2 Weeks in Thailand & Singapore Itinerary

Thailand is not only one of the most beautiful countries in the world, but also one of the most affordable. Whether you are looking for 5 star luxury or hostel hopping, there is something for everyone. Thailand offers everything from amazing food, jaw dropping landscapes, and the best beaches in the world. There is a reason that Thailand is a top destination for backpackers.

I was fortunate enough to spend two weeks in Thailand right before the Pandemic. I have detailed my itinerary to help you plan your next trip to Thailand. I will say that two weeks is the absolute MINIMUM you should visit.

Detailed Itinerary


  • Days 1-5 – Chiang Mai/Chiang Rai
  • Days 6-7 – Khao Lok/Khao Sok
  • Days 8-12 – Phuket
  • Days 13-14 – Singapore

Day 1 – Fly into Chiang Mai

If you are flying from the U.S. then you are going to lose a full day just traveling. The total journey took about 20 hours. You will most likely be arriving late at night so picking your lodging ahead of time is key. We booked an AMAZING Airbnb in Old City Chiang Mai called Villa Nittra Singharaj. We arrived at 11:30pm but the hosts were there to greet us with a full Thai feast, which was much needed after such a long flight. I highly recommend staying there if you can!

Day 2 – Explore Temples in Chiang Mai

The best way to get over jetlag is to get out and explore. On your first full day, explore all the temples in Old City. The Old City of Chiang Mai is a walled off part of the city with centuries-old temples. There are many restaurants and street food stands all around and they are CHEAP. My personal favorite were the watermelon shakes! I had to get one with every meal.

In the evening, head to the Chiang Mai Night Market where you will find unlimited street food, clothing and trinket shops, and live entertainment. We were able to get a plate of Pad Thai and a beer for just $2.

At the end of the day, reward yourself with a Thai Massage. Massages are a big part of Thai culture you can find them for as little as $10 for an hour session (sometimes cheaper)!

Day 3 – Day Trip to Chiang Rai

If the temples in Chiang Mai weren’t enough, take a day trip to Chiang Rai to see the famous Wat Rong Khun (White Temple) and Wat Rong Suea Ten (Blue Temple). The White Temple is one of the coolest pieces of architecture I have ever seen. The white color symbolizes Buddha’s purity and is guarded creatures and dragons.

Chiang Rai is a 3 hour bus ride from Chiang Mai. We decided to stay overnight but it can be done as a day trip as busses leave hourly both directions. If you stay overnight I recommend staying at the Le Meridien Chiang Rai.

Day 4 – Go to an Elephant Sanctuary

A visit to Thailand is never complete without a visit to an Elephant Sanctuary. I recommend going to Elephant Nature Park. This is an Elephant rescue and rehabilitation park where you can feed and bathe the elephants. This is one of the most ethical parks in all of Thailand and the elephants are well taken care of.

Day 5 – Final Day in Chiang Mai, Relax Day

On the final day in Chiang Mai, we spent the day getting traditional Thai Massages and eating as much food as we could. This is a good reset before the next leg of the journey. With the food and massages being so cheap, you can definitely get your money’s worth!

Day 6 – Fly to Phuket and Taxi to Khao Lok

On day 6, book an early morning flight to Phuket. Inter-country flights are extremely affordable. We flew on Air Asia and our flight was under $40. From Phuket you will take a taxi to Khao Lak which is a 75 minute ride. There are several beach resorts in this area but I recommend staying at the Le Meridien Khao Lak. This is an affordable 5 star resort because it is far away from the touristy Phuket. Spend the day at the beach and pool. The following day will be a full day of adventure.

Day 7 – Visit Khao Sok National Park

Khao Sok National Park was by far my favorite part of Thailand. It is about a 90 minute drive from Khao Lak and you’ll want to book transportation in advance. We decided to hire a driver for the entire day as it was cheaper than booking a tour. Khao Sok has giant limestone rock formations that surround the man-made Cheow Lan Lake and is best seen by Longboat. The views are absolutely mind blowing and it is one of the most beautiful places in the world.

The boat ride takes about 2-3 hours but you can always go longer if you choose. Out of all my recommendations, this is one you cannot miss!

Day 8-12 – Patong Beach

The final four days in Thailand we spent at the famous Patong Beach in Phuket. Full disclosure, if you are looking for a more relaxed vibe, this is not the place. Patong beach is very lively with many bars, pushy street sales, and loud music. If you are looking for a quieter place, there are many other beach towns in Phuket to choose from.

There are endless Airbnb’s near Patong beach, but if you are wanting to stay at a resort I recommend staying at Le Meridien Phuket Beach. If you couldn’t tell, there are many Le Meridien resorts in Thailand!

While in Patong Beach, you will find no shortage of activities. There is unlimited street food, fancy restaurants, massage spas, and live entertainment everywhere. If you are looking for a dinner with an amazing view, make reservations for the Patong Sunset View Bar. If you are looking for live entertainment, take a stroll down the famous Bangla Road. The entire road is all bars and live music with floods of people.

Day 12-14 – Fly to Singapore

For the final two days, we took a short flight over to Singapore to complete our 2 week trip to Southeast Asia. With only a short time in Singapore, we visited the famous Marina Bay Sands Rooftop, the Botanical Gardens, and Clarke Quay which is where the nightlife is. Singapore was the cleanest, most futuristic city I have seen. It is the perfect way to end your trip.

If you would like to see more from the trip, here is my Youtube highlight!