Table of Contents

This trip was a challenge to plan, in part because it’s longer than usual. But since we’re literally going halfway around the world — and hey, we went around the world getting there and back! — we wanted to make the most of our time while we were there. We also want to cut down on individual flight times by making a stopover on the way there and back. (We did this when we went to Australia and New Zealand and it worked well for us.)

I thought about combining Thailand with a guided tour of Vietnam and Cambodia, then decided the only thing I was really interested in was Angkor Wat, so I considered doing just that as a tour from Bangkok. But Thai visas require you to get permission to leave and return which sounded like a hassle. So we nixed that. 

We hit more laid back Chiang Mai first, then Bangkok, then with cultural interests satisfied, focused on nature and beaches for the remainder of our time in Thailand. Then we ramped up again with Singapore and Japan. This was our first visit to Asia.

Food & Beverage $18 per day*

Average per person per day. Generally breakfast and one other meal per day. Thailand and Singapore were cheapest.

Lodging $20-101 per night*

In Thailand. Chiang Mai set a new low record; Phuket was highest. Istanbul, Singapore, and Tokyo were higher.

Transportation $628 per person*

Transportation includes flights (to Chiang Mai and Singapore) and ferries plus local tourist passes in Singapore and Tokyo.

Entertainment $402 per person*

Includes three day trips, entrance fees and tickets, and tourist taxes.

* Costs in US dollars at time of trip

Days 1-3: Istanbul

The Plan: I’ve always been interested in Istanbul yet it just isn’t near anywhere else I’d like to visit. So when I saw that Turkish Airlines had nonstop flights to Bangkok I thought “Aha! Now is my chance. We can do a stopover here on the way to Thailand! I even remember reading about how we could do it for free!” Well, we could do it for free if our trip met certain conditions (it didn’t). 

With this brief a stay we plan to spend most — if not all — of our time in the Sultanahmet neighborhood, where the major historic sights are. In addition to the sights listed we’ll likely do one or more of Rick Steves’ walks, as a plan to get to the sights and to have a guided wander around the city. I’ve tried to prioritize so that if we run out of time — or energy — we’ll still have seen our top priorities.

The Reality: We ended up with even less time than planned because our flight arrived late afternoon. So we hit our top priorities our first full day. We’d planned to go to the Grand Bazaar the day we left for Thailand but walking a mile each way in the rain was unappealing. 

  • Day 1: Travel day
  • Day 2
    • Topkapi Palace
    • Haghia Sophia
    • Basilica Cistern
    • Blue Mosque
    • Hippodrome
  • Day 3
    • Grand Bazaar
    • Fly to Thailand

Days 4-8: Chiang Mai

The Plan: I wanted to hit Chiang Mai first, since it’s smaller and probably less intense than Bangkok. We need to go by way of Bangkok, however. The current plan is to fly into Bangkok, spend the day there, and then take the night sleeper train to Chiang Mai. It’s cheaper than flying (though flights are pretty cheap) and will be a new experience. 

Then we’ll have four full days to explore Chiang Mai and the surrounding area. Since we will be jet lagged we didn’t want to pack these days too tight. We should be able to fit in some down time around the temples and shopping if we want. 

The Reality: We dropped the sleeper train idea in favor of a better night’s sleep and flew onto Chiang Mai the day we arrived. The temples were easier to see than we imagined. We ended up seeing all of them in a single day and had plenty of down time. 

  • Bangkok
    • Wat Traimit
    • Chinatown
    • Night train to Chiang Mai
  • Day 1
    • Fly to Chiang Mai
    • Walking street
    • Traditional massage
  • Day 2
    • Wat Phra Singh
    • Wat Chedi Luang & Wat Phan Tao
  • Day 3
    • Wandering the old town and more temples
  • Day 4
    • Mae Peng River boat trip
  • Day 5
    • Shopping and relaxing

Days 9-11: Bangkok

The Plan: Now that we’re somewhat recovered from jet lag and have eased into Thailand a bit, we should be ready for Bangkok. We plan to fly there to save a little time. Otherwise it would take an entire day to travel between the two. In Bangkok we’ll focus on temples with a museum or two if we can fit them in. And as usual do some wandering. I expect we’ll stay in Banglamphu for price, proximity to restaurants, and because it’s such a budget travel mecca. 

The Reality: We did manage to get to all the temples except Wat Arun, which we saw from the river. We didn’t make it to any museums, going to Chinatown instead. 

  • Day 1
    • Travel from Chiang Mai
    • Wat Saket (Golden Mount)
    • Thanon Kao San
  • Day 2
    • Wat Phra Kaeo and the Grand Palace
    • Wat Pho (Wat Phra Chetuphon) and Wat Arun
    • Dinner on the river
  • Day 3
    • Chinatown
    • Jim Thompson’s House
    • The National Museum
    • Suan Pakkad Palace Museum

Days 12-16: Koh Tao

The Plan: Island time begins! It will take us a day to travel from Bangkok to Ko Tao. It sounds like a bus/boat combination might work best. Snorkeling will be a priority here. It sounds like there might also be hiking opportunities. And some beach time. We won’t be scuba diving, even though the island is known for that. 

The Reality: The bus/boat combination worked great. We did some snorkeling from the beach and otherwise spent time there, though our bungalow was so close we could sit on its porch. No hiking, no boat tours. Just relaxing. The beach was too nice. 

Days 17-21: Koh Samui

The Plan: It shouldn’t take long to get to Koh Samui from Koh Tao. Koh Samui will be mostly about beach time. We’re spending time here because this is one of the places Elephant Hills picks people up for their tours.

The Reality: Chaweng Beach was even nicer than Sairee Beach so once again we ended up just hanging out at the beach. 

Days 22-23: Khao Sok National Park

The Plan: I’m really excited about the Elephant Hills tour that includes interacting with elephants plus spending the night in a floating tent on the lake. And since they will pick you up and drop you off at certain hotels, this will also act as our transfer from the gulf coast to the Andaman coast. 

The Reality: Elephant Hills was everything I was hoping for. Besides hanging out with elephants and floating on a lake, we got to see all kinds of spectacular scenery. And it made transferring from one coast to another simple. 

Days 24-26: Krabi Town

The Plan: Elephant Hills does transfers from Krabi so the plan is to stop here for a couple of days and tour the east side of Phang Nga bay and check out the area. Krabi is also a good jumping off place to the southern islands.  

The Reality: We ended up going to Koh Phi Phi rather than Phang Nga bay. I still think we would have liked the Hong Island trip better but hey, now we’ve been to Koh Phi Phi and don’t have to go back. Krabi Town was not that interesting in itself. Ao Nang would be another good base if you want to be by the beach. 

Days 27-31: Koh Lanta

The Plan: Koh Lanta sounds like it has enough going on that we won’t get bored yet is not a frenetic party island.  

The Reality: That pretty much described it. we did a snorkel day trip and otherwise played on the beach and relaxed. 

Days 32-36: Koh Lipe

The Plan: Sounds similar to Koh Lanta but more of a party island?  And proximity to some beautiful islands further south, for day trips if we want. 

The Reality: We enjoyed snorkeling from the beach in front of our hotel so much we didn’t bother with a day trip. There might have been parties. We didn’t run into them or care to. The sand was fine and white. 

Days 37-39: Phuket

The Plan: Phuket is another starting point for tours of Phang Nga bay. We will likely stay in Phuket Town and travel to the beach if and when we want to. We can also fly to Singapore from here without backtracking, which is why Phuket is at the end of our time in Thailand. 

The Reality: By the time we got here we didn’t really need more time at the beach. We spent a day wandering the old town and doing some shopping and our last day on a Phang Nga bay tour to James Bond Island (and other islands). 

Days 40-43: Singapore

The Plan: I’ve been curious about Singapore for a while and since it’s relatively close to Thailand I thought we’d include it on this trip. The manmade “trees” are one of the must-sees for me here but it sounds like there is plenty to see otherwise, as you can probably tell from our itinerary! I’m looking forward to the blend of British colonial, Chinese, and Indian cultures.

The Reality: The Supertrees were every bit as cool as I’d hoped. So was the mix of modern and traditional architecture. The vertical use of greenery was especially interesting. We did most of what we’d planned, though not always on the day we’d planned. We could easily have filled another day.

  • Day 1
    • Colonial District 
    • Temples (Sri Mariamman, Buddha Tooth Relic, Thian Hock Keng)
    • Bukit Pasoh Road
    • Pinnacle@Duxton
    • Night Safari
  • Day 2
    • Emerald Hill bars
    • Gardens by the Bay 
  • Day 3
    • Jungle Breakfast
    • Sri Veeramakaliamman temple
    • Tekka Market and shopping
    • Botanic Gardens
    • Singapore River evening cruise

Days 44-47: Tokyo

The Plan: I was looking for a stopover between Singapore and home and arrived at Tokyo by researching nonstop flights from Singapore and nonstop flights from Detroit. The two likely options were Seoul and Tokyo and of the two Tokyo sounded more interesting. (I looked at middle eastern options first but Dubai seemed the best of those options and we both thought it sounded like Vegas in the middle east which did not appeal.)

Japan isn’t a priority for us but this seems like a good way to at least sample Japan. Who knows, we may like it. I consulted different guidebooks to see what they recommended and came up with this itinerary, which sounds like the mix of historical and modern frenzy that I’m looking for. I lean toward staying in Shinjuku since there’s a particular hotel that is recommended by multiple sources. Hotels are pricy, as expected, but not impossible. 

The Reality: We liked Japan a lot and I think we got the mix I was trying for. We did end up staying in Shinjuku and it worked well. Tokyo is so big that nowhere is really central. Shinjuku had good transport connections. We roughly followed our planned itinerary for each day but mixed up the days to accommodate scheduling we weren’t aware of, like Elvis impersonators. 

  • Day 1
    • Sensō-ji temple
    • Asakusa-jinja shrine
    • Ueno-kōen, Tokyo National Museum, temples and shrines
    • Ameya-yokochō market
    • Tokyu Hands
    • Sensō-ji lit up
    • Craft beer at Ryōgoku
  • Day 2
    • Meiji-jingū
    • Omote-sandō
    • Shibuya Crossing and Shibuya Center-gai
    • Yanaka neighbourhood 
  • Day 3
    • Tokyo Metropolitan Government Building observatories
    • Tsukiji Market
    • Hama-rikyū Onshi-teien gardens
    • Shinjuku, Golden Gai
    • stroll around Ginza
    • Tokyo Bay?
    • Akihabara?