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If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiating out from the bay on the Atlantic Ocean that was discovered by Juan Ponce de León. More than a third of the island's nearly 4 million citizens proudly call themselves sanjuaneros. The city may be rooted in the past, but it has its eye on the future. Locals go about their business surrounded by colonial architecture and towering modern structures.
By 1508 the explorer Juan Ponce de León had established a colony in an area now known as Caparra, southeast of present-day San Juan. He later moved the settlement north to a more hospitable peninsular location. In 1521, after he became the first colonial governor, Ponce de León switched the name of the island—which was then called San Juan Bautista in honor of St. John the Baptist—with that of the settlement of Puerto Rico ("rich port").
Defended by the imposing Castillo San Felipe del Morro (El Morro) and Castillo San Cristóbal, Puerto Rico's administrative and population center remained firmly in Spain's hands until 1898, when it came under U.S. control after the Spanish-American War. Centuries of Spanish rule left an indelible imprint on the city, particularly in the walled area now known as Old San Juan. The area is filled with cobblestone streets and brightly painted, colonial-era structures, and its fortifications have been designated a UNESCO World Heritage Site.
Old San Juan is a monument to the past, but most of the rest of the city is planted firmly in the 21st century and draws migrants island-wide and from farther afield to jobs in its businesses and industries. The city captivates residents and visitors alike with its vibrant lifestyle as well as its balmy beaches, pulsing nightclubs, globe-spanning restaurants, and world-class museums. Once you set foot in this city, you may never want to leave.
You can easily explore all of Gustavia during a two-hour stroll. Some shops close from noon to 3 or 4, so plan lunch accordingly, but stores stay open past 7 in the evening. Parking in Gustavia is a challenge, especially during vacation times. A good spot to park is rue de la République, alongside the catamarans, yachts, and sailboats.
Antigua's capital, with some 45,000 inhabitants (approximately half the island's population), lies at sea level at the inland end of a sheltered northwestern bay. Although it has seen better days, a couple of notable historic sights and some good waterfront shopping areas make it worth a visit. At the far south end of town, where Market Street forks into Valley and All Saints roads, haggling goes on every Friday and Saturday, when locals jam the Public Market to buy and sell fruits, vegetables, fish, and spices. Ask before you aim a camera; your subject may expect a tip. This is old-time Caribbean shopping, a jambalaya of sights, sounds, and smells.
When colonists arrived in Madeira in July 1419, the valley they settled was a mass of bright yellow fennel, or funchal 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 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.
Spread over a string of seven hills north of the Rio Tejo (Tagus River) estuary, Lisbon presents an intriguing variety of faces to those who negotiate its switchback streets. In the oldest neighborhoods, stepped alleys whose street pattern dates back to Moorish times are lined with pastel-color houses decked with laundry; here and there, miradouros (vantage points) afford spectacular river or city views. In the grand 18th-century center, calçada à portuguesa (black-and-white mosaic cobblestone) sidewalks border wide boulevards. Elétricos (trams) clank through the streets, and blue-and-white azulejos (painted and glazed ceramic tiles) adorn churches, restaurants, and fountains.
Of course, parts of Lisbon lack charm. Even some downtown areas have lost their classic Portuguese appearance as the city has become more cosmopolitan: shiny office blocks have replaced some 19th- and 20th-century art nouveau buildings. And centenarian trams share the streets with "fast trams" and noisy automobiles.
Lisbon bears the mark of an incredible heritage with laid-back pride. In preparing to host the 1998 World Exposition, Lisbon spruced up public buildings, overhauled its subway system, and completed an impressive second bridge across the river. Today the former Expo site is an expansive riverfront development known as Parque das Nações, and the city is a popular port of call for cruises, whose passengers disembark onto a revitalized waterfront. Downtown, all the main squares have been overhauled one by one.
In its heyday in the 16th century, Lisbon was a pioneer of the first wave of globalization. Now, the empire is striking back, with Brazilians and people from the former Portuguese colonies in Africa enriching the city’s ethnic mix. There are also more than a few people from other European countries who are rapidly becoming integrated.
But Lisbon's intrinsic, slightly disorganized, one-of-a-kind charm hasn't vanished in the contemporary mix. Lisboetas (people from Lisbon) are at ease pulling up café chairs and perusing newspapers against any backdrop, whether it reflects the progress and commerce of today or the riches that once poured in from Asia, South America, and Africa. And quiet courtyards and sweeping viewpoints are never far away.
Despite rising prosperity (and costs) since Portugal entered the European Community in 1986, and the more recent tourism boom, prices for most goods and services are still lower than most other European countries. You can still find affordable places to eat and stay, and with distances between major sights fairly small, taxis are astonishingly cheap. All this means that Lisbon is not only a treasure chest of historical monuments, but also a place where you won’t use up all your own hard-earned treasure.
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