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  • Gateway Arch Trail, St. Louis, MO 63102, USA
    The unofficial symbol of St. Louis, the Gateway Arch is the tallest man-made monument in the United States, rising 630 feet into the air. It sits at the center of Gateway Arch National Park, which was established in 1935 to commemorate Thomas Jefferson’s vision of a transcontinental America. In 2018, the park emerged from a five-year, $380 million renovation, which added a grassy pedestrian walkway over the interstate as well as a revamped museum with new exhibits about the construction of the arch and how the expansion of the United States affected Native American communities. Tour the new sites, then take the four-minute, vertigo-inducing tram to the top of the arch, where you can see up to 30 miles east and west on a clear day.
  • Rua Senhora Saúde 6B, 1100-390 Lisboa, Portugal
    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.
  • Every December 7 at Pearl Harbor, there is a memorial to those who died in the awful attacks that day in 1941. Survivors gather here, though fewer every year remain alive. Oil still rises from where the USS Arizona lies in the harbor. The horrific events of December 7 are still a raw part of the history here. Several months ago, the civil defense sirens went off all over Oahu. It was a glitch in the system, but I remember an elderly woman in downtown Honolulu who said she looked at the sky because she remembers when there really was an air raid, and the sirens bring her back to that time of eminent danger when what seemed impossible unfolded in front of her young eyes. For history buffs, students, and all sorts of tourists, this is a “must visit” National Park on Oahu. Tickets to take the boat to the memorial are cheap (but do require an advanced booking of a couple days), and there are several other activities and museums at Pearl Harbor to explore including a walk through the USS Bowfin.
  • 1214 Queen St. West, Toronto
    Among the neighborhood’s art-minded hotels, the Gladstone is the most interactive, with shows, classes, and ongoing events. The 37 rooms, all designed by local artists, have breathed new life into the 128-year-old icon, which filmmaker Christina Zeidler took over in 2003 and revitalized in 2005. The Victorian landmark, named for its avenue (in turn named after four-time Canadian Prime Minister William Gladstone), has been a gathering spot for over a century. And it was home to legendary Toronto characters like cowboy Hank Young, who became a fixture at the hotel as a country singer in 1961 and manned the hand-operated elevator from 2005 to 2009, and Peter Styles, former host of Karaoke Night, with applause sign in hand. The legend of Hank lives on in a framed photo in the stairwell en route to the second floor.

    The Gladstone continues to push the boundaries of community and culture with creative events like its educational workshop series, Get School’d, and its annual alternative design event, Come Up to My Room (CUTMR), which runs alongside the city’s Interior Design Show. Begin your stay in this architectural gem with a drink at the Café or Melody Bar (that is, if you’re not first thrust into Fameless Karaoke Night).
  • 79 Carriage House Ln, Philipsburg, MT 59858, USA
    In 2007, hedge fund investor Jim Manley bought a working cattle ranch on the site of a historic silver-mining claim to stake as his bigger-than-life family retreat. In 2010, he opened up the Ranch at Rock Creek, a toy-filled haven in southwest Montana’s Big Sky Country, with 13 houses with one to five bedrooms, luxurious canvas cabins for “glamping,” or a nine-room granite lodge. All are decorated by designer Jet Zarkadas and feature Oriental carpets, deep leather chairs, cow skin and woven Navajo rugs, custom duvet covers, and period Western photos and memorabilia. Despite the remote location and 5,200-foot elevation, all accommodations have landline, working Wi-Fi, and cell phone coverage; some have moose antlers, a private sauna, outdoor hot tub, and indoor copper bathtub.

    Open year-round, the 10-square-mile property encompasses meadows, high country lakes, grassy ridges, and stunning vistas of the Pintler and Sapphire mountains. This self-contained adventureland offers horseback riding; heli-hiking; fly-fishing; river floating; high-tech mountain biking; rope courses; trap shooting; and archery on a 3D course using powerful hunting bows to shoot life-sized models of animals. Weekly rodeo and stagecoach rides underscore the Western theme; in winter, guests cross-country ski, ice skate, and snowshoe on-site. A kids’ club frees parents for spa time and other pursuits.
  • Cape Point, Cape Peninsula, Cape Town, South Africa
    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.
  • 3, 2 Khao Rd, Khwaeng Wachira Phayaban, Khet Dusit, Krung Thep Maha Nakhon 10300, Thailand
    There is nowhere else in Bangkok quite like the Siam Hotel. For starters, it’s owned and run by a Thai rock star, Kamala Sukusol, and her son Krissada. The boutique property includes mid-century timber buildings built by the legendary silk baron Jim Thompson, as well as open and modern structures, with a focus on harmony and comfort, designed by one of Asia’s best-known architects, Bill Bensley. But beyond the glamorous background, it’s the design of the Siam that makes it stand out the most. There’s a 1920s jazz theme mixed in with some Asian colonial flair; the result—with lots of open spaces, natural light, antiques, potted plants, and a black-and-white palette—is simply beguiling. The views of the river here lack temples or interesting landmarks, but it’s a lazy spot to watch boats go by, which adds to the relaxing atmosphere. Service is personalized and extremely professional, as you’d expect from a property of this caliber. In all, this is the closest thing one can find to a resort in Bangkok, and it is one of the most stylish accommodation choices to boot.
  • 1007 York St, Denver, CO 80206, USA
    There’s more to the Botanical Gardens in Denver than just the pretty face of its landscaped grounds and beautiful flowers. It’s also a world-class research center with a mission to connect people with plants (especially the plants endemic to the Rocky Mountains) and to encourage understanding of the ecosystems in which they thrive. The 23-acre location on York Street has a variety of gardens (many based on typically western climates like mountains and plains), popular exhibits, and a shop; it additionally hosts a summer concert series and nighttime events. The institution’s second main location, at Chatfield Farms on the southwest edge of greater Denver, focuses on native flora and agriculture; there’s a working farm on its 700 acres. Both spots offer extensive educational opportunities as well as incredible events like York Street’s Blossoms of Light holiday show.
  • San Juan-Caguas-Guaynabo, PR, Puerto Rico
    This is my favorite hike by far. Cueva Ventana (“Window Cave”) is a beautiful, scenic hole in the side of a mountain that opens up to a lush, green valley down below. You’ll trample through mud, hunker down under low-hanging stalactites, dodge around stalagmites, and never look up (there are bats, of course) while wandering through the cave. All this winding around through two caves leads you to one of the most spectacular views in all of Puerto Rico (but I may be biased). The hike to this cave is half the fun. You climb down into a small opening under enormous, ancient tree roots, and you get the feeling of a tomb raider. But, if you’re claustrophobic or don’t feel up to lowering yourself down a cave wall, there’s an additional path that bypasses the first cave and leads you straight to the easier hike to Cueva Ventana. There’s something for everyone! I’m pretty sure I saw one Puerto Rican woman doing the whole thing in heels. This is a must-visit site for anyone touring the northwest central part of Puerto Rico. Another tidbit is that it’s practically free! You can find the directions on PuertoRicoDayTrips.com, park at the adjacent Texaco gas station. UPDATE (2014): There is now an easier way to access this awesome view! There are now boardwalks for ease of access, and you must pay $11 to tour the site. You get a flashlight and hardhat for safety.
  • 5315 Big White Rd, Kelowna, BC V1P 1P3, Canada
    At the Big White Ski Resort there is more to do than ski and snowboard which is especially useful to know when you’re not a skiing Canadian like myself. Instead of hitting the slopes there are snowshoe excursions, ice wall climbing, sledding with inflatable tubes, ice skating, sleigh rides, dog sledding, and, even more importantly, delicious restaurants and bars full of beer and locally produced wine.
  • Supai, AZ 86435, USA
    There’s a reason this is one of the most iconic spots along the Grand Canyon. Located on the Havasupai Indian Reservation and hidden deep within a 20-mile round-trip hike, Havasu Falls’ sparkling turquoise waters are a popular destination for seasoned hikers who come for the amazing views, rock climbing, and swimming. The hike to the falls and back is best enjoyed with a preplanned route and plenty of stops for rest, food, and water. Because tribe members of the Havasupai, which means “people of the blue-green waters,” maintain the trails and work to keep their land as unspoiled and pristine as possible, reservations for campsites are limited and day hikes and drones are not allowed.
  • Piazza del Duomo, Milano MI, Italy
    The historic and modern center of the city, the Piazza del Duomo (the square surrounding the cathedral’s base) remains a popular meeting place, hangout and hub of Milanese life. Local vendors setup shop (selling fresh coconut in the summer, toys and tourist wares), kids run and play (free from traffic) and shoppers trickle in from the walking street surrounding the huge plaza. The statue of Victor Emmanuel II, the first king of Italy, is the best place to meet, sit, recharge and watch the city go by.
  • Piazzale Michelangelo, 50125 Firenze FI, Italy
    One of the best views of Florence can be savored from the Piazzale Michelangelo, a short walk across the Arno River from downtown Florence. For a fun afternoon head to the square and enjoy an enchanting panorama of the city, followed by a relaxing alfresco lunch at one of the nearby restaurants. The Piazzale Michelangelo is also worth a visit at night to get a very different glimpse of Florence. The lights of the Duomo and the buildings surrounding it make for a magical nighttime scene.
  • Pariser Platz, 10117 Berlin, Germany
    Napoléon and his armies marched through it; revolutionaries and Nazis gathered beneath it; the Berlin Wall ran right behind: It’s safe to say that Berlin’s iconic Brandenburg Gate, completed in 1791, has pretty much seen it all. Designed by Carl Gotthard Langhans, who drew inspiration from the entrance to the Acropolis in Athens, the gate is best approached via Unter den Linden, the tree-lined boulevard that runs between the gate and the former Royal Palace. You can combine a visit here with nearby sights such as the Reichstag, Tiergarten Park, and the Memorial to the Murdered Jews of Europe. Since 2016, an impressive high-tech museum at the gate has offered a history of the city through the perspective of the iconic structure.
  • Poschiavo, Switzerland
    Poschiavo is one of the last stops along the UNESCO-listed Rhaetian Railway before it descends towards Tirano, Italy. It’s also one of the few Italian-speaking villages in Switzerland outside of Canton Ticino. The seemingly untouched medieval town is a jolt back in time, with a full-on baroque piazza boasting a stone campanile and a museum stuffed with 16th-century furnishings and antiquities. Don’t leave without stopping for a nibble at its Wednesday market: Local specialties include pizzoccheri (a buckwheat pasta), burrata, local truffles, anise-flavored bread, wine from Campascio in the surrounding valley, and cheese from Caseficio Valposchiavo, a nearby organic dairy. The market is held every Wednesday on Poschiavo’s main piazza.