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Happy holidays! This post is brought to you by .
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Whether it’s off on an exotic beach getaway or back to a snow-filled hometown, it’s no secret that the holidays are a crazy popular time to travel. Despite that I’m on a self-imposed six-month travel sabbatical, even I couldn’t resist getting in on the fun. Right now, I’m off on a six-day, seven-night getaway that I’m just plain giddy about. I might live in a postcard on Koh Tao, but this particular paradise is just thirteen square miles — a little adventure off the island every once in a while is not only required by visa restrictions, but generally a good way to ward off claustrophobia.

But a trip doesn’t start as the plane takes off — nope, I’ve been working on this one for months. As I’ve recently been sharing my own travel planning system in the Wanderland Guide to Travel Planning, I thought it would be fun to show you a real life example of how all the pieces of one of my shorter trips came together. Here’s how we got from daydream to departure gate on my trip to Bangkok and Siem Reap.

Travel Planning

1. Picking a Destination

When Ian and I arrived in Thailand in late September, we sat down to plot out our visa extensions (necessary every sixty days after entering the country) and visa runs (necessary every thirty days after that) and noticed we’d have to leave the country in late December. Rather than go on a quick but boring bounce to the Burma border and back to activate the second entries in our visa right before Christmas, we decided to go on a holiday getaway.

First step? Picking a destination! The parameters: We had to leave the country to restart our visas, so it had to be an international trip. We had just a few days, so it had to be a neighboring country in Southeast Asia. And while I knew I was willing to splurge a bit for the holidays, I also wanted to take advantage of the great value that can be found traveling in this region. Using the go-anywhere feature on we discussed several ideas, including a weekend away in Penang (accessible via direct flights from Koh Samui!) or a short hop to Singapore (an easy flight from Surat Thani).

Kayak Explore

Right as our musings started to get serious, I was approached by a resort in Siem Reap generously asking if I’d like to come be their guest and learn more about their wellness programs. I quickly realized they were the perfect fit for Meihoukai in Wanderland, and started daydreaming about mornings at Angkor Wat followed by afternoons on the yoga mat. The timing was perfect. We set our sights on Cambodia.

Cambodia Travel

2. Booking Flights

Our next step was to book our flights. The good news? We found flights from Koh Samui to Siem Reap that had just one stopover and coordinated with the ferry times to and from Koh Tao. The bad news was, those flights arrived late at night and left early in the morning — and were over $1,000 for the two of us. Say what?! That wasn’t going to fly. (Get it?)

So we started to get creative. Expanding our search to Bangkok revealed that we could nab flights for just $220 each round-trip on one of Asia’s low cost carriers, Air Asia. Even better, we’d be able to arrive early and leave late from Siem Reap. Next, we had to get ourselves to and from Bangkok.

Kayak Travel Tools

To get from Koh Tao to Bangkok, we decided to take an overnight ferry ($15 each) to an early morning Nok Air flight from Chumphon to Bangkok ($33 each)! There was a tight connection, so we booked a private cab ($15 each) to take us the hour from the ferry port to the airport. On the way back, we decided to suck it up and take the Lomprayah overnight bus from Bangkok to Chumphon, the morning ferry to Koh Tao ($27 each). So while the travel was more arduous, we totalled $310 each, or $620 for both of us to travel round trip to Siem Reap through Bangkok. A far cry from the nearly $1,100 we would have spent traveling via Koh Samui. Now, $480 is more than my monthly rent, so that’s a pretty significant savings!

Thailand Travel Tip: If you’re staying in or traveling through the Gulf of Thailand long term, grab a Lomprayah loyalty card. Just take 200 baht (about $6) and two passport photos to any office to apply. You’ll save 150 baht (about $4) on each ferry or bus journey — the cost of a lovely lunch in Koh Tao!

Booking Flights

3. Creating an Itinerary

Because this is a very short trip, creating an itinerary was simple and went hand in hand with Step 2. However, based on our flights we did decide to expand our trip from one city to two.

Clearly, two nights of overnight travel to spend three nights at your destination is not ideal. But we had an easy solution: adding two nights in Bangkok to make the trip worthwhile. So our final plan became: two nights in Bangkok, three nights in Siem Reap, and two nights of overnight travel. Considering how obsessed we are with Bangkok, it was far from a sacrifice. After all, Bangkok was just named one of KAYAK’s !

I can see why — I’ve been a million times and yet I still love a few days in Bangkok to go see all the movies, go eat all the food, and go do all the shopping. I’m even going to fit in a bit of medical tourism, but more on that in a future post!

Bangkok Travel

4. Booking Accommodation

Next up, booking accommodation. Our accommodation in Siem Reap was sorted from the start. We’ll be staying at the , where we’ll laze around in one of the three onsite pools, indulge on the nutritional wellness menu, take in a few of the onsite yoga classes and spa treatments, and take advantage of our complimentary tuk tuk and driver (one comes with every room!) to explore around town. I can’t wait.

Navutu Dreams

But for Bangkok, we had a big decision to make. We tossed around several different Bangkok hotels on our wish list, but ultimately landed on , an offbeat eco-hotel tucked down the Chao Phraya. We thought it would be the perfect compliment to our lush and laid back digs in Siem Reap, and have long been itching for an excuse to stay here. We snagged a deal at $100 per night.

Bangkok Tree House

5. And beyond…

Finally, all the fun stuff that comes after the big stuff is booked and sorted — finding restaurants, picking tours, and filling up days with adventures.

Because I’ve been to both these destinations before (Siem Reap twice and Bangkok about a billion times), my research was a little less exhaustive than usual. For Bangkok, it mostly consisted of looking into transportation options since we’d be staying slightly out of the city center, and combing Tripadvisor and travel blogs for restaurant recommendations. You guys often ask how I find the restaurants and cafes I stumble upon and here’s one kind of loopy example: Originally, I’d been super keen on attending the in Pattaya. Due to time and money constraints (basically, we went on this trip instead) it didn’t work out, but I spent so long drooling over the list of food vendors at the festival that I realized most are pop up versions of hip Bangkok restaurants — so we decided if we couldn’t go to the festival, we could at least go to those.

Bangkok Travel

Hence, our two day plan for Bangkok is built around a morning brunch at  on our first day and dinner at lively  on our second, followed by drinks at Bad Motel and a movie at Siam Paragon. In between, we’ll hang around Bangkok Tree House, go on their evening firefly tour and take advantage of their complimentary bikes.

The next morning, we’ll fly to Siem Reap. For my Siem Reap travel planning, I really only turned to three sources — my own memory, the website, and . The former is the travel blog of acclaimed travel writers Lara Dunston and Terence Carter, who live in Siem Reap and are absolute experts on the area.

Grantourismo

In fact, I so trust their opinions that we decided to enlist Lara to take us on a  bespoke itinerary while we are in town. Our four day plan in Siem Reap consists of the requisite tour of Angkor Wat, yoga classes and spa treatments at Navutu Dreams, meals inspired by posts on Grantourismo, and an evening with Lara that will include a cocktail making class as well as a cocktail crawl through the city’s most unique and inspiring bars. And yes, hour-by-hour itineraries for all six days have been drafted.

Siem Reap Travel

No two trips are ever alike, and thus, the planning for each is an entirely new process. I hoped you enjoyed this behind-the-scenes peek at how this one came together! To see this plan in action, follow along right now on and . And let me know if you have any last minute suggestions in the comments!

Did you plan a trip for the holidays? Tell me all about your planning process below!

Still planning a holiday getaway of your own? Check out KAYAK’s tool, and then let’s brainstorm in the comments! 

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46 Comments...
  • Bryan
    December 17 2015

    No trip for our holidays. We wanted to spend our son’s first Christmas at home. I enjoyed the post though. Perfect timing for use in planning 2016 travels. Thanks for the inspiration!
    Bryan recently posted..

    • Meihoukai
      December 23 2015

      I can imagine that would add an extra layer of fun to the holidays, Bryan! Have an awesome Christmas!

  • Amanda | Chasing My Sunshine
    December 17 2015

    I LOVE reading about your travel planning. Totally nerding out over all of these posts. I’m headed to Toronto at the end of this week, but I’ve done absolutely no planning, aside from booking an AirBnB. I actually miss it!
    Amanda | Chasing My Sunshine recently posted..

    • Meihoukai
      December 23 2015

      I know — one of my fave things about my new suuuuuuuper slowed down travel itinerary is having time to plan the minutiae of each and every trip! I so enjoy it!

  • Kereta Sewa Shah Alam
    December 17 2015

    just discover your site from somewhere. great sharing your story & experiences. i will recommend this site to my friends out there.

    • Meihoukai
      December 23 2015

      Thanks for reading and sharing — happy to have ya here!

  • Kellie
    December 17 2015

    I didn’t know about the loyalty card, that’s a great tip for the next time I visit Thailand again. Thanks for sharing. Also saw a picture on your Instagram of the treehouse hostel in Bangkok, oh my goodness. Too perfect!
    Kellie recently posted..

    • Meihoukai
      December 23 2015

      Pretty darn photogenic, right? We loved it!

  • Craig
    December 17 2015

    Enjoyed this, a good read. Looks like you got some really good deals! I go to Australia in January for a year so that Travelpony link may come in handy 🙂
    Craig recently posted..

    • Meihoukai
      December 23 2015

      Good luck, Craig. It’s a great resource!

  • Dani
    December 17 2015

    My next trip will be on the last week of January, on my birthday! I’ll be roaming around Hanoi for three days. The way I planned it was quite similar to your process but slightly jumbled up. I booked a flight and chose the destination at the same time. I chanced upon a seat sale and got really excited, so I just picked whatever I could afford at the moment. I booked accommodations a week after. I’ll only be getting to the itinerary over the Christmas break. 🙂

    • Meihoukai
      December 23 2015

      That sounds awesome, Dani. Yeah, the steps are often muddled into one big crazy stroke of genius — or chaos 🙂

  • Ashley
    December 18 2015

    Thank you for the Thailand Travel Tip! That will come in particular use in another month so I really appreciate it.

    Also, Grantourismo? I just pulled up their sight and am using their suggestions to fill my “chill” day tomorrow with cafes and restaurants. I better be tired and hungry because I have a lot to fit in one day! Too bad I didn’t stumble across their site myself before arriving in Siem Reap.

    Oh, and enjoy your mini-vacay! The weather had been fantastic the last couple of days.
    Ashley recently posted..

    • Meihoukai
      December 23 2015

      Their site is THE BEST. Glad you came across it just in time!

  • Marie
    December 18 2015

    Thanks for sharing about the loyalty card. I didn’t have any idea about it until now. Great post!
    Marie recently posted..

    • Meihoukai
      December 23 2015

      It’s a great little insider secret for traveling in the Gulf of Thailand 🙂

  • Leigh
    December 18 2015

    Looking forward to all the posts from this trip – I’ll be there at the end of March and still haven’t decided between the bus or a flight from Bangkok to Siem Reap. The spa and resort in Siem Reap sounds awesome!
    Leigh recently posted..

    • Meihoukai
      December 23 2015

      Oh man… having done both, I’d say take the flight 🙂 It’s not a very fun border crossing, and the flights from DMK are very reasonably priced. Check KAYAK! 😉

  • Noel
    December 18 2015

    Hi Meihoukai! First time poster, and newer reader that spent the last few months reading your blog from the start! I’m actually heading to Thailand on New Year’s Eve as my birthday gift to myself. I started reading your blog as I was planning my trip 🙂 I’ll be in Bangkok for 4 days, then taking the train up to Chiang Mai, and then Koh Tao for my first time diving! Right now I only have the Bangkok hotel booked, 2 days/1 night at Elephant Nature Park, flight from CM to Koh Samui, ferry to Koh Tao, and my booking with Roctopus and Roctopus hotel! I’m so excited, thank you for all your useful tips along the way. Other than that, I think we’ll wing it and hope that we can find accommodations even though it is busy season in Thailand. Can’t wait for what I’m hoping will be the trip of a lifetime!

    • Meihoukai
      December 23 2015

      Hey Noel! Enjoy! Say my blog name at Roctopus for 5% of your courses — and enjoy 🙂

  • Jael
    December 19 2015

    From the sounds of the Lomprayah card, it’s already worth your baht if you’re going to take 2 or more trips (300baht saving vs 200baht application fee)! Would you recommend it to short term travelers who only intend to use the Lomprayah ferry to island hop between Tao, Phangan, Samui and Surat Thani? Not that I’ll be using it, since I’m eyeing for SeaTran ferries that arrive and depart from Bangrak pier in Samui!
    Any plans to do a review of the night boats? I heard it’s a classier facility these days

    • Meihoukai
      December 23 2015

      Going between Samui and Phangan, there is only a 100 baht discount — all other journeys it seems to be 150 baht. I think it’s great for expats and long term travelers but might not be worth the hassle for those just taking a few trips (you do have to bring two passport photos, fill out a form, etc.) As for the night boats, there are a few different ones and they vary in quality. I have a hard time keeping them all straight! It’s hard to write a post on them since their schedules change so often, but maybe I’ll give it a go…

  • amanda
    December 19 2015

    OMG, I’m also at Koh Tao and just find your blog. Your blog is so nice with amazing pictures and som much good information about Thailand:) Really glad I find it and I hope you will continue having a lovely time at Koh Tao:)

    • Meihoukai
      December 23 2015

      So glad you’ve found it helpful, Amanda! That makes me so happy to hear — enjoy Koh Tao!

  • Julia Nix
    December 19 2015

    Penang would have been a wonderful addition to your list. Local food is top notch, heritage shophouses and always a pitstop for backpackers into/from Thailand border by land.

    • Meihoukai
      December 23 2015

      Definitely hoping to get there someday!

  • ‘Lovely to read your thought process lol!
    When I’m travelling solo, I plan by choosing the destination first and everything else after. And the plan can be based on something as simple as “there’s a river” or “there’s an exhibition” that I want to see and off I go! If I’m planning our family holiday, I choose the transport first, as there’s a husband, a tween and myself and then take it from there as to where we’re staying and what we’re doing. With the family, it’s much more planned day to day. Travelling solo, I’ll see.
    When I get there lol!
    [email protected] The British Berliner recently posted..

    • Meihoukai
      December 23 2015

      Ha, I know how you feel! My trips are always more tightly planned when there are other people involved — I’d just prefer to have all the “where to stay, how to get there” conversations beforehand, and not when we’re on the road with our backpacks on.

  • Joella
    December 19 2015

    I find researching and finding flight deals so oddly satisfying! I dont mind spending a bit of time reaearching if I get a good deal. A couple of years ago we did a 3 week trip over Christmas Beijing-Mandalay-Koh Samui-Bangkok-Beijing and on first look the flights were shocking. But after digging around a bit I found some really great deals.I like Kayak but recently I’ve been using Google flights a lot.
    Joella recently posted..

    • Meihoukai
      December 23 2015

      Nice! I agree. It’s a satisfying feeling for sure. Asia has so many great low cost airlines, it’s a hunt but there’s a big payoff!

  • It’s always great to see the method behind other people’s travel planning! I think many people don’t realize that just the planning aspect of a life of perpetual traffic is a lot of work!
    Jenny @ Till the Money Runs Out recently posted..

    • Meihoukai
      December 23 2015

      Indeed. I’ve really enjoyed slowing down so I can savor the planning process again, and not just rush through it in order to stay on the move!

  • Mary B
    December 19 2015

    Planning your itinerary around meals?? Between this and the Martha’s Vineyard restaurant round up, I’m starting to think you’re becoming a foodie! Does your picky eater post need an update? 😉
    Mary B recently posted..

    • Meihoukai
      December 23 2015

      Ha, it definitely does need an update! I’ve definitely become a slightly more adventurous eater but the emphasis is still on slightly… still no seafood and very sensitive to spice which is enough to make most of my dining companions roll their eyes. That said, I love design and I love atmosphere and I love creativity so it’s a fun challenge to find restaurants that have all three — but still have something on the menu I can order!

  • Kristin @ Camels & Chocolate
    December 20 2015

    This looks like a dream trip! As you know, I’m also an obsessive planner and plot many of my future trips based on deals I find on Kayak. Favorite trip planning tool by far!
    Kristin @ Camels & Chocolate recently posted..

    • Meihoukai
      December 23 2015

      I love getting to benefit from that beautiful planning impulse — your emails this summer set my heart aflutter with their minute by minute itineraries 🙂

  • Ahmed Gusto
    December 21 2015

    I can’t agree more that Bangkok is a city of food, yummy food and shopping. one can’t get bored there in bangkok, the hotels, food and even shopping is cheap. looking forward to your article about medical tourism. BTW, my fav hospital is Bumrungrad International Hospital
    Ahmed Gusto recently posted..

    • Meihoukai
      December 26 2015

      Love that hospital too! Have been there many times and had pretty great experiences.

  • Ian Hammond
    December 23 2015

    Thanks for the info. I land in phuket late jan’16. for a long slow cycle tour around S.E. asia. I haven’t been there before so lots to learn.

    • Meihoukai
      December 26 2015

      That sounds like quite the first trip 🙂 Enjoy, Ian!

  • Britt
    December 24 2015

    What a smart way to save money on flights! I actually love the satisfaction of taking something like a $1000 flight and finding the cheapest way possible to do it. It’s a great feeling- I feel like a genius! Especially when it meant a stopover in Bangkok for you, I just want to go back to Chinatown and eat all of that streetfood!

    For me personally, I try not to do too much research on specific sites and places in a city or town because I don’t want to ruin it for myself, and also because I’m a notorious planner and not doing proper destination research is my way of trying to break that a little bit.
    Britt recently posted..

    • Meihoukai
      December 26 2015

      Yeah, I can definitely occasionally over-research a trip. I haven’t done it in a while as I’ve been traveling too frequently to be able to enjoy the pre-planning process, but it’s definitely a risk again now that I’ve got so much time between getaways!

  • Ashby Night
    December 26 2015

    Great post! When I go to Thailand I will have to check out the Tree House hotel, it looks super comfortable and beautiful.

    • Meihoukai
      December 26 2015

      It’s a very funky experience 🙂 Not for everyone, but we loved it — I’ll be writing a post on it soon!

  • Jenn Flo Taylor
    December 28 2015

    Wonderful post- looking forward to hearing your thoughts on the Treehouse hotel in Bangkok. It’s been top of my list of places to stay for some time. I’m headed there in April so am keen to hear others experiences. I’ll stay tuned! Thanks!
    Jenn Flo Taylor recently posted..

    • Meihoukai
      January 2 2016

      I’ve been dying to go for ages as well. A few quick tips until I get to the full post — if you want relaxation go during the week, if you want lively go on the weekends when the place is packed with Bangkok locals escaping the city and bikers just passing through for a drink and to gawk. Bring a bottle of wine and watch at least one sunrise and one sunset! And unfortunately, I have to recommend bringing some snacks as we were very disappointed with the food. But overall, I loved it and I’d go again.