Unless you own your own jet with the ability to land and take off with your crew and all their gear? St. Thomas is always easier and less expensive. The downside of St. Thomas is St. Thomas has far, far fewer boats. If you can find the boat you need for your dates on St. Thomas go that direction. The first and last nights for us anchored off St. John always works for us.

Try to find a boat that works for you on STT. If that fails then you always have the massive overbuilt in inventory of boats on Tortola.