 day forecast. You have a 32nm open ocean reach (4-5 hrs on a bigger cat or mono) between St John and St Croix. This trip requires a bit more self-sufficiency and skill than the usual 7 day loop around Tortola. You'll encounter few charter boats along the way. There will be no boat boys (or Boaty Balls). You'll have only one Customs & Immigrations encounter to deal with when you enter the Spanish Virgin Islands (ie Puerto Rico), but this can be handled electronically on your phone using the CBP ROAM app.

I've done this loop several times starting from CYOA Yacht Charters in St Thomas. What I really appreciate is that you have wonderful backup options if you arrive in the islands and get snakebit with several days of 25+ kt winds and 10+ ft seas or a large north swell (as we did this January with nearly a week of 30+ kt winds followed by several days of 10+ ft north swells). At least with my wife and crew, they have no interest in long open water passages in those conditions. Instead we simply adjust our plans and stay within the more protected waters around St John and the BVI (with numerous anchorages to choose from that are protected from high winds and/or large north swell) until the conditions improve.

CYOA in St Thomas has a great selection of boats (though no power cats) and offers excellent service.