Christmas winds would put a damper on that itinerary. The advantage of starting in St Thomas is that you could always head east if you have high winds or a big north swell. It's been blowing 25-30 kts since Thursday when we arrived so we headed to St John and BVI instead of SVI. We've had gusts of 34-36 kts the past 3 days with 8+ ft seas.

If you do have a favorable weather window, I suggest reversing your itinerary. Head to St John first (Salt Pond Bay or Lameshur Bay). This will give you a much better angle on the 32 nm sail to Christiansted or Buck Island, St Croix. You can then enjoy a nice long downwind sail to Vieques, an 11nm reach from Punta Este, Vieques to Ensenada Honda, Culebra, and then it's only a ~3 hr upwind return to Charlotte Amalie, St Thomas.