I Help Run the Four Seasons Private Jet With Around-the-World Trips

This as-told-to essay is based on a conversation with Chenin Matthews, director of guest experience for the Four Seasons Private Jet. It has been edited for length and clarity.

I came straight from college as one of the managers in training at the Four Seasons Hualalai, in Hawaii. For the last three years, I’ve had the pleasure of calling the jet program my main focus.

Travel is often exciting just because of the end destination, but it can also be a bit cumbersome. That’s not the case with the Four Seasons jet.

It’s a customized Airbus A321, with 48 first-class lay-flat Italian leather seats, so it’s absolutely stunning. In the back, we have a standing-room lounge that creates this social atmosphere.

A normal week varies whether I’m grounded or in flight.

Grounded, it’s making sure that we feel really great with our logistics, working with our Four Seasons teams and properties.

When we are traveling with the guests, every three days you’re in a new destination. I’m on about four of these trips a year.

We’ve got some regional trips that are $148,000, and then we’ve got our longer, 24-day trips that are more from there.

Some of our guests are successful in their own world where they handhold every single detail, and then they’ve allowed us to step in and take over. It’s really interesting to see the relaxation that comes to them.

You never touch your luggage, you don’t have to worry about where your boarding pass is, or which gate you’re going to — we’re there all along the way.

We’re talking with the guests to make sure we are delivering any wants and needs, customizations, and bespoke experiences.

We have an executive chef doing the catering, so it is always going to be three courses.

They’re either focusing on something from where we just came or where we’re going. Coming out of Japan, we have some wagyu beef on board. That’s always a favorite.

Even though we have a menu, it doesn’t mean that’s where it stops.

Oftentimes, we’ll have requests from people who are missing a little bit of home, like an American-style grilled cheese. We had some British folks who were missing fish and chips, but our chef made sure to have it.

I couldn’t tell you my favorite itinerary. It’s like choosing your favorite child. They’re so diverse and they offer such different things.

Ancient Explorer, which we just launched for 2027, is very ambitious. We’re going to Petra, the Great Barrier Reef, Easter Island, and Bangkok — all over the place.

Uncharted Discoveries, the itinerary that takes you through Latin America, features Cartagena, one of our newer properties coming online, and a ship trip to Antarctica.

When I first started, we used to say it was once in a lifetime experience, and we had to remove that because we have people who keep coming back.

We have a fair amount of people who travel solo, but 24 days later, it’s a group of friendships.

There’s a bittersweet element to the last flight. Guests have broken out into song and dance. It was “(I’ve Had) The Time of My Life” from Dirty Dancing.” One time, we had a captain on his last flight before retiring, and so people sang “For He’s a Jolly Good Fellow.”

I can’t say that there are any downsides to my job.

Part of the fun of travel is the unique moments that arise. There was a seaplane from another company that had an emergency landing, but there’s a reason that we have Champagne on board to stall us a little bit.

Sometimes it’s someone who has stumbled across a location that they remember from their honeymoon 20 years ago.

The first time I went to Bhutan with guests, people came out having emotional experiences from being up in Tiger’s Nest. It’s quite a pilgrimage to do the hike up there. Or when we go on a safari in the Serengeti and it’s people’s first time seeing a cheetah.

These moments are very powerful, to see how things unexpectedly touch people in different ways.

I was just on a trip a few months ago, and one of our guests was really touched by this moment that he had with a monk, so he actually wanted to donate about 2,000 kilograms of rice to this particular monastery.

Travel is intoxicating. To be able to experience, touch, and connect with different people, cultures, and food, is something that is special to me.