Day 1 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 2 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 5 Cabo San Lucas, Mexico

Cabo San Lucas, a resort city on the southern tip of Mexico's Baja California peninsula, is known for its beaches, water-based activities and nightlife. Playa El Médano is Cabo's main beach, with outdoor restaurants and numerous bars. Past the marina is Land's End promontory, site of Playa del Amor (Lover's Beach) and El Arco, a natural archway in the seacliffs.

Day 10 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 12 Panama City, Panama

Expect incredible morning views as you arrive into the port for Panama City. Tinged with a silver pre-dawn light, the city will metamorphosise into a golden glow as the sun rises above it. And from then on expect one stunning view after another. Very interesting in its own right, Fuerte Amador is obviously overshadowed by its proximity to Panama City. So should the Miraflores museum of the Canal, which offers a comprehensive and immersive tour of the Canal including a 3-D experience, four exhibition halls, an observation deck, and a surprisingly good restaurant not interest you then there is always the option of lovely Casco Viejo – literally the old quartier of Panama. The grand old colonial houses, cobbled streets, independent boutiques and buzzing street scene make this a must stop on your itinerary. And if you like seafood, you will not want miss the many restaurants and market stalls serving different variations of so-fresh-it's-still-practically-swimming ceviche. Best eaten like the Panamanians do, with salty crackers and a cold beer on the beach. And if money is no object, a cup of geisha coffee – supposedly the world's best and definitely the world's most expensive at $7 a shot is definitely a pick me up! Cool cosmopolitan capital aside, Panama has a skyscraper filled skyline that is worthy of some of its North American counterparts. But if urban utopia is not your scene then fear not, the sandy beaches and lush rainforests are never more than a short cab ride away.

Day 15 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 19 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 22 Samaná, Dominican Republic

Samaná (pronounced sah-mah-NAH) is a dramatically beautiful peninsula, like an island unto itself, of coconut trees stretching into the sea. It's something of a microcosm of the Dominican Republic: here you'll see poverty and fancy resorts, brand-new highways as well as bad roads, verdant mountainsides, tropical forests, tiny villages lined with street-side fruit vendors, secluded beaches, and the radiant warmth of the Dominican people. Samaná is the name of both the peninsula and its biggest town, as well as the bay to the south. It's worth noting that to locals, Samaná denotes only the largest town, Santa Bárbara de Samaná, which makes a great departure point for whale-watching or an excursion to Los Haitises Park across the bay. The bay is home to some of the world's best whale-watching from mid-January to late March. It is now the site of Puerto Bahia Marina and Residences and the Bannister Hotel, contemporary, luxurious yet moderately priced. This complex has brought an entirely new level of tourism to this area, and given yachts a full-service facility in what has always been a desirable cruising destination.A visit here is really about two things: exploring the preserved natural wonders and relaxing at a small beachfront hotel. The latter is most readily accomplished in Las Terrenas, the only true tourist center, where you can find picturesque restaurants, accommodations of all types (including the new oceanfront Sublime Samaná and the luxury condo-hotel, Balcones del Atlantico), and great beaches. At Las Terrenas you can enjoy peaceful playas, take advantage of the vibrant nightlife, and make all your plans for expeditions on the peninsula. The other pleasures are solitary—quiet beaches, the massive national park Los Haitises, and water sports and hiking. A relatively new toll road connects Santo Domingo to the peninsula; it's about a 2- to 2½-hour drive. Small El Catey International Airport is near Las Terrenas and is now being served by twice-weekly JetBlue flights (Wednesday and Saturday). On the Dominican Republic's Samaná Peninsula, the green mountains teem with coconut trees and dramatic vistas of the ocean. The area is full of hidden beaches reachable only on foot or by sea, protected coves, and undeveloped bays. A visit to Samaná is really about two things: exploring its preserved natural wonders and relaxing on the beach. There are a number of all-inclusive resorts where you can hang your hat, quaint and low-key beachfront hotels, as well as new world-class properties, where you can find complete relaxation and tranquillity.

Day 24 Oranjestad, Aruba

Aruba's capital is easily explored on foot. Its palm-lined central thoroughfare runs between old and new pastel-painted buildings of typical Dutch design (Spanish influence is also evident in some of the architecture). There are a lot of malls with boutiques and shops—the Renaissance mall carries high-end luxury items and designer fashions. A massive renovation in downtown has given Main Street (a.k.a. Caya G. F. Betico Croes) behind the Renaissance Resort a whole new lease on life: boutique malls, shops, and restaurants have opened next to well-loved family-run businesses. The pedestrian-only walkway and resting areas have unclogged the street, and the new eco-trolley is free and a great way to get around. At this writing, Linear Park was well and will showcase local merchants and artists. There will be activities along a boardwalk that will eventually run all the way to the end of Palm Beach, making it the longest of its kind in the Caribbean.

Day 26 Gustavia, Saint Barthélemy

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.

Day 27 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 30 Hamilton, Bermuda

With a permanent resident population of 1,500 households, Hamilton doesn't qualify as a major metropolis. Yet it has enough stores, restaurants, and offices to amp up the island's energy level. Moreover, it has a thriving international business community (centered on financial and investment services, insurance, telecommunications, global management of intellectual property, shipping, and aircraft and ship registration), which lends it a degree of sophistication seldom found in so small a center. The central parishes cover the large area of Paget, Warwick, and Devonshire. These parishes are much sleepier than Hamilton and provide great nature and beach respites when you tire of city life. Convenient bus and ferry connections connect the parishes, so trips outside of Hamilton are easy and a fun way to get off the tourist track.

Day 31 Hamilton, Bermuda

With a permanent resident population of 1,500 households, Hamilton doesn't qualify as a major metropolis. Yet it has enough stores, restaurants, and offices to amp up the island's energy level. Moreover, it has a thriving international business community (centered on financial and investment services, insurance, telecommunications, global management of intellectual property, shipping, and aircraft and ship registration), which lends it a degree of sophistication seldom found in so small a center. The central parishes cover the large area of Paget, Warwick, and Devonshire. These parishes are much sleepier than Hamilton and provide great nature and beach respites when you tire of city life. Convenient bus and ferry connections connect the parishes, so trips outside of Hamilton are easy and a fun way to get off the tourist track.

Day 33 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 34 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.