The 32 square miles that make up the island of St. Thomas is not just limited to clear waters and white sand beaches. It has an appeal and its own flair outside of being a tourist hotspot, with a large university, commerce, and a charming, sometimes gritty locale. It’s a gem if you’re willing to treat it as more than a refreshing change of scenery.
St. Thomas remains among the most accessible islands within the Caribbean, sometimes touting mid-January flights from New York for $480, and flying in still remains the easiest method with many flights from major cities in the U.S. having only one stop over (if not offering direct). Once you’re there, renting a car will give you unfettered island access, and is much cheaper and easier than paying questionably expensive “island taxi” fares. Remember (standard island rules), drive on the left!
As with most major Caribbean islands in the last few years, accommodation trends have been leaning more and more into villa rentals and Airbnbs, moving away from the expensive, high-end chain resorts. If you’ve never lived much on the coast, just browsing the Airbnb listings is uncomfortably enticing. Mind you, if you’re prepared to drop some serious cash, these resorts have some of the best, most exotic facilities at the likes of the Ritz-Carlton and Marriott. To make the most of the cheaper, more island-experience of villa rentals, try to book at least a few months in advance.
If you’ve got a rental car or scooter, you can’t go too wrong in picking a location for your stay; you’re usually never more than a 15-minute drive to the beach from anywhere on the island. While St. Thomas isn’t unsafe, it still pays to exercise caution as you would anywhere else; try not to wander the back streets after some heavy bar exploration, and make sure you keep track of your belongings wherever you go.
After getting set up, you may be ready for some adventure. Avoiding the cruise-ship crowd is easy enough, as most of it is contained dockside right next to the ships in the Havensight area. But even with this in mind, there’s still some absolutely fantastic joints in the area, crowd or no. My personal favorites are the Barefoot Buddha coffee shop, equally popular among locals and the tourists. For nightlife, go to the Rum Hut. This simple tiki hut, surrounded by swings instead of bar stools, makes for an airy, lighthearted setting to chat with some interesting folk — this particular bar attracts all sorts of people.
You’ll notice a chairlift up to Paradise Point from Havensight, with a pricey restaurant at the top. If you’re up for it, skip the chairlift and spend 30 or so minutes getting a sweat on, and grab a drink at the end to soak in the views of the island’s capital below you. If you’ve yet to experience a view atop an island peak, I recommend it be your first priority. It allows for a great lay of the land and for planning what spots you might check out. Seeing 360 ocean views is a strange, surreal moment.
Two other iconic views are Drake’s Seat and Mountain Top, both accessible by car, where you’ll be able to look down upon Magens Bay, a staple to any St. Thomas visit if you don’t mind the crowds. If you do go, stop by a place called the Udder Delite Dairy Bar, just at the turnoff on Magens Bay Road. It serves fantastic booze-spiked milkshakes and other treats — it’s a fun little place.
Lindquist Beach, a lesser known, tucked away beach, is located on the island’s eastern side. It’s everything you’d put on a checklist for a Caribbean beach; the sand almost looks pink. Bring your snorkeling gear if you have any, although you could probably get by without it since the water is so clear and calm. You could comfortably devote an entire day here.
If you’ve got the time, it’s worth spending some of it on daytime urban exploration of Charlotte Amalie, especially between Frenchtown and Fort Christian. It’s a hilly city, with an interesting network of stairs and walkways sprinkled with quaint, seemingly miniature parks filled with fountains and benches that afford a better view the higher you go. Try and make it to Blackbeard’s Castle, affording one of the best views of Long Bay. You get a sense of the history of the island, which was only purchased by the U.S. around 100 years ago from the Danish.
In the evening, especially on a Friday or Saturday, go check out Emancipation Garden, a commemoration for the freeing of the slaves in 1848 in St. Thomas. It's a local hangout joint almost always complete with informal live music and dancing; it’s quaint, charming, and laidback.
This column is taken from the January 2021 issue of Dockwalk.