South Beach & Southeast Asia: Trading One Dream for Another
Updated: Sep 1
South Beach
Miami, Florida
January 2026
I had dreamed of visiting South Beach for years.
I’d planned to spend a whole week there after six weeks traveling through the Caribbean—Saint Lucia, Martinique, Dominica, and Guadeloupe—before flying home to San Francisco.
By the time I arrived in Miami, I just had two nights.
It would have been easier—and cheaper—to stay near the airport.
But even with only two nights, I wasn’t giving up my dream.
I was going to South Beach, home to one of the greatest concentrations of Art Deco architecture in the world.
I’ve loved Art Deco for as long as I can remember.
As a child, I was captivated by old black-and-white movies from the 1930s—Katharine Hepburn and Cary Grant in their screwball comedies, Nick and Nora in The Thin Man, and especially Fred Astaire and Ginger Rogers in Top Hat.
The stylish world those movies created fascinated me. Everyone seemed impossibly sophisticated, living in elegant apartments, wearing fabulous clothes, trading witty lines, and dancing in glamorous nightclubs.
The music was part of it too—Cole Porter, Irving Berlin, those wonderful old standards I still love today. Apparently, I was retro even as a child.
Watching Fred and Ginger glide effortlessly together, moving in perfect rhythm with the music, enchanted me. I wanted to dance like that someday.
For my 30th birthday, I threw a 1930s-style costume party, and everyone got in the spirit. We decorated with old radios and an antique telephone, and my friends arrived dressed in their best Art Deco finery. I wore a fabulous black taffeta eyelet dress I’d found years earlier in a vintage shop in London.
And now I was finally going to see South Beach.
I checked into Dream South Beach, an Art Deco hotel in the heart of the Art Deco Historic District.
One thing I’d learned in my Points-and-Miles classes was to book a room that would be good enough, then shortly before arrival ask whether a complimentary upgrade was available.
This time, there was.
I walked into a lovely suite, with a sofa and plenty of room to spread out. I felt like I’d stepped back in time. I half expected Nick and Nora, cocktails in hand, to walk in from the other room.
But I had unfinished business.
My carry-on had been damaged getting off the ferry from Dominica, leaving its telescoping handle permanently extended. In Guadeloupe, I’d wheeled it from shop to shop looking for a replacement, chased promising leads, and even tried to find what had become, to me, the Mythical Mall.
And so the Great Carry-On Quest crossed international borders.
I remembered that Ross usually carried luggage.
I looked up the closest Ross—a discount store that carries quality merchandise—and found one less than a mile away. Even better, it was open until 11pm.
But Ross is always a gamble. They don’t stock a regular inventory, so there was no way to know what I’d find when I got there.
But at least I could have dinner first and still try to find a new carry-on that night. If I got lucky, my one full day in South Beach would be entirely free for Art Deco.
After dinner, I emptied my broken carry-on onto the sofa and called an Uber. Ross was close, so I decided to ride over and walk back.
Five minutes later, I wheeled my broken carry-on into Ross and started looking.
I knew exactly what I wanted: the same size or slightly smaller than my current carry-on. Three days after I got home, I was leaving again for six weeks in Southeast Asia, where I’d be flying on smaller planes with stricter carry-on limits.
I wanted a soft shell with a good outside pocket for my work, and some shade of blue to go with the rest of my luggage.
There were plenty to choose from.
And almost immediately, I saw it.
A lovely light blue. Slightly smaller than my old carry-on. A great outside pocket. Better quality than anything I’d found in Guadeloupe.
And cheaper.
In five minutes.
I spent longer waiting in line to pay than I had finding the perfect suitcase.
I left the broken carry-on at Ross and walked back to my glamorous Art Deco hotel, wheeling my beautiful new blue suitcase behind me.
The Great Carry-On Quest was over.
Ross to the rescue.
My One Full Day in South Beach
Oh my God. I’m in love.
I kept saying some version of that all morning.
The blue sky. The palm trees. The pretty pastel colors. One playful Art Deco building after another drew me farther down the street.
And then I’d catch a glimpse of another one up ahead, as if it were winking at me.
Oh, what’s that?
I had to go see.
That was the thrill for me. As someone with the trait of High Sensation Seeking — what I call Reach — I don’t need to fling myself out of an airplane or off a bridge to feel adventurous.
Sometimes all it takes is the tantalizing glimpse of something around the next corner.
So I kept walking.
One building led to another, and then another—the geometric details, the bold shapes, the exuberance of it all.
Earlier that morning, I’d walked down Ocean Drive to the Art Deco Welcome Center. I picked up a map—and ended up talking with the woman there for half an hour.
She told me about Barbara Baer Capitman, who had led the fight to save South Beach’s Art Deco buildings when many were threatened with demolition, helping found the Miami Design Preservation League in the 1970s.
I felt so grateful to Barbara. Decades before I arrived with my map, marveling at one building after another, she and others had understood that these buildings were worth fighting for.
The Welcome Center was right by the beach, so of course I walked over to take a look.
South Beach.
One of the most famous beaches in the world.
Meh.
After the beaches of the Caribbean, this famous stretch of sand felt surprisingly underwhelming.
I realized that I like a beach with a sense of embrace.
Sugar Beach in St. Lucia was tucked into a spectacular cove. Pointe Marin in Martinique curved gently around the water.
Curves, a cove, some containment—inviting and protective.
South Beach was different.
Broad, straight, flat, exposed. A vast expanse of sand separated Ocean Drive from the water.
I walked all the way down to the sea anyway. Once I got there, the surf looked gentle enough that I might try it someday.
But not today.
Today I had Art Deco to explore.
Who knew I would choose buildings over a beach?
I spent the rest of the day wandering, following whatever caught my eye.
One day wasn’t nearly enough. I wanted to come back, take the architectural tours, go inside the buildings, and give myself time to discover more.
But for now, I had my one day.
My Last Morning in South Beach
I wasn’t ready to leave.
After breakfast, I went back upstairs to my beautiful Art Deco suite and started repacking my luggage, including my brand-new perfect carry-on.
But I was excited about what came next.
It wasn’t as simple as packing to go home after my six-week adventure in the Caribbean.
San Francisco would be only a three-day layover before I left again—this time for six weeks in Asia.
As I packed, I was already sorting things in my mind: what would stay home in San Francisco and what would be coming with me to Asia.
In some ways, I was returning.
In other ways, I was going for the first time.
The last time I’d traveled through Asia, I was in my early twenties, finishing my undergraduate studies at UC Santa Cruz.
One of my majors was cultural anthropology, and I had joined a program through Stanford called Volunteers in Asia. About twenty of us were headed to posts across Asia, traveling together for part of the journey.
We spent a month in Japan, staying with Japanese host families.
I hadn’t been particularly drawn to Japan before I went, but from the moment I arrived, Japan captured my heart.
Early in my life, I discovered that it’s possible to fall in love with a country—and not always the one I expected.
We traveled around Japan and spent a magical week in the mountains at a Buddhist monastery in Koyasan, learning about Buddhism and getting to know the monks who lived there.
Then we continued to Hong Kong, while our group gradually grew smaller as volunteers left for their individual posts.
Eventually, I reached my post in Sumatra, where I lived with an Indonesian family and taught English at the Department of Health. I learned enough Indonesian to communicate, and when my six-month assignment ended, I traveled around Indonesia on my own.
When it was time to go home, I changed my route so I could return to Japan. I had loved it so much that I wanted to visit my host families again before going back to San Francisco.
Altogether, I spent nearly a year in Asia.
Southeast Asia was a very different place then.
The Vietnam War had ended only a few years earlier. Cambodia was in the grip of the Khmer Rouge, and Laos had only recently emerged from years of civil war.
Vietnam especially had haunted my imagination for decades.
Hanoi. Saigon. Da Nang.
As a small child, I had first known those names through the war—places associated in my mind with battles, bombings, and images of terrible suffering on television.
Decades later, I was finally returning to Southeast Asia.
This time, I would travel through places I hadn’t been able to explore on that first journey: Cambodia, Laos, and Vietnam.
Thailand had been high on my bucket list for years, and now I had a good reason to go. Ben, the teacher of the Points-and-Miles classes I’d been taking, was Thai and was leading a group of his students to Thailand starting on January 17.
When I told him I’d join him the following year, he said he wasn’t doing the trip next year.
It was now or never.
Once I decided I was going to Thailand, I started studying the rest of the map of Southeast Asia. So many of the places I wanted to see were only a short flight from one another.
I’d wanted to see Angkor Wat since my first time in Asia—the magnificent temple complex in Cambodia.
On my first Asian journey, I’d had a choice of layovers: Singapore or Kuala Lumpur. I chose Kuala Lumpur.
Singapore became the road not taken, a place I’d wondered about ever since.
And Nancy, a longtime client who had traveled extensively herself, made me promise to visit Laos. It was her favorite country in Southeast Asia.
So I began building my own six-week adventure around the Thailand trip.
There was just one problem.
Time.
The Thailand trip had a fixed starting date, and I wanted to arrive a day early.
I have the trait of High Sensitivity—what I call Depth. I’ve learned that one of the best things I can do for my sensitive nervous system is build spaciousness around arrivals and departures.
I didn’t want to land after a long journey and rush straight into group activities with people I didn’t know yet.
There are no direct flights from San Francisco to Thailand, so I needed to pick a place to change planes after the long-haul flight. My choices were Japan, Hong Kong, or Taiwan.
Since I’d already been to Japan and Hong Kong, I chose Taiwan.
Taiwan had never been high on my bucket list. I just didn’t know very much about it.
But I don’t like to pass through a country just to say I’ve been there. I want enough time to meet some locals, explore, learn about the culture, take a few day trips, and get a taste of what the place is actually like.
And after six weeks of traveling through the Caribbean, followed by three frantic days at home in San Francisco, I also wanted time to recover from the long flight, adjust to the time change, work with some clients, and breathe before setting off again.
I decided to give Taiwan five nights.
Those nights had to come from somewhere.
South Beach.
I was sorry to cut my week in South Beach so short. But Miami would be easy to return to. Taiwan might not be.
So I left South Beach, promising I would come back.
Taiwan, on the other hand, was a blank slate.
A Note Before You Go
If you recognized yourself in this story, you’re not alone.
I’ve created a free 30-second quiz and a free short booklet, An Introduction to Depth and Reach, to help you learn a little more about these two traits.
I hope they help you understand yourself a little better.
I’d love to share them with you.
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