Oranjestad, St. Eustatius, is the island's capital and only town. It is possible to leisurely walk the entire town in one day. Orangestad (or Orange City) consists of Lower Town, which is on the water, and Upper Town, which sits atop a cliff.
Begin your sightseeing at the St. Eustatius Historical Foundation Museum in Upper Town, which relates the fascinating history of the island. The museum is housed in the Simon Doncker House, where British Admiral George Rodney stayed after invading the island in 1781. Plan to spend at least an hour at the museum, which—given the island's history—is one of the most engrossing in the Caribbean. You'll see luxurious furniture and fine china used by wealthy European ship captains, as well as the more humble relics of the Salanoids, Statia's original pre-Columbian inhabitants.
Pause to admire the view from Fort Oranje, which was built in 1636 on the site of an earlier French fortification. It still holds giant cannons, and the courtyard has several memorial plaques—look for the one that U.S. President Franklin D. Roosevelt presented to commemorate Statia as the first foreign land to recognize the U.S. Declaration of Independence. The tourist office is also at the fort: Be sure to pick up the Walking Tour Guide, which details a self-guided tour of Oranjestad that includes many old buildings that have been renovated.
Among the sights is Honen Dalim. Said to be on of the oldest synagogues in the Western Hemisphere, it was built in 1739 but is now in ruins (http://www.statiasynagogueproject.org). The Dutch Reformed Church, just a block from the main square, is even less intact thanks to hurricane damage. The church was built in 1774, mainly from hand-hewn rocks and yellow and red ballast bricks. Restoration is ongoing.
Take a few minutes to explore the cemeteries of both the synagogue and the church. Legend has it that Statians hid their valuables in coffins and buried them in the Dutch Reformed Church cemetery during Admiral Rodney's raid. As the story goes, islanders were foiled when Rodney noticed the unusual number of recent burials and ordered the graves to be opened. Read the old epitaphs for a glimpse into the past—if you can. When we were there, the goats lounging on the cool stones made it a bit difficult.
To get from Upper Town to Lower Town, you can walk down the stone-walled Bay Path (also known as Old Slave Road), which offers fabulous views but can be slippery on rainy days, so wear appropriate shoes. The ruins of warehouses and other old buildings in Lower Town continue for about 1 mi/1.6 km along the water in a parklike setting. They give an idea of what this bustling trade center was like in the 1700s, when there were hundreds of warehouses, taverns, shops and homes in the area.
Recent improvements to warehouses and buildings have created a more desirable neighborhood with cafes, restaurants and shops. A maritime museum is located in the original customs house, in cooperation with several U.S. universities' underwater archaeology departments.
There are more historic sites outside of Oranjestad. The remains of 19 fortresses and batteries mark old defense posts around the island. Do explore some of them if you have time—either hire a taxi for the day or engage the services of a local historical-tour guide.
Two of the town's highlights are Fort de Windt and Fort Amsterdam. Fort de Windt (circa 1753-1775) offers spectacular views of St. Kitts and Nevis, islands to the south. It's located at the end of the road called Weg Naar White Wall. Fort Amsterdam (more correctly called Concordia Battery) is poised on a cliff overlooking Great Bay on the eastern side of the island. Historians believe this fort was built in 1781, after the French recaptured the island from the English.
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