The photo everybody comes home with — the one where Magens Bay curves below you in three shades of turquoise and the British Virgin Islands stack up on the horizon — is taken from a pull-off on the north-side ridge. It takes about two hours to do the whole loop properly, it costs almost nothing, and from our hillside villa it starts five minutes from the front door.
Here's how we'd run it.
Drake's Seat
A roadside overlook on the ridge, named for the story that Sir Francis Drake watched for ships from here. Free, no gate, no ticket. You park on the shoulder, walk a few steps, and the whole of Magens Bay opens up underneath you.
Fifteen to thirty minutes is plenty. The reason to come is the angle — you're looking straight down the bay with St. John and the BVI behind it, which is a view you can't get from sea level anywhere on the island.
Go early. Before ten the light is behind you and the pull-off is quiet. By midday the tour vans arrive in waves and the shoulder gets tight. There are usually a couple of vendors set up; it's cash, it's low-key, nobody hassles you.
Mountain Top
Fifteen minutes further along the ridge is the highest point on St. Thomas. There's a viewing deck, a gift shop, and the banana daiquiris the place has been known for longer than most visitors have been alive. Entry is free — you're paying for a drink if you want one.
Budget thirty minutes to an hour. The view here is wider than Drake's Seat and faces a slightly different direction, so it's worth doing both rather than picking one. On a clear day you can see a long way out over the Atlantic side.
Same advice on timing: ships in port means buses, and buses mean the deck is three deep. Early morning or late afternoon.
The stop most people skip
Phantasea Tropical Botanical Garden sits on the same hilltop stretch — orchids, bromeliads, palms, and a quiet harbour view. It's $15–20 a head and takes an hour or two. It is the opposite of a bus stop, which is exactly the point. If you've got a morning and the overlooks took less time than you expected, this is where the rest of it should go.
The drive itself
Two-lane, steep, switchbacked, on the left side of the road in a left-hand-drive car. It sounds worse than it is — everyone moves slowly because the road insists on it. We wrote the whole honest version in driving on St. Thomas.
Allow more time than the map says. The map always lies about this island, and the pull-offs between the named stops are half the reason to do the drive at all. Real drive times are here.
Putting it together
The loop that works: Drake's Seat first thing, Mountain Top next, then drop down the north side to Magens Bay ($5 entry) for the rest of the morning. You're back at the villa for lunch having done the island's two best views and its most famous beach before the day got hot.
From Mahogany Seaview on the north-side ridge, all of that is inside fifteen minutes — the overlooks are essentially your neighbourhood. From Sapphire Beach on the east end it's a twenty-five to thirty minute drive over the ridge, which makes it a proper half-day outing rather than a before-breakfast errand.
Either way, do it on a clear morning early in the trip. It's the drive that makes the rest of the island make sense — you see how small it is, where the bays sit, and which side of the ridge your beach is on. Open weeks for both places are on the deals page.