14 Day Thailand Itinerary- perfected
Things to consider when planning:
Best Time to Visit: November–December
Personally, I recommend visiting Thailand in November or December, as it’s the perfect shoulder season. The weather is generally dry and comfortable, the crowds are lighter than during peak season, and prices for accommodations and tours are often more reasonable. Plus, you can avoid the heavy rains of Thailand’s wet season (May–October), which can make certain areas, like islands and national parks, difficult to explore. For me, this time of year strikes the best balance between comfort, cost, and an authentic experience.
Day-by-Day Itinerary
Day 1–4: Chiang Mai
Day 1:
Arrive in Chiang Mai, settle into your hotel, and explore the Old City.
Visit iconic temples like Wat Phra Singh and Wat Chedi Luang for an introduction to the city’s history and culture.
Tour suggestion: 3 Hour Old City and Temples Guided Walking Tour
Day 2:
Spend the day at an ethical elephant sanctuary. Feed, bathe, and learn about these gentle giants in a meaningful and unforgettable way.
Tour Suggestion: Elephant Sanctuary, Waterfall & Bamboo Rafting
Day 3:
Take a day trip to Doi Inthanon National Park, known for its stunning waterfalls, nature trails, and the highest peak in Thailand.
Tour Suggestion: Doi Suthep Temple & Wat Pha Lat Hike
Day 4:
Stroll through Chiang Mai’s vibrant markets, such as the Night Bazaar or Sunday Walking Street Market.
Optional: Take a Thai cooking class to master local dishes.
Tour Suggestions:
Accommodation Suggestion: Stay in a boutique hotel within the Old City for convenience and charm.
Where we stayed: Baan Ratchiangsaen - Short walk outside old city walls, good value
Other options: Rendezvous Classic House- In old City
Unique Stays: Tree Scape Retreat Resort or Phor Liang Meun Terracotta Arts
Day 5–6: Khao Sok National Park
Travel: Fly from Chiang Mai to Surat Thani or Phuket, then transfer to Khao Sok National Park. A private air-conditioned car transfer to the pier is recommended for convenience. Arrange with your resort for a pick-up at the dock.
Day 5:
Check into a floating resort on Cheow Lan Lake (e.g., Panvaree The Greenery).
Spend the day kayaking, soaking in the limestone cliffs, and listening to jungle sounds.
Enjoy included boat tours, where guides will point out local wildlife.
Day 6:
Take a guided jungle trek to explore caves and spot exotic wildlife.
Transfer to a budget-friendly jungle resort for an authentic, rustic experience—or stay another night at the floating resort if your budget allows!
Accommodation Suggestion: Split your stay between a floating resort and a jungle bungalow for variety.
Day 7–10/12: Krabi Ao Nang
Travel: Take a bus or private transfer from Khao Sok to Krabi Ao Nang. The bus ride offers a glimpse into the countryside and is a surprisingly pleasant experience, despite some chaotic moments!
Day 7:
Arrive in Ao Nang and settle into your beachfront resort.
Relax on the beach or take a stroll along the lively Ao Nang promenade.
Day 8:
Visit Railay Beach, accessible only by long-tail boat, and one of my favorite spots in Krabi. Spend the day exploring caves, marveling at the limestone cliffs, and soaking up the serene atmosphere.
Day 9:
Join a multi-island hopping tour, visiting spots like:
Bamboo Island
Phi Phi Islands
Snorkel in vibrant waters and enjoy the beauty of these famous destinations.
Day 10:
Take a day trip to Phra Nang Beach. Explore the Princess Cave, kayak along the mangroves, and enjoy the peaceful surroundings.
Optional Additional Days in Ao Nang, or Phuket, for additional beach time!
Spend an extra day relaxing with a Thai massage or spa day.
Explore Krabi Town’s markets to pick up unique souvenirs and enjoy delicious local food.
Transfer to Phuket, if departure is more affordable.
Day 12:
Depart from Krabi or transfer to Phuket for your flight home.
Accommodation Suggestion: For an awesome value, and quiet stay at one of the many cliff view resorts, like Poonsiri Resort Ao Nang. For a more local experience, consider staying at Aonang Guesthouse. For a luxury experience, stay at a beachfront hotel like Centara Grand Resort Ao Nang
Stopover Suggestion: Seoul or Tokyo
If you have extra time, consider breaking up the long journey with a 2-3 day stopover in:
Seoul: Explore bustling Myeongdong, visit ancient palaces, and indulge in delicious street food. We did a 4 day layover in Seoul on our second trip to Thailand and it was awesome!
Tokyo: A vibrant city where tradition meets modernity—enjoy sushi, iconic sights, and unique cultural experiences.
Tip: Book multi-city flights to make the most of your time and avoid unnecessary backtracking.
Tips for Success
Timing: November–December is the best time to visit for great weather and fewer crowds.
Packing: Bring lightweight, breathable clothing and comfortable shoes for all the exploring!
Tours vs. DIY: Group tours for island hopping are often more affordable and better timed than private options. Instead, wake up early to beat the crowds to the local beaches!
Flexibility: Adjust the itinerary based on your pace and interests—this is your adventure!
Cheow Lan Lake, Koh Sok National Park, Thailand
You know the trip was good, when you can’t wait to go back!
Jake and I fell in love with Thailand during our first trip in 2017, so much so that we couldn’t resist going back in 2019! [Read more about our first adventure in 2017 here.]
On our return trip, we wanted to do a multi-country trip, so for our leg in Thailand we focused on exploring the Krabi Ao Nang region, but the real highlight was Khao Sok National Park—hands down the most beautiful place I’ve ever seen. The limestone cliffs are absolutely jaw-dropping, and the experience was nothing short of magical.
We stayed at a floating resort, the Panvaree The Greenery, which was a splurge for us at the time but completely worth it. Picture this: kayaking on a serene lake surrounded by towering cliffs, the soothing sound of cicadas in the background, and ultimate relaxation. While it did take some effort to get to Khao Sok and find the port where the resort picks up guests, it was all part of the adventure—and totally worth it!
After our night at Panvaree, we balanced our budget by staying at Koh Sok River & Jungle Resort, which is shockingly affordable. This resort offers a more rustic, authentic experience with charming open-air villas and mosquito-net-covered beds—perfect for soaking up the jungle vibe. The quaint town nearby adds even more character to the experience.
Thailand never fails to amaze us, and these experiences are just a few reasons why it holds such a special place in our hearts.
After leaving the jungle, we hopped on a local bus from the village center to Krabi Ao Nang. Navigating the bus system with the language barrier was a bit of a challenge, but it ended up being an incredible value and a memorable part of the trip!
The ride itself was surprisingly pleasant—with air conditioning, beautiful views of the countryside, and a couple of hours to just relax. The bus had a mix of tourists and locals, which made the experience feel authentic. That said, don’t expect traditional bus stations—things are very casual here!
At one point, we were ushered off the bus in Krabi and dropped off at what looked like an auto shop. 🤔 Confused? So were we! Turns out, it was actually a mini transfer station where we boarded a second bus to Ao Nang. Thankfully, the Thai bus operators knew exactly what they were doing, even if we didn’t!
It might not have been the most glamorous part of the trip, but it added to the adventure and gave us plenty of stories to tell. Sometimes, the unexpected moments are what make travel so memorable!
Rediscovering Ao Nang and Falling in Love with Railay Beach
Returning to Ao Nang felt like coming home to one of our favorite destinations. This charming beach town quickly became the perfect hub for our adventures, and we couldn’t resist visiting Railay Beach multiple times. Accessible only by long-tail boat, Railay is a true paradise surrounded by dramatic limestone cliffs, crystal-clear waters, and a serene atmosphere. Every visit was a unique experience—whether we were exploring caves, soaking in the views, or simply relaxing on the soft sand. By the end of our trip, we knew: Railay Beach was our absolute favorite spot in the area!
Our Bamboo Island Splurge Gone Wrong
Back in 2017, we did a multi-island hopping tour, and Bamboo Island was the standout highlight. The stunning white sand, vibrant turquoise water, and peaceful vibes made it unforgettable. When planning our 2019 trip, we couldn’t wait to return—this time without the crowds. To make it special, we splurged on a private boat tour to beat the rush and enjoy the island all to ourselves.
Unfortunately, things didn’t go as planned. The water was incredibly rough that morning, and the boat ride out was anything but smooth. Jake ended up getting seasick, which made the experience even harder to enjoy. When we finally reached Bamboo Island, we were informed that due to the tides and the time of day, we could only stay for 10 minutes.
To make matters worse, the locals who booked our private boat had known about the tides in advance but didn’t warn us or offer any alternatives. It was incredibly frustrating to realize that we’d spent so much money on an experience that felt rushed and poorly planned.
Our Advice for Future Travelers
If you’re considering visiting Bamboo Island or planning a similar excursion, here’s what we learned:
Stick to group tours for popular destinations like Bamboo Island. They’re more affordable, and the operators usually have better timing for tides and conditions.
Take advantage of the amazing long-tail boat rides to closer beaches like Railay and Phra Nang. They’re easy to organize, budget-friendly, and just as breathtaking.
While our Bamboo Island trip didn’t live up to expectations, it’s a reminder that not every travel experience goes perfectly—and that’s okay. The moments we spent at Railay Beach and exploring Ao Nang made up for it, and the journey (even with seasickness!) always leaves us with stories to tell.
A Love Affair with Thailand
Our two trips to Thailand, filled with breathtaking landscapes, cultural discoveries, and unexpected adventures, solidified it as one of our favorite destinations. From the serene beauty of Khao Sok National Park to the vibrant charm of Ao Nang and the unforgettable experiences (even the imperfect ones) like Bamboo Island, Thailand continues to amaze us with its diversity and wonder.
Travel, after all, is as much about the challenges as it is the rewards. It’s the moments of awe, the laughter over missteps, and the stories we carry home that make each journey special. For us, Thailand holds a treasure trove of memories—some planned, some spontaneous—that keep calling us back.
If there’s one thing we’ve learned, it’s that no trip is ever perfect, but every trip is worthwhile. And Thailand? It’s a destination we’ll keep dreaming about until we find our way there again.
So, whether you’re planning your first trip or your fifth, don’t hesitate to embrace the adventure. Thailand is waiting, and it might just steal your heart like it did ours.
