Sunset here is quick. You get maybe forty minutes of the good stuff and then it's dark, with almost no dusk — that's what being close to the equator does. So the question isn't really where the best view is. It's where you can already be standing when it starts.
The free ones are the good ones
Drake's Seat is the classic, and it's free, and it takes ten minutes. It's a pull-off on the ridge road looking down over Magens Bay and the outer cays. You are not the first person to find it, so there will be other cars and often a vendor or two, but the view does the work. It faces north rather than due west, which means you're watching the light change on the water and the islands rather than staring at the sun itself — which is honestly better.
Mountain Top is higher, has a parking lot and a gift shop and a famous banana daiquiri, and looks out over Magens Bay from about 1,500 feet. It's more of a stop than a sit. Get there before the light goes rather than during.
The ridge road itself — the stretch running along the spine of the island — has a dozen unmarked pull-offs. Half the best sunsets we've seen were from a place with no name, because we happened to be driving at the right hour.
The ones worth a reservation
Paradise Point above Charlotte Amalie has a skyride up and a view down over the harbor. It's touristy in the way that things are touristy when they're actually good.
Sunset Grille does what the name says — a table with the water in front of it, timed for the hour. Book it, because everyone else had the same idea.
On the east end, Sapphire Beach Bar and Iggies both put you on the sand with a drink in hand. Neither is a west-facing sunset in the postcard sense, but the light on the water and the cays at that hour is the thing worth showing up for, and you don't have to drive anywhere afterward.
For an actual dinner rather than a drink, SeaSalt is our standing recommendation on this side of the island.
Why the north side wins
If you're staying on a hillside, you don't go anywhere. That's the entire pitch.
Our Mahogany Seaview villa sits up on the north-side hillside above the coast, and the last hour of light happens on the deck. You watch the weather move across the water from miles out, the color change on the outer cays, and the lights come on across the water afterward. Nobody drives to a viewpoint because the viewpoint is where you're already sitting with a drink.
That's the honest trade of an ocean-view place versus a beachfront one. Down at Sapphire you're in the water all day and you walk up salty at dusk. Up at Mahogany Run you're not stepping onto sand in thirty seconds, but you get elevation, constant trade wind, and this hour every single evening without planning it. We own one of each and the side-by-side comparison is the most useful thing we've written for people trying to choose.
One practical note
Check the sunset time and subtract an hour. Between the shortest and longest days the difference here is only about an hour and a quarter, so it's roughly 5:45 in December and 6:55 in June — but the roads are narrow and dark, and you don't want to be finding a pull-off in the last five minutes of light.
Then drive slowly on the way back. The ridge road is not a road to hurry on after dark.
More on getting around in the rental car guide, and open weeks are on the deals page.