No hassles at all if you've given yourself the time after landing. Easy to stumble out and pick up a taxi if you don't have one reserved. You'll typically pay per-person and per-bag, so it will seem steep to pay $20-25 for two to share a packed van for a 10-minute ride, but who cares when you're on vacation. Buy a 1-way ferry ticket for the next one leaving (confirming that they haven't broken down or are on a delay). Arrive in Road Town, small line, check through customs. Catch another taxi depending on your charter plans. You're on your way. Just in reverse on the way back, which typically takes longer. You were probably thinking of the optional porter at the STT airport when you're leaving. I don't have experience with them (but may consider it), but I understand that can help you move through the security line faster during a busy day or season. But getting on the ferry from the airport is easy. Have fun!