Almost everyone who stays with us lands at Cyril E. King (STT), on the west end of the island, and stays on the east end. That's the whole island, end to end, on your first day with luggage and no bearings. It is not a hard drive. It's just longer than the map suggests, and the order you do things in decides whether you're in the water by four or eating gas-station crackers at nine.
How long it actually takes
Plan on roughly 45 minutes to the east end, and more if you land in the middle of a cruise-ship afternoon or at rush hour through Charlotte Amalie. The distance is small; the roads are two-lane, hilly, and busy near town. Nobody is in a hurry here and you won't be either after the first ten minutes.
Taxi or rental car
Taxis and private drivers work on a per-person rate — budget in the range of $10–15 per person for shared runs, more for a private transfer or a longer haul — and the drivers know the roads better than you will all week. There are stands at the airport, at Red Hook, in Charlotte Amalie, and at Havensight.
The rental car question is its own conversation, and we wrote it up in do you need a rental car on St. Thomas. Short version: if you're staying on the hillside at Mahogany Seaview, you want a car. If you're staying at the Sapphire Beach condo, you can get away without one for days at a time, and some guests skip it entirely.
If you do rent: you'll be driving on the left, in a left-hand-drive car, on steep switchbacks. It's manageable. It is not the moment to learn on a scooter, and it's worth doing that first drive in daylight if your flight lets you.
The order that works
Groceries first, then the villa, then the water. Stopping at Moe's on the way in costs you forty-five minutes of a day you'd already given to travel; doing it tomorrow costs you a beach morning. Our full grocery run guide has the list.
Then check in, put the perishables away, and go get in the ocean before you unpack a single suitcase. The unpacking will still be there. The light won't.
Small things that help
Have some cash — taxis, roadside spots, and smaller shops don't all take cards. Keep swimsuits and sunscreen in your carry-on so your first swim doesn't depend on checked luggage arriving. And leave your return-day plans loose: the airport wants you three hours early for departure because of customs, which is the one genuinely annoying piece of travel logistics here.
Open weeks and current discounts at both places are on the deals page.