The Perfect Itinerary for an Epic Adventure in Thailand

When we said goodbye to our expat jobs in Singapore, we didn’t realize that it would be five long years until we’d be back in Southeast Asia once again. One of the greatest perks of working and living in Singapore was the ability to easily travel throughout the region, whether for a long trip or just a cheeky weekend away.  

After visiting almost every country in Southeast Asia, we can easily say that Thailand was our favourite. We’d been there a dozen times or more, usually for pleasure but occasionally for work (how I miss those all-expense paid trips that typically involved a luxury hotel and a rooftop bar). We’d ziplined in Chiang Mai; toured the floating markets of Bangkok; rock climbed in Railay; and explored some of Thailand’s most famous beach destinations from Phuket to Phi Phi to Phangan and more. 

Suffice it to say, we felt pretty confident in crafting what we considered to be the perfect itinerary for a month-long journey in Thailand. We’d travel from south to north and then back to Bangkok, ticking off a lineup of our old favourites plus a few new discoveries. 

Brief stop in Koh Samui

The timeframe for the trip was scheduled for late September so we made it a priority to start in the Gulf of Thailand, where the rainy season runs from October to December. We guessed (correctly, as it turned out) that we could still enjoy sunny skies if we headed there first. 

After an exhausting journey of three flights — from Toronto to Copenhagen to Bangkok to Koh Samui — we finally collapsed in the stylish and welcoming arms of the Zazen Boutique Resort. While we usually choose furnished apartments, this trip featured a mix of Airbnbs, boutique inns and even a couple luxury hotels like the Zazen, thanks to credit card points and judicious scanning for online deals.

Koh Samui is, of course, a very popular destination in its own right but it was just a one night stop for us. We had limited interest in its busy streets, underwhelming eateries and overpriced resorts, although we did enjoy our brief stint of being pampered with high thread count sheets and a respectable breakfast buffet at the Zazen. 

Instead, we were in pursuit of a lower key, off-the-beaten path, bohemian beach vibe that could be found on the neighbouring island of Koh Phangan, just a 30-minute ride away on a fast ferry.

Beach life on Koh Phangan

Koh Phangan has a number of beaches with plenty of accommodation options to choose from. It was important to select our location wisely as that can affect the entire tone of one’s stay. We wanted to be steps away from the beach and decent dining – always important when the scorching midday heat makes even the shortest walk feel like a debilitating expedition – but as far away as possible from any late-night party scene. 

We ended up choosing a bungalow by Hin Kong beach and couldn’t have been happier with our location. This is a quieter beach as its extensive sandbar makes swimming almost impossible. That said, the sunrise and sunset walks along the sandbar are just phenomenal, especially sunrise when we had the entire beach to ourselves. We were also minutes from a number of popular restaurants and the always-essential 7-11, our go-to spot for a few groceries and a blast of air conditioning. Our Airbnb was small and simple but offered an excellent view of palm trees and ocean from the hammock on our balcony.

We quickly found that we needed our own set of wheels to explore Koh Phangan. Between the scorching heat and the steep hills that characterize the island, we could only get so far on foot. Many travellers choose to rent a scooter but we felt more confident about tackling the terrain in a car, taking the minimum three-day rental. 

We toured the local temples, not seeing a single other tourist but getting a chance to watch a Buddhist ceremony at a respectful distance. We also rented snorkeling gear from a local hotel and took a look at the fish and coral off Mae Haad beach. And we had a chance to catch the buzz at the very popular and busy Haad Yao beach and feel very pleased with ourselves for choosing the more laid-back Hin Kong beach instead. 

A big part of each day was dedicated to exploring the local dining options. By the end of our time, we had a well-vetted list of favourites, including Happiness Thai Restaurant for fresh seafood at a reasonable cost; Indigo Cafe for international veggie mains and baked goods; the adjoining Chana Masala for Indian food; Segal’s for hummus and other Israeli classics; and Kikekla for somewhat pricey Thai dishes in a stylish beachfront setting.

The hidden paradise of Wai Nam

Hin Kong beach was a pleasant re-introduction to Thailand island life but we still had one more stop on Koh Phangan – and this one would be a complete immersion in the beach lifestyle. It took some work to get there: we had a 30-minute transfer over the steep hills of the island to Haad Rin, and then a 20-minute ride via a longtail boat to the hidden paradise of Wai Nam beach.

Wai Nam offers what we consider to be the ultimate beach experience for Thailand: no big hotels; no hordes of tourists; just a quiet slice of sand and sea enclosed by cliffs and jungle. 

There’s one hotel, the Whynam Beach Resort, which is a combination hotel/wellness centre/hostel/digital nomad retreat with an all-vegan menu and spontaneous dance parties on the beach. Meals are taken at low tables with pillows for seating; decorative feathers and flowing scarves are available for sale at the bar. The hippie vibe is palpable. 

We purchased our meals at the Whynam Beach Resort but stayed in what could only be described as a legitimate shack on top of the nearby cliffs. It was a charming, old wooden bungalow that was lightly restored and given a lick of paint by an expat couple. There was no air conditioning but we could catch an ocean breeze on the tiny porch. These were true barefoot luxury conditions, if luxury means a toilet that flushes once a bucket of water is poured in. 

Mornings were for sunrise yoga on a cliffside platform. I spent afternoons reading while Gillian hunted down that day’s mellow dance party (Bambu Jungle Lounge on Sunday was her favourite). And then we had evenings of vegan meals and people watching at the Whynam restaurant. It was perfect. 

On the morning of our departure, we were glad to have plenty of time to get to the ferry dock in Haad Rin. Our pre-arranged longtail boat had engine trouble and we had to wait 30 minutes in the blazing sun for another boat to be sent our way. After a jam-packed ferry ride back to Koh Samui (I was very relieved to see a light jacket at every seat), we had an overnight stay in a largely forgettable hotel and then onward to Chiang Mai by plane the next morning.

Food and temples in Chiang Mai

Once again, weather played an important role in the timing of our visit; we were hoping our arrival in Chiang Mai would coincide with the end of its wet season. In fact, we were fortunate to just miss a period of intense flooding that shut down many areas of the city and had an even greater impact on communities further north. 

We had originally considered renting a condo in the trendy Nimman area, possibly with a pool in the building as an escape for the heat. However, we were very happy with our final choice: a bright and chic studio apartment located in one of the many charming back alleys of Chiang Mai’s walled city. We were thrilled to have a small but serviceable kitchen again and immediately stocked up on a few essentials at Rimping Supermarket, a gourmet grocery store. 

After so many easy-going days at the beach, it was time to ramp up the tourist activities. We kicked off our time with an excellent exploration of local food with A Chef’s Tour. This tour ended up being a private experience: just the two of us and the guide on the back of a songthaew truck, making our way across the city from one tasty hole-in-the-wall restaurant to another. 

While it was incredible to re-acquaint ourselves with Chiang Mai classics like khao soi, we had to be willing to forgo our often-vegetarian/sometimes-pescatarian diet and embrace meat eating for this one day. We tried to make up for it by frequently lunching at Tien Sieng Vegetarian Foods, a local eatery that was also popular with Buddhist monks. Generally, we found it quite challenging to follow our usual, healthy, sugar-free, mostly vegetarian diet; Thai cooking is big on meat and the liberal use of palm sugar. 

Other highlights included touring our way through the city’s most significant temples; visiting the high-end Maya Lifestyle Shopping Centre; and exploring some of Chiang Mai’s many markets including the Saturday night Wua Lai Walking Street, the Sunday night market on Ratchadamnoen Road and, our favourite, the daytime Jing-Jai Market. We also found respite from the heat and a decent cappuccino in the beautifully-designed Kalm Village, a free museum and cafe tucked away in the old town. 

Finally, our favourite activity was hiking the Monk’s Trail all the way up to Wat Phra That Doi Suthep, an impressive Buddhist temple with views of the whole city. The first half of the hike was well signed and we quickly made our way to a small, picturesque temple that feels quite hidden away. 

From there, the path was largely washed out and we found ourselves scrambling up steep hills with no signage in sight, just our AllTrails map to guide us. Eventually, however, we emerged from the jungle and had a lovely wander through the temple grounds. For those interested in this hike, be sure to check AllTrails for the latest reports on trail conditions – this is a hike to avoid after a rainfall. 

Northern Thailand beyond Chiang Mai

We were looking for a taste of northern Thailand beyond Chiang Mai and considered all the popular options: a visit to Pai, a favourite among backpackers; a hill tribe trekking experience; or maybe a road trip along the 600km Mae Song Loop. 

In the end, we decided that what we wanted most was a brief sojourn in a beautiful setting, a taste of village life, and absolutely no exploitative hill tribe or elephant tourism. And we also wanted a relatively short drive from Chiang Mai as we didn’t relish the thought of spending hours on bumpy backroads. 

We chose a short stay at the lovely Lisu Lodge, an eco-friendly boutique lodge surrounded by rice fields and orchards, just an hour away from Chiang Mai. The lodge has a close, working relationship with a nearby village that is predominantly populated by the Lisu people. We were able to have a non-intrusive guided tour of the village and learn about the customs and lifestyle of this tribe.  

Gillian also worked out a clever hack for our transportation to the lodge. Instead of booking a relatively expensive transfer from Chiang Mai, we joined a fun cooking class at Maetang Lanna Thai Cookery School, located in a nearby village. They picked us and our luggage up in the morning and then dropped us off at Lisu Lodge in the afternoon – all included in the cost of the class. 

Indulging in affordable luxury in Bangkok

We said goodbye to the peace and quiet of rural Thailand and flew into Bangkok for the final stop in our journey. Home for the next few days was a spacious room in the luxurious COMO Metropolitan Bangkok, which we had snagged for a great price after keeping a watchful eye for deals. The immediate neighborhood was not to our taste as it was largely dominated by large hotels and corporate buildings, but Lumphini MRT station was just a short walk away. 

While we had been to Bangkok many times before, I had never visited the Grand Palace and neither of us had toured the Jim Thompson House Museum, making these both must-visit sights. 

The Grand Palace, as spectacular as the name suggests, has been the official residence of the Kings of Siam since the 18th century. We had a fascinating walk through this highly decorated complex, with the obligatory peek at the Emerald Buddha housed inside what is considered the most sacred temple in Thailand. Pro tip: get to the Grand Palace as soon as it opens since the crowds can be overwhelming to even the most seasoned travelers. 

Our next stop was truly memorable. We both love touring historic homes that retain the original art and furnishings so the Jim Thompson House Museum was an easy win. The house is the former residence of American entrepreneur and art collector Jim Thompson, who is credited with revitalizing the Thai silk trade. The home, built in a traditional Thai style, was so lovely that I would have been happy to move in immediately. 

The theme for the rest of our time in Bangkok was self-indulgence.

We made the mandatory visit to our favourite massage place in Bangkok: Health Land, a chain of high-end spas where two hours is the minimum time allotted for a Thai massage. We snacked our way through the vast selection of dishes available at the Khlong Lat Mayom Floating Market, one of the less touristy markets. And we took part in one of our favourite Bangkok traditions: a buffet lunch at a luxury hotel, this one being La Scala at the Sukhothai Bangkok Hotel. For deal hunters, our best tip is to download the Eatigo app to access discounts for many Bangkok restaurants; we snagged our La Scala brunch at an incredible 50% discount. 

With that, our adventure came to an end. Our tour of Thailand’s greatest hits was everything we hoped it would be. We had impressed ourselves with the number of sights and activities that we managed to pack into the month while still leaving plenty of downtime for leisurely sunrise walks along the beach. And our experience was a wonderful reminder that even the beaten path has room to explore around its borders.