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Cape Town’s Table Mountain National Park, which hugs the perimeter of the city, is so popular that the line for the cable car to the top can be longer than a queue for a Disneyland ride. But why stand in line when you can put your feet to use? There are several routes that lead to the top of the 3,562-foot, flat-topped mountain, including the two-mile Platteklip Gorge trail. Yes, it’s steep, but startling views of the city and the Atlantic await. Trek, get hungry, then picnic on local provisions—crackers, Dutch-style Gouda, and biltong, the thick-sliced South African jerky—before riding the cable car back down.

Dedicated to everything olive, Uje sells superior extra-virgin olive oils, olive wood cutting boards and olive tapenade, as well as other favorite tidbits such as hams and cookies. Uje also runs an oil bar (Dominisova 3), an eatery offering olive oil tastings and an olive oil-centric menu.

When it comes to Kindred, you can forget your preconceived notions of vegan restaurants. The South Park spot features killer cocktails, filling food, and an edgy design, complete with a coffered ceiling, a white-marble bar, and a demon-wolf-head sculpture mounted on the wall. Pair the refreshing Place of Certainty (vodka, elderflower, Aperol, lemon, Thai basil, winter melon bitters, and cucumber) with Kindred’s take on the charcuterie board (smoked golden beets, kale pesto, and red-chili-and-orange-fennel seitan), or order something more substantial, like the beet risotto or the seared cauliflower steak with squash puree and steak sauce. The restaurant also offers an excellent weekend brunch with everything from cinnamon rolls and banana bread French toast to pancakes with bourbon butterscotch.

The most enviable address in Waikiki, the beachfront Halekulani is all about restrained elegance and pitch-perfect service. The hotel dates back a century, though it was entirely rebuilt in the 1980s—and the room decor—fifty shades of white and plantation shutters framing the turquoise sea—complements the scene outside. The beach itself is small and usually mobbed, but the pool is a dream—a giant oval big enough for laps, and quiet enough (few kids here) for a long doze under your chaise’s umbrella. The grassy courtyards and seaside restaurants are just as improbably serene; some might say stuffy, but for others, the reliably hushed atmosphere is a welcome tonic to the hubbub of Waikiki, just outside the Halekulani’s marbled entrance.

The most northern of the Northern Beaches, Palm Beach makes for a relaxing day or weekend trip. Here, a sandy isthmus straddles ocean waves and harbor sails, and the Barrenjoey Lighthouse stands watch a short hike up the hill. Snag a spot on the deck of the Boathouse—a Hamptons-style beach shack complete with crab traps, striped awnings, and all manner of flowers and produce on display—for a bacon and egg roll, croissant French toast, or beer-battered flathead and chips overlooking the water. After finishing that cappuccino, which started with an anchor stamped into the foam, take the ferry across the inlet to the Basin campground in Ku-ring-gai Chase National Park to swim, stand-up paddle board, and search for wallabies in the wild.

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.

In a valley only five miles from the Pacific Ocean, Folktale Winery lives up to its name: The Old World French-style château appears like a castle from childhood fables amid the vineyards and oak trees. On arrival, visitors are greeted with a taste of sparkling brut (NV). Like many winemakers in the area, Folktale focuses on chardonnay and pinot noir, but its wines stand out for their bright acidic style and the minerality of the terroir. Daily tasting hours run into the early evening, and individual glasses and bottles are available, as well as flights of Folktale and reserve wines from single vineyards. The restaurant serves such seasonally inspired small plates as brie and pear bruschetta, shared plates (the crispy octopus is a local favorite), salads, and cheese or charcuterie boards. Pro tips: Save room to sample wine ice cream pops, made of rosé or grenache. Tours (which require reservations) include visits to the vineyards, cellar, and barrel room. And check the winery’s events calendar for yoga classes in the vines, special workshops, and concerts.

Housed on a 1,100-foot stretch of beachfront, Grace Bay Club is as stylishly current as it was in 1993, when it became the first luxury hotel to open on the then nearly empty sands of Grace Bay. From its original 21 rooms, the upscale property has grown to 82 suites, each of which features ocean views, a private veranda or patio, and chic interiors by renowned designer Thom Felicia. Guests can also look forward to superior service, including a personal concierge available day or night via a provided cell phone.

When hunger strikes, there’s the oceanfront Infiniti Restaurant & Raw Bar, which boasts sea-to-table fare and the longest bar in the Caribbean, as well as several other family-friendly venues, including The Grill. If it’s pampering you seek, make time to visit the spacious Anani Spa, where you’ll find six treatment rooms, including one just for couples. A spa tent is also available for beachfront massages.

The Hotel Telluride is close to town and the slopes but just removed enough from the action to feel like a tranquil mountain getaway. Here, the warm lobby welcomes guests with a large fireplace, comfy couches, and board games, as well as a dedicated check-in area for pets, who are allowed for a small fee and treated to house-made biscuits. Rooms have kitchenettes, private balconies, and humidifiers to combat the dry mountain air, while suites feature separate living and dining areas. It’s been said that The Hotel Telluride also boasts the most comfortable bed in town, triple-sheeted with custom-made linens.

The small, on-site restaurant, West End Bistro, serves a hot breakfast and simple dinner items like kale-and-quinoa salad and Colorado beef burgers—plus freshly baked chocolate chip cookies for an après-ski treat. Guests also have access to a sun deck with hot tubs and outdoor saunas as well as free cruiser bikes and shuttle service to the gondola and downtown Telluride. If desired, the hotel can even arrange for in-room massages or guided day trips to forage for wild mushrooms.

The Château Dufresne might not be high on most visitors’ lists of sights to see in Montréal, but as it is just across the street from both the city’s botanical garden and the Olympic Stadium, you may want to drop in if you are in the neighborhood. The mansion was constructed from 1915 to 1918 in the Beaux-Arts style popular in Montréal in those years. The 20,000-square-foot building is modeled on the Petit Trianon at Versailles and is actually two homes in one, as the brothers Oscar and Marius commissioned side-by-side mansions. The château served several different purposes after the Dufresne family lived there, first as a boarding school and later as the home of the Musée d’Art Contemporain. Today many of the rooms have been decorated with early 20th-century pieces, and a permanent exhibition provides an introduction of life in Montréal’s East End a century ago. Temporary exhibitions cover a range of topics, including some that highlight the collections of prominent Montréal patrons and others that focus on leading artists in the city.

Food trucks often frequent the mellow North Shore surf-town of Hale‘iwa—and Giovanni’s remains the fan favorite! Each platter contains two scoops of rice and a dozen jumbo shrimp: lemon-butter, hot and spicy, or the classic garlic-rich scampi-style. Add hot sauce or a side of homemade mac salad... or go rogue with a garlic hot dog smothered in scampi sauce. The truck was initially crisp and white, but has been steadily graffitied with the signatures of chefs and customers since the mid-90’s. Today it parks across from McDonald’s, but has added a pavilion and picnic tables. Or visit the original Giovanni’s White Shrimp Truck at 56-505 Kamehameha Highway in Kahuku.

White tablecloths may have been cast aside at many Toronto establishments, but Scaramouche doesn’t play by trends. No barn-board tables or Edison bulbs can be found here. This swank uptown restaurant is a classic, having wined and dined customers—and topped many a restaurant list—for over 35 years. Take a tip from regulars and start the evening with the foie gras terrine before ordering entrées like Canadian grass-fed filet mignon or pork with hazelnut spaetzle and white asparagus. And, by all means, leave room for the coconut cream pie.

Every once in a while, the sun shines bright in San Francisco and every city residents flocks to the nearest park or beach to soak up the sun and day drink. Baker Beach, in the confines of SF, seems worlds away from city life. The view of the Golden Gate Bridge is spectacular, and the diverse group of Baker Beach visitors is a testament to what a hodge podge San Francisco truly is. Parking can be a pain in the butt; take the 29 bus and save yourself the hassle.

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

Every story about Chatham Bars Inn surely features the veranda, a wide porch with companionable groupings of wicker armchairs and table service that alleviates the need to fetch your own drink—so you never have to look away from the serene view of sailboats and swooping seabirds.

Chatham Bars Inn excels memory making and, in addition to spaces like the verandah that make you feel you’re part of a generous and grand tradition, this Cape Cod resort has created intimate places (a small library, a settee in front of a fireplace, a private deck outside your cottage, chairs arrayed around a fire on the beach) where your private traditions will be forged.

It faces the aptly named Pleasant Bay, calm waters sheltered from the Atlantic surf by barrier islands. And you’ll find it’s impossible to forget where you are: The fleet of sailboats and fishing boats and runabouts keep the ocean top of mind while the creative menus in the dining venues (centered around the catch of the day and the seasonal produce from their own eight-acre farm) are likely the most locavore of any property of this caliber.

Originally built as a private hunting lodge, the inn has been in business since 1914, which means many guests have been coming here since childhood. This curated version of a Cape Cod beach vacation is a decades-long habit for those guests—and one that new arrivals may be inspired to adopt. Pride of place is strong here and guests get caught up in it, too. While you don’t have to shuck the clams or dig the potatoes yourself (though those could probably be arranged upon request), you will never feel insulated from the experience of this distinctive part of New England.