A rising junior at the University of Florida, Josh Rosen was slated to spend his 2020 spring term studying in Florence, Italy, participating in an eclectic academic program that ranged from international business to art and wine tasting. But the coronavirus pandemic had other plans, and his program—like most everyone’s study abroad programs—was canceled. Almost immediately, his parents began planning a family trip to Italy—to celebrate his 2022 graduation.
“He missed this big opportunity, and it kind of put things in perspective for all of us,” says Sherrie Rosen, Josh’s mother. “Our other son is starting college, and we’ll be entering a new phase of life, but right now we’re all home, sitting around the dining room table every night, and we had plenty of time to talk about it, to do research. It’s a long way off, but it has also become clear that life is short, and we didn’t want to miss any more big opportunities. In that vein, we’re already thinking about his brother’s graduation in 2025.”
The Rosens aren’t alone. More and more people have begun looking at their travel ambitions the same way they’ve long considered their finances: setting goals and making multiyear plans, five and even 10 years in advance. There are many good reasons to map out your bucket-list trips.
Some require long lead times, especially when limited permits are required, such as the increasingly hard-to-secure ones for treks to Peru’s Machu Picchu or the red-hot Milford Track hiking trip in New Zealand.
Fantasy adventures requiring a higher level of fitness, like gorilla trekking in Rwanda, are better done sooner in life than later. There is no such thing as a last-minute around-the-world cruise, as the best ships offer these voyages only every few years, and they book up fast.
Jack Ezon was an early pioneer in this niche of the industry. As founder and managing partner of Embark Beyond a luxury lifestyle and travel agency, Ezon is one of the world’s most prominent travel advisors, with numerous professional athletes, celebrities, and other high-net-worth individuals as clients. For years he has been pushing what he calls “meaningful travel.”
“Just like a financial advisor, we really want to understand our clients’ life goals and work backward from that,” he says. “They each have their own personal lifestyle and goals. The strategy is to help them enhance those life goals by using travel as a platform to fulfillment. To do that, we try to chart a course over five or 10 years to deliver on those goals and make it more meaningful than one-off, ad hoc trips that don’t further their needs.”
For clients with children, for example, Ezon created a program called Journey to Global Citizenship, under which he tailors vacations to school curricula. Know that your daughter will be studying biology during her sophomore year? That’s the perfect time to schedule a trip to the Galápagos Islands.
Whatever the reason for your dream vacation, it starts with a list—and many travel agencies are making that brainstorming process easier for their clients. Virtuoso an international network of high-end independent travel agencies, for example, recently developed Wanderlist, a software platform for mapping each client’s bucket-list aspirations.
Cate Caruso, owner of True Places Travels a travel agency structured more like a consulting firm, was one of the first Virtuoso advisors in the world to use Wanderlist. “This concept of the long-term travel portfolio has actually been around for a while,” Caruso says, although she notes that the software streamlines the planning process.
Now, I start by asking things like, ‘Why do you travel? What was the first trip that changed you? How does travel improve your life? ’ Then we look at all the milestones, big occasions, birthdays, anniversaries, graduations, births, grandchildren, retirements. That’s a big one: People set a timeline for travel around retirement, especially for bucket-list things like an around-the-world cruise. We usually make a five-year plan.” Tania Swasbrook, VP of operations at Travelworld International Group, meanwhile, is planning her family’s travel with her 8-year-old daughter in mind. “The legacy I want to leave her is to be a citizen of the world,” she says. “It’s important to me that she hits all the major civilizations—Mexico, India, China, Japan, Greece, Egypt, and so on but you can’t just do that off the cuff; you have to be strategic.”
The key, she stresses, is to make a list and start simple. For her, that means saving trips to Japan or Egypt for when her daughter is older, since there’s so much to learn. “Planning is for the future—not just Christmas vacation or where to go next summer, but years down the road.”
Of course, travel has looked a little different this year. The old adage, “You don’t know what you got till it’s gone” has proved especially true for leisure travelers during the pandemic, and the silver lining may be that travel will become an even more important priority when normalcy returns.
Acknowledging the uncertainty of life goes hand in hand with realizing the importance of making every trip count—and not putting off the ones that are personal musts. Time spent in isolation can be used productively to discuss, reflect, research, and ultimately emerge with a better sense of the places you want to visit, not to mention the people you want to go with. “More than ever, people crave human contact in their travel,” Ezon says. “Multigenerational travel with families and reunion travel with friends were already big trends, but they will greatly accelerate after this. We are already seeing increased interest.”
Typical bucket-list items include safaris and trips to UNESCO World Heritage sites and the polar regions, but increasingly, travel industry experts note a shift away from places and toward experiences. For instance, people want to go on a safari to engage with wildlife and experience Africa, not just to say they’ve been to a specific country, such as Kenya or Tanzania or Botswana. “It’s not just where and when anymore, it’s why,” Caruso says. “Even though this is a list, the kinds of trips people are putting on it are about experiencing something, not just checking them off.”
Ezon also uses Wanderlist, but he says making the initial list is just the start of the process. “We want clients to move away from thinking about travel in terms of destinations and think in terms of aspirations. When someone tells me their bucket list includes Machu Picchu, I ask, ‘Why? That’s one day. What else do you want to do in Peru? ’ If it’s all about seeing ruins, maybe we could look at alternatives that are a better fit for them and the other things they enjoy.’
Life is short, and the world is a big place. Make a list.
To help you with doing so, here are some of the best places worldwide that deserve a place on your bucket list.

Polar Regions
“We call it the ‘penguin and polar bear’ fantasy, and the Arctic or Antarctic are always in the top five bucket-list trips for our clients,” says travel advisor Cate Caruso. Most of these journeys are on smaller cruises. National Geographic Expeditions, for example, leads excursions to Antarctica, Russia’s far east, Greenland, and more, and puts learning at the forefront, with a team of specialists—biologists, geologists, naturalists—giving science lectures to accompany travelers’ evening Champagne. nationalgeographic.com

Italy
Nearly a third of Wanderlist users picked ltaly as their dream destination. Tuscany is an oft-cited vacation spot, but travel fantasies abound throughout the country. History buffs head to Rome, fashionistas to Milan, artists to Florence, romantics to Venice. And no matter where you go—from the cliffs of the Amalfi Coast to Lakes Garda and Comothere’s incredible food and wine at every turn. Devising your own trip is doable, but arranging private tours with a company such as Imago Artis will make a good trip great. iatravel.com

African Safari
Getting up close and personal with wildlife—especially lions, cheetahs, leopards, giraffes, hippos, elephants, and endangered rhinos on their own turf—is the dream journey for many. Planning is essential: The best lodges, with uncrowded private reserves (typically found in South Africa and Botswana, and also in Tanzania, Zambia, and Namibia), are very small, with just five to 15 rooms, and often book up well over a year in advance.
Great safari options abound; one of our favorites, Micato Safaris, offers full-service treks in East and South Africa, generally lasting 10 to 17 days. micato.com

Around-the-World Cruises
You can see it all! Typically stretching from around 100 to well over 200 days, global circumnavigations are the textbook definition of a “once-in-a-lifetime experience,” and they tend to be offered by the more luxurious lines on their midsize ships just once or twice per year. Oceania Cruises recently supersized its popular “Around the World in 180 Days” offering; the upcoming Epic World Quest onboard the Insignia sets sail in December 2021 and lasts 196 days, visiting about 100 ports across more than 40 countries and six continents. oceaniacruises.com

Australia and New Zealand
Considering the vast size, immense variety of natural beauty (the Great Barrier Reef, the Bay of Islands, Aoraki/Mount Cook National Park), vibrant cities, and the long flights to get there, trips to Oceania tend to be saved until they can be done as multiweek experiences. If you need help putting together your excursion, Southern Crossings, a 34-year-old luxury tour company, will work with you on arranging accommodations, guides, activities, and more. southern-crossings.com