Two facts collide on St. Thomas. You drive on the left, and the cars are left-hand drive — mainland cars, steering wheel on the side you're used to, on the side of the road you're not. It sounds like a nightmare and it isn't. It's about twenty minutes of concentration and then a week of mild vigilance at intersections.
The left-side thing, practically
Your body will be fine on straight road within a mile or two. The two places it bites are turns onto an empty street and pulling out of a parking lot — there's no traffic to copy, so the habit takes over. The fix is a sentence you say out loud every time: stay left. Passengers should say it too.
Roundabouts go clockwise. Yield to whoever's already in it. Everything else is ordinary driving at slow speeds.
The hills are the real story
Grades here are steeper than almost anything you drive at home, and they come with blind switchbacks and no shoulder. That's why nearly every rental on island is an SUV and why you should take one — not for off-roading, for the low gear and the ground clearance on a driveway that starts at a 20% pitch.
Go down hills in low gear rather than riding the brakes. Use your horn on blind corners; here it means "I'm here," not "you idiot." And if a local is behind you, pull over and let them past. They've done this road ten thousand times and they're not sightseeing.
North side vs. east end
Getting around the east end — Red Hook, Sapphire, the beaches — is mostly flat, straightforward, and short. If you're at the Sapphire Beach condo you can do a whole trip with very little driving; plenty of guests skip the rental car entirely and take taxis for the occasional dinner out.
The north side is where the driving becomes part of the vacation. The climb up to Mahogany Seaview and the roads across the ridge are steep, narrow, and genuinely beautiful — the picture above is that hillside. You'll drive them a few times a day, and by day three you'll like it. Read what the north side is really like before you decide which side of the island suits you.
A few last things
Gas is sold by the gallon and costs more than the mainland. Parking in Charlotte Amalie is limited and worst on cruise-ship days. Plan the first drive in daylight. Skip the scooter — these are not scooter roads.
And if none of the above appeals, don't force it: taxis run in the $10–15 per-person range for common routes, and our rental car guide walks through when you actually need one.
Open weeks at both villas are on the deals page.