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We were offered the chance to visit Pompeii or Herculaneum when we docked at Sorrento. People rave about Pompeii because it’s absolutely huge and gives you a great sense of just how sophisticated Roman civilisation was. Herculaneum, by contrast, was a Roman seaside town, a sort of holiday resort, and doesn’t offer the same kind of scale. Still. I remembered my Latin lessons, and how we’d learned that while Pompeii’s buildings were smashed and burned by the falling volcanic ash, Herculaneum was actually preserved in the thick mud that engulfed it. And it’s true: wandering around the archaeological remains of the town, you feel like you’re in a place that’s only recently been abandoned. The wine shop (above) still has its amphorae stacked to the side, the houses have beautifully preserved frescoes and mosaics. What it lacks in size it more than makes up for in detail.

No matter how many postcards you’ve seen of Rome’s iconic Colosseum, you just don’t get it until you pass beneath its crumbling arches. Built by Emperor Vespasian in 72 C.E., the huge amphitheater held 50,000 spectators and marked its opening with 100 days of brutal spectacles like gladiator combat and animal fights. The Colosseum was in use for four centuries, and now you can tour the ruins. Walk through the Hypogeum, an intricate series of tunnels and elevators originally used to transport animals, slaves, and gladiators, to the performance above, or take a moonlit tour to have one of the world’s most storied structures all to yourself.

While it’s not in Mexico City proper, the sacred pre-Hispanic city of Teotihuacan is close enough–about 30 miles– for an easy day trip if you’re interested in architecture, archaeology, and indigenous history. The site’s primary structures, the Temple of Quetzalcoatl and the Pyramids of the Sun and the Moon, have been designated by UNESCO as World Heritage Sites, and it is possible to explore the pyramids–and even climb them–either independently or with a guide. After ascending nearly 250 steps on the Pyramid of the Sun, you’ll have a greater appreciation for these ancient structures and the civilization responsible for having built them. In addition to the pyramids, an on-site museum documents the history of the so-called “City of the Gods,” and displays archaeological finds, including pottery, bones, and other important objects.

The Castelo de São Jorge, is one of the Alfama neighborhood’s most historically significant monuments. Plan a visit late in the afternoon so that you can explore every nook and cranny and learn about the castle’s abundant history. Stay for golden hour so that you can capture the light as it dances on the castle walls, and later to watch the sunset dip below the horizon.

Mexico City has no dearth of luxurious boutique hotels, but Las Alcobas is a special option. Designed by famed firm Yabu Pushelberg, the hotel is full of gorgeous details, from hand-stitched leather wall coverings to a spiral staircase that surges up from the lobby. Upon arrival, guests enjoy a welcome drink as a bellman leads them to their room; explains the technology that controls the light, sound and temperature; and offers them a selection of handmade soaps. Once settled in, they can lounge in plush robes on their goose-down comforters while sampling snacks from the minibar. For a heartier meal, Las Alcobas offers two excellent restaurants. Just outside the hotel’s front door, there’s also Presidente Masaryk, Polanco’s main avenue full of restaurants and high-end boutiques.

Petra flourished more than 2,000 years ago, trading with Rome as an equal before being abandoned after a series of earthquakes in the 4th and 6th centuries C.E. It wasn’t until the 19th century, when European explorers “rediscovered” it, that the ancient city returned to the public consciousness. Now, visitors can walk down the narrow canyon of the siq to the city entrance—as dramatic an approach as any to a tourist attraction on the planet. The canyon opens up onto the carved facade of the Treasury, Petra’s most iconic site. From there, you can explore the cliffside tombs with their colorful bands of sandstone, the Street of Facades, and the amphitheater hewn from living rock. The ancient center lies some distance off, along with the splendid old Monastery, which sits at the top of a steep but rewarding climb. Consider buying a three-day ticket and visiting at different times of day to enjoy the changing light—early in the morning is best for the Treasury, while late afternoon is better for the Royal Tombs.

High above English Harbour in Nelson’s Dockyard National Park sits the Blockhouse, a brick ruin. On a perch overlooking the southeastern coast of Antigua, the circa-1787 site encompasses an officer’s quarters and those of servants, as well as stables. An ammunition-storage space, a catchment and a cistern have been restored in recent years.

Stretched out from the northwest corner of the island like a small arm, Pigeon Island is a historical landmark and a satisfying all-in-one nature, beach, and hiking escape minutes from Rodney Bay Marina. The 44-acre mountainous green plot is home to the preserved ruins of British military forts and garrisons; the Brits chased the Caribs out and used the islet to monitor French activity. Walk among the ruins, and hike up to the cannons of Fort Rodney, where the lookout point offers a breathtaking panoramic view of St. Lucia’s coastline and the sea below, dotted with sailboats. Hike down to the beach for a swim and a toast to history at Jambe de Bois, a restaurant on the water.

Swift streams and waterfalls continue to carve these vertiginous and rugged valleys as they pour into the sea. One of the most stunning wilderness areas on earth, it also contains ancient Hawaiian ruins of graves, temples, house platforms, and terraced fields. The fear factor increases past the initial two-mile path to Hanakāpīʻai Beach (best visited in summertime, as winter swells tend to wash it away). Only experienced hikers in good condition and with proper gear should venture further along the famous 11-mile Kalalau Trail. Check for path and park closures before making plans and don’t forget the $20/night permit to crash at a campsite. However long you trek, stay on the main path and pack out what you brought in.

Housed in a 1964 structure whose modern lines and central fountain greatly complement what’s on view, this anthropology museum is a repository of the most important pre-Hispanic treasures modern Mexico has discovered. The works are displayed in exhibits that trace the entire history of the Americas’ indigenous population, from the Bering migration to the present day. Exhaustive (and sometimes exhausting) in scope, many visitors choose to jump ahead to “greatest-hits” galleries focusing on name brands like the Aztecs (to see their misnamed calendar stone); the Maya and their artifacts; or the Olmec culture, famed for its colossal (and quite sensual) head sculptures dating back to Mesoamerica’s earliest recorded eras.

What do Al Capone and Bruce Willis have in common? They both did time here at Eastern State Penitentiary. (OK, Willis wasn’t an inmate, but he did shoot the film 12 Monkeys here.) The facility’s first inmate was brought through these doors in 1829, and the prison was in use until 1971. After closing, it became a target for vandals and housed a sizable colony of stray cats. Real estate developers proposed repurposing it as condominiums (high-security, of course), but preservationists won out. They raised funds to stabilize the crumbling interior and remove trees that were growing inside some cells. Wander through its stark interior and learn about the fascinating history of this unique site and its previous tenants, including Capone. Don’t miss the special art installations that are on display here all year round.

Just behind the Pantheon hides the church of Santa Maria Sopra Minerva, a gem in its own right. The only Gothic church in Rome’s center, it’s a breath of fresh air from over-the-top Baroque opulence. Plus, it has gorgeous frescoes by Filippo Lippi (an early Renaissance master), the body of Italy’s patron saint Catherine of Siena, the tomb of painter Fra Angelico, and a statue done—at least partly—by Michelangelo himself.

Take in views of a hot spring–fed waterfall, a dramatic ravine, and the Dead Sea from a resort that sits more than 800 feet below sea level. A cliff-top outdoor restaurant serves organic greens from the garden. Evason Ma’In, (800) 591-7480, from $300. This appeared in the December/January 2010 issue.

Considered the largest Roman city gate north of the Alps, the Porta Nigra has been designated a World Heritage Site.

The Palace of Holyroodhouse remains the official residence of Queen Elizabeth when she visits Scotland, and guided tours here include her public reception rooms in the main part of the pile. History buffs, however, will want to see the palace’s oldest section, where the personal assistant to Mary Queen of Scots was assassinated—a bit of skulduggery orchestrated by Mary’s husband, Lord Darnley. In adjacent rooms are exhibitions linking Mary to Queen Elizabeth I, while the grounds feature beautiful gardens and ruins of the original abbey.