Whether for family reunions or girlfriend getaways, big groups can get the most out of their trip with Tremblant Living’s three- to eight-bedroom rental chalets located in and around Mont-Tremblant Resort village.
Design: Wooden beams and stone fireplaces provide a rustic backdrop for chic contemporary furnishings and modern, high-end appliances.
Amenities: Request a chalet with a sauna, billiard table or even an indoor pool.
Dress Code: Casual layers will take you from sunny daytime hikes in the Laurentian Mountains to chilly evenings around the firepit.
Drink: A pint of home-brewed beer (seasonal specials include Raspberry Ale and Oktoberfest) from La Diable microbrewery.
Dish: Lobster poutine enjoyed on the terrace of Patrick Bermand’s eponymous restaurant.
Outing: Nature lovers can spend the day zip-lining above the trees and looking out at the mountains and river, while spa devotees can find bliss at nearby Scandinave Spa’s outdoor Nordic bath circuit.
Don’t Miss: The Pierre Plouffe Nautical Centre offers watersports ranging from tubing to wakeboarding, as well as boat rentals, for a perfect day on Lac Tremblant.
Lastarria Boutique Hotel
Named for the hip quarter in which it occupies a central address, Lastarria Hotel is the ideal launch pad for exploring the modern side of Santiago.
Design:Art Deco meets pop art in a setting that combines its history as an upscale 1920s residence with the bohemian character of its recently revitalized neighbourhood.
Amenities: The knowledgeable front-desk staff can prepare a half- or full-day itinerary including museums, parks, shopping and sightseeing.
Dress Code: You’re equally at home in heels or a pair of sneakers.
Drink: Afternoon tea (a Chilean ritual) is complimentary in the restaurant every day from 4 to 6 o’clock.
Dish: The Tabla Aire Mar y Tierra presents a sampling of Chilean surf and turf, all made for sharing.
Outing: For a one-stop intro to the country’s top wines, visit nearby Bocanáriz, a restaurant where every server is a sommelier and the small-plate menu is designed around regional pairings.
Don’t Miss: The poolside terrace is a courtyard-garden oasis that will make you forget you’re in a city of over 6 million.
Set over 160 sloping hectares on Mount Liamuiga, this brand new (and still growing) resort puts sustainable cuisine front and centre with an organic farm, edible landscaping and a signature restaurant that’s already one of the best in the Caribbean.
Design: West Indian architecture meets infinity pools and villas, plus a plantation-inspired bar built using stones from the property.
Amenities: The daily fruit basket isn’t just for show – it’s full of pineapples, bananas and anything else ripe for the picking, all from the property.
Dress Code: Take a cue from the staff’s crisp jeans and linen shirts, created by Caribbean designer Claudia Pegus.
Drink: The cellar comes care of sommelier Isabelle Legeron, the world’s leading expert on natural wines.
Dish: Harvest vegetables on the farm with the chef, then watch him turn it all into a healthy meal.
Outing: Head down to the black-sand Dieppe Bay beach for seafood at Arthur’s.
Don’t Miss: The organic, Ian Woosnam-designed golf course. It’s closed one day a week for weeding and you’ll find fruit trees throughout.
Shelborne Wyndham Grand
Retro glamour reigns at this iconic South Beach property, first built in the 1940s then restored and reopened in late 2014.
Design: Find Miami Art Deco style throughout, with vintage-car-inspired decor (chrome lamps, leather accents) in the 200 guest rooms.
Amenities: The prime oceanfront location means you can choose between lounging by the pool, strolling the boardwalk or heading out to the beach.
Dress Code: Fun and floral by day, dress-to-impress from sunset on.
Drink: Cocktails in the Drawing Room are separated into categories like Aphrodisiacs and Stimulants – take your pick.
Dish: Tuna belly tartare and A5 Wagyu beef from Iron Chef Masaharu Morimoto’s South Beach outpost.
Outing: Head to Artsee Eyewear for standout sunnies and Alchemist for designer collaborations, then marvel at 1111 Lincoln Road, a parking garage/design destination by Swiss firm Herzog & de Meuron.
Don’t Miss: Morimoto executive pastry chef Manabu Inoue’s exotic macaron flavours – including guava, yuzu and black sesame.
Prince Edward County, Ontario
The Drake Devonshire Inn
This restored historic iron foundry building in Ontario wine country is the latest outpost of Toronto’s Drake Hotel Properties.
Design: Big, bold, modern design and local artist collections complement the building’s original architectural elements.
Amenities: Comfy made-in-Canada “hoodie” bathrobes by Shared. Throws from PEI’s MacAusland Woollen Mills.
Dress Code: West Queen West cool meets country-casual.
Drink: Unwind firepit-side on the shores of Lake Ontario with a glass of Vintner’s Daughter Chardonnay by local winery Rosehall Run.
Dish: Prinzen Farms rotisserie chicken and Hagerman’s heirloom tomato salad from chef Matt DeMille’s local farm-and-lake-to-table menu.
Outing: After a day of antiquing in nearby Bloomfield and visiting wineries along the Millennium Trail, settle into the hotel’s Glass Box rec room for a rowdy game of Ping-Pong.
Don’t Miss: Splurge for the Owner’s Suite, an A-frame lodging with peaked ceiling, a bedside fireplace and stunning lake views from the private patio.