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Trip Ideas

Where Would You Go if Travel Were Free?

We at Jetsetter have big dreams (wanderlust comes with the job, after all). So hand us a fat stack of cash, and you better believe we'd be on the next flight out to some incredible far-flung destination. From yachting around Greece to hiking the Himalayas, here's the once-in-a-lifetime trips we'd be taking if we were gifted the ultimate all-expenses-paid vacation.

Chelsea is Brooklyn-based travel writer, editor, and photographer. When not home eating her way through NYC, she's gallivanting across the globe, sailing the coast of Croatia or hiking the peaks of Peru. Her superpowers include booking flight deals and sleeping in small plane seats.

See recent posts by Chelsea Bengier

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Flying around the world on a private jet

If I were given any free trip, it’d be the Four Seasons Private Jet Experience. Essentially, the Four Seasons sends passengers on a 24-day trip around the world, stopping in cities across Asia, Africa and Europe; flying on their private jet; and staying at the chain’s most exclusive properties (ahem, Four Seasons Resort Seychelles at Desroches Island) — all to the tune of $135,000 per person. The cities you stop in depend on the month you depart, but my perfect itinerary would be Seattle-Tokyo-Beijing-Maldives-Serengeti-Istanbul-St. Petersburg-Marrakech-Boston. A girl can dream…

— Siobhan Reid, Writer

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Getting schooled in Central America

I love a good road trip, so I’d take my family of four on a month-long journey through Central and South America. Although my kids have passport stamps from 10-day max excursions, I’d jump at the opportunity of an extended vacation to immerse them in various cultures, landscapes and flavors. How cool would it be to study biology in the rainforests of Belize? Or ditch the gym for surfing along the Costa Rican coastline? Now, that’s my kind of classroom!

— April Ellis, Senior Photo Editor

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Yachting around the Aegean

I’d take to the sea on a private yacht (with a personal chef and clean-up crew, of course) for my family and friends to tour the Greek Islands. I’d start in Santorini, with a couple nights’ stay at the Andronis Luxury Suites, then hop in the boat to cruise around Mykonos, Naxos, Paros, Skiathos, Zakynthos and all the other Aegean gems.

— Clara Sedlak, Executive Editor

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Seeing the Northern Lights in Iceland

I’ve been eyeing Iceland for ages — between the Northern Lights, adorable icelandic ponies and scenic Ring Road, it had me sold. I’d splurge for a stay at Ion Luxury Hotel, then spend my days swimming in waterfalls, bathing in hot springs and hiking volcanoes. The landscapes are so gorgeous, I’d bring every single roll of film I own (and then some).

— Lauren Dishinger, Associate Photo Editor

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Road Tripping through the Southwest

Foot my gas and film, and I’ll be on the road faster than you can say Route 66. Shooting my way through New Mexico, Arizona, and Southern California for a month seems like the perfect antidote for the pre-winter blues. On my list of photo-centric places: Truth or Consequences, White Sands, Carlsbad Caverns, Monument Valley, The Cinders, Saguaro National Park, The Domes, Death Valley, and Salvation Mountain, just to name a few!

— Rebecca Enis, Photo Intern

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Going on the ultimate Roman holiday

When I drop dough, it’s always on food and wine (I do have priorities, people). So I’d make a beeline for the culinary capital of the world: Italy. I’d bring my appetite for a few weeks of la dolce vita, hitting all of the destinations on my bucket list, including Venice, Positano, Cinque Terre, Tuscany, Puglia and more.

— Jamie Ratermann, Head of Social Media

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Exploring Antarctica and South Africa

If I were handed a blank check to blow on a once-in-a-lifetime vacation, I wouldn’t just stay in one place. I’d check into the One&Only hotel in Cape Town for a few nights before departing on an eight-day expedition to Antarctica. For a mere $70,000, I would bunk down in a domed suite at the White Desert luxury camp (think: cozy interiors with fur-pelt blankets to snuggle up in), and spend my time exploring cobalt-blue ice caves, hiking glacial mountains, kite-skiing on snow drifts and playing with Emperor penguins. Afterwards, I’d defrost back in South Africa, going on game drives and spotting the Big 5 at either the Lion Sands Sabi Sand or Singita Lebombo safari lodges just south of Kruger National Park.

— Chelsea Bengier, Editorial Assistant

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Adventuring around Asia

Those who know me know I have big dreams — and expensive taste! If money were no object, I would spend an epic month hiking the Himalayas, visiting Bhutan’s tiny tea houses, Buddhist temples, and high-altitude monasteries before jumping over to Nepal and diving into Sherpa mountain culture. My final destination: Everest Base Camp.

Lindsey Olander, Editor

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Driving through South America

I’m guilty of always trying to squeeze the maximum amount of activities into one break, so I would take a month-long drive through South America. Starting in Peru, I’d hit the Sacred Valley and Machu Picchu, then head to the Atacama Desert in Chile. Argentina’s up next, with a few days on an estancia (cattle ranch), horseback riding and drinking mate with the gauchos. But, I’d make sure to mix in a bit of leisure time: Drinking wine in Mendoza surrounded by vineyards and the snowcapped Andes sounds like the perfect way to reboot, before traveling to Patagonia. Last but not least, I’d top off the trip with a couple afternoons of eating, drinking, and reading by the pool at Garzón, a small hotel and restaurant in a rural town near the southern coast of Uruguay.

— Gretchen Moosbrugger, Photo Editor

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Heading to the Scottish Highlands

Hand me the winning ticket to the travel lottery, and I’d book the next flight to Scotland. Bunking down in a charming cottage or B&B, I’d soak up the raw beauty of the Highlands on long, aimless walks through the countryside. A train ride from Edinburgh to Mallaig would also be a definite must, especially on the ultra-luxe Belmond Royal Scotsman, which has postcard views of the glistening lochs and picturesque villages. Plus, there’d be stops in Inverness to check out the castles, Loch Ness — because how could I not — and the Isle of Skye to see the waterfalls and fairy pools.

— Chelsea Stuart, Editorial Intern



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