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The city’s iconic wood-paneled Tram 28 rambles along a 4.3-mile route from Campo de Ourique to Praça Martim Moniz, navigating tight turns and steep inclines as it passes some of Lisbon’s most endearing attractions. Originally commissioned in the 1930s, these classic Remodelado trams were in fact enlisted for their ability to handle Lisbon’s hilly terrain. They can get painfully crowded—wait times can be outrageous in the high season—so catch an early ride (5:40 a.m. most weekdays, or 6:45 a.m. on Sundays) for unobstructed views of hilltop neighborhoods like Graça and the Alfama.

Graceful palms and lush gardens greet guests at Grotto Bay Beach Resort. Situated on 21 acres, this peaceful colony of cottage-style rooms overlooks the beautiful blue water of Bailey’s Bay in the Parish of Hamilton. Tangerine salt body scrubs, sweet milk and lavender facials, and hot stone massage will melt away all of the exertion of snorkeling excursions, golfing, exploring the resort’s on-site cave, or bicycling around the island. On the other hand, why not take it easy and lounge by the pool, which features a swim-up bar, or on one of the resorts private beaches. Dine among the island ambience of palms, rattan furnishings, and ceiling fans in the Hibiscus Room or Palm Court Dining Room. Afterwards, you can enjoy drinks and tropical breezes on the terrace before retreating to guest rooms outfitted in bright prints and tropical tones.

Sitting near Mount Hollywood in Griffith Park, the Griffith Observatory has a vantage point that allows visitors great views of the HOLLYWOOD sign during the day, and even more fantastic views of the stars at night. The space has plenty of telescopes for stargazing, but it’s also a great informal setting for learning about the universe, thanks to a large exhibit space and a 290-seat planetarium that puts on rotating shows about topics ranging from the northern lights to water—and possibly alien life—on other planets. There is no entrance fee for the institution and just a small admission price for the planetarium itself.

Mount Royal Park starts at the edge of the city just beyond the McGill campus and runs alongside neighborhoods like Plateau before rising to the top of 764-foot-tall Mount Royal (Mont Réal), the hill that gives the city its name. The twisting roads and paths of this crown jewel of Montréal’s park system were initially laid out by Frederick Law Olmsted, who also designed New York’s Central Park. While Olmsted’s plan was not followed in all its details, the final result was true to his vision of a woody park that takes advantage of the site’s hilly topography. There are two belvederes with views of the city skyline and the St. Lawrence River, and one of Montréal’s iconic landmarks, a 103-foot-high cross, sits at its northern end. The park is most popular in summer, but residents flock here in every season, to enjoy the colorful foliage in the fall and the cross-country ski trails and toboggan runs in the winter.

The Roman Forum is where ancient Rome began. The sprawling archaeological park gives us just a hint of what the Roman Empire once was—a dominant and diverse society. The Forum itself was the political, social, religious, and commercial focal point for the Roman Republic and eventually the whole Empire—for the most elite members of society as well as the common plebs. Walking through the Forum is a walk through history, from its beginning as a valley with small hilltop communities (8th century B.C.E.) to its rise as the capital of an empire. The ruins of basilicas, temples, public forum spaces, and shops can be explored, and the adventure leads to Palatine Hill, an area of high-society patrician homes including the house of Caesar Augustus.

If, like most visitors, you head for Tucson between Thanksgiving and Easter, you’re probably seeking sun and warmth while the rest of the country deals with the winter blahs. And you’ll most likely find what you’re looking for. There’s a reason why golfers, cyclists, hikers, and runners flock to southern Arizona this time of year. But, once or twice a decade, the lush Sonoran desert might get a snowfall—it never lasts for long, but every saguaro, ocotillo, cholla, and prickly pear cactus will be edged in ephemeral white. As soon as the sun comes up over the mountains, you’ll start hearing the drip drip drip of the inevitable melting...And by the next day you’re likely to be wearing shorts again. Saguaro National Park, which flanks both the western and eastern edges of Arizona’s second-largest city, is the ideal place to go for a hike in the rare desert snow. The Eastern (Rincon Mountain) division of the park has a hilly eight-mile one-way loop road with access to numerous trails. Drive slowly and yield to the runners and senior-citizen-cyclists-in-spandex with thighs of steel. Get out and up into the saguaro-studded hills before the unlikely landscape disappears...Keep your eyes open for bobcats, mule deer, and the pig-like javelina. (You’re less likely to encounter a rattlesnake in the winter months, but this is still desert wilderness.) And if there’s no snow, you might be treated to spring wildflowers. Don’t forget your sunscreen...

Far above the city streets on the 52nd and 53rd floors of the Roppongi Hills building, the Mori Art Museum houses contemporary works by primarily Japanese and East Asian artists in a range of mediums, including photography, design, fashion, architecture, and video installations. There’s also an observation deck on the 52nd floor with an open-air Sky Deck, a lounge, a café, and a restaurant with outstanding views of the city. Keep in mind, though, that there are a myriad other dining options as well on the lower floors of the Roppongi Hills building, one of the tallest in the city.

Located in East End Village and painted in Anguillan flag colors, the Heritage Collection is Anguilla’s only museum. It showcases the island’s history and geology from the time of the Arawaks to the 1969 Anguillan revolution, with additional displays on the British invasion (derisively called the “Bay of Piglets” by the press) as well as on Queen Elizabeth II’s royal visit. Established in 1996, its collection includes photographs and artifacts from the island’s major eras, including the days of slavery and the phosphate trade. If you’re lucky you’ll meet Colville Petty, the museum curator and founder, and garner some of his unique insight on Anguillan history.

On the first Saturday of the month, locals shop for vintage apparel and antique home decor at this flea market.

On the still-bucolic site of a former coconut plantation just west of Montego Bay, Round Hill is another of the legendary hotels created in the early 1950s to accommodate wealthy Brits and Americans who were discovering the pleasures of a Jamaican winter. Since then, it has evolved into a thoroughly modern resort that manages to retain its original, exclusive, clublike spirit. In the beginning, Round Hill consisted of a group of shareholders (British playwright Noel Coward was one) who rented out their private villas when they were absent. That’s how it still works, although the celebrity shareholder most mentioned these days is designer Ralph Lauren, who rents neither of his two villas. Along with 27 other villas, which can be divided into 86 suites, there’s the Pineapple House, a seafront block of 36 rooms, all decorated, predominantly white on white, by Lauren. The ambience is quiet luxury, the service is relatively formal (the doorman wears white), and the children among the guests are treated as the heirs and future holiday decision makers that they are. Almost every villa has a story, whether it has to do with Coward, the Kennedys, or How Stella Got Her Groove Back. And Montego Bay, whose city lights can be seen only from the highest villa (#28), is still another world away.

For a classic American diner experience, the Cherry Hill Diner in, yes, Cherry Hill, New Jersey, is the place to go. This 24/7 locale has been around for decades, and is as renowned for its freshly baked cakes as it is for its gargantuan omelets. If you can, try to swing by at night when the lights are aglow and the whole vibe harkens back to the days of mid-twentieth century USA.

A private-island resort six minutes by boat off the coast of Antigua, Jumby Bay is one of the Caribbean’s top luxury, all-inclusive stays, and one of its most environmentally aware. A $28 million renovation in 2010, which included the addition of 28 suites and a first-ever spa, gave it all the digital-age essentials: 42-inch flat-screen TVs, iPod docking stations, Bose sound systems, free Wi-Fi. Yet its underlying spirit of environmental responsibility, highlighted by its hawksbill sea turtle preservation program and its banishment of wheeled vehicles except for golf carts and bicycles (every room comes with two bikes), continues to reign. Rosewood manages the resort, but it belongs to an association of island homeowners, some offering their properties for rent. So if, say, a 1,346-square-foot beach-view pool suite isn’t big enough, it is possible to do as celebs such as Hillary Swank, Jim Carey, and Paul McCartney have done and plop down up to $20,000 per night for a private villa or estate home. Couples can be perfectly content here, but it is especially attractive to families, who appreciate programs like the Rose Buds kids’ club.

One of the more bizarre landscapes in the Philippines is Bohol’s Chocolate Hills, a 20-square-mile area that contains some 1,700 hills. To date, these natural formations still baffle geologists, though legend claims the hills are rocks once thrown by battling giants, or tears cried by a giant who lost his love. The hills are green during wet season and turn into brown mounds during the dry season, hence the name. Climb up to the viewpoint to get a 360-degree view and unleash your imagination. Some people say the hills look like giant Hershey’s Kisses; others just see mounds left behind by enormous moles. Before you leave, buy some local Peanut Kisses to help you remember your visit—perhaps inspired by the Hershey’s chocolates, they are shaped like the hills.

Driving along the countryside in northern Portugal near Oporto I saw the spectacular hillside vines of the famous Douro Valley spread out in front of me for miles. The sight was breathtaking. I saw the steep hillsides with the vines on the terraces. The vines were loaded with grapes that in a couple of weeks would be ready for harvest. The vineyards were first established in the 12th century by Cistercian monks. There are numerous Cistercian monasteries in the area. UNESCO declared the Douro Valley a World Heritage Site in 2001. The Douro Valley produces the grapes for port, red, and white wines. Douro tours are available and run from a few hours to a few days. The cruises run from April to October. If you want to see the harvest picking of the grapes plan your tour for September. A drive through the Douro Valley or a cruise down the Douro River is an experience to savor. If you get to northern Portugal, look into a side trip to the Douro. You won’t be disappointed.

Tucked into the hilly northwestern corner of Jordan, Umm Qais (or ancient Gadara) commands grand views of the Sea of Galilee and the Golan Heights from the edge of its plateau. It was here that Jesus is said to have performed the miracle of casting demons out of men and into pigs. The town has existed since the Hellenistic period, but is best known for its Roman ruins, which once sat along a prosperous trade route. Many ancient streets and buildings are still intact, as are several Ottoman-era stone houses, which remained occupied all the way until the 1980s. Grandest of all the ruins is the black basalt theater, located along the wide Decumanus Maximus that still holds its original paving stones. Visitors should also be sure to check out the small museum in what was once the home of the Ottoman governor, as well as the celebrated restaurant in the old Ottoman school. In recent years, Umm Qais has become a pioneer of community tourism in Jordan, and it’s even possible to take cooking classes, nature walks, or tours with a local beekeeper after enjoying the ancient ruins.