Look beyond the pricey shops, T-shirt vendors, and bustling crowds for a glimpse of the island's history. The city served as the capital of Denmark's outpost in the Caribbean until 1917, an aspect of the island often lost in the glitz of the shopping district.
Emancipation Gardens, right next to the fort, is a good place to start a walking tour. Tackle the hilly part of town first: head north up Government Hill to the historic buildings that house government offices and have incredible views. Several regal churches line the route that runs west back to the town proper and the old-time market. Virtually all the alleyways that intersect Main Street lead to eateries that serve frosty drinks, sandwiches, and West Indian fare. There are public restrooms in this area, too. Allow an hour for a quick view of the sights.
A note about the street names: in deference to the island's heritage, the streets downtown are labeled by their Danish names. Locals will use both the Danish name and the English name (such as Dronningens Gade and Norre Gade for Main Street), but most people refer to things by their location ("a block toward the Waterfront off Main Street" or "next to the Little Switzerland Shop"). You may find it more useful if you ask for directions by shop names or landmarks.
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Windward Passage Hotel
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