SmartFlyer

SmartFlyer Global travel agency with roots in New York City. Introducing clients to amazing places since 1990.

06/23/2026

One of Cabo’s most iconic resorts just entered its next chapter.⁠
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At the end of 2025, Waldorf Astoria Los Cabos Pedregal completed a multi-year transformation spanning all 112 accommodations. Led by the resort’s original designer, Paul Duesing, the refresh introduces contemporary touches while celebrating the Mexican craftsmanship, artistry, and cultural heritage that have defined the property from the beginning. The result feels both refreshed and unmistakably Pedregal.⁠
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If you’re interested, chat with your SmartFlyer travel advisor.⁠
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Located in the heart of Tuscany, Castelfalfi offers an authentic taste of one of Italy’s most iconic regions. Surrounded...
06/22/2026

Located in the heart of Tuscany, Castelfalfi offers an authentic taste of one of Italy’s most iconic regions. Surrounded by vineyards, olive groves, and rolling hills, the restored medieval borgo serves as the perfect home base for exploring the countryside.⁠
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From yoga in the woods and afternoons spent poolside to truffle hunting, medieval villages, and sunset aperitivos overlooking the hills, we’ve mapped out our idea of the perfect day in Tuscany.⁠
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While some experiences—like truffle hunting—are seasonal, there’s no better time to start dreaming about a future escape. Consider this your inspiration for planning ahead.⁠
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Find the full guide at the link in bio, plus more recommendations for experiencing Tuscany through Castelfalfi.⁠
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Some of life’s most important lessons aren’t taught in a classroom. They’re learned through new cultures, unfamiliar pla...
06/21/2026

Some of life’s most important lessons aren’t taught in a classroom. They’re learned through new cultures, unfamiliar places, and shared experiences. Today, we’re celebrating the SmartFlyer dads bringing those lessons to life through travel.⁠
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Friday Flight Mode: Art Basel, but make it Basel.
06/19/2026

Friday Flight Mode: Art Basel, but make it Basel.

With The Bear’s final season hitting streaming services on June 25, the whole world’s about to be hungry for Chicago aga...
06/18/2026

With The Bear’s final season hitting streaming services on June 25, the whole world’s about to be hungry for Chicago again. So, we thought we’d tap a seasoned city vet to get the real take on it’s dining scene.⁠
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After 25 years on the Magnificent Mile, no one knows this city quite like The Peninsula Chicago. A quarter-century of sending guests to the best tables in town—the icons, the new openings, the neighborhood spots worth the trip—makes them exactly the kind of insider we trust. So we asked them where they actually send people, and this is what they said.⁠

For ultimate Chicago weekend guide, click the link in bio.
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06/12/2026

What’s new and next in luxury travel? Right now, it’s less about where you’re going and more about what you’re going for. Hotels are turning into stages, expeditions are being built around once-in-a-lifetime moments, and the world’s biggest events are reshaping how (and when) people travel.

That’s what’s new and next. For more on what’s new in the travel word, head to Stay Awhile, a Substack by SmartFlyer, link in bio.

This year’s retreat took us to Big Sky, where we immersed ourselves amidst the peaks of One&Only Moonlight Basin, One&...
06/11/2026

This year’s retreat took us to Big Sky, where we immersed ourselves amidst the peaks of One&Only Moonlight Basin, One&Only’s first stateside property and one of the most anticipated openings in recent years.⁠
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It didn’t take long for us to deeply settle into Montana mornings on the yoga deck, lakeside lunches, helicopter rides over Yellowstone, and long evenings together around a fire.⁠
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Congratulations to the eighteen agencies that achieved SmartFlyer ONE 2025. We love coming together to celebrate you.⁠
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MARCHAY, MARCHAY
Michael Schertz, Michael Schertz
Robert Merlin, Robert Merlin, Travel Advisor
Judy Stein, the stein collective
Addie Bell, Addie | Luxury Travel Planner
Jacqui Weidman, Jacqui Weidman
Elisa Brown, Elisa Brown, Founder
Kyle Seltzer, KAX Lifestyle
Michelle London, Away We Globe | Luxury Travel
Kara Slater, Kara Levy Slater
Betsy Polatsch, Betsy Polatsch
Deborah Director, Deborah Director
Rachel Braylovksy, Rachel Brylovsky
Teddy Betesh, Teddy Betesh
Ash Chin, Sojourns Of
Betsey Brown, Betsey Brown, Travel Advisor
Julie Palo Hayes, Julie Palo Hayes, Travel
Albert Valera, Albert | Everything Travel Guy
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And a special thank you to the partners who brought it all to life:⁠
Kerzner International
One&Only Resorts
One&Only Moonlight Basin
Akira Back Moonlight Basin
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bigsky

If you’re looking for the pleasures of a seaside Italian escape without the frenzy that now defines much of peak-summer ...
06/10/2026

If you’re looking for the pleasures of a seaside Italian escape without the frenzy that now defines much of peak-summer Amalfi and Capri, you’re not alone. ⁠
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More and more, the best of Italy’s coast is found in the places that haven’t yet been discovered by everyone else, the quieter islands and stretches of shoreline where summer still moves at its own pace. Knowing where to look, and when to go, is where a good advisor makes all the difference. Here are a few of the coastal escapes our team is sending travelers to this season.⁠
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For more recommendations around Italy, click the link in bio.⁠
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