Day 1 Fort Lauderdale, Florida, United States

Like many southeast Florida neighbors, Fort Lauderdale has long been revitalizing. In a state where gaudy tourist zones often stand aloof from workaday downtowns, Fort Lauderdale exhibits consistency at both ends of the 2-mile Las Olas corridor. The sparkling look results from upgrades both downtown and on the beachfront. Matching the downtown's innovative arts district, cafés, and boutiques is an equally inventive beach area, with hotels, cafés, and shops facing an undeveloped shoreline, and new resort-style hotels replacing faded icons of yesteryear. Despite wariness of pretentious overdevelopment, city leaders have allowed a striking number of glittering high-rises. Nostalgic locals and frequent visitors fret over the diminishing vision of sailboats bobbing in waters near downtown; however, Fort Lauderdale remains the yachting capital of the world, and the water toys don't seem to be going anywhere.

Day 4 Saint Thomas, U.S. Virgin Islands

If you fly to the 32-square-mile (83-square-km) island of St. Thomas, you land at its western end; if you arrive by cruise ship, you come into one of the world's most beautiful harbors. Either way, one of your first sights is the town of Charlotte Amalie. From the harbor you see an idyllic-looking village that spreads into the lower hills. If you were expecting a quiet hamlet with its inhabitants hanging out under palm trees, you've missed that era by about 300 years. Although other islands in the USVI developed plantation economies, St. Thomas cultivated its harbor, and it became a thriving seaport soon after it was settled by the Danish in the 1600s. The success of the naturally perfect harbor was enhanced by the fact that the Danes—who ruled St. Thomas with only a couple of short interruptions from 1666 to 1917—avoided involvement in some 100 years' worth of European wars. Denmark was the only European country with colonies in the Caribbean to stay neutral during the War of the Spanish Succession in the early 1700s. Thus, products of the Dutch, English, and French islands—sugar, cotton, and indigo—were traded through Charlotte Amalie, along with the regular shipments of slaves. When the Spanish wars ended, trade fell off, but by the end of the 1700s Europe was at war again, Denmark again remained neutral, and St. Thomas continued to prosper. Even into the 1800s, while the economies of St. Croix and St. John foundered with the market for sugarcane, St. Thomas's economy remained vigorous. This prosperity led to the development of shipyards, a well-organized banking system, and a large merchant class. In 1845 Charlotte Amalie had 101 large importing houses owned by the English, French, Germans, Haitians, Spaniards, Americans, Sephardim, and Danes. Charlotte Amalie is still one of the world's most active cruise-ship ports. On almost any day at least one and sometimes as many as eight cruise ships are tied to the docks or anchored outside the harbor. Gently rocking in the shadows of these giant floating hotels are just about every other kind of vessel imaginable: sleek sailing catamarans that will take you on a sunset cruise complete with rum punch and a Jimmy Buffett soundtrack, private megayachts for billionaires, and barnacle-bottom sloops—with laundry draped over the lifelines—that are home to world-cruising gypsies. Huge container ships pull up in Sub Base, west of the harbor, bringing in everything from breakfast cereals to tires. Anchored right along the waterfront are down-island barges that ply the waters between the Greater Antilles and the Leeward Islands, transporting goods such as refrigerators, VCRs, and disposable diapers. The waterfront road through Charlotte Amalie was once part of the harbor. Before it was filled in to build the highway, the beach came right up to the back door of the warehouses that now line the thoroughfare. Two hundred years ago those warehouses were filled with indigo, tobacco, and cotton. Today the stone buildings house silk, crystal, and diamonds. Exotic fragrances are still traded, but by island beauty queens in air-conditioned perfume palaces instead of through open market stalls. The pirates of old used St. Thomas as a base from which to raid merchant ships of every nation, though they were particularly fond of the gold- and silver-laden treasure ships heading to Spain. Pirates are still around, but today's versions use St. Thomas as a drop-off for their contraband: illegal immigrants and drugs. To explore outside Charlotte Amalie, rent a car or hire a taxi. Your rental car should come with a good map; if not, pick up the pocket-size "St. Thomas–St. John Road Map" at a tourist information center. Roads are marked with route numbers, but they're confusing and seem to switch numbers suddenly. Roads are also identified by signs bearing the St. Thomas–St. John Hotel and Tourism Association's mascot, Tommy the Starfish. More than 100 of these color-coded signs line the island's main routes. Orange signs trace the route from the airport to Red Hook, green signs identify the road from town to Magens Bay, Tommy's face on a yellow background points from Mafolie to Crown Bay through the north side, red signs lead from Smith Bay to Four Corners via Skyline Drive, and blue signs mark the route from the cruise-ship dock at Havensight to Red Hook. These color-coded routes are not marked on most visitor maps, however. Allow yourself a day to explore, especially if you want to stop to take pictures or to enjoy a light bite or refreshing swim. Most gas stations are on the island's more populated eastern end, so fill up before heading to the north side. And remember to drive on the left!

Day 5 Antigua, Antigua and Barbuda

Day 6 Tortola, British Virgin Islands

The bustling capital of the BVI looks out over Road Harbour. It takes only an hour or so to stroll down Main Street and along the waterfront, checking out the traditional West Indian buildings painted in pastel colors and with corrugated-tin roofs, bright shutters, and delicate fretwork trim. For sightseeing brochures and the latest information on everything from taxi rates to ferry schedules, stop in at the BVI Tourist Board office. Or just choose a seat on one of the benches in Sir Olva Georges Square, on Waterfront Drive, and watch the people come and go from the ferry dock and customs office across the street.

Day 7 San Juan (Puerto Rico), Puerto Rico

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.

Day 9 Half Moon Cay, Bahamas

The Half Moon Caye is a natural monument situated at the southeast corner of Lighthouse Reef Atoll. The crescent-shaped caye is a protected marine reserve that was established as a World Heritage Site in 1996. The pristine caye has breath-taking walk-in snorkelling from the beach, idyllic sandy beaches and magnificent wildlife both in the sea and within the littoral forest.

Day 10 Fort Lauderdale, Florida, United States

Like many southeast Florida neighbors, Fort Lauderdale has long been revitalizing. In a state where gaudy tourist zones often stand aloof from workaday downtowns, Fort Lauderdale exhibits consistency at both ends of the 2-mile Las Olas corridor. The sparkling look results from upgrades both downtown and on the beachfront. Matching the downtown's innovative arts district, cafés, and boutiques is an equally inventive beach area, with hotels, cafés, and shops facing an undeveloped shoreline, and new resort-style hotels replacing faded icons of yesteryear. Despite wariness of pretentious overdevelopment, city leaders have allowed a striking number of glittering high-rises. Nostalgic locals and frequent visitors fret over the diminishing vision of sailboats bobbing in waters near downtown; however, Fort Lauderdale remains the yachting capital of the world, and the water toys don't seem to be going anywhere.

Day 13 Cartagena, Colombia

Cartagena's magnificent city walls and fortresses, now a UNESCO World Heritage Site, enclose a well-restored historic center (the Cuidad Amurallada, or walled city) with plazas, churches, museums, and shops that have made it a lively coastal vacation spot for South Americans and others. New hotels and restaurants make the walled city a desirable place to stay, and the formerly down-at-the-heels Getsemaní neighborhood attracts those seeking a bohemian buzz. The historic center is a small section of Cartagena; many hotels are in the Bocagrande district, an elongated peninsula where high-rise hotels overlook a long, gray-sand beach.When it was founded in 1533 by Spanish conquistador Pedro de Heredia, Cartagena was the only port on the South American mainland. Gold and silver looted from indigenous peoples passed through here en route to Spain and attracted pirates, including Sir Francis Drake, who in 1586 torched 200 buildings. Cartagena's walls protected the city's riches as well as the New World's most important African slave market.

Day 14 Fuerte Amador, Panama

Day 15 Fuerte Amador, Panama

Day 17 Puntarenas, Costa Rica

This town is not on the Nicoya Peninsula, but rather on Costa Rica's mainland. It is best known as a cruise-ship port and launching pad for ferries heading southeast to the coast of the Nicoya Peninsula and for cruises sailing out on the Gulf of Nicoya. Puntarenas is also a major fishing port with a lively fish market. The town's reputation suffers from the unimpressive parts you see from your car as you roll through town on the way to the ferry dock. But the town has a lot of character off the main drag, thanks to its illustrious past as an affluent port town and principal vacation spot for San José's wealthy, who arrived by train in the last century. Once the port was moved and roads opened to other beaches, Puntarenas's economy crashed, but it's making a comeback. Sitting on a narrow spit of sand—punta de arenas literally means "point of sand"—that protrudes into the Gulf of Nicoya, the town boasts a beautifully groomed, wide Blue Flag beach with views of the Nicoya Peninsula and spectacular sunsets, along with a public swimming pool, the San Lucas Beach Club, and a marine-life museum. Ticos arrive by bus and car to enjoy the beach and stroll the Paseo de los Turistas, a beachfront promenade lined with tree-shaded concrete benches and seafood restaurants. Crowds of locals, called porteños, cruise by on bicycles, the town's most popular form of transport.

Day 19 Acajutla, El Salvador

Day 20 Puerto Quetzal, Guatemala

Puerto Quetzal is Guatemala's largest Pacific Ocean port. It is important for both cargo traffic and as a stop-off point for cruise liners

Day 21 Puerto Chiapas, Mexico

Day 23 Manzanillo, Mexico, Mexico

Day 24 Puerto Vallarta, Mexico

Puerto Vallarta is a resort town on Mexico's Pacific coast, in Jalisco state. It is known for its beaches, water sports and nightlife scene. Its cobblestone center is home to the ornate Nuestra Señora de Guadalupe church, boutique shops and a range of restaurants and bars. El Malecón is a beachside promenade with contemporary sculptures, as well as bars, lounges and nightclubs.

Day 27 San Diego, California, United States

San Diego is a vacationer's paradise, with year-round temperatures in the seventies and near-constant sunshine. One of America's most family-friendly cities, San Diego is home to LEGOLAND, the New Children's Museum, and the famous San Diego Zoo. Sunbathers and surfers are guaranteed to find their perfect beach, and foodies find delights in artisanal breweries, local bistros, and gourmet restaurants. From the Broadway excitement of La Jolla Playhouse to the European feel of Little Italy to the nouveau-chic of the Gaslamp Quarter, San Diego has something for everyone.

Day 29 San Francisco, California, United States

With its myriad hills and spectacular bay, San Francisco beguiles with natural beauty, vibrant neighborhoods, and contagious energy. From the hipster Mission District to the sassy Castro, from bustling Union Square to enduring Chinatown, this dynamic town thrives on variety. The city makes it wonderfully easy to tap into the good life, too: between San Francisco's hot arts scene, tempting boutiques, parks perfect for jogging or biking, and all those stellar locavore restaurants and cocktail bars, it's the ultimate destination for relaxed self-indulgence.

Day 32 Vancouver, British Columbia, Canada

Vancouver is a delicious juxtaposition of urban sophistication and on-your-doorstep wilderness adventure. The mountains and seascape make the city an outdoor playground for hiking, skiing, kayaking, cycling, and sailing—and so much more—while the cuisine and arts scenes are equally diverse, reflecting the makeup of Vancouver's ethnic (predominantly Asian) mosaic. Vancouver is consistently ranked as one of the world's most livable cities, and it's easy for visitors to see why. It's beautiful, it's outdoorsy, and there's a laidback West Coast vibe. On the one hand, there's easy access to a variety of outdoor activities, a fabulous variety of beaches, and amazing parks. At the same time, the city has a multicultural vitality and cosmopolitan flair. The attraction is as much in the range of food choices—the fresh seafood and local produce are some of North America's best—as it is in the museums, shopping, and nightlife.Vancouver's landscaping also adds to the city's walking appeal. In spring, flowerbeds spill over with tulips and daffodils while sea breezes scatter scented cherry blossoms throughout Downtown; in summer office workers take to the beaches, parks, and urban courtyards for picnic lunches and laptop meetings. More than 8 million visitors each year come to Vancouver, Canada's third-largest metropolitan area. Because of its peninsula location, traffic flow is a contentious issue. Thankfully, Vancouver is wonderfully walkable, especially in the downtown core. The North Shore is a scoot across the harbor, and the rapid-transit system to Richmond and the airport means that staying in the more affordable 'burbs doesn't have to be synonymous with sacrificing convenience. The mild climate, exquisite natural scenery, and relaxed outdoor lifestyle keep attracting residents, and the number of visitors is increasing for the same reasons. People often get their first glimpse of Vancouver when catching an Alaskan cruise, and many return at some point to spend more time here.