Blackbeard's Castle

Book direct Stay the night at the landmark.

The Castle Journal

Paradise Point St. Thomas: 7 Things to Know Before You Ride (2026)

Paradise Point St. Thomas is the view every cruise passenger has already seen in a photo and can’t quite place: the full sweep of Charlotte Amalie Harbor, the ships lined up at the dock, green hills falling away on both sides. It sits roughly 700 feet above the Havensight cruise terminal, and you can be standing up there about fifteen minutes after you walk off your ship. Here is what it actually involves, what to watch out for, and how to fit it into a day that also includes the historic side of town.

What Is Paradise Point St. Thomas?

Paradise Point St. Thomas is a hilltop observation deck above the Havensight dock, reached by an aerial tram known as the Skyride to Paradise Point. The ride takes about seven minutes and climbs some 700 feet, with the harbor opening up behind you the whole way. At the top you’ll find a viewing platform, a bar, a small restaurant, a cluster of shops, and a short nature trail.

It’s privately operated and it isn’t affiliated with us. Blackbeard’s Castle is the other hilltop in town, about a mile west, above the historic district of Charlotte Amalie. Visitors ask us about Paradise Point constantly, so this is the straight rundown rather than a sales pitch.

How to Get to Paradise Point

The Skyride to Paradise Point (the easy way)

The Skyride’s base station sits directly across from the Havensight cruise terminal, a two-minute walk if your ship is docked at WICO. You can buy tickets at the base station or online ahead of time, and online is usually a little cheaper. Rates and operating hours shift seasonally, and the tram shuts down in high winds, so check the operator’s current schedule the morning of your visit instead of trusting an older blog post.

If your ship is at Crown Bay rather than Havensight, you’ll need a taxi to reach the base station. Budget ten to fifteen minutes each way plus a wait. Not sure which dock you’re on? Our St. Thomas cruise port guide breaks down both terminals, and the VI Port Authority publishes the official berthing schedule.

By taxi or rental car

You can also drive up Flag Hill Road to the top instead of riding the tram, which some visitors prefer if they’re uneasy about heights or traveling with someone who has mobility limitations. The road is steep and narrow with tight switchbacks. Open-air safari taxis run the route regularly and drivers will usually wait for an agreed fare.

Walking up is technically possible and almost nobody enjoys it. It’s a hot, shadeless climb on a road with no sidewalk. Skip it.

Charlotte Amalie Harbor at sunset, the harbor view visitors ride up to Paradise Point St. Thomas to see
Charlotte Amalie Harbor from the hills above town.

What to Do Once You’re at the Top

Realistically, this is a viewpoint with amenities rather than an attraction that fills an afternoon. Most visitors spend forty-five minutes to an hour up there. What’s waiting:

  • The observation deck. The reason you came. On a clear morning you can pick out St. John, Water Island, and on a good day the British Virgin Islands on the horizon.
  • The bar. Known island-wide for a frozen banana daiquiri that has been on the menu for decades. Worth one, even if rum drinks aren’t usually your thing.
  • The nature trail. A short loop with signage on local plants and a decent chance of meeting an iguana who is entirely unbothered by you.
  • Shops. A small cluster of souvenir and jewelry stands. Fine for a magnet; downtown is better for real duty-free shopping.
  • Live music. Often on busier ship days, usually around midday.

Is Paradise Point St. Thomas Worth It?

Yes, with a caveat. If it’s your first time on the island and you want one photograph that says exactly where you were, this delivers it better than anywhere else you can reach in fifteen minutes. The tram ride is genuinely fun, and it’s about as close to the dock as a shore excursion gets.

The caveat is that it’s a short experience for what you pay, and it gets crowded when three or four ships are in port. If you only have four or five hours ashore and you want more than a photo out of them, weigh it against the historic district. Plenty of people do both, which is exactly what we’d suggest below. For a wider look at what else competes for those hours, see our guide to St. Thomas excursions and the full list of things to do in St. Thomas.

Best Time to Go and How Long to Budget

Go early. The base station opens around the time the first ships clear, and that first hour is the quietest and the coolest. By eleven on a three-ship day you’ll be standing in line.

Light matters too. Mornings put the sun on the harbor and the ships; late afternoon gives you softer light but more haze. If you’re staying on the island overnight rather than sailing out at five, sunset is the better call. Our guide to the best time to visit St. Thomas covers the seasonal side of that.

Budget about ninety minutes door to door from the Havensight dock: fifteen minutes each way including waits, plus forty-five minutes at the top.

How to Pair It With Blackbeard’s Castle

Here’s the itinerary we’d actually recommend if you have five or six hours ashore.

Ride up in your first hour off the ship, while the line is short and the light is good. Come back down, take a taxi into town (about ten minutes), and give the rest of your morning to the historic district: Fort Christian, the waterfront, the shopping streets, the 99 Steps. Finish at the top of Blackbeard’s Hill.

Blackbeard’s Castle is built around the Skytsborg Tower, a Danish watchtower raised in 1679 and one of only five National Historic Landmarks in the U.S. Virgin Islands. A $15 day pass covers the castle grounds, a tour of the tower, and a sampling in the rum room. Children under 10 get in free, and USVI residents get in free with island ID. We’re open 9am to 9pm daily, so there’s no closing time to race.

The poolside swim-up bar at Jolly Roger's, a ten-minute taxi ride from Paradise Point St. Thomas
Jolly Roger’s is free to walk into, pass or no pass.

Jolly Roger’s Restaurant & Pirate Bar sits on the property and is always free to walk into. No admission needed to eat or drink. It’s open-air and poolside with the harbor in front of you, and if you’re not sailing until evening, the sunset from up there around six is the part people actually remember. The self-guided walking tour fills the time in between.

And if you’re staying the night rather than sailing away, the hotel on the castle grounds has reservations open, with rooms looking out over the same harbor. Prefer a longer plan? Our St. Thomas cruise day itinerary maps the whole thing hour by hour.

Paradise Point St. Thomas: FAQ

How much does the Skyride to Paradise Point cost?

Pricing changes seasonally and there are separate adult and child rates, so check the operator’s current rate rather than relying on an older article. Booking online in advance is typically cheaper than buying at the base station.

How long does the Skyride take?

About seven minutes each way. Most visitors spend forty-five minutes to an hour at the top, so plan on roughly ninety minutes total from the Havensight dock.

Can you drive to Paradise Point St. Thomas?

Yes. Flag Hill Road runs to the top and taxis make the trip regularly. The road is steep and narrow with switchbacks, so take it slowly in a rental car.

Is it wheelchair accessible?

The tram cabins and the main observation deck are generally manageable, but the nature trail and some of the terraced areas are not. Contact the operator ahead of time if accessibility is a concern.

What else is nearby?

The Havensight shopping complex sits at the base of the tram. Charlotte Amalie’s historic district is about ten minutes west by taxi, and that’s where you’ll find Fort Christian, the 99 Steps, Blackbeard’s Castle, and the rest of the island’s historical sites.

Make the View the Start of Your Day, Not the Whole Thing

Paradise Point St. Thomas earns its spot on a cruise-day itinerary. Just don’t let it be the only thing you do, because the island’s story is in the town below it. Climb the 99 Steps, take the tower tour, and end the afternoon at the swim-up bar with the whole harbor spread out in front of you. See what the $15 day pass includes, or grab yours here.

Plan Your Visit

Tonight’s Sunset
Golden hour from the Jolly Roger’s terrace.

Plan Your Day at the Castle

The $15 day pass covers the castle grounds, a tour of the 1679 Skytsborg Tower, and a rum room sampling. Locals get in free with island ID.

Free St. Thomas Guide

One Perfect Day in St. Thomas

A local’s hour-by-hour guide to the best beaches, the island’s best view, and where to catch the sunset. Drop your email and we’ll send it straight to your inbox.