Your 2020 Travel Calendar: When to Go Where

December 28, 2019 by Allison Reiber DiLiegro

Great Plains Zimbabwe Camps


A new year of travels is here, if you just decide where to go. To help you choose where 2020 will take you, we’ve assembled a month-by-month guide to some of our most fabulous destinations. We’ve highlighted 12 outstanding trips around the world at the times when lovely weather and low crowds collide. Here’s to another year of adventures.

January: Trisara, Phuket, Thailand


If beachy days and balmy nights are calling, Trisara awaits. The Andaman Islands are at their best in January and February, when the weather is warm and dry. Trisara is set on 35 acres of jungle, tropical gardens and white sand beach, with private pool villas scattered on the hillside for total seclusion. Days are spent lazing by the pool, snorkeling right off the beach, and diving into Thai culture in Phuket town. If you’re on a wellness kick this January, head to Trisara’s hilltop Jara Spa. There are body treatments, yoga, meditation, fitness classes and personalized wellness programs.


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February: HabanaLive, Cuba


For some sunshine that’s a little closer to home – just 90 minutes from Florida – make the hop down to Cuba. With sunny weather and little rain, February is a beautiful time to be on the island. HabanaLive designs bespoke itineraries through Havana and beyond that highlight the country’s rich history, art, music, or whatever interests you most. In addition to insider access in humming Havana, HabanaLive can arrange private villas on Cuba’s beautiful beaches.


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March: Chablé Maroma & Chablé Resort, Mexico

It’s spring break, which means it’s time for Mexico (though not that type of Mexico). Sister properties Chablé Maroma and Chablé Resort offer two unique experiences, both rooted in wellness and Mayan mysticism. Chablé Resort is set in the lush jungle on the Yucatan peninsula, with a focus on spa and transformative wellness experiences. There are Mayan rituals, yoga classes, and sweat sessions in the traditional temazcal saunas. For a wellness experience that’s more relaxed – think: indulgent beach resort – there’s Chablé Maroma. Guests can spend their days practicing yoga and soaking in the spa, or sipping a cocktail in the sand.


Contact Reservations: Chablé MaromaChablé Resort

April: TIME + TIDE Miavana, Madagascar


Looking to get far, far away? Set on the white sand island of Nosy Ankao off Madagascar, TIME + TIDE Miavana is as castaway as it gets (just with all the creature comforts). There are private butlers, private pools, spectacular seafood and sprawling villas with indoor/outdoor spaces. The decor is modern and playful, with pops of turquoise that play off the Indian Ocean’s many shades of blue. While not swimming in the gin-clear waters, Miavana is a perfect base for exploring northern Madagascar’s extraordinary landscapes and creatures, like lemurs and chameleons.


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May: The Norman & Six Senses Shaharut, Israel


Spring is a beautiful time to visit Israel, particularly when there’s a new Six Senses in town. Start at The Norman in Tel Aviv, a glamorous boutique property set in a former mansion. From there, take the 3.5-hour drive to Six Senses Shaharut, just south of the dramatic Negev Desert. Guests can spend their days mountain climbing and biking, taking camel safaris and dune walking with Bedouins. Or admire the biblical landscapes from home with pampering treatments that blend Eastern and Western medicine in the spa.


Contact Reservations: The Norman & Six Senses Shaharut

June: Kālesma, Mykonos


Sunny but right before high season, June is a perfect time to travel to Mykonos. For the feel of a traditional Cycladic village-gone-glam, head to boutique resort Kālesma. A good choice for couples or families, Kālesma epitomizes traditional Greek hospitality. There are lush suites and spacious villas, each with a private pool, as well as excellent modern Greek cuisine. Admire the Aegean views from the pool or get out and explore – it’s ten minutes from Mykonos Town but a world away.


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July: The Brando, French Polynesia


For a summer vacation that goes beyond the expected, there’s The Brando. Set on Marlon Brando’s private island, The Brando is eco-friendly yet ultra-luxurious. It’s also exclusive, with just 35 villas on six square kilometers of pristine nature. Guests spend their days exploring the lagoon on a kayak or outrigger, snorkeling and scuba diving, or stargazing with a naturalist. After a day in the sun, there’s the Varua Te Ora Polynesian Spa, inspired by the Royal family, who used to come to the island for beauty rituals. The all-inclusive pricing means that once you arrive, you’ll feel like the island is all yours.


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August: Great Plains Zimbabwe Camps


If safari beckons, buck the expected and head to Zimbabwe. Great Plains has four luxurious camps throughout the country. Mpala Jena Camp and Mpala Jena Suite are set in Zambezi National Park, with buffalo, elephant, lion and bird-watching and easy access to the UNESCO-recognized Victoria Falls. Sapi Explorers Camp is set in the wild Sapi Reserve. The sprawling Sapi Reserve was once a hunting concession that Great Plains took over to protect. Today, you’ll feel like one of the early explorers as you tour the reserve on foot or by canoe. August is one of the most beautiful months to visit Zimbabwe, with sunny, mild days and excellent wildlife spotting.


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September: Heckfield Place & The Fife Arms


When the air turns crisp, the countryside calls. Heckfield Place, 40 minutes from London Heathrow Airport, and the Fife Arms in the Scottish Highlands offer different takes on bucolic bliss. Start at Heckfield Place, the chic hideaway in a Georgian home with outdoor adventures, a cozy spa and excellent seed-to-table cuisine. From there, head out into the Scottish Highlands for a stay at the Fife Arms, an art-filled inn with unforgettable design and easy access to the great outdoors. Hike through the Highlands, explore the Queen’s Braemar Castle and taste whisky, all in a day’s work.


Contact Reservations: Heckfield Place & The Fife Arms


October: Crillon Tours, Bolivia


Bolivia has many climates, but October hits most of them right. Thankfully, that’s not up to you to plan. With their wealth of expertise, Crillon Tours arranges bespoke itineraries through this incredible country. Cruise the waters of Lake Titicaca, explore the otherworldly landscape of the Uyuni Salt Flats and delve into the beauty of Bolivian cuisine in La Paz. Off the beaten path and adventure-packed, Bolivia is ideal for family trips to honeymoons.


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November: Matakauri Lodge, The Farm at Cape Kidnappers & The Lodge at Kauri Cliffs, New Zealand


If you’re planning a trip to New Zealand, spring (September – November) is a glorious time to visit. And the Robertson Lodges are glorious places to stay. A trip through the three lodges will bring you to inspiring landscapes on the North and South Island. On the North Island there’s The Lodge at Kauri Cliffs for world-class golf and sweeping Pacific views as well as The Farm at Cape Kidnappers for rolling hills, rugged cliffs and more golf. On the South Island, Matakauri Lodge is set on Lake Wakatipu for stunning views of the mountains. Prepare for action-packed days of adventuring, world-class cuisine and nature like you’ve never experienced.


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December: Six Senses Bhutan


Touch down in the Himalayas for an unforgettable adventure. Six Senses Bhutan is a circuit of luxury lodges that brings guests through the many landscapes and magnetic culture of Bhutan. Days are filled with cultural experiences like hiking to temples, touring the Dzongs – Bhutanese fortresses – visiting local festivals and meditating with monks. Each property has its own unique spa, perfect for unwinding and reflecting after days of exploration. Weather in December is lovely; some valleys are warm and sunny, while some mountains are snowy for a little holiday cheer.


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If you’re looking for more seasonal inspiration, we’re happy to help. Contact Hidden Doorways at for more intel on when to go where.

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