Thailand in two weeks: an itinerary suitable for over-55 travellers

A two-week Thailand itinerary – seeing a lot, without feeling the need to see everything

Two weeks in Thailand: the itinerary

This two-week Thailand trip is built around a fairly sensible pace and a logical route. This is unsurprising as it was designed by a travel agency. These people tend to know what they’re talking about. There’s a bit of everything: busy cities, temples, a river, the jungle, beaches, and the occasional weird experience that made us laugh. Well – it did after I’d recovered from the shock. I’m talking about you, River Kwai!

I’ve kept the day-by-day stuff flexible and fairly concise, so you can glance at it without getting a spreadsheet headache. Where it’s useful, I have added (or in most cases: will add) links to more detailed posts. Think Bangkok markets, northern adventures, jungle stays, and beachy escapes.

If you like the idea of a Thailand trip where you can have a lazy morning, take a wrong turn without consequence, and maybe spend a few hours doing nothing at all in a comfortable airconditioned room or at the side of the pool (highly recommended), this itinerary should work nicely.

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Why we planned the trip like this … not that we did much of the planning.

Technically, we didn’t plan much of this trip at all — it was all laid out by the travel agency because, well, we won it. Cue a mix of excitement and slight disbelief. That said, we did manage a few minor tweaks here and there. These tweaks were mainly to make sure the trip was doable for anyone over 25.

The route made sense: Bangkok first, then Chiang Mai and the north, before heading south for a bit of island bliss. It gave a gentle introduction to Thailand — from the buzz and chaos of Bangkok, to the calmer north, to a proper stretch of sand at the end. Perfect for doing and seeing a lot without feeling completely overwhelmed.

I have to be honest: if I had planned this trip myself I would have gone longer (the longer the flight, the longer I stay and this one was 13 hours). I’d also have included some of the national parks and the islands in the south. Especially Kao Sok is still on the wish list. I would also have stayed in the Kanchanaburi province for a day longer. The resort we stayed in was lovely and we didn’t get to enjoy it for long. Finally, I’d have added an extra day in Bangkok at the beginning.
But generally, it was a great trip that we didn’t need to recover from. I can recommend this itinerary to everyone.

Temple guards at the Grand Palace, Bangkok

Day 1 -2: Bangkok

• After arriving in Bangkok at the crack of dawn, we were more than happy that a friendly driver with a minivan was waiting for us. So much better than having to hail a taxi half asleep! It’s a long way from the airport to downtown Bangkok, so expect to stare out the window of the car for a while.
• We stayed at the Maitria Mode Hotel Sukhumvit, a mid-sized hotel with friendly staff, great breakfast and a rooftop pool we spent most of the first afternoon in. After a little nap, of course. Then some walking around, a lovely dinner at a riverside restaurant and more time in the pool. Not a bad way to start the trip. Interested in this hotel? You can find prices and book here.
• On day 2 we did what every Dutch person has to do when in Bangkok: go on a bike tour. I loved that. Read all about it in this post about our biking adventures
• What I didn’t love quite as much was the tour of the temples and the Grand Palace on the afternoon of the same day. Not because of the temples, but because of our own over-enthusiastic planning. The temples were all incredibly beautiful and the Grand Palace was stunning beyond belief. But at this point the heat and the jet lag had caught up with me and I was utterly miserable after a few hours.

Day 3 – 5: a road trip with a guide and a driver to Kanchanaburi Province.

• Day three started early. And I mean very early. Our guide and our strong and silent driver picked us up at seven. Yes, seven in the morning. Why? We had a long day ahead of us. After getting to know our guide Phoey and driver Gob during the hour it took us to even get out of Bangkok, our first stop was at a train market. Quite bewildering to stand pressed against a wall and see a train pass inches in front of you . And then within half a minute all the market stalls were back like there had never been a train in the first place.
• Stop two on this road trip: the floating market of Damnoen Saduak. A brief boat ride through a sea of vessels, each brimming with vendors eager to sell us their wares. At times, they even latched onto our boat with grappling hooks. We managed to escape mostly unscathed, only surrendering to a bit of mango sticky rice. All this while skillfully avoiding elephant statues, fans, and baskets.
• Stop three: a lunch break, followed by a visit to the WWII cemetery in Kanchanaburi, which left a somber silence. Like the famous Bridge on the River Kwai, it prompted quiet reflection. We were deeply moved by the Burma Railway and its museum—so much suffering, so much loss. Walking along the road hewn through the rocks by prisoners, it’s almost unimaginable what they endured.
• Leaving the weight of history behind, we shifted gears and headed back to more cheerful activities: a drive to the river and a night on a jungle raft. This is where I found out even good swimmers cannot beat strong currents, and where we spent a magical, but hot night in the jungle. Read more about our stay at River Kwai Jungle Rafts here.
• The second day of this trip wasn’t as packed: we took the boat pack to the pier again, where our driver was waiting for us. It was about an hour’s drive to the Erawan falls, where we spent an enjoyable morning hiking up the paths next to the waterfalls, and swimming at almost every level. I do have to say the swimming was decidedly more enjoyable than the hiking. More about this in an upcoming post.
• After lunch the driver took us to our stay for the next night: Home Phutoey River Kwai Resort. Less than a mile as the crow flies from the Jungle Rafts, but worlds away: air conditioning, a lovely pool (no currents!), thermal baths, a restaurant with a view, beautifully landscaped surroundings. Want to check it out? You can find prices and booking options here. I would have loved to stay another night.
• The next day, after a hearty breakfast, it was a long (and I mean four hours) drive to Ayutthaya, with ancient temples, a huge statue of a reclining Buddha looking very blissful, and another divine passion fruit smoothie. It was incredibly hot. So hot that we didn’t mind being left at the station three hours before the departure of our train, because of the airconditioning. Also, we were tired.
• Read more about the sleeper train to Chiang Mai in an upcoming post

Dag 6 -9: Chiang Mai

• On arrival in Chiang Mai, slightly bleary-eyed after the night on the train, we were happy to see a driver holding up a sign with our names. I could very easily get used to private drivers.
• The driver took us to our hotel, De Charme Hotel, where we left our luggage and headed out for breakfast. The rest of the day we spent visiting temples (I have to be honest, they do all start to look alike after a while), lounging by the pool and getting a foot massage. Foot massages are something else I could easily get used to. We took a Grab to the Night Bazar for street food and some light shopping.
• Day two in Chiang Mai was another one of the tweaks I’d asked for: a cooking class. Guide Natty took us to a market, then to the Smile Organic Cooking farm, where we met our fellow wannabe-chefs and prepared a delicious five-course meal. More about that in an upcoming post, but this is the cooking class we did and we really enjoyed it.
• On day three we went to another of my tweaks: an ethical elephant sanctuary in the mountains about an hour from Chiang Mai. I wanted it to be ethical, or as ethical as possible for rescue elephants: no touching, no washing, no direct interaction, just watching. Read about our elephant experience here. Do let me give you a spoiler: this is where I ended up on the muddy hill that made me decide to start writing this blog.
• Day four was another cycling tour, early in the morning, through the rice fields and villages outside Chiang Mai. Very enjoyable, albeit very hot, and a nice way to spend the morning.
• The afternoon we spent lounging by the pool again, before heading back to the station for the night train back to Bangkok.

Day 10 – 14: Koh Samet

• On arrival at Bangkok station, another driver was waiting for us. Off we went to Ban Phe, where the boats to Koh Samet leave. It was a long drive, but in the back of an airconditioned van after a rather restless night, this wasn’t much of a problem.
• The boat ride to Koh Samet took only half an hour. Only later did I realise that we were the only ones not wearing life vests. Slightly too much confidence in ferries I think, being Dutch. This is a mistake I’m not going to make when we travel to Indonesia later this year.
• We checked in at Baan Ploy Sea Hotel and settled into – well, not doing very much at all really. We spent our days on Koh Samet hopping between beaches, eating wherever the locals ate, indulging in another foot massage, and being bounced around in Songtaews—tuktuks on steroids. We squeezed in a book or two, watched a few fire shows, and then witnessed the ultimate spectacle: a massive thunderstorm rolling in from the mainland, putting even the best fire performers to shame.
• We also rented bikes for a day or two. Koh Samet is hillier than you’d think and this time I forgot to check the brakes so this was slightly more adventurous than necessary. We gave the ubiquitous snorkeling tours a pass. I’m too nearsighted to tell a sea turtle from a great white shark unless they’re practically bumping into me. I’d prefer it not to come to that.

Day 15: one more day in Bangkok

• After our island bliss on Koh Samet it was time to head back to Bangkok. By private driver, naturally. Traffic jams galore so this took slightly longer than expected. We were however in time for dinner on Khao San Road and a quick swim.
• On Khao San Road I recommend Madame Musur for dinner (awesome Pad Thai) but Khao San Road itself didn’t really appeal to me—too much weed in the air, too many people trying to sell something, and that skinned alligator on display. This was the first time in Thailand—well, perhaps aside from my revelatory moment on the muddy hill—that I truly felt too old for my surroundings. So Khao San Road is a no for me, although it is conveniently close to all the major sights.
• On our last day in Bangkok we went to the national museum, a few more temples and the Golden Mount, home to Wat Saket temple. Well – we walked around it. It was almost forty degrees, it was 300 steps and it wasn’t like we hadn’t seen temples before.
• After that, we went for another massage—a full-body one this time. Halfway through, I realised it had been a while since my last bone density scan and wondered if this was even safe. Thankfully, no bones were harmed in the process, but I think I’ll stick to foot massages from now on.
• Completely relaxed and smelling of jasmine we hopped into a minivan one last time and headed back to the airport.

Final Takeaways and Possible Tweaks

• This itinerary worked perfectly for us, though it did involve quite a bit of travel between destinations. If you prefer not to handle transportation yourself, Thailand is very tour-friendly—guided excursions, private drivers, and organized trips make it easy to explore temples, floating markets, jungle treks, and local attractions without self-driving.
• Safety in Thailand is generally good, but a little awareness goes a long way. Keep valuables discreet, avoid flashing phones or cash, and stay in busy, well-lit areas, especially at night. Use trusted transport—taxis, rideshares, or arranged transfers—and if you’re on a tour, follow the guide’s instructions. Trust your instincts: if something feels off, move on.
• The food in Thailand was incredible and very affordable. Lots of vegetarian options, fresh fruit, and we loved all the food markets. Don’t worry too much about eating the food. Stick to where the locals eat. Skip the tap water, and keep up basic hygiene. Usually that’s enough to stay safe, though nothing’s guaranteed. If you have dietary requirements inform your guide and your hotels.
• For a two-week trip, focusing on Bangkok and the surrounding region, followed by Chiang Mai, with a bit of Koh Samet added to the mix, gives a perfectly balanced experience of city life, culture, beach relaxation and northern Thailand’s landscapes.
• If you have more time, you could add a few days in Khao Sok National Park for a jungle and river adventure, or spend extra days on a southern island such as Koh Lanta or Koh Yao Noi for more beach time and relaxation.

If you’d like to read more about Thailand, take a look at the country hub.

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Too rushed?

Although this itinerary was quite full and involved a lot of travel between locations, it didn’t feel too rushed for us. This may be different for you. Want to take a more serious look at whether an itinerary is too rushed or exhausting? Download the trip-planning checklist below. You can use it for any future trip to decide whether changes are needed. No sign-up needed, direct download. If you would like to receive occasional emails with tips and stories, you can subscribe to our newsletter.

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