Our group of 3 couples is considering a SVI charter in January or April of 2021. Leaning toward a St Thomas-based charter having done our last two charters from there. Our previous itineraries included St John and the BVI but we would like to change it up. Assuming appropriate weather/conditions, we would sail downwind to Culebra and Vieques, then to St Croix before returning to St Thomas - the plan being reaching instead of beating and an opportunity to see St Croix. All our previous trips have been in April, but considering mid-January next time around. How concerned should I be about Christmas winds. If anyone has some advice, I would welcome it!

The itinerary seems fine - wouldn't be too concerned with wind on those long reaches to/from STX. Easterly winds are usually most of Jan.

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.

Thanks for the advice - I hope the winds ease a bit for you.

I am planning the same trip in May with boat from CYOA. I was going to follow the Don Street itinerary of STT- Culebra- Vieques- STX- USVI but I am liking BarrdJ's suggestion of reversing the track that time of the year due to more E, ESE winds.

Having East winds: the Vieques -STX -STT trip idea is fine - Beating back to STT from Culebra or Vieques is what you are trying to avoid in general.
The Beat up to Salt Pond to start, and the Beat up to STT at the end of the SVI trip are not necessary and I would avoid that plan if ease of sailing is the objective. [Just my opinion]