5 Days in Hong Kong: My Spontaneous & Itinerary-Free Trip

My spur of the moment trip to Hong Kong was born from a late-night conversation with a travel-hungry friend 10,000 miles away.

It was a wild, impulsive, and indelible adventure; a chance journey that wasn’t really meant to take place, but played out perfectly nonetheless.

Our five-day meet-up was a blur of world-class food, bumpy ferry rides to distant destinations, passionate karaoke with locals, adrenaline-pumping blackjack hands, frenzied markets — and plenty of other captivating adventures in between.

And when it was time to fly our separate ways, we’d been left in awe of what Hong Kong has to offer. Neither of us was quite ready to leave, and we both made stern-faced promises that we’d return one day and recreate the magic.

So, here’s our story. Our Hong Kong highlights, if you will.

How My Impulsive Trip to Hong Kong All Began

I was having an unassuming late-night conversation with my lifelong friend, Riley, on a quiet March evening. He was busy getting a house-renovation business set up in Colorado, U.S.A. and I was half a world away, working on my blog in Chengdu, China.

The chat had been rather uneventful until I sent him a few pictures from my 32nd birthday Chengdu street food marathon from just a few days earlier. It was then when our conversation instantly took a turn. The photos of the tantalizing street food had sparked something inside of him.

“I want to see Asia. I just started searching for flights. Let’s meet in Hong Kong on Monday. I hear they have some of the best food in the world.” he suggested.

“I’m in, but do you really think that’s going to happen? You don’t have a passport. Monday’s five days away. Who’s going to watch your kids?” I answered skeptically.

“I’ll make it happen. The kids are out of town. I’m buying tickets. I’ll expedite the passport. Let’s do this.”

And five days later, I packed my bag and boarded a plane to Hong Kong.

My Partner in Crime

Meet Josh Riley — known by friends simply as “Riley.” He’s the impulsive soul who pulled the trigger on a 15-hour plane ride halfway across the world on five days’ notice without a passport.

My last-minute trip to Hong Kong was Riley’s wild and hair-brained scheme that he carefully willed into fruition. I’m giving him all the credit.

Since we met in middle school 19 years ago, the two of us have had a knack for adventure. We’ve weathered wild storms high in the Colorado mountains, taken seedy Greyhound buses cross-country, and even picked up our lives to move to Hawaii. (At one point we packed five people into a dingy two-bedroom Honolulu apartment.)

So, when Riley stepped off a bus and we found each other in the crowded streets of Hong Kong, we both knew unpredictable opportunities were waiting on the horizon.

Map of Our Hong Kong Highlights

Interactive map of our Hong Kong highlights

Click a marker on the map to reveal information about its destination. I’ve included every location mentioned in this post, so zoom out if you can’t find exactly what you’re looking for. Most destinations are easily accessible by public transportation or taxi.

Getting Lucky in Macau

Our first day in Hong Kong — Southeast China’s autonomous and densely-packed cultural wonderland of 7 million — was fairly short-lived. But, worry not. We’d be back.

Just a few hours after Riley landed in Hong Kong, we boarded a ferry and rode east towards Macau, Asia’s gigantic and gaudy equivalent to Las Vegas. Bringing in over $37 billion in 2018 (more than triple that of Las Vegas), Macau is unquestionably the gambling capital of the world.

Super-sized Las Vegas? Right up our alley.

When we arrived in Macau, we excitedly dropped off our bags at our hotel and set off towards the swanky Grand Lisboa Casino. We were ready for some low-stakes blackjack, free drinks, and top-notch people-watching. You know, all the familiarities we’d become accustomed to over our multiple trips together to Las Vegas.

But we hadn’t done our research. Macau and Vegas are nothing alike.

Low-stakes gambling does not exist in Macau. And the casinos don’t serve alcohol either. The only people hanging out in the streets are bored cab drivers, taking long drags off cigarettes and waiting to give their next ride.

So, we reluctantly walked up to the cheapest blackjack table we could find — $40 minimum per bet. I took a deep breath, sat down at the only open seat amidst a down-on-their-luck Australian bachelor party, and put my money on the table.

My brief dive into blackjack was only three hands long. Each deal of cards was an agonizing and nail-biting experience, but I ultimately edged out the dealer each time. Knowing that my luck could (and probably would) run out at any moment, I grabbed my chips and stood up. I’d won $200 in under five minutes.

After a lengthy contemplative chat with Riley about luck, limits, and life, we decided it was time to ditch the casino and walk away on top. Macau’s high-stakes tables would chew us up and spit us out if we stayed much longer.

We weren’t cut out for Macau, and we both knew it.

A Wild Night with New Friends

Since we’d banned ourselves from entering any more casinos, we retreated back towards our hotel and wandered into a nearly empty restaurant for a late dinner. Sure, we’d won a good bit of money, but we hadn’t found the excitement we’d been anticipating in Macau. The first day of our adventure was fading to an uneventful end.

Were we really going to visit the gambling capital of the world just to play three hands of blackjack and eat a quiet meal?

But then, a man at a nearby table stood up with a large bottle of beer in his right hand and gestured wildly to his eight tablemates, and gave what I can only assume was a rousing speech.

He was speaking in Chinese and, although neither Riley nor I had the slightest clue what he was saying, we answered his heartfelt words with applause. He took a look over at us and smiled. We liked his passion and he liked our enthusiasm, so he invited us to come and join his table.

For the next few hours, the ten of us enthusiastically drank beer and baijiu, Hong Kong’s favorite grain alcohol, and communicated through wild gestures, basic broken English, and laughter. We chummed it up like old friends who hadn’t seen each other in years. By the end of the night, the table was littered with empty beer bottles, cigarette butts, and half-eaten plates of food.

Soon enough, the clock had crept well past midnight and the restaurant staff started stacking chairs on the tables around us. The beer ran dry shortly after and we all decided to part ways, hugging and wishing each other happy days ahead.

Hong Kong Mansion Hopping

Our brief stay in the luxurious Macau Crowne Plaza Hotel was our big splurge to start the trip. After a sleepy check out, we hobbled onto a bus back towards Hong Kong and retreated to more suitable confines for a couple of shoestring travelers – the Chungking Mansions.

Made famous by Anthony Bourdain, the Chungking Mansions are a set of old, funky high-rises, home to a large slice of Hong Kong’s immigrant population. Each of the mansion’s 16 stories is full of life – packed with cramped businesses, wandering aromas, and tiny budget hotels.

Yeah, you guessed it, we’d come for the budget hotels.

Once we arrived at the Mansions, we wandered about the buzzing ground floor. Chattering food vendors beckoned us to have a seat at their stalls. Shopkeepers peddled counterfeit watches, SIM cards, and discount tailored suits. The sights, smells, and sounds jumped out at us from every direction. We strolled around slowly, soaking it all in.

We then checked into our miniature hotel room at the Premium Lounge (which was barely bigger than my camper van), flipped on the clunky air conditioning unit, and fell into a peaceful afternoon nap as the restless outside world continued to buzz and throb outside our window.

The Food, The Glorious Food

After resting up in the Chungking Mansions, we hit the town to explore Hong Kong’s world-renowned food scene and were overwhelmed with the choices. I’m a glutton for quality Chinese food, so the choices in Hong Kong were pushing all the right buttons.

Whether it was a golden-roasted goose hanging in an oily window, a greasy grab-and-go waffle shack on a noisy street corner, or a muggy dim sum restaurant with steam spilling out the front door – the wide array of food options in Hong Kong frequently stopped us dead in our tracks.

Eventually, a tiny 10-seat sushi restaurant beckoned us, so we wandered in and started filling out a menu. From the moment the first plate arrived, we were in heaven.

Sea urchin, eel, mackerel, raw shrimp, seared salmon – our selections hit the table one after another in a blissful blur of fresh flavors. We soon returned to the register to order a second round of sushi – a third – a fourth. High-quality Japanese food is abundant all over Hong Kong and we were reaping the delicious benefits.

And this experience was only a sign of things to come.

Hong Kong’s top-notch cuisine blew us away time and time again for the duration of our trip. Steamed buns, beef brisket noodles, egg tarts, you name it – we had as much mouth-watering food as our stomachs could handle, and we always hit the streets in search of more.

Cruising the Ferry to Lamma Island

The following morning, we pushed and squeezed our way through Hong Kong’s ever-congested sidewalks to the Central Ferry Pier. From there, we hopped aboard a ferry, this time bound for Lamma Island. We were a bit beat up from the first couple of action-packed days of our trip and decided an island escape would recharge our batteries.

After about 20 minutes on the barge, we disembarked at a quiet fishing village on the south of the island. We bee-lined into the first café we saw and quickly threw back six shots of espresso between the two of us.

Gripped by the energy of a few fresh hits of caffeine, we set off on a paved 6 kilometer (3.6 mile) hiking trail that would take us through the middle of the tropical island to its northern shore. We huffed and puffed up hills, and past the empty houses of fishermen at sea as the powerful sun radiated down.

Within an hour and a half, we reached our destination where we walked up and down a small lonely beach. A fisherman, perched on a rock in the distance, cast out a line. Hungry seagulls swirled in the sky above us. Barges inched across the South China Sea on the distant horizon.

We kicked around the sand, chatting eagerly about what Hong Kong might have in store for us next. Soon, a ferry arrived to take us back towards the frantic city we’d become so enamored by, and we hopped on.

The Insanity of Lan Kwai Fong

A quick breather back at the Mansions and another trip to our beloved sushi spot turned day into night. Once fully recharged, it was time to set off on the subway towards our next adventure: Hong Kong’s wild bar district, Lan Kwai Fong.

From the moment we arrived, the neighborhood was absolutely buzzing. Hordes of raucous people spilled out of bars, posted up along storefronts, and swarmed chaotically into the streets. We both knew that Lan Kwai Fong wasn’t really our style, but we’d have a great time anyway.

We set off into the night, wandering in and out of crowded bars for a drink when the moment struck — completely taken aback by the insanity that surrounded us.

Inside one venue, a man sat playing acoustic guitar and singing passionately as oblivious bargoers brushed past him. The next bar was playing host to a risqué drag show much to the delight of its tipsy patrons. People from all corners of the world filled the streets, flowing through the wild night without worry. Lan Kwai Fong was loose and crackling with energy.

Midnight came and went as we drifted around, chatting the evening away with strangers in the streets. But our fleeting energy fled, and the exhaustion of international travel sideswiped us. We flagged down a taxi, crawled in, and made our way back towards the refuge of our tiny hotel room for a much overdue night of sleep.

High Stakes Horse Racing (Almost)

Our ensuing Sunday morning got off to a sluggish start, but a stroll down Hong Kong’s lively Nathan Avenue jolted us awake once again. Now fully alert, we set off towards the Happy Valley Racecourse for some of Hong Kong’s world-renowned horse racing. We’d heard that Hongkongers take horse racing very seriously and we were more than ready to place a few wildly uninformed bets on the races.

Our excitement took a hit, however, when we arrived and realized that we’d shown up at the wrong racetracks. The races were about to start at Sha Tin Racecourse – over an hour away on crowded public transportation. Damnit.

But Happy Valley was still open for business – they were accepting bets and streaming the races on a swath of big-screen TVs – so we went in anyway. We’d gotten a brief taste of gambling in Macau and we’d been itching for more ever since.

This might be the day we strike it rich. That’s what we told ourselves at least.

We frantically Googled “how to horse bet” and scrambled through the confusing ins and outs of it all on our smartphones as the first race drew closer. It didn’t take long for us to approach the counter and place a few longshot bets that would never come close to panning out.

After a couple of hours and a few too many failed bets, we consoled ourselves with a greasy bag of comfort food from a nearby McDonald’s. We climbed high into the racetrack’s bleachers to sit and stare at the distant, glittering skyscrapers.

Wandering Through the Hong Kong Night

After our brief foray into the world of horse betting, we retreated back to our hotel to nap and recharge for a few hours. When night fell, we were once again back on the prowl, searching for our next adventure.

Our first stop was along Hong Kong’s Avenue of Stars to soak in the well-known Symphony of Lights – a choreographed spectacle of multi-colored lasers beaming and flashing out of skyscrapers across Kowloon Bay. Accompanying music played in the background.

Next, we walked through Kowloon Park, a mid-city escape from the hectic buzz of city life. The park was swarmed with countless large groups of people enjoying the humid Sunday evening. Grill tops full of sizzling meat spewed out smoke, music blared from portable speakers, and circles of joyful people danced the night away. Hong Kong was packed with life in every corner.

Further along, we found a small, quiet park where we sat on a bench and watched two men playing an intense game of chess, slamming the timer emphatically after every move. To our right, three men casually played cards, stopping frequently to engage in seemingly devious transactions with the occasional passersby.

Hunger eventually struck, so we walked to a nearby seafood restaurant and climbed a pair of tall metal stools at a cramped table. We capped off another successful day with a dinner of razor clams, baked mussels, pork belly, and cold Tsingtao beer.

Hong Kong’s Bustling Markets

Riley and I began our final day in Hong Kong by walking the ever-packed sidewalks and soaking in the chaos that reverberates in every direction.

First, we stopped at the Wan Chai Market – a claustrophobic collection of stalls peddling mountains of fresh seafood. From the moment we stepped inside, our senses were overwhelmed.

Live shrimp splashed and wiggled about in cheap over-filled plastic bowls. Vendors wearing thick rubber gloves shouted across the market as they de-scaled the day’s fresh catch. Freshly cut filets of fish lay across beds of ice, their hearts left attached and still beating.

Oysters. Clams. Mussels. Prawns. Sea snails. Crabs. Scallops. Geoduck. Seafood was everywhere. The unmistakable aroma of fresh ocean creatures permeated the air as we wandered the crowded corridors in amazement. We left only after we’d ogled every last stall.

A few more hours of captivating city-walking eventually brought us to Temple Street Night Market, a pedestrian-only street packed with kiosks selling kitschy knick-knacks, handmade goods, counterfeit electronics, silly t-shirts, and other touristy trinkets.

We spent an hour bartering and haggling with amused vendors, accumulating numerous gifts for Riley’s family and friends back home. When the dust settled, Riley donned a t-shirt of two cats reenacting the famous Titanic “I’m flying!” scene and had two plastic bags bulging full of knock-off goods. Success.

The urge to find amazing food hit once again, and we stopped for yet another top-notch meal – this time of grilled scallops, mantis shrimp, razor clams (again), and cold Tsingtao (again). The food in Hong Kong was a non-stop highlight for us – it never let us down.

Belting Out Karaoke with Locals

Full of seafood and cheap beer, Riley and I dived back into the bustling streets but quickly realized we needed to find a bathroom — any bathroom — in a hurry. In a desperate search, we poked our heads down a dark, greasy alley where we heard the faint echoes of a keyboard and off-tone vocals in the distance.

We followed the sounds into the back door of a dimly lit lounge with soft red lighting and cigarette smoke hanging in the air. A middle-aged couple shared the microphone – singing together passionately to a Cantonese ballad. The moment we set foot inside, we knew we’d stumbled upon our destiny for the evening – Hongkongers love karaoke, and so do we.

A few locals spotted us (clearly, we looked a bit out of place) and invited us to their table. They ordered a round of drinks, brought us a book of songs, and chatted to us in broken English.

It didn’t take long for our new friends to force us into picking out a couple of songs. They wanted to hear us sing badly, so we really had no choice in the matter. We’d be singing in front of strangers whether we were ready or not.

It was Riley’s turn first. He took the stage and promptly began butchering “It’s Been a Long Day’s Night.” His delivery was a bit erratic, so the elderly house keyboard player slowed down and sped up in an attempt to coax Riley back to the basic melody. His attempts were futile.

After watching a few more locals sing their hearts out, it was my turn to take the stage. I clutched the microphone and gave “Take Me Home, Country Roads,” my very best attempt. I was met with blank stares and half-smiles from the audience. Nobody had the slightest clue what song I was singing.

Meanwhile, Riley had disappeared. He’d taken to the streets in search of an ATM and had been gone for nearly an hour. Where the hell did he go?

Just as I was getting worried, he called frantically over a choppy public WiFi connection. He’d become hopelessly lost in the Hong Kong night and needed me to come and find him.

“Tell me your intersection and don’t move,” I told him as I sighed and dropped my head into my hands.

I typed his location into my phone, grabbed his heaping bags full of gifts, and started walking along the deserted city sidewalks. Fifteen minutes later, I found Riley standing under a flickering streetlamp with a shit-eating grin on his face. I shook my head in disbelief.

We regrouped with a basket of fried seafood and began our stumble back towards the Chungking Mansions. Dawn was just around the corner and Riley had a flight to catch in six hours.

What a trip. What a wild and ridiculous trip.

Hong Kong Raised the Bar

For as much fun as we had, Riley and I left countless stones unturned in Hong Kong. Hopefully, this wasn’t our final trip to Hong Kong together – there was too much left unseen. We’d seen only a sliver of this shining city in five days, and it left us hungry for more.

We made a good start of it, though – the high-stakes blackjack, the late nights with new friends, the worldly cuisine, the lively markets, the free-wheeling karaoke – it all happened because a couple of thrill-seeking old friends got itchy feet and decided it was time for an adventure.

And I must say we chose the perfect city to embark on that adventure.

Hong Kong is a striking place full of dynamic and eye-catching travel opportunities. To walk its spirited streets is to elevate all five senses into overdrive.

Our fascinating five-day tour of Hong Kong was a brisk stream of highlights – one after another, after another – on repeat.

Neither Riley nor I know if or when our trails will ever lead back to Hong Kong. We have no idea what the future will bring.

But what I do know is that our remarkable journey to Hong Kong has left me hooked, humbled, and patiently on call to return at a moment’s notice.

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Have any questions about my Hong Kong highlights that didn’t make this article? Have some memorable Hong Kong stories of your own? I’d love to hear your feedback in the comments below!

Last Updated on April 29, 2023