The Windmill Bar St. John: History, Sunsets & The Best View in the USVI

The Windmill Bar sits at roughly 900 feet of elevation on the spine of St. John, perched on the stone bones of a sugar plantation that has watched over the island for nearly 250 years. It is, by almost any honest measure, the best sunset view in the U.S. Virgin Islands — and one of the few places where a cold Carib comes with a side of genuine Caribbean history.

This is the story of how a 1780s windmill, a Crucian land deal in the 1940s, and three generations of one family turned a quiet hilltop into the most beloved gathering place on St. John.

A Sugar Mill That Outlasted an Empire

Long before there was a bar, there was a windmill.

Estate Susannaberg was a working sugar plantation in the late 1700s, one of dozens that covered the steep, sun-baked hills of what was then the Danish West Indies. According to records held by the Library of Congress, the stone windmill tower at Susannaberg was erected between 1780 and 1800, making it the second-oldest windmill on the island of St. John. The wooden sails, the gearing, and the grinding stones are long gone — claimed by hurricanes, rot, and time — but the conical stone tower still stands, every bit as solid as the day enslaved Africans laid its mortar.

That tower is the soul of the place. You can walk right up to it, run your hand along walls almost three feet thick, and look out the same arched openings the millers used to gauge the trade winds more than two centuries ago.

The Richards Family: Three Generations on the Hill

The modern chapter begins in the mid-20th century, when a Virgin Islander named Neptune Richards bought the old Susannaberg estate. The Richards family has owned the land ever since, and the property today — windmill, bar, restaurant, campground, and disc golf course — operates collectively as Neptune's Lookout.

In 2025, Boston's WCVB Chronicle traveled down to St. John to film a feature called "Legacy on the Lookout," documenting how the Richards descendants turned an inherited hillside into one of the Caribbean's most distinctive destinations. The story they tell is not one of outside investors or resort developers; it's a family story about land, stewardship, and refusing to sell to the highest bidder.

That decision is why The Windmill feels nothing like a typical tourist bar. It feels like a backyard — because, in the truest sense, it is one.

The View

From the open-air deck, the eye sweeps roughly 180 degrees across some of the most photographed water on Earth.

To the north and west you'll see Hawksnest Bay, the long arc of Virgin Islands National Park coastline, and the green humps of Lovango, Congo, Mingo, and Grass Cays rising out of Pillsbury Sound. Beyond them, the east end of St. Thomas stretches toward the horizon, and on a clear evening you can pick out boats threading between the islands like tiny white sparks.

When the sun drops, it drops into that view — slipping behind St. Thomas in a slow burn of orange and magenta that turns the entire sound into hammered copper. Regulars will tell you the green flash happens here more often than anywhere else on St. John. They are not exaggerating.

The Vibe: Picnic Tables, Painkillers, and No Pretense

There's no dress code, no host stand, no velvet rope. You park along Centerline Road, walk up the path, and find a seat at a picnic table or a stool at the bar. Dogs are welcome. Kids are welcome. Sailors who just hiked up from the dinghy dock at Cruz Bay are very welcome.

The crowd is a mix that you'll find almost nowhere else on the island in such easy proportion: born-and-raised St. Johnians, long-haul liveaboards off the boats in Coral Bay, snowbirds from New England, charter guests in damp swimsuits, and the occasional honeymooning couple who stumbled in for one drink and stayed for four.

The soundtrack matches. Live music plays most nights — solo steel pan, acoustic duos, full reggae and rock bands — and the Virgin Islands Jam Fest, a three-day music festival now in its sixth year, takes over the property each spring. Sunday Bingo from 4 to 6 PM is an institution; the prizes are silly, the heckling is merciless, and the regulars guard their cards like state secrets.

Food and Drink

The kitchen is small and the menu is tight on purpose — everything is made to be eaten with one hand while the other holds a drink and your eyes stay on the water.

Highlights worth ordering:

• Island Bowls — built on rice and beans, naturally gluten-free, generous enough to share and endlessly customizable
• Buffalo Chicken Dip — creamy, spicy, served bubbling hot with fried corn tortilla chips
• Seafood Dip — a house favorite, rich and briny, the kind of app that disappears before the second round arrives
• Peel-and-Eat Shrimp — chilled, perfectly seasoned, the ideal sunset snack
• Burgers — proper, juicy, griddled the old way; a Beyond Burger is available for vegetarians
• Painkillers — the unofficial drink of the Virgin Islands, poured strong

Happy Hour runs daily from 12 to 3 PM: $4 Truly, $4 Carib, and $6 Blue Chair Bay Windmill Breeze — a coconut-rum-and-pineapple house pour that tastes exactly like the breeze it's named after.

Practical Information

Address: 17A Susannaberg, St. John, USVI 00830
Hours: Open daily, 11 AM – 8 PM (kitchen until 7:30 PM)
Phone: (340) 514-4798 · Text: (912) 657-2564
Reservations: Not needed — first come, first served

Getting there from Cruz Bay: Take Centerline Road (Route 10) up the hill past Dolphin Market. At one mile you'll hit Supreme Corner — a sharp hairpin to the right. Continue another mile, passing the Myrah Keating Smith Clinic and Paradise Lumber on your left. The Windmill Bar entrance is on the right. Total drive: about 8 minutes from the Cruz Bay ferry dock.

From St. Thomas: Catch the passenger ferry from Red Hook to Cruz Bay (about 20 minutes), then taxi or rental jeep up Centerline. If you're charter-bound, most Cruz Bay-based captains know the spot and will happily build a sunset stop into your day.

Best time to go: Aim to arrive at least 90 minutes before sunset. Tables along the western rail fill up first, and the light show in the half-hour after the sun drops is arguably better than the sunset itself — the sky goes through every color in the box while the lights of St. Thomas blink on across the sound.

Why It Matters

There are flashier bars in the Caribbean. There are bars with bigger menus, longer wine lists, and infinity pools that lean over the cliff for the Instagram. The Windmill Bar has none of that, and it doesn't need any of it.

What it has is a 1780s stone windmill still standing where it was built, a family that has tended this hill for three generations, and a view that makes strangers turn to each other and say the same thing every single evening: "I can't believe this is real."

That, more than anything else, is why The Windmill Bar has quietly become the place every St. John local recommends first when a friend asks where to go.

Come early. Stay late. Order a second painkiller. And when the sun finally drops behind St. Thomas, look up at the old stone tower behind you — and tip your glass to Neptune Richards, who saw what this hilltop could be a long time before anyone else did.