Charlotte Amalie is one of the most walkable capitals in the Caribbean. Within a few blocks of the waterfront you have centuries of Danish colonial history, the best duty-free shopping in the region, and one of the most remarkable hilltop views in the islands.

This is a guide to doing it properly — on foot, at the right pace, in the right order.

Start at the waterfront

Begin at Fort Christian, the deep-red fortress at the water’s edge. Built in 1672, it’s the oldest standing structure in the U.S. Virgin Islands. Even if you don’t go in, a walk along its perimeter gives you the scale of what the Danes built here.

Main Street and the alleys

A block inland, Dronningens Gade — Main Street — runs parallel to the harbor. The duty-free shopping is genuine; the covered alleys branching off it (Royal Dane Mall, Palm Passage, A.H. Riise) are worth the detour. Give yourself 45 minutes here and resist spending the rest of your day in the shops.

Up the 99 Steps

A few blocks from Main Street, turn uphill. The 99 Steps — hand-cut Danish brick, probably 18th century — climb through a neighborhood that hasn’t changed much since the Danes left. The steps were built so soldiers could sprint from the harbor to the tower. You can take your time.

Blackbeard’s Castle

At the top of the steps, the Skytsborg tower has stood since 1679. The view from the top is the best reason to make the climb: the full harbor spread below, the islands in the distance, the cruise ships at anchor. Allow an hour on the property — the tower, the garden terraces, Jolly Roger’s for a drink before you head back down.