St Thomas: Charlotte Amalie (revisited)

February 2026

After Puerto Rico, the first real tropical island I ever visited was St Thomas. Puerto Rico is an island, but it is so large that it does not always feel like an island per se. The Virgin Islands are small and the sea is always in sight. The feel is definitely "island" everywhere. When I was at Georgetown, my friend Ivan D and I flew to St Thomas from San Juan for a weekend. We explored Charlotte Amalie a little, but the main focus of that trip was to see St John. In fact, we did very little in the capital of the US Virgin Islands other than visit some shopping arcades and stay in a nice, small hotel in the hills.

That first trip set the bar for tropical islands for the rest of my life - and it was a very high one to match. Some places I traveled eventually exceeded it, but not many. Finally, after several decades I was returning to St Thomas. Was it really like I remembered?

Upon leaving the immediate cruise ship zone (filled with small shops selling tourist shlock) I came to the incredibly upscale Yacht Haven Grande, for those who had arrived in town on their own boat. The place felt like a luxury hotel setting minus the rooms. The main thing I noted was how empty it was. The yacht club is large, yet I didn't see many people (and most of the shops weren't open). It appeared oddly desolate (but very well-maintained). Was there a "yacht season"?

And, at the entrance was an old turret. I think it might have been an original fortification that was incorporated into the place.

At the yacht club stand three statues of guys on stilts (Moko Jumbie)

A Moko Jumbie is a traditional stilt walker or dancer associated with Caribbean Carnivals for over 200 years. Derived from West African traditions, Moko Jumbie cultural practices were introduced to the Caribbean island by enslaved Africans during the 19th century.

(Wikipedia)

I had never heard of Carnival in St Thomas nor of these stilt-walking guys. Apparently, my knowledge of the region was extremely limited. The USVI was clearly more than a cruise port.

Upon exiting the Yacht Haven Grande, I started a sun-drenched walk along a lovely esplanade to reach the edge of downtown.

At the end of the waterside walk lies the Legislature Building (Capitol) of the United States Virgin Islands.

Right in front of the Capitol is Fort Christian, one of the original forts protecting town.

Fort Christian in Charlotte Amalie, named for Christian V of Denmark, was built between 1672 and 1678 and is the first and largest fort in the Virgin Islands. Constructed on a rocky peninsula in the bay, its tall, thick walls of stone and brick, supported by large buttresses, stand as a testament to early colonial engineering. Timber, bricks, and other materials were imported, while lime for mortar was likely produced locally. The fort was established under the leadership of Jørgen Iversen Dyppel, who oversaw construction, colonial administration, and labor, which included indentured European workers and enslaved Africans. The central building, Trygborg (“safe castle”), housed the governor, staff, and essential functions, while the star-shaped bastions and surrounding palisades provided defense against pirates and foreign attacks. By 1680, Fort Christian was fully operational, with chapels, kitchens, guardrooms, offices, and storage spaces forming a self-contained colonial community. The fort, along with watchtowers and outposts around the harbor, formed the core of Charlotte Amalie’s early fortifications, ensuring the safety of the settlement and shaping the island’s colonial history.

https://www.stthomashistoricaltrust.org/fort-christian-1

I had forgotten that the US bought "half" of the Virgin Islands from Denmark!

Finally, I reached the part of town I remembered, with old buildings climbing up the hills. I noted some still showed hurricane damage (Maria, 2017).

I climbed some stairs to the famous Hotel 1829 overlooking the harbor. It is still in use.

That part of Charlotte Amalie is filled with stairs rather than roads for people to travel up and down to the lower town.

Someone has a lovely house just under Blackbeard's Castle

The iconic Blackbeard's castle created a bar and swimming pool for day use overlooking town. I was happy to have huff and puffed up all those stairs for the view.

Note: the "castle" is just an old Danish watchtower; someone later cashed in on the "Blackbeard" legend to make the place sound more interesting.

I thought about the expensive cable car near the cruise ship port promising great views. Indeed it was higher, but farther removed from town. The view from Blackbeards is quintessentially Charlotte Amalie. I was happy I made the effort.

On the way back to the lower town I came upon the famous 99 Steps. I was curious why those steps got such recognition since there are similar stone stairways all over the hills.

I descended an even longer set of stairs all the way to the lower town and its beautiful old homes.

St Thomas is completely set apart from other islands in the region for its degree of renovation of heritage buildings. Since my last visit it had greatly improved, even after a devastating hurricane.

I was reminded of all the luxury shopping available upon arrival to the heart of old downtown, too.

Compared to the past, old downtown is mostly restaurants, bars, and luxury shops. All the cheap tourist shops have moved closer to the cruise ship pier (at least it appeared that way). As I felt years ago: who would travel to the Virgin Islands to buy a Rolex or diamonds? Was it really that much cheaper?

The famous Palm Passage was not nearly as lovely as I remembered (but still nice). I think that's because all the small alleys (gades) have been renovated nicely and it doesn't appear as special as in the past.

I crossed the very busy highway to have a look again at the blue-water harbor.

The shopping streets are lovely, but I noticed many were closed. Was it oversaturation? TWO huge cruise ships were in port and it didn't feel that busy.

I felt tired and hot. It was time to head back to the ship. I returned via a different street and caught the front part of Fort Christian. A bus had just pulled up and a large group was about to enter.

Back on the ship I pondered my visit. It was a good walkabout where I saw much more of Charlotte Amalie than Ivan and I ever had. The day exceeded my expectations - I was happy.

Final takeaway:

St Thomas has actually improved a lot in the intervening years from my first visit (in terms of development). Islanders have an incredibly high standard of living compared to their neighbors (they are Americans after all). Of course, St Thomas is expensive and hurricane-prone, but it is still beautiful and being developed responsibly. The island has some limitations it cannot escape - one of them being water. Everyone gets their water from rainfall via cisterns. Unless the islands invest in desalination (expensive and energy intensive), they will never be able to support a large population. That puts the brakes on runaway development even more than the small land area.

Charlotte Amalie for me remains one of the most beautiful seaside towns of the Caribbean (or anywhere). I felt lucky to have returned, but unless I come into a lot more money (or visit again on a cruise), I don't think I will need to return.

St Thomas - still A+