Rolling out on the Niña, Pinta and Santa Maria with 90 men and fame and fortune on the brain, Christopher Columbus sailed off in 1492 to find the New World. The trip was fraught with illness, death, near-mutiny and some serious technical difficulties. Oh, and the fact that the world he found wasn’t new. People had been living there since long before his ships arrived.

Columbus’s journey was mainly about finding a new trade route to Asia, but his financiers back in Europe didn’t frown on imperialism. It took him and his crew seven months to launch from Spain, make a pit stop in the Canary Islands off the coast of Africa, cross the Atlantic, wind around the Caribbean and then sail back home. On the occasion of Columbus Day, Playboy wanted to know how the contemporary traveler could reenact the explorer’s journey, sans plundering, of course. While telling the tale of Columbus’s voyage, we’ve created an itinerary that traces his path, finding ample natural beauty and culture to experience along the way—and accomplishing the trip in less than three weeks instead of seven months.

Columbus’s Crew:
Spanish royals Isabella and Ferdinand, still giddy from conquering Granada and reclaiming their country from the Moors, agreed to finance Columbus’s pursuit of a transatlantic trade route to Asia in April 1492. Columbus had shopped the idea to European royal courts for a decade, appealing to England, France and Portugal. Wanting to catch up with their Iberian neighbor’s colonial reach, the Spanish king and queen agreed to co-fund Columbus’s gambit in hopes of conquering new land. They agreed to pay Columbus one-tenth of all the gold, spices and other booty he recovered on his journey. Before departure Columbus spent months around Huelva, gathering crew and supplies. Eventually, on August 3, he launched from Palos de la Frontera on the southeastern edge of Spain.


Modern Explorer: No longer a bustling port, contemporary Palos is small and lovely to look at, with medieval architecture and beautiful gardens. Today, the attractions are a little heavy on Columbus hero worship. Paintings, statues and museums devoted to the guy litter the region, like the statue pictured above, situated on the Wharf of the Caravels. The wharf also includes full-size replicas of the Niña, Pinta and Santa Maria. Before leaving, visit the 14th century church of San Jorge and see the monolith inscribed with the names of the town’s 70 sailors who traveled with Columbus, then prepare for departure. But instead of launching from Palos, as Columbus did, head to nearby Huelva, where a cruise ship awaits.

Columbus’s Crew (seven days en route):
Columbus always intended to stop in the Canary Islands before heading west; he just didn’t expect to get stuck there for so long. The island of La Gomera was an ideal launch point to cross the Atlantic. It was under Spanish control, close to the Southern trade winds and full of natural resources for stocking up. However, the ships needed extensive repairs and the winds didn’t cooperate, so they languished for a month. On September 8, Columbus noted in his diary, “At three o’clock this morning, the NE wind began to blow, and I set my course to the west.”


Modern Explorer (28 hours en route): Seafaring accommodations in 2013 are slightly better than in Columbus’s day. Naviera Armas’s cruise ship from Huelva to the Canary Islands features a swimming pool, a store for supplies and several restaurants to stave off scurvy. Once the ship reaches the islands, hop a ferry to La Gomera, “the Whistling Island,” so named for how the local children speak to one another from miles apart. In a language passed down for centuries, the Gomerans communicate through a series of whistles, using the rocky ravine-filled landscape as a microphone. Trek into the island’s jungles on an open-top jeep tour, and listen for the secret language of the locals.

Columbus’s Crew (37 days en route):
Captaining the Santa Maria, Columbus guided the three ships across the Atlantic. Along the way they saw shooting stars, killed a porpoise with a harpoon, got slowed by a tangle of weeds, had multiple false sightings of land and fended off a mutiny. As days wore on, some of the crew began to turn on Columbus because they feared they’d never find land. They plotted to throw him overboard if he didn’t turn back toward home. On October 10, he made a deal with the crew that they’d travel only a few days further before turning around. It was a deal he didn’t have to worry about following through on. On October 12, after sailing more than 3,000 nautical miles, they made landfall, and Columbus named the island San Salvador. He searched the islands for gold to bring back to the royals but found only trinkets worn by villagers. Hoping to find pearls and gold, on October 27 he left for what the natives called Cuba, though he believed it was Japan.

Modern Explorer (35 hours en route): In his journals, Columbus wrote that upon losing sight of land on the first full day of sailing from La Gomera, men openly wept. He had to console them with promises of riches and land at their destination. The prospect of 35 hours of flying from airport to airport may make the present-day traveler just as emotional. The reward for today’s trip is not riches but a beach paradise. (Unfortunately, no direct flight is available. Expect layovers in Madrid, Miami and Nassau before finally landing on the island.) San Salvador, also known as Columbus Isle, is a diving and fishing mecca. Check in to the Riding Rock Resort, which features more than 50 dive sites and miles of deserted white beaches for you to lazily conquer. But don’t just colonize the beach, take control of the water too. The resort offers specialty courses that include deep sea diving, search and salvage, and a general diving class.

Columbus’s Crew (one day en route):
Maybe the natives of San Salvador just wanted Columbus out of their hair when they promised him gold awaited in Cuba. Unfortunately for Columbus, there was barely any to be found. However, he loved the natural beauty of the island and discovered tobacco there. But Cuba is where the expedition began to fracture. On November 21, the Pinta, captained by Martín Alonso Pinzón, separated from the other ships against Columbus’s orders and traveled east, exploring the Inaqua, Caicos and Grand Turk islands. Although Columbus had always commended Pinzón for his competence, animosity between the two seems to have arisen. Pinzón decided to leave the expedition, thinking he could better find gold on his own.


Modern Explorer (two hours en route, plus the hassle of sneaking in): For U.S. citizens, pesky politics have kept Cuba off-limits for far too long, but visiting isn’t impossible. Flying in from Nassau to Havana using circumvents most of the difficulties related to visiting the embargoed country. However, American visitors must purchase temporary medical insurance unless they have coverage from somewhere other than the U.S. Arriving in Havana, you may think the plane from Nassau was a time machine. The old Buicks and Plymouths, brought to the island before the revolution, make the place look like it’s stuck in the 1950s. Even so, the culture in Cuba is still vital, and the communist restrictions are easing, allowing for more privately owned restaurants to open. Get immersed in Havana’s best nightlife and head to the downtown Vedado district. For Rat Pack era exploits, visit El Gato Tuerto (the One-Eyed Cat), a slick café and bar that offers live music, mostly jazz trios and quartets with singers performing Latin classics into the wee hours of the morning.

Columbus’s Crew (one day en route):
Columbus tooled around Cuba for nearly a month in search of riches, but found few. The native Tainos told him about a fierce tribe of cannibals on a nearby island whom the Cubans greatly feared. Columbus chalked the rumors up to cowardice and embarked for Hispaniola anyway, landing on the northern shore of what is now Haiti. While exploring Haiti’s coast on Christmas Eve, Columbus’s ship, the Santa Maria, ran aground and wrecked. He ordered the men on the ship to stay on the island and establish a Spanish colony. When he returned to Haiti on his second voyage the following year, he found all the men he’d left behind were dead.


Modern Traveler (five hours en route): Haiti’s lush forests, jagged mountains and beautiful ruins make it a great hiking destination. In fact, the translation of the Creole Ayiti is “land of high mountains.” However, social unrest makes it advisable to use a tour guide. Hiking Haiti offers mountain biking, horseback riding and treks ranging from easy walks to challenging 10-hour hikes. One of the best spots to traverse is about 160 miles north of Port-au-Prince. Built in the early 19th century, Sans-Souci Palace was home to the first monarch of an independent Haiti, King Henri Christophe. Built in the wake of the slave rebellion that gave Haiti its independence, the palace is now a ruin that in 1982 UNESCO declared a World Heritage Site.

Columbus’s Crew (47 days en route):
Though Pinzón had deserted Columbus back in November, the Pinta and the Niña unexpectedly reunited off the coast of modern-day Dominican Republic on January 6. Ten days later, they departed from Hispaniola to head home. A massive storm in the Atlantic separated the two again, with Columbus coming ashore in the Azores briefly and then landing in Lisbon on March 4 to repair his boat for a return to Spain. He arrived in Barcelona on March 15, and Spain greeted him as a hero. He would make three subsequent voyages, setting off a wave of colonization by European powers. And while Spanish explorers carried disease that wiped out native populations, modern epidemiologists believe they returned the favor, sending syphilis back with Columbus.


Modern Traveler (14 hours en route): In an ideal world, a return to Europe syphilis-free takes half a day by plane instead of nearly two months. But the journey isn’t complete. Check out a building Columbus himself may have visited in 1493. Perched atop the hill that overlooks the city is the Castle of São Jorge, which dates back to the sixth century. Climb one of the castle’s towers, stroll around the ramparts and take in a sweeping view of Lisbon below. Now it’s time to relax after a long journey, at the Altis Belem Hotel & Spa. Situated on the water, this hotel with an ultra-modern, minimalist aesthetic boasts five-star amenities, a heated pool and a Michelin-starred restaurant. Had Columbus had access to such luxury, he probably would have thought twice about setting out for the New World again.

This article was originally published on Playboy for iPhone. For more exclusive content and the best articles from the latest issue of Playboy, download the app in the iTunes Store.


Photos by Edward the Confessor/Wikimedia Commons (ships); Marcin Polak/Flickr (Columbus statue); Till Krich/Flickr (Canary Islands); © Stephen Frink Collection/Alamy (San Salvador diving); Tony Hisgett/Flickr (Havana); Remi Kaupp/Flickr (Sans-Souci Palace); fulviusbsas/Wikimedia Commons (Castle of São Jorge)