One sister plans everything. Another wings it. They still travel.

Issa Okamoto has been traveling since she was little, but not necessarily with her parents. 

“Honestly, seeing my mom on a flight, I’m like ‘What is happening?’” the 22-year-old content creator and Oberlin College and Conservatory student said on a call with her consummate travel companions: her sisters. 

When Issa was 4, Ameya was 7 and Nadya was 9, they moved to Oregon with their mom while their dad stayed in New York. For years afterwards, the trio would fly back and forth between parents, unaccompanied. 

“We’ve been traveling alone together a while,” said 28-year-old Nadya, a content creator and entrepreneur. 

Nearly two decades later, the Okamoto sisters still stick together. 

“We actually all live like across the street from each other,” said 26-year-old Ameya, who's an artist and influencer.

They live in New York and still travel together, too, but no longer because they have to. 

“It's been really fun to kind of see how both sisters travel and then figure out how we each individually do so, too,” Issa said. 

The big sister

"Then and now, the dynamic is I've always been the stressed-out older sister,” Nadya said. 

As the eldest, she was the one left in charge on their cross-country flights. 

“I used to feel like I could not sleep on the plane in case someone took one of them. And so, I would stay up all night, and either they would watch the JetBlue Cartoon Network TV with me, or they would sleep, and I would force myself to stay awake because I was always nervous,” Nadya recalled with a laugh. “My mom would be like, 'Don't let anybody take them because they'll be human trafficked.’” 

“She did say that to us,” Ameya echoed.  

Nadya says she still gets anxious when things go wrong. 

“I think I’ve missed one flight from sleeping in, and I thought like the whole world was ending,” she said. 

To stay on top of things, she meticulously updates her Google Calendar, carving out set times for specific tasks, such as getting ready for a meeting or getting to the airport. 

“I calendar out everything,” Nadya said. “If anything adjusts, like we leave for the airport let's say 30 minutes later than my calendar, I adjust the calendar invite.” 

She loves itineraries and color coding. 

“I also think that Nadya does enjoy planning,” Issa added. 

“She likes being in charge,” Ameya joked. 

“Yeah,” Nadya chuckled. “For me, there's no such thing as over-planning. It just gives me more peace of mind.” 

The middle child

Ameya didn’t always appreciate Nadya calling the shots.  

As a kid, the self-described classic middle child recalled thinking, “well, I'm only a little bit younger.” But she sees the benefits now, like not having to worry about anything while “blindly following" her big sister.

Unlike Nadya, Ameya said she’s always been a good sleeper. 

“I don't think that I would have gotten to the point where I'm so comfortable sleeping in public and on planes if I didn't probably know that I had an older sister who would make sure I woke up on time, make sure the transfer was happening, make sure I got my immigration forms filled out, all of that,” she said. 

It’s different, however, when Ameya travels solo or with others. 

“I actually think that when they're on their own, they’re very organized,” Nadya affirmed. 

“I always have a schedule for myself in my head,” said Ameya. “The trick for me, though, is the fact that I'm not married to it.”  

If she misses a flight, which she said has only happened once or twice, she’s fine with catching the next one. “I get where I need to go, but it's like in my own timing and my own way,” Ameya said, adding that she can lock in when needed and take the lead if she’s traveling with a group that’s not her sisters.  

Even when she’s making the plans, Ameya prioritizes flexibility and the chance to “choose your own adventure.” 

“My best travel experiences and best travel stories are all about impulsivity,” she said. “You meet someone, and it changes your whole itinerary.” 

The youngest 

Issa falls somewhere in between her sisters’ styles. 

“I think that honestly has been a gift to me, that I've been able to adapt,” she said. “And that kind of transfers in a lot of areas of our life, more so than traveling.” 

“I don't color code my calendar, but I have a Notes app where I'm like 4:30 here, 5:30 here, 6:30 here,” she added. “I have that kind of general outline, and then maybe I have the Airbnb booked, but I don't have dinner and reservations.” 

Issa said her approach to travel has evolved as she’s gotten older and become more financially independent. 

“When I was first starting out as a content creator, making my own money, it definitely was a financial limit,” she said of having to plan carefully and budget. 

“As I've grown up, it's kind of been a privilege where ... I can miss a flight, and I'll just hop on the next one or I'll get there and just figure it out and book the closest, nicest hotel that has the best reviews," she said. 

However, the sisters sometimes switch roles as they've grown up.

“I think it's been a healing process though for us, as we've all entered our 20s, to see Nadya, sometimes when we travel, like she steps back and Ameya and I will take the plate on,” Issa said, prompting immediate, good-natured protest from Nadya.  

“You want some proof?” Issa added, producing a photo of Nadya dozing off on a flight. 

“Sometimes I nap on the plane,” Nadya acknowledged.