14 min read
Somewhere over the Andaman Sea, watching limestone cliffs slide past a longtail boat, I started keeping a notebook. Not an itinerary — a scorecard. After enough trips, every new place quietly gets ranked against the last one. The beach that ruined other beaches. The single best thing I ever put in my mouth. The adventure that scared me, and the one that quietly rearranged me.
Ten countries and a stack of stamps later, here’s that notebook, opened up. Not a “top 50 things to do” list scraped from everyone else’s blog. My actual rankings — the real winners, the honest letdowns, and the calls I’d defend across a dinner table. I’ll tell you who won each category, who came close, and at the end, the handful of lessons that turned out to matter more than any single destination.
Grab a coffee. This one’s a long one, the way the best trips are.

🏖️ Best Beach: Railay, Thailand — but it’s a fistfight
Railay Beach in Krabi is accessible only by boat. That’s the first clue you’re somewhere special — there is no road in. Sheer limestone cliffs drop straight into water so clear it looks edited. You step off the longtail into bathwater-warm shallows with rock climbers dangling off the walls above you, and the whole place feels like it shouldn’t legally be allowed to be that beautiful.
What seals it for me isn’t just the postcard. It’s everything around it. A short boat away you’ve got the Emerald Pool — a jungle spring the color of a gemstone — and a hot spring waterfall where warm water spills over smooth rock into cool pools below. The contrast of climbing a cliff in the morning and soaking in a natural hot tub by afternoon is the kind of day Krabi just hands you.
But this category is a brawl, so here are the real contenders:
- San Blas, Panama — 365 islands run by the indigenous Guna Yala people, most of them nothing but a sandbar and a few palm trees. You sleep in a rustic cabin, snorkel reefs with no one else around, and stargaze with zero light pollution. It’s the closest I’ve come to falling off the edge of the modern world.
- Lanikai, Hawaii — powder sand, calm turquoise water, the two little Mokulua islands floating just offshore. The most effortless beautiful beach on this list; you don’t earn it, you just walk up.
- Seven Mile Beach, Negril, Jamaica — home-team bias fully disclosed, but the sunsets there are a religious experience and I will not be taking questions.

The call: Railay for sheer drama, San Blas for soul. If you only get one in your life, go where the road can’t follow. The friction is the filter.
🌊 Best Day on the Water: the Phi Phi Islands
If Railay wins the beach, the Phi Phi Islands win the day. We took a speedboat out from Krabi and it turned into one of the most surreal days I’ve ever had with a passport.
Crystal water, limestone cliffs rising on every side, and a string of stops that each could’ve been the highlight: Maya Bay, the cove made famous by The Beach; hidden lagoons you reach by ducking through gaps in the rock; Monkey Beach, where a colony of monkeys runs the shoreline; a Viking Cave painted with ancient art. We snorkeled over coral thick with color, swam into a dark sea cave with bats overhead, and watched bioluminescence light up the water like it was plugged in. It genuinely felt like a different planet for eight hours.
Lesson baked into that day: the boat tours that pack four or five stops into one route are some of the best money you’ll spend traveling. You see more, you skip the logistics, and a good captain knows exactly when to hit each spot before the crowds do.

🍜 Best Single Bite: Khao Soi in Chiang Mai
I’ve eaten my way through a lot of countries, and one dish still lives in my head rent-free: Khao Soi, the northern Thai curry noodle soup, eaten at a little spot called Kao Soy Nimman in Chiang Mai. Creamy coconut curry, soft noodles, a tangle of crispy noodles on top for crunch, a squeeze of lime, a little pickled mustard green on the side. I think about it on random Tuesdays in the middle of meetings.
Chiang Mai actually deserves its own food medal. We took a half-day cooking class on an organic farm outside the city — picked the herbs and vegetables ourselves, learned to pound curry paste from scratch, and I ended up leading our group’s cooking demo. I came home able to recreate maybe a tenth of it, but the appreciation stuck.
The rest of the food podium:
- Chicken paella in Madrid, demolished after walking nearly six miles through the city. Hunger is the best seasoning, and Spain knows it — the tapas scene alone is worth the airfare, plates of jamón and patatas bravas and a glass of something cold while the whole city is out walking.
- Fresh lobster at Lobsteria in Casco Viejo, Panama, plus the country’s famous Geisha coffee — one of the most sought-after and expensive cups on earth, grown in the Panamanian highlands.
- Anything home-cooked in Enfield, St. Mary, Jamaica. No restaurant has ever beaten my family’s kitchen, and no restaurant ever will. Oxtail, rice and peas, fresh fish, a Sunday spread that takes all day. That’s not a meal, it’s an inheritance.
- Mango sticky rice from a Bangkok street cart, for about a dollar, that embarrassed desserts costing twenty times more.

The pattern I noticed: my best meals were almost never the fancy ones. They were street carts, family kitchens, and tiny neighborhood spots a local pointed me toward. Spend your food budget low and local. The expensive restaurant is usually selling you the room, not the food.
🐪 Best Adventure: a night in the Sahara
Some experiences rearrange you a little. Mine was the overnight camp in the Moroccan Sahara, at the end of a three-day road trip out of Marrakech, over the High Atlas Mountains and past thousand-year-old kasbahs clinging to the hillsides.
You ride a camel into the dunes as the sun drops and turns the sand the color of fire. You eat tagine around a low table. Then the Berber camp staff start drumming and singing, and you look up at a sky so absurdly full of stars — no city light for a hundred miles — that it stops feeling real. I’d met half the people in that circle three days earlier. By the end of the night, far from anything, they felt like old friends. It is still the single most awe-inspiring thing I have ever done while holding a passport, and I’ve chased that feeling ever since.
Runners-up for the adrenaline and the awe:
- Climbing the 1,200 steps to Tiger Cave Temple, Krabi — brutal, sweaty, calves screaming, absolutely worth it for the 360° view at the top.
- Dunn’s River Falls, Jamaica — climbing a terraced waterfall hand-in-hand with a human chain of strangers, water rushing over you the whole way up. Bring water shoes; thank me later.
- Parasailing and jet-skiing off Oahu, then a sunset sail to close the day — Hawaii makes it almost too easy to stack adventures.

🏙️ Most Underrated City: Panama City
Everyone sleeps on Panama City, and they’re wrong. In one place you get the colonial charm of Casco Viejo — where we kicked off the trip salsa dancing at Teatro Amador, a historic theater turned nightclub thumping with live Latin music — and a skyline like a mini-Miami across the bay. You get a tropical rainforest inside the city limits at Metropolitan Natural Park, where you can hike past wildlife twenty minutes from downtown. You can rent a bike and ride the Amador Causeway out over the water with the skyline on one side and the canal on the other.
And then there’s the Panama Canal itself. Standing at the Miraflores locks watching container ships the size of buildings get lifted by nothing but water — as an engineer, that genuinely short-circuited my brain. A hundred-year-old machine still doing one of the most important jobs on the planet, every single day. Worth the trip on its own.
Honorable mention: Toledo, Spain — a medieval city stacked on a hilltop that feels like a time machine, an easy day trip from Madrid. And Nice, our base on the French Riviera, where the Mediterranean is exactly the blue everyone promises.

🌅 Best “I’d Go Back Tomorrow” Place: Jamaica
I’m biased — it’s home. But even setting the family aside, Jamaica punches so far above its size it’s almost unfair. Seven Mile Beach in Negril for the sunsets. Doctor’s Cave in Montego Bay for the clear water. Frenchman’s Cove in Port Antonio for the quiet. The Blue Mountains for serious hiking and the best coffee in the world. A lazy bamboo-raft float down the Martha Brae, poled by a guy who’s done it ten thousand times and has the stories to prove it.
But the version of Jamaica I love most isn’t on a map. It’s Enfield, in the hills of St. Mary — a small, bushy community where I spent part of my childhood. No itinerary, no checklist. Just family, home-cooked food, familiar paths, and swimming in a cool river that’s exactly as cold as I remembered. That’s the side of travel no resort can sell you: going somewhere that means something.

🎭 Best Cultural Whiplash: Marrakech at sunset
Some places change character with the light, and nowhere does it like Marrakech. By day, the great square of Jemaa el-Fnaa is a loose scatter of orange-juice carts, henna artists, and snake charmers. But as the sun drops, it transforms into a full open-air spectacle — food stalls fire up their grills and send smoke curling into the dusk, and storytellers, drummers, and acrobats all compete for the same patch of attention. We walked through it three or four times just to keep feeling it shift.
Step off the square into the souks and you’re in a different world again — a maze of stalls selling lanterns, spices, leather, and rugs, where haggling isn’t rude, it’s the expected conversation. Then duck into a riad, one of the traditional courtyard guesthouses, and the noise vanishes completely: cool tile, a quiet fountain, mint tea. That whiplash between chaos and calm, all within a few hundred feet, is the most alive a city has ever felt to me.

😬 The Honest Letdown: getting lost in Fez
I’m not going to pretend every moment is a highlight reel. The hardest hours of any trip I’ve taken were our first few in Fez, Morocco. The old medina is a thousand-year-old maze of unmarked alleys, we arrived during Ramadan, and we got thoroughly, stressfully lost — while being trailed by “faux guides” who make a living steering confused tourists in circles and then demanding payment.
Here’s why I’m telling you, because the way it got fixed is the actual travel lesson. We finally identified the two main thoroughfares that act as the medina’s arteries, linked back up with friends we’d made on the Sahara tour, and hired one real local guide for a proper walking tour. Suddenly the same city that felt hostile became one of the most fascinating places I’ve ever walked — the centuries-old leather tanneries, the oldest university on earth, tilework so intricate it stops you mid-step. A good local guide for a few hours is the highest-ROI money in all of travel. Buy it early, especially anywhere built before street signs existed.
💳 Best Trip on Points: Thailand, by a mile
Two weeks across Bangkok, Chiang Mai, Phuket, and Krabi — boutique hotels, rooftop pools, a hillside resort where villas sat tucked into the trees — and a stunning amount of the lodging was booked with credit card points. Free breakfasts, upgrades, the works. Thailand is the rare place where the dollar stretches and the points stretch, so you get genuine luxury at a fraction of what the same experience costs in Europe.
This is where the finance brain and the travel brain shake hands. A well-run travel-rewards setup quietly pays for the best trips of your life — I rarely book a flight or hotel without first running it through a points card. The math on a disciplined points strategy beats almost any “deal” you’ll find hunting for cheap fares, and it compounds: every trip funds a little of the next one.
🎒 What I Actually Pack (After Learning the Hard Way)
Gear won’t make a trip, but the wrong gear can quietly ruin a day. After ten countries, this is the short list I never travel without:
- A travel-rewards credit card — books the flights and hotels, racks up the points for the next trip, and covers you on foreign transaction fees. The single highest-leverage thing in my bag, and it’s not close.
- Water shoes. Railay’s rocks, Dunn’s River Falls, the Emerald Pool, any rocky beach — grippy aqua socks have saved my feet and my dignity more than once.
- A power bank and a universal adapter. A dead phone in an unfamiliar city is a real problem. Offline maps don’t help if the battery’s gone.
- Offline maps downloaded before you land. The single best defense against “faux guides” and wrong turns in a place built before street signs.
- Packing cubes. Boring, life-changing. They turn a chaotic suitcase into something you can actually find things in across a multi-stop trip.
- One nice outfit. You’ll get invited to something — a dinner, a rooftop, a wedding — and you’ll be glad you can show up looking like you meant to.
Everything else you can buy there, usually cheaper, often better.
🗺️ The Notebook’s Bottom Line
Ten countries in, here’s what the scorecard actually taught me — and notice that none of it is about a specific beach:
- Go where the road doesn’t. Every one of my peak moments — Railay, San Blas, the Sahara — required an extra boat, an extra 4×4, an extra day of effort. The friction filters the crowds. The best places make you work for them a little.
- Eat low and local. Street carts and family kitchens beat white tablecloths nearly every time, for a tenth of the price. Ask the person who served your coffee where they eat.
- Buy the guide. A few hours with a real local turns a stressful, confusing place into the best day of the trip. It’s the cheapest insurance in travel.
- Leave a day completely unplanned. Some of my favorite memories — a rainforest hike in Panama, a slow afternoon wandering Casco Viejo, a quiet river swim in St. Mary — came from the days we deliberately scheduled nothing.
- Use points like a system, not a gimmick. The trips look expensive. Run right, a lot of them aren’t.
- Travel with people, not just to places. The strangers around that Sahara campfire are the reason I remember the night at all. The destinations are the setting. The people are the story.
I keep adding to the notebook. There are stamps I don’t have yet — Japan is high on the list, a real run down Italy’s coast, more of Africa, somewhere with snow — and the rankings will shift as I go. That’s the entire point. The best trip is almost always the next one.
So: where’s your notebook pointing next?
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