How To Plan The Perfect Multi-City (And Island) Thailand Itinerary

A two-week Thailand itinerary complete with must-sees and hidden gems.

By Chris Schalkx

11 October 2019

More than 30 million tourists visit Thailand every year—and for good reason. From the lush jungles in the Northern mountains to the pearly white beaches in the South, Thailand has something to offer for everyone. Mix in world-class cuisine, swoon-worthy resorts and friendly locals with smiles as warm as the country's year-round balmy climate, and you’ve got a destination that’s hard to beat—whether you're traveling for your honeymoon, with kids, a group of friends or solo.

This 14-day Thailand trip itinerary brings you to the diverse highlights The Land of Smiles has to offer—including must-see temples, viewpoints and tucked-away restaurants where you’re unlikely to bump into another tourist. More of this, less of that? Journy builds its custom itineraries from scratch, keeping your preferences, budget and interests in mind.

Bangkok: Temple-Hopping And Bar Crawls

Well-intended friends will inevitably advise you to get out of the Thai capital as soon as possible. Ignore that. Beyond its traffic-choked streets and dime-a-dozen shopping malls, you’ll discover hidden temples, hip speakeasies and ancient neighborhoods bursting with old-school cool. It’s also one of the most exciting foodie destinations in Southeast Asia, whether you’re after curbside noodles prepared on flaming woks, or crisp white tablecloth affairs.

Chiang Mai: Coffee Beans And Jungle Dreams

Thailand’s second city couldn’t be more different from its capital. Here, skyscrapers make way for jungle-clad mountain backdrops, and while traffic on its outer ring road oftentimes rivals that of Bangkok, most of its streets remain blissfully quiet. Crumbling temples and quaint cafes dot the moated Old City, while outdoor adventures await in the valleys further out.

The Southern Islands: Beach Bliss

The word of Southern Thailand’s azure waters and powdery beautiful beaches has been out for decades, but with the right insider intel, it’s not impossible to find some of the best beaches all to yourself. The hundreds of kohs (Thai for ‘island’) fringing the coastlines on both sides are as beautiful as they are diverse. Whether you’re after world-class diving or foot massages in the sun, you’re bound to find a Thai island to your liking.

A Sample 2-Week Thailand Itinerary

Stop 1: Bangkok (3 nights)


Sample Day 1: Bangkok's oldest corners

Albeit thronged with tourists, the shimmering pagodas of the Grand Palace and neighboring Wat Pho are must-visits. Avoid the crowds by starting early (the gates open at 8 AM)—with a pinch of luck, you’ll have the grounds all to yourself – even if it’s just for a few moments to check out one of the famous floating markets. Wat Pho’s traditional massage center is regarded as the Harvard of massage schools, and its students are coveted candidates for high-end spas around the region. An expert Thai massage here will only cost you a fraction of their future rates.

Hop on the Chao Phraya river ferry and alight at the Si Phraya pier in the Bang Rak district. Here, old buildings provide new homes for contemporary art galleries like ATT19 and creative hotspots such as restaurant-slash-boutique Warehouse 30. Seek out Someday Everyday for a lunch of top-notch Thai curries by Michelin-starred chef David Thompson, then set off northwards to Chinatown, stopping for a coffee at one of the many hip cafes along the way. You can seek out Chinatown highlights such as Wat Traimitr, but simply getting lost in the maze of cacophonous alleys and wet markets is just as fun.

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For dinner, brave the queues for fluffy omelets with giant chunks of fresh crab meat at Raan Jay Fai, Bangkok’s first (and only) Michelin-starred street food joint. Alternatively, Sala Rim Naam at the iconic Mandarin Oriental hotel is a more romantic vibe option, where royal Thai cuisine comes with river views and traditional Thai dance performances. End the night partying at Soi Nana, a cluster of switched-on cocktail bars (start at Tep Bar or Ba Hao) with drinks made from Chinese herbs and local moonshine that pay tribute to its location on the fringe of Chinatown.

Sample Day 2: Bangkok's modern side

Now that you’ve seen Bangkok's oldest corners, discover what makes this city such a modern metropolis. After finishing your hotel breakfast at a leisurely pace, set off to the Jim Thompson House, a leafy cluster of beautifully preserved teakwood dwellings filled with Buddhist artwork and Asian antiques collected by Thailand’s most legendary silk trader. From here, it’s just a short hop to BACC (short for Bangkok Art and Culture Centre), where ever-changing art exhibitions showcase work from local artists alongside snazzy concept stores and specialty coffee shops.

BACC bookends Siam, Bangkok’s premier shopping district. Malls line the road, with Siam Discovery and Siam Center offering the most in terms of fashion-forward Thai design. Don’t forget to cross the street to the warren of alleys that make up for Siam Square, where Bangkok’s art school students and up-and-coming designers have set up indie boutiques and boba tea shops. When your legs start to ache, book yourself a private onsen session at the luxurious Panpuri Spa in Gaysorn Village.

Come sunset, visit one of the many night markets scattered around the city or take an elevator to the top of the MahaNakhon tower, Thailand’s tallest skyscraper and home to its highest observation deck. Thrill-seekers should shuffle around its glass-floored skywalk on the 78th floor, while the rest of us opt for excellent cocktails and pan-Asian fine dining at the sky bar two floors below.

Sample Day 3: Day trip from Bangkok to Ayuthaya

About two hours from Bangkok, the ancient temple-studded capital of Ayuthaya makes for a great day away from the city. Leave your hotel early (your Journy trip designer can advise on transportation options) to arrive before the afternoon heat sets in. Rent a tuk-tuk to explore the crumbling ruins of Wat Chaiwatthanaram and the gigantic reclining Buddha at Wat Lokayasutharam. Skip the elephant riding tours—for obvious reasons. Opt to visit one of the few elephant sanctuaries when you arrive in Phuket or Chiang Mai. You’ll find plenty of options for a simple lunch along the river (better yet, vendors will likely find you first)—but Summer House and the restaurant at boutique hotel Sala Ayutthaya are much more atmospheric.

If you’re not taking the night train to Chiang Mai (more on that below), a sunset dinner cruise on the Chao Phraya river is a romantic way to cap off your time in the Thai capital. Not every boat ride is created equal (book the wrong one, and you’re in for bad buffet food and loud karaoke), but Supanninga Cruise, with authentic Thai fare and Champagne, is a solid option.

Stop #2: Chiang Mai

Chiang Mai

Transport from Bangkok: Flights to Chiang Mai leave throughout the day from both of Bangkok’s airports. A first-class cabin on the overnight train from Hua Lamphong station is a romantic alternative—there’s nothing quite like watching the sun rise while rolling into the Northern countryside.

Sample Day 4: Cafe and temple hopping

Spend your first day in Chiang Mai hopping from temples to cafes and tucked-away street food joints in the walled Old City. Crumbling Wat Chedi Luang (once home to Thailand’s most sacred Buddha statue) and the beautifully restored Wat Phra Singh are must-visit buddhist temples, but do venture out to some of the lesser-known wats, such as Wat Saen Fang (just west of the Tha Phae Gate) to find peaceful temple grounds all to yourself.

Between temple visits, there are cafes aplenty to refuel (this is Thailand’s coffee capital after all). Graph Cafe and the industrial-chic Gateway Coffee Roasters are worth seeking out for their excellent brews from local beans. Also carve out some time to sample Chiang Mai’s signature dish, khao soi, a spicy coconut curry soup that has foodies salivating by the mere mention of it. Try a bowl at Khao Soi Khun Yai, located north of the Old City and widely regarded as one of the best, and you’ll undoubtedly become a fan of this Thai food, too.

Head to the hip Nimmanhaemin district for dinner. Home to some of the city’s most progressive tables (try to grab a reservation at the teeny-tiny chef’s table Blackitch) and best bars (stop at Yayee Rooftop Bar for Thai craft beers with misty mountain views), this is where Chiang Mai’s hip young things and fashion-forward expat community comes to play.

Sample Day 5: Exploring Chiang Mai's mountaintop temples, national parks and countryside

A visit to Chiang Mai isn’t complete without a stroll around Wat Phra That Doi Suthep, the mountaintop temple visible as a speck of shimmering gold from everywhere in the city. Rent a motorbike, and head out early to dodge the crowds (and the mid-day heat). It’s a sturdy drive uphill, through lush jungle and on winding roads, but the view from the top is worth the effort. On the way back, make a pitstop at the Huay Kaew Waterfall for a refreshing dip.

From Doi Suthep’s base, it’s an easy 30-minute drive to Mae Rim, the countryside district bordering Chiang Mai city. The road swirling between Doi Suthep and Mon Cham is peppered with interesting stops, from pottery workshops to vintage-filled artist retreats (The Ironwood is a great lunch stop). Make your way to the perfectly manicured Queen Sirikit Botanic Garden for an insight into the region’s wildly diverse flora and fauna, then continue westwards until you reach the sign for Moncham. From here, zip through villages and rice fields until you reach the Mon Cham Viewpoint, where mountain vistas fill the horizon as far as the eye can see.

Back in Chiang Mai, the sleepy riverside district of Wat Ket is a lovely spot for dinner. The Riverside Bar & Restaurant, with its terrace right on the Mae Ping, is an oldie but goodie, and also offers candlelit cruises. Head to Jack Bain’s Bar, just a few blocks away, for a nightcap in a stately teakwood mansion on the leafy grounds of the posh 137 Pillars House hotel.

Sample Day 6: Day trip to Chiang Rai

Get up at dawn to explore more of Northern Thailand on a day trip to Chiang Rai, a sprawling mountain town about three hours from Chiang Mai. Its main draw is Wat Rong Khun (better known as The White Temple), a modern temple conceived by Thai architect Chalermchai Kositpipat. The unconventional all-white design, including skulls, dragons and a pit of severed hands, seems to have come straight out of a fever dream but is endlessly photogenic.

Just North of the town center lies Baan Dam, another eclectic sight. Here, Thai national artist Thawan Duchanee has erected a range of structures inspired by Lanna temples and otherworldly dwellings and filled them with furniture from animal bones, crocodile skins and tribal statues. Somewhat creepy, but definitely spellbinding. Less nightmarish is Wat Rong Seur Ten (or ‘The Blue Temple’), an azure-hued modern temple complex which can be visited on the way back to Chiang Mai.

Keeping up with the weird-and-wacky theme, book a table at Bad Boy Valley for one of Chiang Mai’s most unique dining experiences. Hidden deep inside the countryside, this eccentric artists’ hideout doubles as a chef’s table and dishes up inventive Thai fare amidst elaborate flower arrangements, exotic taxidermy and priceless Buddhist art.

Stop #3: Southern Thailand

You could spend months island hopping around Southern Thailand and still only scratch its surface. With eight days, you’ll be able to maximize your beach time by splitting your itinerary into two four-day trips. The following three islands each have a unique character, are relatively easy to get to and make for a great tropic-tinged getaway on a four-day jaunt.

Option #1: 4 days in Phuket
For ritzy resorts and Michelin cuisine

Phi Phi Islands, Phuket

If you’re looking for a one-stop-shop of everything Southern Thailand has to offer, Phuket is your best bet. This might be Thailand’s most populous—and touristy—island, but on the 30 miles stretching from north to south, Phuket offers plenty of tranquil temples, lush jungles and beaches only in-the-know sun-seekers hang out at. Spend your days sipping cocktails at buzzing beach clubs like Cafe del Mar, a top-class dinner from locally farmed produce at Pru, or lounging at one of the many private beaches of some of the country's plushest resorts.

On the sightseeing front, Phuket's Old Town is worth leaving your villa for. The colorful Sino-Portuguese style villas and shophouses lining its main street are home to fantastic local restaurants (seek out Michelin-recommended Raya for authentic Phuket fare) and quirky souvenir shops. Also free up a day to explore the islets dotting surrounding Phang Nga Bay, where you can expect hidden beaches, seaside BBQs and pristine coral reefs. Or, take a ferry ride to Railay Beach, located not too far from Ao Nang and close enough to visit Krabi before returning to Phuket. Your Journy trip designer can recommend a reputable tour company.

Avoid the tumultuous southern beaches if cheeky nightlife isn’t your thing—the further north you go, the classier the crowds get. Here you’ll find Trisara, where each secluded villa comes with its own infinity pool, and only guests have access to the resort’s private beach. Also up north, Sala Phuket is more wallet-friendly and is fringed by Mai Khao Beach, one of Phuket’s prettiest and least developed stretches of sand. Alternatively, opt for an away-from-it-all experience at Six Senses Yao Noi, a luxurious eco-resort on Koh Yao Noi, a 40-minute speedboat transfer away from Phuket’s east coast.

Getting to Phuket from Chiang Mai: Scores of flights leave for Phuket from Chiang Mai airport every day. Direct flights will take about two hours, those with a stop in Bangkok will take up to five.

Option #2: 4 days in Koh Tao
For underwater adventures and jungle treks

Sai Nuuan Beach, Koh Tao

Koh Tao is the smallest of a trio of islands in the Gulf of Thailand, and while it doesn’t have the star-studded resorts of nearby Koh Samui or the legendary beach parties of neighboring Koh Phangan (though you’ll certainly stumble into a fiesta or two), it’s a down-to-earth slice of Thai paradise.

This is Thailand’s main scuba diving hub—and whether it's your first time or you are an experienced diver, the dozens of diving schools fringing the island will have something to fit your wishes, from expert-led deep-sea dives to 4-day PADI certification courses. If you rather stay onshore, there are plenty of cooking classes, jungle hikes (trekking to the Tanote Peak viewpoint for unbeatable views for any backpacker), rock climbing, and yoga classes to stay busy between sunbathing sessions at one of Koh Tao’s many golden beaches.

Koh Tao’s accommodations are a little less luxurious than the resorts you’ll find in Phuket or on Koh Samui—but this also means they’re much more affordable. If you still want to splurge, book a stay at one of the ultra-spacious villas of Casas del Sol, which come with private pools and killer views over the Chumphon Archipelago. Or opt for one of the thatched-roof villas at Jamahkiri, with direct access to the semi-private Tian Ok Beach.

Getting to Koh Tao from Chiang Mai: Bangkok Airways operates twice-daily flights from Chiang Mai to Koh Samui, from where you can connect to Koh Tao by ferry. Alternatively, fly to Bangkok first, then fly to Surat Thani or Chumphon where ferry connections to Koh Tao await.

Option #3: 4 days in Koh Lipe
For barefoot beach bliss and lazy days

Koh Lipe

Deep down south on the border with Malaysia, dreamy Koh Lipe boasts postcard-perfect beaches and some of the clearest waters in all of the country. Thanks to its remoteness, it sees far fewer crowds than Phuket or Koh Tao, but it’s main beaches, Pattaya Beach and Sunset Beach, offer enough comfort creatures to pamper yourself during your stay. There isn’t a whole lot to do on the island, but therein lies its charm. Spend your days at the beach with powdery white sand between your toes and a coconut –or mojito– in hand at one of its many bohemian beach bars, or head out to snorkel for a full day of colorful marine life just off its shores.

For a change of scenery, join a day trip to nearby Koh Ra Wi and Koh Adang, two unspoiled islands just off Koh Lipe’s coast where even more crystalline waters await. If you’re keen on adventure and don’t mind roughing it, there are tent rentals on Koh Adang available for an unforgettable overnight experience.

Idyllic Concept Resort, located at the quiet end of Sunrise Beach offers direct beach access, lush tropical gardens and some of the best bungalows on the island. If you’re looking to splurge a little more, some of the rooms at Asara Private Beach Resort sport open-air Jacuzzi tubs with ocean views.  

Getting to Koh Lipe from Chiang Mai: Air Asia operates one daily flight from Chiang Mai to Hat Yai, from where you can reach Koh Lipe with a fairly straightforward bus—and ferry transfer the next morning. If you want to make the trip in one day, you can catch the last ferry out if you board a very early morning flight to Hat Yai through Bangkok.

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