If you have access to PHL airport? You should also be able to use JFK and Newark. Between those three airports you should be able to find an early morning flight any day of the week direct arriving at STT or SJU near noon. A midday arrival at either place is a reasonable chance you will make Tortola on the same day even if you are delayed. The same is true on the return. The flights to Philly leave at 2 from STT. There is ample time to get from Tortola to St. Thomas to catch a 2PM plane. Note: To many STT is a miserable place to be trying to depart on any weekend. Always book yourself on the first flight south outgoing day and the last plane of the day on return direct to any of those three airports.

Right now the JFK flights are $188 a leg leaving STT at 3:30.

Trying leave the dock the same day you land is a recipe for misery. We gave that up long ago and never rush away from the dock. We leave when the boat is ready and everyone in the crew is ready. We do try to arrive back at the base early and with zero delay moving the boat on the last morning. Have everyone packed before the boat hits the dock to be on our way home. To us using hotels on the way in and out is more hassle than it is ever worth. We will not take a charter without a sleep aboard.