Seven-Month Flashpacking Odyssey Through Southeast Asia
We have elected to extend our break from constantly being “on the move” and drop anchor on one of our absolute favorite islands in the world… Maui. We’re settling in for a two-month stint here before heading off to “The August Place to Be” (aka The Spa) to hang out and wager on the ponies with our gang for a month. Once September rolls around, we’ll pack our bags and continue chasing the sun to different regions on our round-the-world journey.
Now that we’ve left Southeast Asia behind (for the time being), it feels like the perfect moment to look back through the binoculars and deliver a summary of our seven-month flashpacking odyssey through the region.
Southeast Asia is a truly amazing place to explore. Once you get adjusted to the initial culture shock, you find yourself completely letting go of the worries, routines, and stress that normally weigh you down at home. When you travel around Asia for an extended period, you learn to release yourself from the daily grind and discover a whole new concept of reality. The region simply moves at a much slower pace. What I love most is that time here works in approximations rather than specifics. No worries, no stress. It is so incredibly relaxed that you basically just sit back, go with the flow, and trust that it will all somehow work out in the end.
The Logistics
Southeast Asia is the perfect region for extended travel, but it requires a serious investment of time to really dig down and explore properly—something that just isn’t possible if you’re only staying for a few weeks. It’s the ultimate destination if you happen to be in a gap between jobs, retired, or fortunate enough to be granted a sabbatical.
Because the region is so compact, moving between countries by air, sea, or bus is incredibly easy and relatively inexpensive. The freedom to effortlessly hop across borders into entirely different cultures—the classic definition of “Same Same but Different”—is what makes this part of the world so special. Because Barbie and I had zero time constraints, we took our sweet time in each location to truly observe the unique local lifestyle.
If you too decide to drop out of society, find yourself with plenty of time, and no longer have to answer to “the man,” a month in each country is usually sufficient to cover the main highlights. The one major exception is Indonesia—it is so vast that you will absolutely need more time to do it justice.
Traveling is no longer just a luxury for the wealthy. We realized early on that world travel can be done very cheaply if you get a little creative. If you’re itching to see the world but are terrified of the costs, let me assure you: it does not have to break the bank.
💰 Top 3 Rules for Preserving Your Moolah:
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Travel Slowly: Moving fast is what kills a budget. Traveling slowly brings down your transportation costs dramatically. Opting for long-term stays is definitely the way to go because it unlocks the absolute best rates on accommodations.
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Eat Local and Hit the Street Stalls: Avoid the ubiquitous, overpriced tourist-trap restaurants. As you acquire more experience on the road, you’ll develop a keen eye for spotting and avoiding these tourist traps instantly.
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Integrate into Daily Life: Avoid the urge to constantly book group day tours and commercial excursions. They are almost always overpriced. You will save a ton of money—and get a far better, more authentic experience—by doing those exact same day trips independently.
The Southeast Asia Lowdown
The internet is a massive part of everyday life in Asia, particularly when it comes to social media. To say Asians have a love affair with Facebook would be an understatement. It is by far the most popular app on the continent. Every single person—from the wealthy elite to the poor villagers—utilizes it as their primary news source. The ease with which articles, stories, and opinions are shared on the platform has made locals incredibly plugged into global events and acutely aware of what the rest of the world is saying about their home countries. Many less affluent folks who can’t afford a television get 100% of their information straight from their cell phones. The old “one laptop per child” dream will probably never come to fruition out here, but “one smartphone per human”—which is just as capable in many ways—has officially arrived.
When it comes to hardware, iPhones are the undisputed top dog and the ultimate status symbol. Samsung comes in a distant second for those who want a brand name but can’t quite spring for Apple prices. I noticed that a shiny iPhone is in the hands of just about every beautiful young Asian woman. Those who want to look like hipsters but can’t afford a brand-new device simply buy refurbished models. If you’ve ever wondered what happened to all the old iPhones you traded in over the years, they are being put to excellent use sitting in the hands of people all across Southeast Asia.
On the downside, environmental pollution is a massive, serious problem out here. I cannot think of a single thing that pisses me off more than seeing garbage floating in the ocean or littering a beautiful beach. Thailand is unfortunately a major global contributor to the sheer volume of plastic waste found in our seas. Plastic bags are so incredibly ubiquitous, the country’s largest plastic bag manufacturer is actually launching an IPO next month. It really makes you wonder what these nations can do to curb the madness. Look at Hawaii—supermarkets there are no longer allowed to hand out plastic bags to customers; you have to bring your own canvas bags. It seems like a pretty good place to start.
Is it safe to travel through Southeast Asia?
Absolutely. It is a incredibly safe place to navigate, with violent crime rates that are significantly lower than what you’ll find in most major Western cities. While we’ve been out here on the road for the past seven months, there have been about a dozen tragic public shootings back in the United States. My best advice to you is to turn off CNN and Fox News because they completely pollute your mind. Their news coverage constantly portrays foreign countries as unsafe. I can tell you firsthand that Barbie and I never felt the least bit threatened out here, even when walking entirely alone down dark country roads at night.
And what about the street food?
Not only is it safe, it is also some of the best food you will ever taste in your life! You haven’t truly lived until you’ve eaten high-quality dishes whipped together right in front of you at a busy street stall. Sure, the Loose Stools Index is bound to take a temporary hit here and there, but the culinary rewards are well worth the risk. A good, simple rule of thumb to follow is this: if you see a massive line of locals waiting at a stall, odds are the food is fresh, delicious, and totally safe. Get your ass in that same line immediately!
Beyond the food, there is a distinct list of reasons why Southeast Asia is just such an incredibly relaxed place to exist:
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Zero Wardrobe Stress: It is shorts and flip-flops 100% of the time. I didn’t even pack a single pair of long pants for this entire seven-month trip. Your clothes can be wrinkly, dirty, or completely mismatch, and nobody gives a damn.
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The Freedom of the Beard: You can go days without shaving because physical appearance means absolutely nothing out here. Nobody cares what you look like; what matters is that you are a righteous dude.
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In-Your-Face Wildlife: The nature is spectacular. I love waking up to raw jungle noises, geckos chirping, and roosters crowing. Being able to recognize exactly which wild animal was making a specific noise always put a massive smile on Barbie’s face.
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Flavorful Fruit: Buying fresh fruit straight from the farms via street and beach vendors is an absolute pleasure. I remember buying fruit from supermarkets back in Las Vegas and it never tasted like anything. Out here, every single bite is bursting with flavor.
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The Price of Freedom: Many of the absolute best things in life out here are totally free. There’s no need to spend your days shopping, no getting ripped off at overpriced celebrity-chef restaurants, and no parking your car in a $50-per-day garage. Instead, you get to snorkel in a crystal-clear sea, hike up to breathtaking viewpoints, watch world-class sunsets, or just wander the vibrant streets looking at wacky stuff on every corner—all at zero cost.
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Tropical Cold Showers: Who needs hot water when you’re living in a tropical climate anyway?
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Multi-Purpose Oils: Using the exact same natural oil to repel mosquitoes and keep myself smelling attractive for Barbette.
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The Barefoot Connection: Any place where you can walk around barefoot most of the time is a win in my book. Some people say walking barefoot connects you directly to the earth and grounds you. BFD buys that.
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No Planning, No Stress: Going with the flow and refusing to plan anything for days at a time completely eliminates stress from your life.
Traveling through this region absolutely fascinates me and has taught me more than I could ever learn sitting back home. I learned about the sheer hardship that others have to go through just to survive. I learned that at our core, we are all exactly the same, even if the ways we live our lives look different. I witnessed the genuine friendliness of total strangers and fell in love with the massive smiles on the faces of the locals. Most importantly, I learned that you won’t achieve true freedom by making more money. You find real freedom by working less and spending less.
The Country Breakdown
The reason travelers flock to Southeast Asia in droves is obvious: the incredibly low cost of living compared to Western countries, the year-round warm weather, world-class beaches, rich culture, awesome food, unique aromas, and an endless abundance of outdoor activities.
Here is my personal, direct assessment of the countries we’ve tackled:
🇹🇭 Thailand
Thailand used to be my absolute favorite country in Southeast Asia, but I have to admit I was slightly disillusioned by the scene during this visit. In the major tourist destinations, prices have skyrocketed and mass tourism has started to hinder the vibe. The Land of Smiles has slowly transformed into the “Land of… Give Me Your Baht,” with many locals appearing understandably jaded by the sheer volume of tourists. There are still great spots left, but you have to get way off the beaten path and far away from the massive crowds of freshly minted tourists who often fail to know how to behave.
Thailand Update 2026: After 10 full years on this round-the-world journey and many, many return visits to Thailand, I have to completely rewrite the script on our above assessment. My opinion has officially come full circle.
I now recognize that what we were experiencing back then were just the growing pains of a nation that was rapidly developing. Today, Thailand has morphed into a way more advanced, modern country, and Barbie and I absolutely love the current-day prosperity and world-class advancements it offers. From the seamless infrastructure to the elevated comforts, it is a flashpacker’s absolute dream. Consequently, we have fallen deep in love with the Land of Smiles all over again, revisiting the country over a half dozen times in subsequent years for extended, multi-month stints. Whether we are hanging out in Bangkok, exploring Chiang Mai, or relaxing on the beaches of Phuket and Koh Lanta, Thailand has firmly solidified its spot as one of our absolute favorite countries on the planet.
🇰🇭 Cambodia
A fantastic place and an absolute must-visit. The people have a wonderful attitude despite their history, and the culture is incredible.
🇲🇲 Myanmar (Burma)
An absolute gem. You need to get your ass here before the tourism floodgates open completely and change the landscape forever. Traveling is ultimately about emotions, and our journey through Myanmar was one of the richest, most emotionally rewarding experiences we’ve ever had. It is a real favorite of ours. Do not rush through it; you need a bare minimum of three weeks to properly cover the main areas of interest.
🇲🇾 Malaysia
(Note: This is strictly regarding Peninsular Malaysia, as we haven’t hit Borneo yet). It’s a perfectly fine place to visit if you have extra time on your hands, but we found the other Southeast Asian countries to be a bit more engaging. That said, we are highly looking forward to checking out the wild jungles and wildlife of Borneo on a future leg, which should offer a completely different perspective.
🇸🇬 Singapore
A completely different vibe than the rest of the region. This island nation seriously has their shit together—it is easily the most organized place on the face of the earth. Bring your wallet, prepare to spend some moolah, and eat your heart out!
🇮🇩 Indonesia (Bali & Lombok)
Bali is a beautiful place, but the massive flood of tourists into popular areas like Ubud, Kuta, Seminyak, Canguu and Legian has turned them into a total clusterfuck. You will be much better served exploring the lesser-known corners of the island. The absolute best beaches are found on the Bukit Peninsula but that area has all the signs of future overdevelopment. The Gili Islands off the coast of Lombok are incredibly fun, laid-back beach spots, but try your best to avoid peak season to miss the heavy crowds.
🇵🇭 Philippines
I am honestly not sure how this country has managed to avoid the overwhelming mass tourism plaguing the rest of Southeast Asia. If you are a righteous dude who loves super friendly people, the ocean, and world-class beaches, get your traveling butt over here immediately. The islands are unbelievably laid-back, and so are the people.
🇱🇦 Laos
Definitely worth including on your next itinerary. It is incredibly chill. For novice travelers who might be a bit intimidated by Asia, the town of Luang Prabang serves as a perfect, easy, and gentle introduction to the region.
🇻🇳 Vietnam
We visited Vietnam on our previous journey and fully plan to revisit it when we return to the region. I know many Americans still associate the country with the horrors of the Vietnam War and are skeptical about visiting. Big mistake. Vietnam opened its borders to tourism about 20 years ago, and it is an absolute must-visit on any extended trip through the region.
Thru the Binocs
🕵️♂️ Binocular Observation: Coming Home
There is a great quote from The Curious Case of Benjamin Button that always sticks with me:
“It’s a funny thing coming home. Nothing changes. Everything looks the same, feels the same, even smells the same. You realize what’s changed, is you.”
We’ve changed, no doubt about it. But hopefully, after all this time on the road, I’ve also changed to become a much better horse handicapper. Saratoga, here we come!