Day 1 New York, New York, United States

From Wall Street's skyscrapers to the neon of Times Square to Central Park's leafy paths, New York City pulses with an irrepressible energy. History meets hipness in this global center of entertainment, fashion, media, and finance. World-class museums like MoMA and unforgettable icons like the Statue of Liberty beckon, but discovering the subtler strains of New York's vast ambition is equally rewarding: ethnic enclaves and shops, historic streets of dignified brownstones, and trendy bars and eateries all add to the urban buzz.

Day 4 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 5 Philipsburg, Sint Maarten (Dutch part)

The capital of Dutch St. Maarten stretches about a mile (1½ km) along an isthmus between Great Bay and the Salt Pond and has five parallel streets. Most of the village's dozens of shops and restaurants are on Front Street, narrow and cobblestone, closest to Great Bay. It's generally congested when cruise ships are in port, because of its many duty-free shops and several casinos. Little lanes called steegjes connect Front Street with Back Street, which has fewer shops and considerably less congestion. Along the beach is a ½-mile-long (1-km-long) boardwalk with restaurants and several Wi-Fi hot spots.Wathey Square (pronounced watty) is in the heart of the village. Directly across from the square are the town hall and the courthouse, in a striking white building with cupola. The structure was built in 1793 and has served as the commander's home, a fire station, a jail, and a post office. The streets surrounding the square are lined with hotels, duty-free shops, restaurants, and cafés. The Captain Hodge Pier, just off the square, is a good spot to view Great Bay and the beach that stretches alongside.

Day 6 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 7 Road Town, Tortola, British Virgin Islands

Day 8 Puerto Plata, Dominican Republic

San Felipe de Puerto Plata is the capital of the Puerto Plata province on the Dominican Republic's Atlantic north coast. The city is best known for its beaches. Playa Dorada's lengthy beachfront is backed by resorts and an 18-hole golf course. The city's old colonial-era center is dominated by the 16th-century Fortaleza San Felipe, a Spanish fortress that now houses historical and military artifacts.

Day 11 New York, New York, United States

From Wall Street's skyscrapers to the neon of Times Square to Central Park's leafy paths, New York City pulses with an irrepressible energy. History meets hipness in this global center of entertainment, fashion, media, and finance. World-class museums like MoMA and unforgettable icons like the Statue of Liberty beckon, but discovering the subtler strains of New York's vast ambition is equally rewarding: ethnic enclaves and shops, historic streets of dignified brownstones, and trendy bars and eateries all add to the urban buzz.