Destinations: North America

Visiting a new destination is more than an exploration of unfamiliar lands—it’s an exploration of self. If you’re willing to cast off traditional ideas about travel and welcome something different, perhaps even something that pushes you beyond the limits of personal comfort, you can unleash your creativity, shift your perspective in subtle yet extraordinary ways, and experience the world with intention.

Follow four bold travellers to some of their favorite destinations and learn how these places and their experiences there shaped the way they view the world and connect with it. You’ll discover that what you fear may be too daring is the starting point for truly transformational travel.

To say Kimi Werner is comfortable in the water is a vast understatement. As a child growing up in coastal Maui, she would often go snorkeling with her father as he free-dove and spearfished (what he caught was the family’s main source of food). And as an adult, Werner continues to find the ocean at the center of her life—and career(s): She is a U.S. National Spearfishing Champion, a bold free diver, a seafood-focused chef, and an ocean conservationist.

Werner has traveled all over the world—even to Antarctica—in pursuit of natural beauty and in service of protecting it, but her favorite place to explore remains her home state of Hawaii. She and her family live on Oahu’s North Store, which, she says, “still does function as a small town.The community is very much in tune with nature, and a lot of people live here because they want nature to dictate their lives, their choices, their schedules.”

Her top destination when it comes to Oahu? “Waimea Bay is hands down my favorite beach, and I think it’s one of the most magical places in the world. Whenever I go, I find myself questioning why I travel so far when I have something so beautiful right here.” For hiking enthusiasts, she recommends Keālia Trail (“I call it the StairMaster of the North Shore”) and Ka’ena Point Trail, where there is a bird sanctuary. All of these breathtaking spots are within a 45-minute drive of Four Seasons Resort Oahu at Ko Olina, which offers a morning or sunset Ma’ili Pillbox Hike for a closer hiking experience.

At Four Seasons Resort Hualālai, situated on an expansive stretch of coastline on the Big Island of Hawaii, you can get a taste of what it feels like to explore the ocean’s depths and push your physical limits via the Kimi Werner Freediving Experience, in which as many as four guests can spend two half-days learning to free dive with the national spearfishing champ. The package includes a four-course private dinner crafted by the resort’s executive chef, Richard Polhemus.

Whether you’re exploring the world or exploring creative pursuits, you’ll find one common thread: The most meaningful experiences occur when things happen unexpectedly. Unplanned adventures and thinking beyond the expectations of a typical vacation may lead to a deeper connection with your destination and yourself.

Just ask photographer and creative director Dave Krugman. His numerous world travel experiences – including time spent in Kyoto – have led him to believe that one of the most essential elements of a successful trip, regardless of destination, is keeping an open mind.

“I try to leave a lot of breathing room for spontaneity and serendipity, because my favourite moments are when something happens, the path diverges, and I’m exposed to this thing that I couldn’t have planned even if I wanted to,” he says.

In Kyoto, those moments could be immersing yourself in the world of geiko and maiko – kimono-clad entertainers who perform traditional song and dance – and an ozashiki asobi dinner in one of the city’s historic geisha districts. Or learning the art of Zen meditation from the deputy head monk of Shoden Eigen-in.

During his stay at Four Seasons Hotel Kyoto, Krugman discovered a variety of new people, environments and experiences: A hotel guide led him on a tour of an ancient bamboo forest, and the Concierge arranged a visit to a local lantern workshop, where artisan lantern-makers taught him how to carefully layer thin sheets of paper over a frame to build his own mini lantern.

Even the Hotel’s atmosphere provided opportunities to connect with the culture and history of the city. Set around the 800-year-old Shakusui-en pond garden – one immortalized in a 12th-century epic poem – every setting at Four Seasons is carefully crafted with purpose.

Krugman cites travel as one of the biggest influences on his photography and his relationship with the world around him. “There is nothing more inspiring and invigorating than travel,” he says. “It always shows me that the world is so much larger than we imagine, so much more diverse. Witnessing this complexity and the vastness of the world is a humbling feeling, and it inspires me. Photography allows me to connect more deeply with all I see and experience.”

There are many valid reasons to talk yourself out of the adventure of a lifetime – a lack of travel companions, language barriers, concerns about food. But writer and entrepreneur Jessica Nabongo believes that embracing the unfamiliar in spite of your worries can improve your life and deepen your understanding of connection. She also believes that being afraid has no place in a travel itinerary.

“I would say that my travel philosophy is to travel without fear,” says Nabongo, the first Black woman to visit all 195 countries in the world. “I’m constantly living outside of my comfort zone. I think my comfort zone is discomfort,” she quips.

In Florence, one of Italy’s most beautiful cities and the centre of the cultural and intellectual revolution that swept through Europe during the Renaissance, Nabongo leaned into the unfamiliar to become uniquely acquainted with the region. A truffle-hunting excursion led her through the scenic Italian countryside, while a Michelin-starred dining experience and tours of iconic landmarks – like the Duomo, with its distinctive terracotta-tiled dome – offered new perspectives of the storied city.

Aside from abandoning fear, Nabongo’s second travel philosophy is to explore new places with a positive mindset: “I always say positive energy coats my stomach, because I’ve never had food poisoning!”

Arguably, sampling local fare is among the easiest ways to connect with a new place, a new culture and new people. In Florence, that could mean queueing up with the locals to eat lampredotto at one of the city’s myriad food stands. Or it could mean indulging in an intimate sunset dinner at the renowned Ponte Vecchio, the city’s signature arch bridge. Available exclusively to guests of Four Seasons Hotel Firenze, the bridge’s only open-air terrace provides a romantic setting for a decadent meal above the glittering jewellery boutique Dante Cardini.

Travelling with a reasonable amount of abandon can alter our perspective and shape the way we connect with the world around us, with others – and with ourselves. It can even change how we think of travel. For Nabongo, each new adventure doesn’t involve leaving home, but arriving there. Her experiences with hospitality in Florence and beyond have taught her to appreciate the fact that any destination is just as much about the people as it is about the location.

“For me, now, home is in people,” she says. “Yes, I physically live in Detroit, but I have homes in London, Accra, Dakar, Bangkok, Rome – I can think of so many places that I have homes because my people are there.”

Trips all too often become mired in travel itineraries: Sights to see, foods to eat, things to do. Recommendations from friends or something you saw on social media. The pressure to check items off a list becomes so great that a long-awaited getaway can quickly turn into a chore instead of a rewarding experience.

Georgina Miranda, who cites yoga and energy practice among her laundry list of talents, thinks about this a lot. She believes travel that’s overly focused on getting things done can limit your ability to truly arrive at a destination and connect with it. Instead, she suggests giving yourself 20 to 30 minutes upon arrival to be present in the moment without any obligatons. “It’s this art of being versus doing,” she says. “And I think Western culture really encourages us to constantly be doing, so we miss out on so much magic.”

Costa Rica is one of the destinations where she lets her senses capture that magic – the sight of verdant rainforests, the sound of waves rushing to shore, the cool mist of a thundering waterfall, the salty scent of the ocean breeze.

“It’s been in the recent years that [I realized] my travelling has changed so much,” she says. “I no longer want to see the world – I want to feel the world. And that really shapes how I travel.”

Tucked between unspoiled beaches on the north Pacific coast, Four Seasons Resort Peninsula Papagayo, Costa Rica, is surrounded by rugged yet tranquil natural beauty that eases into your psyche, connecting you to this lush paradise. This coastal retreat offers unrivalled access to some of the world’s most unique habitats. There, you can witness monkeys leaping from limb to limb during an exploration of the mystical cloud forest Monteverde, or venture into the mangroves and paddle through incredible tree and root systems to see the rich diversity of wildlife found in this serene sanctuary.

“If you’re open enough, you can let a lot of wonderful things come into your life when you travel,” says Miranda. “It snaps you out of autopilot and it gives you the opportunity to wake up to yourself again.” In Costa Rica, that experience could come in the form of a yoga session or meditation class at the Resort’s Spa to help you find your balance or set your intention for the day. The on-site Wellness Concierge can design a custom plan with you to help your best self emerge – centring your breath, body and mind to restore balance.

“There’s a moment when travelling that you realize you will never be the same because of what you’ve experienced,” Miranda says. “You have felt, touched, tasted and been immersed in a new reality, and so now your own reality is different.”