We did the San Juan- Beef Island flight thing. Southwest flies to San Juan and we used miles. Used American miles to get to Tortola. That worked well. I recommend Marriott Courtyard in San Juan near the airport. Beautiful hotel on the beach. You guessed it - used points. My only recommendation is to pick up your beverages at Tico's yourself on the way to Road Town or Nanny Cay. They were 1.5 hours late for our charter which delayed our departure a bit.