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The Best Private Transportation Experiences of the Year

The 2020 Legend Awards.


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The 2020 Legend Awards are meant to serve as inspiration for future travel—when it is safe to do so. Learn more about this year's awards on our methodology page.

The allure of private transportation perhaps starts at the sheer exclusivity of the experience. But really, the appeal is so much more than Dom Perignon enjoyed in a luxury private jet or aboard your very own yacht—though it’s certainly a good start. Nonetheless, a major draw of private transportation is that the logistics revolve entirely around your schedule, from start to finish. The in-flight or on-yacht experience is similarly tailored to your preferences, from brand of caviar to WiFi speed to accomodations for your pet.

Private travel also puts near-inaccessible parts of the world within your reach as a traveler. With their ability to navigate narrow channels or restricted airspace, our Legend Award honorees for best private transportation deliver access to highly sought-after parts of the globe. These are the best private transportation services of the 2020 Legend Awards:

Wheels Up and Delta Private Jets

Wheels Up and Delta Private Jets came together in 2019 to fuse the intimate and elite service of Wheels Up with Delta’s global reach. They’re now responsible for one of the largest owned and managed private fleets—available to members with 24 hours notice.


PELORUS offers private, super-exclusive yacht charters with 100% customizable itineraries. One of our favorite PELORUS charters is aboard the LEGEND, a 77.4-meter superyacht that can accomodate 26 guests as it treks to Antarctica. A week on the LEGEND through PELORUS starts at $550,000 and brings luxury travelers to see chinstrap penguins, seals, and whales, swim in geothermal waters, and hike Antarctic glaciers.


One of the reasons we love VistaJet is their subscription that allows passengers to pay exclusively for hours in-flight, a rarity in the private aviation industry. VistaJet is also one of our go-to family-friendly private jet programs, with plenty of entertainment geared toward children. And most recently, they’ve announced the arrival of the Global 7500 aircraft, two years ahead of anyone else in the industry.

Uber Black and Uber Copter

We've long since been fans of Uber's ​​​​​luxury offerings. Among our favorites are, of course, Uber Black, which instantly pairs travelers with a high-end black car driven by an experienced professional. In the last year, we’ve also become Uber Copter converts, as a way to get from lower Manhattan to JFK in seven minutes flat.

Dream Yacht Charter

Dream Yacht Charter puts luxury vessels at your fingertips, with their fleet of 1,202 yachts, catamarans, floating villas, and monohulls in 50 destinations around the world. Dream Yacht Charter is the only company to offer fractional sailing ownership on a global scale. You can secure a chartered yacht with a full crew or sail your own ship.


NetJets debuted their partnership with Northrop & Johnson, a luxury yacht industry leader, in late 2019. NetJets owners can now charter yachts and access selected Northrop & Johnson’s VIP experiences, bringing NetJet’s top-tier sky experience to the water.

TCS World Travel

TCS World Travel plans private jet vacations for luxury travelers seeking the best jet amenities. Each all-inclusive bespoke TCS jet vacation can take you to 10 hard-to-reach destinations on one trip.


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