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Gaze at the beautiful floor to ceiling mosaic that pictures the marine life and coral reef in Grand Cayman as you climb the double helix staircase to the top of the 75ft observation tower. Located in Camana Bay, this tower offers 360 degree panoramic views of Seven Mile Beach, George Town, and the North Sound. Not up for the big climb? No worries, there’s a full service elevator available to take you to any floor for observation, including the very top.

Controlled by the François Pinault Foundation, the same trust in charge of Christie’s auction house, this is a museum-worthy gallery in the heart of Venice. Set inside a 17th-century customs house, it showcases Pinault’s impressive private collection, comprised of some 2,500 pieces of modern art. The location, at the point of land where the Grand Canal meets the Giudecca Canal, is equally spectacular. After you’ve finished browsing the art collection, grab a pastry or a small bite at the in-house Dogana Cafe.

In the winter months Waimea Bay is a favorite surf destination and home to the Eddie Aikau Big Wave Invitational competition. Eddie is a legendary Hawaiian surfer and the first lifeguard of the North Shore of Oahu. Eddie Would Go, T-shirts and bumper stickers abound, immortalizing the courage of this lifeguard that would swim out to rescue surfers when no one else would. The Eddie Aikau surfing tournament started in 1984, but in the 25 years running has only been held eight times due to the condition that waves been at least 20 feet high. We just happened to be there for lucky number eight as Waimea delivered an event of legendary proportions as waves of up to 50 feet rolled in for the 25th Anniversary. If you are in Hawaii...GO TO WAIMEA BAY! It is gorgeous, whether you’re hanging out on the beach or hitting the waves. We hiked to a sacred burial site located just up the cliffs from Waimea while we were there.

Parque Forestal is Santiago’s lung and central park. Created for the first centennial celebration in 1910, the park has become an iconic area of the city with elegant residential apartment buildings along the perimeter. One of the most enjoyable ways to spend an afternoon is walking under the century-old trees and then strolling the cobblestoned streets of the adjoining Lastarria area. Parisian-style facades, cafés full of intellectual life, boutiques, museums like Bellas Artes (a copy of the Petit Palais in Paris), restaurants, and bars all bring this neighborhood to life.

Hello, rooftop pool! Leave it to Chicagoans to remain optimistic that summer will be amazing, even if winter lasts well into May. The rooftop pool (open to restaurant as well as hotel guests), occupies a prime spot on one corner of Six Points, that crazy intersection where three major shopping streets cross paths. That means the regulars are a mixed bag, but all come in for a good time, whether that means for brunch in the newly redesigned Café Robey street-level restaurant, to drink until dawn at the poolside Cabana Club bar, or to sneak up to its new sister, the Up Room, at the top of the deco tower.

Guadeloupe’s outdoor markets are an important part of daily life and a sight for sore eyes. Fragrant cooking spices compete with colorful bottles of homemade rhum, women in traditional madras head ties smile at passersby, zouk music or gwo-ka drums blast in the background, and the calm Caribbean Sea is the backdrop. Saint-Anne Market, on Grande-Terre Island, is a favorite. It borders a beautiful white-sand beach, steps from a row of casual restaurants and bars.

Kailua Beach is always named one of the best beaches in the world. It has the most deliciously soft sand, gentle surf, and maybe a turtle ( honu) to swim with. Kailua Beach is actually many beaches. For a fascinating study on ancient beach names, take a look at the historical Hawaiian names in John R.K. Clark’s book “The Beaches of Oahu.” In modern times the beach names are three. Oneawa ( AKA Castles), lies to the north near the house the President favors for holidays. Kalama sits in the middle of the crescent named to honor Queen Kalama the wife of King Kamehameha III, former owner of the entire Kailua district. Kailua Beach Park is thirty acres with parking, picnic facilities, lifeguard and restrooms. Kayak rentals are close by and you may pull the boats across the street, stopping for a custom made sandwich at Kalapawai Market, and paddle out to one of the Mokulua islands. If you want a quieter experience albeit with no facilities or life guard, try Kalama Beach via any marked public right-of-way along Kalaheo Avenue beginning in 300 block and proceeding north. Pay attention to no-parking signs; find parking down a side street off Kalaheo Avenue TOWARDS the mountains. Leave nothing of value in your car, take chairs, towels, sunscreen, hats, a cooler of water and perhaps lunch. If winds pick up, pack up and head to docile Waikiki.

Glück is a genius combination of café and kids’ playroom. Parents pay for each child’s entry so that the kids, supervised by café staff, can amuse themselves with a full array of toys and games while the parents relax, have coffee, and wedge in some adult conversation. Tables come with electrical outlets so harried moms and dads can plug in and catch up with everything they should have done two days earlier. The menu features coffees and infusions, sandwiches, and pastries, all done nicely. Private babysitting is available at extra cost.

Originally a 15th-century convent, followed by stints as the headquarters of the Dutch Admiralty and Amsterdam’s town hall, the Sofitel Legend The Grand Amsterdam—or simply, The Grand—presides over the heart of the old city. With its imposing brick facade flanked by canals and its location within a stone’s throw of Dam Square and De Oude Kerk, The Grand would be a legend even without Sofitel’s designation. The majestic entrance courtyard hasn’t changed since its construction in the 17th century—a fact that’s reinforced by the hotel’s horse-drawn carriage, which offers guests a different way to explore the city center—and even before the building became a hotel, landmark figures in European history stayed on site, including William of Orange.

While today’s interiors are starkly modern, the designers alluded to the hotel’s storied past in the decor and textiles featured in the 177 rooms and suites, which overlook either the interior courtyard and gardens or the canals, and come with touches like rainshowers and signature MyBed mattresses. The private Canal House Suites—especially popular with the dignitaries and celebrities who frequent the hotel—may appear boldly contemporary, but accents like round windows and wood-beamed ceilings hint at their past as the private homes of Dutch admirals. The hotel’s five dining options include the Michelin-starred Bridges restaurant—set in what was once the town hall’s canteen—as well as the casual, all-day Bridges Bistro, traditional Flying Dutchman café, sophisticated Library D’Or lobby lounge, and peaceful Garden Terrace. The two-floor SO Spa houses a gym, heated indoor pool, wet area with Turkish hammam, and treatment rooms for French-inspired services.

Founder’s Note: Uncommon Travels

This bar in Gros is one, as the locals say, ‘de toda la vida’. A lifelong place to stop and enjoy one of their spectacular anchovy and tuna pintxos (I recommend the one that looks like a mountain of mayonnaise) or a pintxo moruno, a hanging kebab that is a house specialty. The pintxos are classic and delicious. Always a great ambience.

At Salt Water Farm, students return to the land—and the sea—to learn forage, fillet, and feast.

I just love the huge space and the glass ceiling of Galleria Umberto. It is located across from Teatro di San Carlo and despite its modern look, I was surprised to find out that it was built between 1887–1891. The Galleria was named for Umberto I, King of Italy at the time of construction. It was meant to combine businesses, shops, cafes and social life — public space, with private space in the apartments on the third floor. Don’t miss it! The architecture is breath taking all year long.

It may look a little like your childhood summer camp, but Phantom Ranch feels like the Ritz by the time you make it to the bottom of the Grand Canyon, whether by foot—a steep 10-mile hike—mule, or boat down the Colorado River. Set near a creek in the shade of a cottonwood grove, the lodge is the only property located beneath the rim of the canyon, making it an extremely popular destination. Book early; the concession uses a lottery system for reservations beginning 14 months in advance. There are two lodging options: log cabins that sleep up to 10 people and are furnished with cold water sinks and toilets (there are common shower facilities), and four dormitories—two each for men and women—that sleep 10 in five bunk beds. Linens are provided and, thankfully, all of the buildings have air-conditioning in the summer and heating in the winter. Also be sure to reserve meals ahead of time. Seating in the canteen is limited, and the steak and meat-stew dinners, served family style, are surprisingly tasty.