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When colonists arrived in Madeira in July 1419, the valley they settled in was a mass of bright yellow fennel, or funcho in Portuguese. Today the bucolic fields are gone, and the community that replaced them is the self-governing island's bustling business and political center. Funchal is the only town of any size on the island and the base for the bulk of its tourism thanks to the plethora of hotels, restaurants, bars, cafés, phenomenal coastal and hillside views, and—of course—Madeira wine.

Despite the tropical vegetation, Funchal’s center feels decidedly Portuguese, though there's a heavy British influence, which is a holdover from the mid-16th-century marriage of the Portuguese Princess Catherine of Bragança to England's King Charles II. The marriage contract gave the English the right to live on Madeira, plus valuable trade concessions. Charles in turn gave Madeirans an exclusive franchise to sell wine to England and its colonies. The island's wine boom lured many British families to Funchal, and many blue-blooded Europeans and famous vacationers such as George Bernard Shaw and Winston Churchill followed the pack to enjoy the mild winters.

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