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The winding streets of ancient Genoa all lead in one direction—straight up. Lace up your tennis shoes and keep climbing. Eventually you will reach a small park at the edge of the city, the entrance to one of the many fortresses that speckled its 17th-century walls. From here you’ll be treated to one of the best views of both old and new Genoa. Come at dusk for a stunning sunset over the urban edge of the Ligurian Sea. (And if you are too tired to walk back down, catch the funicular for less than two euros!)

One of the delights of Valparaíso is exploring the colorful hillsides that ramble down towards the sea. Take the century-old funicular elevators Ascensor Concepción (Turri) or El Peral near the main plaza, constructed between 1883 and 1911. Once high into the hills of Cerro Concepción & Alegre, explore the meandering alleyways and cobblestone streets on foot. There are boutiques, cafés, mom-and-pop shops, old school bakeries, bars, restaurants, art galleries, and church bells tolling. It often feels more like a small village than a city. Climb up and down the many staircases often lined with bright graffiti. In the distance, the bay gleams in sunlight and the busy port never tires. At dusk, the lights twinkle like fairylight. Grab a table at a spot like Café Turri for a view of the sunset and a cocktail.

The village of Fira clings to the side of a cliff overlooking the Santorini caldera in the southern Aegean Sea. If you arrive by ship, you’ll likely be conveyed up to town by funicular, or on a donkey, unless your cardiovascular prowess can take the 500 narrow stairs that climb the side of the steep cliff. On the old volcano’s rim, the street level is actually above many of Fira’s restaurants and bars, which mark their entrances with facade doorways at the top of their steps. From the terraces of these establishments, guests are treated not only to some of the most delicious fare in the Cyclades, but also to breathtaking, panoramic views of the Santorini Archipelago.

It was raining when we arrived in Donostia-San Sebastian, but the skies cleared on our second day, and we rode the funicular railway up Mount Igueldo to take in the view back on the city, La Concha Bay, and the empty beach. The “low” travel season had just begun, and the strange little children’s amusement park on the mountaintop had shuttered up for the fall and winter, adding just the right disorienting touch of weird desolation to the Basque country panorama.

The description may sound daunting: a 2,000-vertical-foot gain in less than a mile. OK, it is a little daunting—but the trick is to take your time. This nearly mile-long wooden stairway was converted from a funicular railway that washed out in a rock slide in 1990. Averaging a 24-degree slope, it has a few “false summits,” where it looks like you’re about to get to the top only to discover there’s still more to go. The reward for this effort is an incredible view looking out from the foothills over Colorado Springs. Up for the speed challenge? The current record was set on Sept. 25, 2015, by U.S. mountain-running team member Joseph Gray, who did it in 17 minutes, 45 seconds. Good luck.

The Aubrey sits at the edge of Barrio Bellavista, a few steps from Santiago’s bottle-green 1925 funicular (which takes visitors up to Cerro San Cristóbal) and just below the zoo (sometimes guests can hear the animals when they’re lying by the pool). Open since 2010, this 15-bedroom boutique hotel is housed between two 1920s mansions built by the same architect. The larger of the two houses once belonged to famed Chilean railway magnate Domingo Durán. Today, the hotel is owned by a Brit and an Aussie who spent $3 million and several years transforming it into its current state.

The bedrooms are split between the two mansions, and there’s also an outside block housing a few pool suites. A cobbled terrace runs between the restaurant and piano bar. The interiors are inspired by the early 20th-century art deco movement and feature statement art deco furniture, printed fabrics, and elaborate wallpaper.

Take the Incline Railway up Lookout Mountain on your way to Ruby Falls and Rock City and you’ll understand why the journey is often half the fun. In operation since 1895, the funicular has a maximum grade of 72.7 percent, making it the world’s steepest passenger railway and earning it the nickname “America’s Most Amazing Mile.” For its age and impressiveness, the railway is now a designated National Historic Site and a Mechanical Engineering Landmark. Before your ride, visit the machine room to see the enormous gears that drive the train, then sit back and enjoy the sweeping views of the valley below as you creep steadily up the track. Sure, you could just drive to the top of Lookout Mountain, but where’s the fun in that?

After nine years and nearly $600 million, it’s not an exaggeration to suggest that the re-opening of the iconic Bürgenstock resort—set on 148 acres of ridgeline above Lake Lucerne—was one of the most widely anticipated of the decade. Originally opened in 1873, the family-owned resort grew into a moneyed playground, where Hollywood royalty romped (Sophia Loren lived here for many years) and wed (Audrey Hepburn married Mel Ferrer in a chapel on the property). It then endured several years of decline, after which Qatar state fund bought the property, closed it, and began planning a stunning transformation. Bürgenstock now includes four hotels, 12 restaurants and bars, 67 residences, and a 107,000-square-foot spa featuring three pools (including a heated outdoor infinity pool overlooking the lake), hammans, saunas, and private treatment rooms. Both the 102-room Bürgenstock Hotel and the 160-room Waldhotel—the latter a state-of-the-art medical spa and hotel—are brand-new, five-star additions. The historic Taverne 1879 and Palace Hotel, built in 1904, have also undergone considerable refurbishment. The real star, however, is the dramatic view, optimized from every angle—including at the Spices Kitchen and Terrace, which cantilevers out from the Palace Hotel as if it’s floating above the lake. Speaking of the lake, even getting to Bürgenstock is like something out of a James Bond film, quite fitting since the crew of Goldfinger spent a month here during filming. After crossing the lake by boat, you take a funicular up the face of the mountain and into the Bürgenstock Hotel, landing on the terrace with its arresting views.

While Cape Point is not, in fact, the southernmost tip of Africa—as is often claimed—it is generally accepted that the Indian and Atlantic oceans meet somewhere between here and the real tip, Cape Agulhas. Still, Cape Point is about as dramatic as you can get, with the land falling steeply away on three sides, the wind whipping around the cliffs, and the ocean churning below. The road to the point, at the end of a drive from Cape Town, goes through 20 miles of nature reserve full of baboons and antelopes. For those who don’t want to walk up to the lighthouse, there is a funicular, but to reach the point itself, you’re going to have to hike.

Sitting at the tip of the peninsula of St-Jean-Cap-Ferrat, which juts out into the Mediterranean, the iconic Grand-Hôtel du Cap-Ferrat, is now under the management of the Four Seasons brand. Located halfway between Nice and Monaco in the striking Antibes cape, the beyond-glamorous property first opened in 1908, and remains the epitome of the bonne vie, Jazz-era French Riviera. A destination resort, it has hosted everyone from Winston Churchill to Charlie Chaplin to Pablo Picasso, and is set on multiple lushly landscaped acres full of gardens, pools, and tennis courts that tumble down to the Mediterranean. Rooms are in three buildings. Try for one in the hotel’s original core, as these have soaring ceilings and floor-to-ceiling, sliding-glass-door windows looking out to the sea. The suites are also enormous, but ask for a higher floor for the best ocean views.

Within the 18th arrondissement in Paris France, high atop the city, resides the wonderfully beautiful, hilly neighborhood of Montmartre. This diverse and eclectic section of the city can be a bit busy with tourists, but the views of Paris and the splendor of the Basilica of the Sacré-Cœur are certainly worth it. Riding the funicular is rather novel, but not necessary if you’re willing to climb the 300+ steps to the summit. This is an area to be explored on foot, as is nearly all of Paris. The shops, theaters, and forever famous Moulin Rouge should not be missed. The streets are intimate, the shops unique, and the overall feel of this place speaks of a youthful, colorful Paris.

Atop towering Cerro San Cristóbal, there are two municipal pools where many families go to cool off during the summer: Tupahue and Antilén. Conveniently, these all have fabulous views of the city below. However, they do come with a price tag of US$12 for the lower-elevation Tupahue, and US$15 for Antilén, which keeps crowds to manageable levels in January and February.

Snaking, cracking, shimmering a brilliant blue in places and covered by mystical frost in others, the Mer de Glace displays nature in all its powerful glory. France’s longest glacier stretches for 4.3 miles and is over 650 feet deep. Quite literally a sea of ice, it continues to move under its own weight; its surfaces break up, crevasses appear, and pointed columns of ice known as seracs burst from the surface. Though this glacier continues to amaze, it’s slowly being decimated by climate change—in 1988, you only had to climb down three steps to reach the ice grotto, which is carved out every spring; now, the ice has receded so much that you have to tackle 430 steps.

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.

Set high above the St. Lawrence on Cap Diamant, overlooking Old Québec, this imposing yet inviting landmark is as much a lodging as it is a tourist attraction, borne out of its reputation as the most photographed hotel in the world. Opened in 1893 by the Canadian Pacific Railway to drum up luxury riders for its trains, the castle-like Fairmont Le Château Frontenac feels every bit as grand today as it must have when Roosevelt and Churchill secretly hatched plans for the invasion of Normandy here in 1943—and it continues to be the hotel of choice for A-list celebrities and other notables. A $75 million renovation in 2014 updated the 611 rooms with a more contemporary feel, draping spaces in chic furnishings and soothing shades of gray and cream, plus butter-yellow or soft turquoise accents. The spa features seven treatment rooms adjacent to an indoor pool, whirlpool, steam rooms, and a gym, but the hotel has become a destination for its food: Champlain restaurant is helmed by acclaimed young chef Stéphane Modat and offers a modern take on Québécois cuisine alongside magnificent views, while 1608 Wine & Cheese Bar highlights local wines, cheeses, and charcuteries.