Charlotte Amalie, the 99 Steps & Blackbeard's Castle

Charlotte Amalie is one of the oldest cities in the Caribbean. The Danes established it as a trading post in the 1670s, and for much of the 18th and 19th centuries it was one of the busiest free ports in the Atlantic world. The old city sits on a steep hillside above the harbor, layered in Danish colonial architecture — yellow and red warehouses, shaded alleyways, and a hillside laced with hand-built staircases.

Most cruise passengers spend their time on Main Street, where the duty-free shopping is concentrated. The more interesting city is a short walk uphill from there.

The 99 Steps — and Their Real Count

The staircase known as the 99 Steps climbs from the lower town up through the hillside residential area. Like most of the old city's infrastructure, the steps were built from ballast bricks — heavy ceramic bricks loaded onto ships in Europe as ballast for the westward Atlantic crossing, then offloaded in Charlotte Amalie and used as building material. The same bricks line alleyways, garden walls, and the base courses of colonial buildings throughout the old town.

If you count carefully, you'll find the staircase actually has around 103 steps. The "99" is what everyone calls it, and the name is older than any surviving record explaining it. The steps are steep and get slippery in rain — wear shoes with some grip.

Blackbeard's Castle (Skytsborg)

At the top of the hill, above the steps, stands a five-story stone watchtower that the Danes built in 1679. Its official name is Skytsborg — "fort of protection" in Danish. The purpose was purely practical: a high point from which to spot approaching ships and communicate back to the harbor. Whether the pirate Edward Teach, better known as Blackbeard, ever actually used it is a legend that locals have enjoyed but that no historical record supports. He was active in these waters in the early 1700s, about a generation after the tower was built.

The views from the tower grounds are the main draw — a panorama over Charlotte Amalie Harbor, Hassel Island, Water Island, and on clear days you can pick out the British Virgin Islands on the horizon. There is a bar and restaurant at the complex. Admission is charged to enter the tower grounds.

Fort Christian

Down at the harbor level, Fort Christian is the oldest standing structure in the US Virgin Islands. Construction began in 1671, making it older than most of the colonial cities in the Eastern Caribbean. The dark-red fortress served for centuries as the seat of Danish colonial government — at different times a courthouse, a jail, a church, and a military barracks. It is now a National Historic Landmark and houses a museum of local history. The fort sits at the east end of Emancipation Garden, the small park at the center of the waterfront.

How to Walk It

Start at the waterfront near Fort Christian. Walk west along the harbor to Emancipation Garden, then up through the shopping alleyways (Vendors Plaza, International Plaza) to Main Street. Continue up the hill via Government Hill Road or any of the side staircases — the 99 Steps are on Government Hill — to reach Blackbeard's Castle at the top. The full loop takes about two hours at an easy pace, not including shopping stops. The hillside portions are steep and exposed to sun; go early or bring water.