Expat Holidays Thailand

Classic Thailand – 2 Week Itinerary

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This Thailand 2 week itinerary is perfect for first-time visitors to the country. It includes city, culture, history, nature, adventure and of course beach time.  You will start in the capital city of Bangkok and travel by river to the ancient city of Ayutthaya. After that you will travel North to Chiang Mai — the cultural capital of Thailand — where you will spend time with free elephants at the Elephant Nature Park, take an adventurous jungle trek, ride bamboo rafts down the river and more.  Of course no Thailand holiday is complete without beach time. This itinerary ends with 6 relaxing nights on the most beautiful beaches in Railay and Phi Phi Island.

Holiday highlights
  • Exploring Bangkok using various modes of local transport: sky train, canal boat, tuk tuk, long tail boat and more.
  • Luxury cruise to Ayutthaya and biking around ancient ruins
  • Overnight sleeper train to Chiang Mai.
  • Doi Suthep Mountain.
  • Elephant Camp experience
  • Jungle trekking and visiting local hill tribe villages
  • Chiang Mai famous night markets
  • Relaxation on the best beaches in Thailand
Brief itinerary

Day 1: Arrive Bangkok

Day 2: City tour

Day 3: Cruise to Ayutthaya, bike tour, overnight train to Chiang Mai

Day 4: Old town Chiang Mai and Doi Suthep Mountain

Day 5: Elephant Nature Camp

Day 6: Jungle trekking tour

Day 7: Fly to Krabi and transfer to Railay beach

Day 8: Railay beach

Day 9: Railay beach

Day 10: Ferry to Phi Phi Island

Day 11: Phi Phi Island

Day 12: Phi Phi Island

Day 13: Transfer to Bangkok for last night

Day 14: Departure

Recommended for

Couples, solo travelers, families, can be tailored for a honeymoon.


Upon arrival in Bangkok, meet your driver and transfer to your hotel by private car. The rest of the day is free at leisure. If you like, in the evening we can arrange a Bangkok night tour by tuk tuk. During this tour you will visit some of Bangkok’s temples for a different experience at night and taste the famous city street food.

Meals this day: none


Bangkok is famous for all of its’ various modes of transport. Today you will have a chance to explore the city with our guide — using different types of transport to get around. Highlights of the tour include visits to the Wat Phra Kaew Emerald Buddha Temple, Wat Pho Temple of the reclining Buddha, Wat Arun Temple of the Dawn and a long tail boat tour of Bangkok canals. You will travel around by sky train, canal boat, tuk tuk, long tail boat and river taxi boat. In the afternoon, return to your hotel and evening is free at leisure — we can make reservations for you at one of the famous Bangkok rooftop restaurants.

Meals this day: breakfast, lunch


Today is a big travel day! Pick up at your hotel after breakfast for a joined Ayutthaya boat & bike tour. At 08:30 you will be welcomed on board the Luxury Cruiser at the River City Shopping Complex Pier in BANGKOK. Then you can relax and enjoy the fascinating scenery along the Chao Phraya River. Coffee and other beverages will be served while you enjoy the rich variety of sights along the river banks such as Temple Of Dawn, the Royal Grand Palace and the Royal Barges.

A superb buffet lunch will be served, including a wide variety of oriental and western cuisines. In the meantime, the boat will pass through Nonthaburi province before reaching Wat Chong-lom Pier. At noon, the boat arrives at Wat Chong Lom Pier outside the city of Ayutthaya. Then you continue your journey to Ayutthaya by road.

At 13:00 start exploring the ancient city’s Historical Park by bicycle to see the highlights of this former capital of Thailand. The tour ends around 16:00, at which time you will be transferred to a simple, local guesthouse where you can use the room to freshen up and have dinner.

Then it’s time to board an overnight train from Ayutthaya to Chiang Mai. Overnight on the train.

Meals this day: breakfast, lunch


Your train arrives in Chiang Mai early in the morning. You will be picked up at the station by private car and transferred to your hotel. Breakfast and early check in will be arranged for you so you can relax after the journey. Your hotel will be located in or close to Chiang Mai Old Town where you can walk around and visit all the famous temples. If you wish to have a guide for this tour, we can arrange it. In the afternoon your guide will pick you up for a short trip to Doi Suthep mountain from where the ancient temple Wat Phra That is located. This temple was built in 1383 and is still a working monetary today. From the mountain you can enjoy panoramic views of Chiang Mai. This trip will only take about 2 hours so you this will be a very relaxing day.

Meals this day: breakfast


Enjoy a full day visit to Elephant Nature Park; a natural home and sanctuary for elephants, buffalos, dogs, cats, birds and many other rescued animals. Your visit starts with a picturesque drive through rural countryside to Elephant Nature Park. You will hear the personal stories of rescued and orphaned elephants. See how they became a proud herd and free from abuse for the first time in their lives. Many find their visit to Elephant Nature Park rewarding and very relaxing. Observe free roaming elephants, and other rescued animals enjoying the natural surroundings of our sanctuary. Your visit helps support our regional projects and offers an invaluable opportunity of helping elephant conservation.

Meals this day: breakfast, lunch


Today is a full day jungle trekking tour which will take you through some of the most scenic nature in North Thailand. You will get a chance to visit some of the local hill tribe villages and learn about their daily lives. After lunch you will ride local, bamboo rafts down the river before heading back to Chiang Mai.  In the evening enjoy a traditional Chiang Mai Khantoke dinner with a performance

Meals this day: breakfast, lunch, dinner


Free time until transfer to airport for a 2 hour flight to Krabi. In Krabi airport you will be picked up by your driver and transferred to Railay Beach by land and a short long tail boat ride. Railay is one of our favorites. This bay is part of the mainland but has an island feel since the only way of reaching it is by boat. Rest of the day free at leisure.

Meals this day: breakfast


Next 2 days are free at leisure. You may choose to simply relax and enjoy the beach or you may easily arrange some day trips at the hotel tour desk. There are kayaks available for rent, a great hike to the viewpoint overlooking the bay on both sides. For those more adventurous, Railay is famous for world-class rock climbing — a day tour with a lesson can be arranged at one of the local climbing shops.

Meals this day: breakfast


Get on a 1.5 hour ferry to the famous Phi Phi Island. This is the island you have seen on most of Thailand travel brochures and photos online. The island became famous after the movie ‘The Beach’, starring Leonardo DiCaprio was filmed there. Check into your hotel and rest of the day free at leisure.

Meals this day: breakfast


Free time on Phi Phi Island. We recommend hiring one of the local, long tail boats for a private snorkeling tour around the smaller islands and of course a visit to the famous Maya Bay, where ‘The Beach’ was filmed.

Meals this day: breakfast


Free time until transfer by ferry back to Krabi. In Krabi, pick up by your driver and transfer to airport for departure flight. If the flight times match to connect to your international departure flight, this will be the end of your holiday. If not, you will be transferred from Bangkok airport to your hotel for the final night.

Meals this day: breakfast


Time for some last minute shopping or relaxing before transfer to airport for your departure flight.

Meals this day: breakfast

Best time to go

Best time for this trip is November – March. Chances of rain are small, temperatures in North Thailand are cool in the mornings and evenings while temperatures in South Thailand are perfect for beach days.

March and April are also a great months to go.  It gets very hot, especially up North with chances of rain but the benefit is much lower prices relative to the weather.

May – October is the official ‘low season’ in most places in Thailand.  There can be heavy rains at times but don’t let this put you off – it normally rains hard for a few hours in a day and usually in the evenings.  During this time prices drop dramatically and there are much less tourists.  For these reasons are seeing the low season become more and more popular time to visit Thailand.

Thailand visa information

Thailand allows free visa on arrival for most countries.  Please check the list here for information regarding your country.

Extension options

If you have more than 2 weeks, we would be happy to offer you some trip extension ideas.  You can head to Kanchanaburi and spend a few nights in a luxury tents and floating villas on the river.  You may wish to visit Siem Reap, Cambodia for a few days to explore the Ancient Angkor ruins.  If you are more active, you might like to try one of our overnight trekking tours in North Thailand.  Or simply add more beach time, possibly on another island.

Tailor – made

All of our suggested itineraries are based on holidays that have been very popular with our clients.  However we strongly believe that each holiday should be unique to the traveler.  Absolutely anything in our itineraries can be tailored to suit your requirements, travel style and budget.  Simply contact us and let us design your custom holiday!


We never mix groups during holidays.  All the holidays are arranged for your group only so you can travel at your own pace.

Independent travel

The most consistent feedback from our clients is how amazing our guides are!  We strongly believe that having a guide can add some much value to your travel experience.  With that said, we totally understand that some travelers prefer to explore independently.  If this is your travel style – we can still help you!  We can arrange your holiday without guides, suggest activities that you will enjoy, advise the best way to get around, how much to pay for things, etc.  We simply help you plan a logical itinerary, book accommodation and necessary transfers along the way.

Planning process

We work together with you until you are 100% satisfied with your itinerary.

  • Initial contact by phone or email to ask you some questions to help us fully understand your travel style, requirements, budget etc.
  • We send you a detailed itinerary proposal with prices
  • You review, and if needed, reply with requested changes.
  • We send you updated proposal.
  • Continue this process until you are 100% happy with and accept the proposal.

Prices often vary due to travel period, best accommodation rates during that period, number of persons traveling, etc.  Please send us your holiday requirements and and approximate budget (if you have one in mind) and we will get back to you with a detailed quotation right away.

Free planning. No booking fees.

Our philosophy is simple: our tours will not cost clients more than if they arrange the same tour themselves.  We do not charge any ‘fees’ whatsoever.  How do we make profit?  Our profit comes from suppliers we use – hotels, transport, tour companies, etc.  Rates we get as a travel agency are much lower than direct booking (or booking website) rates.  This allows us to offer tours to our clients at lower prices, or at worst the same, as they would be if booking all the services directly.  To simplify – you save money, time and receive our expert advice for free.

Please provide as much information as possible.  We respond to most requests right away during work hours and always within 12 hours.

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Hotel options for this holiday

These are popular hotels that we have used for this holiday.  If you have other hotels in mind, or would like more options let us know.

Location Economy hotels (room type) Premium hotels (room type) Luxury hotels (room type)
Bangkok Holiday Inn Sukhumvit 22 (superior) VIE Hotel Bangkok (deluxe) Shangri La Bangkok (deluxe river view)
Chiang Mai Raming Lodge Hotel (deluxe) Kodchasri Thani (deluxe) 137 Pillars House (rajah suite)
Railay Beach Sand Sea Resort (grand deluxe) Railay Village Resort (jacuzzi villa) Rayavadee Resort (deluxe pavilion)
Phi Phi Island Phi Phi Bayview Resort (new wing superior) Holiday Inn Phi Phi (deluxe bungalow) Phi Phi Island Village (beachfront junior suite)

Holiday includes

  • Accommodation in category chosen
  • All meals as mentioned in the itinerary (B=Breakfast, L=Lunch, D=Dinner
  • All airport and train station transfers by private vehicle with A/C
  • Train tickets Ayutthaya - Chiang Mai
  • Ferry tickets to Phi Phi Island
  • All private and joined sightseeing as mentioned in the program
  • English speaking guides where mentioend
  • All entrance fees as mentioned in the program

Holiday does not include

  • International flights
  • Domestic flights (can be quoted separately)
  • Travel insurance
  • Any meals and transfers not clearly mentioned in the program
  • Any personal expenses such as tips, laundry etc


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  • My husband and I have been living in SE Asia for 3.5 years and have used Lenny’s services on many occasions! From a night in Bangkok, to Laos, Cambodia and Vietnam, to arranging everything for a trip for my in-laws, he’s been able to manage it all quickly and efficiently! He is very thorough and provides clear details that ensure you have a magnificent experience. I tell everyone I know about Lenny and his services! I highly recommend getting in touch with him to plan your next SE Asia trip!

    Laurie Ranz, expats based in Bangladesh
  • Thank you Lenny and team for making our trip to Thailand so memorable! All the transfers and tours were exactly as described and we felt at ease the whole trip knowing your team were working away making sure we enjoyed it. Thanks for all the recommendations and especially the elephant tour, definite highlight! We’ve already passed your details to others because we know our friends and family will be in good hands when booking their trips through you. Thank you again for taking such good care of us!

    Reena Mandora from UK – Bangkok and North Thailand tour
  • Lenny, I just wanted to pass along some words of thanks. You have done a fantastic job assisting us with our retirement vacation that you tailored to our needs. 6 weeks in Asia was was ambitious but was made stress free through your help. Our hotels were gems, in great locations, with a staff that were more than helpful. Transfers to and from the airport were perfect. It was nice to see a smiling face there for us in each new location that we visited. I would highly recommend this service to anyone looking to book. Your communication to us was amazing (I couldn’t imagine how it could be any better). We always knew what was happening in the next few days. It was nice to have the safety net of being able to get in touch with the owner of Expat Holidays knowing that we would have a response to our inquiry in a short period of time. Our guides were knowledgeable and were easily able to communicate with us. Special thanks to our guide, Mr. Sophy, from Siem Reap. He went above and beyond. Finally, even though we made a few last minute changes, they always went off without a hitch from your end.
    We will be recommending Expat to our friends and family (our daughter is already talking about coming back to this part of the world) when we get home.

    Rob Kruse from Canada – Thailand & Indochina tour in 2016
  • We were a group of 8 touring from South Africa. We contacted Lenny and from day 1 everything he advised us on turned out perfectly. He accommodated our every need and structured our trip according to what we wanted. Lenny even made the effort to meet us at our hotel in Bangkok, for a meet and greet. It is always good meeting the person behind all the arrangements. Everything was well arranged and on time, from our day trips to our transfers to either hotel, airport or train station. The accommodation was also top class. I would highly recommend Lenny and Expat Holidays Thailand, to anyone considering traveling to this beautiful country and its very friendly people. We certainly will be back in the future and will make use of Lenny’s services again. Thank you Lenny, for a great experience.

    Ingrid Bailey from South Africa – Thailand family tour in 2016
  • This company is absolutely amazing. Our tour was organized perfectly from the first minute to the last. The itinerary, the varieties of sightseeing, the service deserve the top prize. Our guide Peter and our driver were very attentive. Peter is knowledgeable, with a sense of humor, and very cheerful. Our accommodation was excellent. I am dreaming now about going back to Thailand and explore more with Expat Holidays Thailand. They are the best!

    Elena Yzgur from USA – 2 day tour of Bangkok and Ayutthaya from a cruise ship