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Whistler Blackcomb receives lots of press about its big-mountain features, but the resort offers plenty of terrain for every family member and skill level. The Whistler Blackcomb Snow School, among the best in North America, is great for both seasoned skiers and kids as young as toddlers. Even tweens and teens can enjoy small-group lessons, which offer equal parts socializing and instruction in the terrain parks and beyond. Welcome on the Whistler and Peak 2 Peak gondolas, non-skiers will have the village to themselves during the day. When back with their group, they can hang at one of the more than 25 on-mountain restaurants.

Tempt fate at the Monkey Paw’s Book-O-Matic machine, where for the price of a toonie you’ll be delivered an archaic tome in the vein of Elementary Arabic, Vol. 3. I’ll let you know how my studying gets on. The Monkey’s Paw is an eclectic vintage bookstore on Dundas with a collection of unique books, vintage maps, and bugs preserved in Lucite.

Even if you aren’t planning to take a cooking course during your visit to San Antonio, a trip to the Culinary Institute of America is worth a visit. It’s a great area to walk around in, and you can try coffee and pastries at the CIA Bakery Cafe. You can also eat at NAO, the award-winning restaurant at the CIA that’s also part of the student’s educational experience. Be sure to make a reservation.

From the porte-cochère entry at the Westin Puntacana Resort & Club, you’ll catch an inviting first glimpse of coconut palms, manicured grass, and a long swimming pool that seems to end at the sea. The view only gets better upstairs, where all 200 rooms—including 16 suites—offer swoon-worthy ocean vistas. On the hottest of days, the high-ceilinged, open-air lobby is a great place to hang with a cold one while catching the ocean breezes. When it’s cooler, have lunch by the pool or at the beachside La Palapa, and plan for dinner at the open-air Brassa. As a guest at the Westin, you also have access to Puntacana Resort & Club’s eight restaurants, two golf courses, tennis center, Six Senses Spa, aquatic center, and Grupo Puntacana Foundation activities.

Key West doesn’t have many swimmable beaches, but this elegant 1920 oceanfront resort sits on the largest private one in town—an 1,100-square-foot strand punctuated with tall palms. While the shoreline itself is on a rocky shelf, a long dock extends out to the shallows for laps and snorkeling. Just off the beach, two large pools are set into green lawns and lush landscaping in front of the Spanish-style main building, which is on the National Register of Historic Places. The hotel’s wooden coffered ceilings, arched entryways, red-tile roofs, and other key architectural details recall the hotel’s glamorous heyday, while the clean, refreshed rooms are entirely modern, with sleek wood-framed beds, white linens and curtains, and ocean views. Children under 16 stay for free and babysitting is available for adults who want to take a break at the Spa al Mare, which has an open-air cabana right on the sand for al fresco massages and treatments.

The hot-air balloon captains of the Masai Mara see themselves more as sailors than pilots. Despite the fact that they are flying, they guide the balloon through the air, adjusting the pulleys and controlling blasts of hot air like sailors harnessing the wind with canvas. The anticipation of takeoff is exhilarating: Guests arrive to an open field in the darkness and lie down on the grass to be hoisted up into the basket, with the roar of the flames overhead. The ride itself is tranquil and relaxing, drifting through the sky, admiring the balloon’s shadow on the golden ground as the sun rises. Rides can be booked in advance while staying at Angama Mara, one of Kenya’s most luxurious lodges.

Only in Berlin could a hulking, aboveground World War II‒era concrete bunker, right in the center of the city, be turned into an art gallery. The structure—too bulky to be blown up after the war—was transformed in 2008 by collector-curator Christian Boros, who lives in a penthouse on top of the building. After extensive renovation, the lower floors house the Boros Collection, around 500 works of art spanning sculpture, installations, paintings, and photography. Works change every couple of years but always feature big international names such as Damien Hirst, Olafur Eliasson, Elizabeth Peyton, Wolfgang Tillmans, Manfred Pernice, Ai Weiwei, and Michel Majerus. You can view the collection only on weekends, as part of a guided tour; book an appointment via the website.

This 12-cottage luxury hotel, 3,100 feet up in the Blue Mountains, is Jamaica without the beaches. It is the Jamaica of misty mornings, cool, cuddle-worthy evenings, and a musical heritage recognized worldwide. First as a private estate belonging to music producer Chris Blackwell and then as part of his Island Outpost collection of hotels, Strawberry Hill has been a creative refuge for performers including Bob Marley, the Rolling Stones, and Willy Nelson. After Hurricane Gilbert destroyed the estate’s great house in 1988, Blackwell commissioned Jamaican architect Ann Hodges, who specializes in historic reconstructions, to build the cottages, a restaurant, and a pool, which were opened in 1994. Yet despite the rock and roll history, and the hanging with like-minded souls up in the mountain mists, what guests seem to remember most is the far-below views of Kingston, especially at night, when the lights glow and sparkle from what must certainly be another world.

Formerly Blue Sydney.

Carefully constructed around support beams and pipes from a 100-year-old wheat and wool wharf, this hotel offers a beautiful mix of old and new that juts out into the Woolloomooloo harbor. The Heritage Level is where you’ll find original wooden pier pilings, metal wheels, and conveyor belts that date to 1910, but classic touches such as early-20th-century photographs of Sydney are scattered throughout the property. Goose down bedding, plush furnishings, walk-in showers, and in-room iPads make modern travelers feel right at home, and the bar that runs the length of the central atrium—hanging Swarovski crystals shine pink and purple in the evening candlelight—often hosts fashion shows and cocktail events. Most rooms have sliding glass doors that take advantage of the hotel’s over-water location between the Royal Botanic Gardens and Rushcutters Bay; they open to either the city skyline or the Potts Point naval base. Maritime history buffs should book the latter and check out the site on the wharf from which sailors boarded ships for Gallipoli.

The bleak, windswept landscape of Connemara in the West of Ireland is characterized by bogs, lakes, mountains, and miles of stone walls. Connemara National Park is one of the best places to appreciate this unique landscape, with more than 7,000 acres of national park encompassing mountains, including some that are part of the Twelve Bens range, plus Western blanket bog and treeless plains that are home to red deer, sheep, and Connemara ponies. Explore for yourself, and find traces of history dating back thousands of years, including 4,000-year-old megalithic tombs and abandoned farms.

The #1 thing recommended to me to see in Portland was the Saturday Market. It lived up to its hype! I spent a few hours Saturday morning wandering around the market and was floored at the talent of the vendors. I was also shocked at how reasonably priced everything was. I purchased a catnip-filled body pillow to bring home for my cat and two hand-painted, extra-large ceramic mugs ($20 each). My only regret was that I didn’t have enough room in my suitcase to bring more stuff home!

Rumour has it that there are over 10,000 chocolate shops in Belgium, and that it would take a full 6 months to tour all of them. To this I say: challenge accepted. (Remind me to pack my stretchy pants) Eating chocolate is undoubtedly one of the most iconic things to do in Belgium, and Antwerp is the perfect place for that. Between the beautiful architecture of the train station, the history of diamonds, the Jewish quarter and the ancient squares, Antwerp doesn’t disappoint. And if somehow it does, make your way to DelRey, my favorite chocolate shop in the city. I visited several, and the owner of this particular one was extremely enthusiastic about his products, and more than willing to give me a free sample. That may or may not have biased my judgement. I will never tell.

The newly refurbished Sheraton Kona Keauhou Bay Resort is stylish, with a large pool and water slide. But it was the history and the view from the hotel (located off the famous Ali’i Drive) that won me over. The hotel gives you an excellent vantage point to the bay around which King Kamehameha III was born (stillborn, as legend has it). He grew up to become Hawai’i’s powerful and benevolent ruler, and sought to unite the people. He called The Big Island his home and is beloved by many. The hotel offers several notable cultural markers, including two heiau (Hawaiian temple) replicas.

After the Grand Ole Opry left the Ryman Auditorium, country legend Roy Acuff said the redbrick building with its Gothic arches and stained glass windows might as well be torn down. The Ryman had been home to performances and broadcasts since the 1940s, but it was in poor condition and lacked air-conditioning and proper dressing rooms. Fortunately, its legacy as “The Mother Church of Country Music” prevailed and, after years of sitting practically empty, the auditorium was renovated and began hosting shows once again. Originally built as a church, the grand hall has spectacular acoustics and a lingering magic in its pews from all those years spent witnessing country music history. A trip here is practically obligatory when visiting the Music City.

Go for the scene, not the food, and enjoy the Art Deco décor and great people-watching at this buzzy Left Bank landmark. Despite a limited menu and steep prices, the place is packed day and night. Order a chocolat chaud and sit on the terrace, watching the world go by.