4 Destinations That Keep Me Coming Back For More

What’s your favorite place in the world?

It’s a hard question to answer if, like me, you love to travel. As a seasoned expat, I’ve been fortunate to call many incredible places “home” over the past two decades.

In 2012, I decided to sublet my apartment in San José, Costa Rica and take a one-way trip around the world, starting in Mexico before traveling up the U.S. Pacific Coast into Canada. Afterward, I hopped over the pond to Europe, Southeast Asia, and beyond.

During those years, I was a full-time digital nomad, spending anywhere from a few days to a few weeks or months in each place I visited… from London to Bangkok to Bali. And while each destination has made a lasting impression, some stand out among the rest.

Below, I share how traveling to 60+ countries has helped me refine what I look for in a home away from home… and which places keep calling me back.

Nosara, Costa Rica

The rate and pace at which I’ve traveled have varied over the years in alignment with my changing age, tastes, and interests. Each era brings new favorite places to travel or live.

In 2000, I became a U.S. national surfing champion. So in the years that followed, I made it a priority to settle near perfect waves so I could train. My favorite stops included world-class surf spots in Hawaii, Puerto Rico, Australia, and Baja, Mexico… but I eventually settled on the beaches of Central America.

When I first arrived in Nosara, Costa Rica in 2005, it was the height of the rainy season and the town was virtually abandoned. The shops and restaurants had closed, the tourists had fled, and the roads (and my clothes!) were often covered in mud from torrential downpours.

Life in my early days there was hard. I lived on a slim budget of $1,000 per month; I didn’t know anyone; and my Spanish was lacking. Plus, I had a few scary encounters with the local wildlife… including a run-in with a crocodile in the Nosara river mouth.

But after a while, I didn’t care. I loved walking to the beach to check the waves each morning, starting my day with a cafecito, and practicing yoga at a studio tucked in the rainforest canopy. Instead of commuting to a corporate job in the U.S., I got to ride my 4×4 through the Nicoya Peninsula.

If you’ve never been to Nosara, it’s a quirky beach town with a colorful, yet controversial past.

In the late 1960s, a developer from the U.S. began buying up nearly 3,000 acres of cattle ranches in the area to create a development that’s known today as the Nosara American Project. Although his master plan was never fully realized, the area remains subdivided into lots buffered by the Bosques de Nosara, a protected wildlife and nature preserve.

The area comprises three beaches: Playas Nosara, Pelada, and Playa Guiones. The Nosara river mouth (yes, where I narrowly escaped that crocodile!) is good for fishing, Pelada is a tranquil cove known for its colorful sunsets and beach bars, while the expansive, white sand beach of Guiones is best for surfing. Every evening, a diverse group of local residents and visitors gather to watch the sunset in Guiones or Pelada, along with their surfboards, dogs, hula hoops, and bongo drums. It’s become a daily ritual that locals and tourists alike are happy to partake in.

Nosara is also located in the Nicoya Peninsula, one of the world’s Blue Zones, with a high concentration of centenarians. Today, it’s the home of multiple yoga and meditation retreat centers, such as Blue Spirit, making it a magnet for yoga enthusiasts, surfers, wellness-seekers, and Hollywood elite.

I’ll tell you more about my move and Nosara’s history below:

Life back then was far from perfect, but it was just right for me… and I continue to visit Costa Rica every few years.

Practical Tips:

1. Located in the northwest Guanacaste province of Costa Rica, Nosara is a four to six-hour drive or bus ride from San José airport. Alternatively, you can fly into Liberia Airport, which is two hours north. You can also catch a shuttle from either airport or hop a local flight with Sansa Air. However, excess baggage on Sansa may be limited.

2. Once in Nosara, renting a car, 4×4, or golf cart makes it easier to get around, as taxis are in limited supply. Enterprise, National, and Alamo have cars there.

3. If you’re looking for a wellness retreat, Nosara is the place. Bodhi Tree Yoga Resort in Playa Guiones and Blue Spirit down the road in Garza are two good options.

Positano, Italy

After my time in Central America, I headed north to Italy where my grandmother’s family hails from. Stepping off the plane in Rome felt like coming home… even though it was my first time there.

In Rome, the fragrant smell of fresh bread and pizza peppered the air, and stylish locals zipped through cobblestone streets on their bikes and mopeds. And when I needed a break from urban life, I escaped to the tiny towns dotting Positano and the Amalfi Coast.

I’ll never forget celebrating my birthday with a multi-course dinner at Torre Normanna Restaurant—the oldest watchtower in Maiori on the Amalfi Coast. The beauty of the Mediterranean at sunset, fireworks exploding over the horizon, was surreal and to this day is among my favorite travel memories.

The following day, my best friend and I hiked the Path of the Gods, which stretches for eight kilometers through villages along the Amalfi Coast. After our trek, a local friend took us to a couple’s B&B and winery in Ravello, where we spent the afternoon rolling handmade gnocchi, tasting wine, and indulging in an Italian farm-to-table feast. The couple didn’t speak English, and we didn’t speak Italian, but we communicated all the same.

That trip reminded me that travel is more about who you’re with and the experiences you share than where you are… although being in a beautiful setting like Italy helps!

In all my years of travel, I’m not sure I’ve been anywhere as picturesque and pretty as Positano and the Amalfi Coast. If you’re looking for a scenic, romantic destination with warm, sunny weather and panoramic views of the Mediterranean, this region of Italy (just south of Naples) is for you.

Practical Tips:

1. For cooler temperatures and fewer crowds, visit in the shoulder season of spring (April to June, when flowers are in bloom) or fall (September to October). July and August are the hottest—and busiest—months.

2. To get to the Amalfi Coast, you can fly or take a train into Naples or Rome, then take a car, bus, or ferry to Amalfi. There are also ferries, buses, and taxis between Positano and Amalfi. You can also rent a car or moped… If you dare to drive the narrow roads.

3. Make sure to try the local lemons, known as Sfusato, that you’ll find everywhere in the region. You can eat the whole fruit, including the peel. You can also sample the lemon flavor in granita, cocktails, and limoncello.

Kyoto, Japan

Although adjusting to the language, food, and customs was at first a challenge, I felt welcomed by the Japanese people, who are among the kindest I have ever met.

Although Tokyo is the most densely populated city in the world, there’s more to see beyond this metropolis. Japan offers an incredible array of nature, as nearly three quarters of the country is covered by forest. From the subtropical islands of the south, through the terraced rice paddies of the Niigata Prefecture, to the mountains of Hokkaido in the north, there’s plenty to explore in Japan year-round.

I especially loved Kyoto for its temples, rivers, and cherry blossom trees. I was fortunate to be there in the spring during sakura, or cherry blossom season. At this time of year, you’ll see locals outside enjoying hanami, which translates to “flower viewing,” often in the form of picnics, parties, and outdoor gatherings with friends and family.

I like to experience hanami along the Philosopher’s Path, where pale pink petals float through the air and carpet the waters of the Lake Biwa Canal. Spring is also prime time for sampling traditional Japanese confectionery, or wagashi, often made with rice flour, fruit, sweetened bean paste, and agar, a type of seaweed.

Some wagashi recipes date back centuries. My favorite is the sakura mochi, a salty-sweet rice ball wrapped with bean paste and a pickled cherry blossom leaf. Even today, its taste reminds me of the rewards of pushing past cultural barriers.

Practical Tips:

1. You can reach Kyoto from Tokyo in about two hours on the high-speed Shinkansen train. A ticket costs between $70 and $100, depending on the date and time of your travel. You can also fly to Osaka, then take a 30 to 45-minute taxi or train to central Kyoto.

2. You can see geiko (Kyoto’s name for geisha, which translates to “artisan”) in public in the Gion district of Kyoto. Be careful not to offend with selfies or photos. Instead, buy a ticket to one of the authentic geiko dance performances or tea ceremonies, such as the Maikoya experience.

3. Don’t miss the Arashiyama District in Kyoto. Here, you can walk through the Bamboo Grove, hang out with monkeys at Iwatayama Monkey Park, and take a boat ride on the Hozugawa River.

Vancouver, Canada

My preference for outdoorsy living has led me to some… well, unintuitive destinations.

I’ve found that tropical islands like Bali, Indonesia, and Koh Samui, Thailand are as invigorating as the bustling cities of Hong Kong and Sydney. And the Arctic archipelago of Lofoten, Norway is just plain cozy!

A destination’s climate and cost of living doesn’t matter as much to me as proximity to water and nature. Hong Kong might be humid, expensive, and crowded, but it’s also surrounded by hiking trails and islands like Lantau, Lamma, and Cheung Chau. In contrast, Lofoten is cold and remote, but the scenic landscapes and hiking trails are breathtaking. It’s a place where you can hike a fjord, forage for wild mushrooms, surf or kayak in the Norwegian Sea, and see the northern lights… all on the same day.

Vancouver, British Columbia boasts that same dynamism… minus the Arctic temperatures.

In downtown Vancouver, modern glass skyscrapers are draped against the snowcapped peaks of the North Shore Mountain Range. Although it’s a modern city, the surrounding greenery, parks, sea wall, and Pacific Ocean provide respite from hurried city life.

Vancouver is a culturally diverse place with distinct neighborhoods, each offering its own unique charm and character. From the historic Gastown to the trendy Yaletown, every area has its own identity. Granville Island is the place to go for arts, culture, and food, offering a lively market, theaters, art galleries, and a marina. When the weather is nice, head over to Kitsilano or English Bay Beaches to enjoy the sun, sand, and waterfront.

Vancouver’s a safe city with good public transportation, a high standard of living, and a multicultural food scene. Here, you can find food from all corners of the world—often on the same block! Whether you’re in the mood for fresh sushi, local salmon and crab, a farm-to-table spread, or Korean BBQ, you can find it in Vancouver.

And if you’re short on time, you can grab a famous Japadog on the street… but there are plenty of vegan and vegetarian options as well.

I especially enjoy the city’s West End and Coal Harbour neighborhoods, which border Stanley Park, a green oasis that exceeds New York’s Central Park in size. Here, you can walk or bike around the nine-kilometer Stanley Park Seawall, ride the Stanley Park Train, or relax on one of the sandy English Bay beaches.

There’s also an aquarium, teahouse, outdoor pool, splash park, and 27 kilometers (yes, 27!) of walking trails. Make sure to snap a photo at the Brockton Point Lighthouse, with a view toward the Vancouver Harbour and North Van.

As Canada’s most densely populated city, Vancouver’s easy to navigate… even as a tourist. You can bike around the downtown peninsula in under an hour. And, if you’ve got a spare couple of hours, you can go from skiing in Whistler (about two hours away) to relaxing on Vancouver Island.

Whistler is home to the Olympic Park and plenty of outdoor activities. In the summer, you can enjoy camping, hiking, mountain biking, golf, horseback riding, ziplining, and more. In the winter, Whistler transforms into a winter wonderland. It’s a world-class ski and snowboard destination and hub for dining and nightlife. The best part: it’s only a two-hour drive from Vancouver, up the picturesque Sea-to-Sky Highway.

Whistler was the last place I went before travel shut down in 2020. But it’s one of my favorite places to snowboard in the winter and practice yoga at the Wanderlust Festival in the summer.

Its central location is a bonus, too. Vancouver has a busy international airport with direct flights to 112 destinations in 23 countries.

Practical Tips:

1. Although public transportation in the metropolitan area is plentiful, having a vehicle will allow you to further explore British Columbia and Calgary. You can rent a car at the airport or at agencies throughout the city. (Try Discover Cars for competitive rates.)

2. Calgary and BC are full of incredible summer and winter sports destinations. While I’ve only been to Whistler and Fernie, other popular towns in the region include Banff, Revelstoke, and Lake Louise. Kelowna on Okanagan Lake is famous for its scenery, fruit orchards, vineyards, and golf courses.

Finding Your Own Favorite Place

In my twenties, I wanted to surf, work, and play hard while making new friends. In my thirties, I wanted to see the world as fast as possible while building my business. And now, in my forties, I’m more interested in slow traveling and getting to know the people, cultures, and lifestyles in different countries.

The more you travel, the more you might find that (like me) your favorite places change over time. You may decide to rotate annually through three different locations. Or, you may stumble across somewhere you love enough to put down roots.

Through more than 25 years of international travel, I’ve found that I have more favorite moments than places: riding my bike through the countryside of Munich, Germany on a crisp fall day, walking the northern route of the Camino de Santiago in Spain, or watching my friends get married in an Icelandic forest… travel has given me more memories than I can count.

If you’re searching for a new corner of the world to call home, first reflect on the type of experience you want. Are you a jet-setting digital nomad, a retiree seeking adventure, or just looking for a temporary change of scenery? Envision yourself living your ideal life. Whatever you can dream up, it’s available somewhere on this big blue marble.

And once you’ve established a list of your favorite places in the world, consider countries that you may have missed before. Often, the most transformative travel experiences come when you go beyond your comfort zone.

In the upcoming years, I hope to explore more of Africa, the Middle East, and Central Asia. So, I’ve been reading up about destinations that are new to me, from Bhutan to Lebanon to Uzbekistan… and I look forward to sharing those stories with you, too.