In this post, I’ll share what went into planning and executing a 17-day, four city trip with my 80-year-old mother and several relatives who joined us along the way in Tokyo, Bangkok, Koh Samui and Hong Kong.
Organizing a trip like this takes a tremendous amount of planning, but with AI, some of it can be automated or at least provide some assistance. I’ll share things that worked well and things that we should have done different.
Background
In the fall of 2024, my father suffered a stroke while on an Alaskan Cruise. He subsequently passed away late last year. He had been sick for more than six years which meant that my mother wasn’t able to leave his side in Vancouver, Canada.
When you lose a loved one, especially a parent, it becomes apparent how short our time on earth really is. For a long time now, I had been wanting mom to experience the life I have in Asia, a life that she helped build through her personal sacrifice.
I wanted her to stay in the same hotels I stay in, eat in the same “hole in the wall” and 3-Star Michelin restaurants I eat in and to see the same glorious waterfront sunrises and sunsets that I love so much.
More importantly, I wanted mom to meet my fur babies, my two rescue dogs living in Hong Kong. She had visited me in Beijing more than 10 years ago but never had the chance to come to Hong Kong where the dogs are.
For anyone that has dogs, you know how big a part of life they are. I really wanted to share that part of my life with her and for them to feel the warmth from my mom too. I knew Arya especially would immediately attach to my mom.
The Plan
The plan was to convince mom to take a trip to at least two cities, Tokyo and Hong Kong. Tokyo to visit her grandson who has lived there for more than five years and to Hong Kong to meet my dogs and see one of the cities I call home.
As the plan evolved, I thought about other cities I wanted her to see since she was already going a long distance. I didn’t want her to come all the way to Asia to only spend one week. I also didn’t want to make each stop too long because it would be hard to find things to keep her entertained.
Therefore, I decided to make it a Friday night to Sunday trip that stretches out for 16 days. I targeted each city to be four nights so that it provides a good taste of the city, but not so much that we’re sitting idle and not sure what to do next.
Family Members
The hardest part in planning a trip like this was to find the right balance between appeasing family members while also keeping the planning momentum going. The main reason that these trips don’t get carried out is because it gets exhausting trying to incorporate everyone’s requirements.
To overcome this, I suggest you need to set a cutoff point and have conviction to enforce it. Set some redlines and then enforce them. For this trip, I took input and then set the cities and timeline and didn’t let anyone modify them after that point. I can assure you my conviction was tested and retested as people requested and sometimes demanded changes.
Mobility & Transportation
Being a “young” 49-year-old myself, I didn’t realize how much mobility gets impacted by age. mom struggled to get into vans (my typical vehicle of choice when being a tourist) and would have preferred normal cars. Places like Japan are best seen via the subway, but this includes a lot of walking; mom would start to get tired beyond 12,000 steps a day.
If you’re planning to take family members on a trip, it will pay great dividends to think through the transportation at each location. The most fun we had in a car was in Koh Samui; we booked a “tourist van” which was like a nightclub in a large van. The interior was well designed with easy access stairs for mom.
The tourist van also had another feature that made the travelling time super fun; we could all fit inside and not have to split across two cars. In places where travel time can be long, this adds high quality time together to the agenda where otherwise it would be boring, downtime.
For the times where it made sense to take transit, we realized often at the worst possible time that people could not get the local transit card to load on their iPhones or Android devices. This was always traced back to them not having a credit card setup on the Wallet apps. I suggest setting up the cards prior to leaving your home country so that there’s a better chance the local transit cards can be setup.
Accommodations
When travelling with a big group, hotels can become very, very expensive. Wherever possible, I tried to book a large suite with multiple rooms. In Bangkok for example, I booked the Kimpton 2-bedroom-suite which was expensive, but cheaper than booking two smaller rooms. The bonus being that we got to spend more time together and had a much bigger overall space.
Another great option would be to choose an Airbnb. For this trip, I didn’t go that route because I wanted mom to experience some of my favourite hotels and the service they provide. However, in a future trip, I’d look at Airbnb to save money and provide a lot more space for the money.
Another tip is to reach out to the hotel to let them know you plan to book multiple rooms; they may be able to offer a better rate, upgraded rooms for free, or at least putting the set of rooms together on one floor for easy access to each other. In Bangkok, The Kimpton Maa-Lai did this for us and we loved being close to each other’s rooms.
Food
This was by far the most contentious and difficult part of the trip to manage. At one point, I had to make a tough call and make tough decisions that made some members of the family unhappy. Everybody has their likes and dislikes and some also have medical allergies or other limitations on what they can eat.
We had one person that cannot eat anything spicy, we had another that asks for everything to be super spicy or “Thai spicy”, a few people that won’t eat anything raw, another that loves raw food, one vegetarian, and another that doesn’t like paying for anything green. The most challenging however was a person that only wanted to eat western food while in Asia.
For the first half of the trip, I tried my best to accommodate everyone, but to achieve that meant we were eating in Italian restaurants or food courts. We would go from restaurant to restaurant and at each stop, people would find reasons why we can’t eat there. We wasted a lot of time and energy.
This was not the experience I wanted for mom so half-way through the trip, I made the decision that I would choose 2-3 restaurants that I knew were good and take a vote. The restaurant with the highest votes is where we went, and people had to figure out a way to select food they could eat. This meant that sometimes, 1-2 individuals ate bread.
This turned out to be an excellent approach. It provided some level of input from the group, while stopping all the time-wasting and aggravating indecision. I was able to show mom the restaurants I really wanted her to experience while appeasing the majority of the group. Freed from having to make their own decisions, people seemed happier with this process and focused on enjoying each other’s company.
Time
Four nights per city turned out to be ideal. I think we could have stretched it to five, but with four, it felt like everyone left the city hungry to come back, which I think is a good way to leave a city. The last thing I wanted was someone to find a city we visited to be boring.
Time with mom is precious at 80-years-old and everyone wanted to spend time with her. Since this trip was something I wanted to do for her, I wanted to spend some quality 1:1 time with her. With so many family members joining different parts of the trip, there were times that I had to be firm that I wanted to spend a few hours with mom alone.
Family members respected this and gave me that time. I had debated whether to say anything because the last thing I want is to restrict anyone from spending time with mom. I’m glad I said something because some resentment would have built up at organizing everything only to have no alone time with mom.
Speaking of time, I realized that it’s important to give some “free time” to people for them to do as they please. It’s also important to try and fill the other time with activities back-to-back to keep the momentum going. Wherever possible, I tried to allocate the more exciting things towards the end of the day to ensure each day ends on a high note.
Before going to bed at night, I would send a message to the group chat with the next day’s itinerary. It would follow this template format:
Itinerary Wednesday March 26th
- 08:30AM Breakfast together at hotel
- 11:30AM Go to Emsphere for shopping
- 12:30PM Food court light lunch
- 03:30PM Return to hotel
- 05:00PM Depart hotel for TukTuk night tour
- 05:45PM Meet guide at BTS Krug Thonburi Station
- 08:45PM Return to hotel
- 09:00PM Dinner at Kimpton
- 11:00PM+ Kids go to rooftop bar
By having a set itinerary each day, it allowed people to plan the next day accordingly. It also prevented anyone from having an excuse as to why they are late. The itinerary is there for all to see so if someone doesn’t show up when they should, they will miss out.
Special Moments
A multi-city trip like this is often hard to remember. Things go by so quickly that places start to blur together. To make sure that each city is memorable in its own way, I would suggest planning a special moment in each city.
For Tokyo, we took mom to see the dazzling neon lights of Shinjuku and took lots of pictures with her there. She loves parks so we took her to the Meiji Shrine. In Bangkok, mom loves tuktuks so we arranged a night tour in a specially designed tukuk.
In Koh Samui, I arranged a beachfront sunset dinner exclusive to my family. It was certainly one of the highlights of the trip and something she’ll never forget. In Hong Kong, it was all about the dogs and for mom to experience a Michel-Star Indian restaurant at New Punjab Club.
By having these special moments lined up, we ensured that mom and the family have something memorable in each city that they can recall long into the future. An unplanned special moment occurred which I’ll go into more detail in the next topic.
Unexpected Moments
After my father suffered a stroke on an Alaskan Cruise, we learned the importance of medical insurance. We had purchased full insurance for mom and I made sure that everyone coming for the trip was fully insured. Thankfully, we didn’t have to use any insurance this time, but we did have a mighty scare!
As mentioned above, I had planned a tuktuk ride for mom as her most memorable moment in Bangkok, however something much bigger was to happen that she’ll never forget. While mom and I were getting laser facials at The Signature Clinic, the beds started to shake violently.
At first we thought it was the staff moving our beds (our eyes were covered due to the laser), but it became apparent something much more troubling was happening. We experienced the first major earthquake in Bangkok in more than 100 years!
While the experience my mom and I had was not too unsettling, we even took the elevator down from the 10th floor of the clinic because we saw no damage, the experience for my family at the hotel was rather startling. They had to run down the fire staircase while the concrete walls were crumbling and concrete dust was filling the air. They thought they were going to die.
Sadly, several dozen people did die in the earthquake when a half-built building collapsed on the construction workers inside.
I want to highlight how incredible Thai people were during this whole episode. We were evacuated and had to stay in open areas outdoors because there were aftershocks. Random Thai strangers would come up to my mom and provide her with water, snacks and several even took pieces of cardboard and used them as fans to cool her down from the 38.5C temperatures.
The warmth and kindness of the Kimpton Maa-Lai staff was exceptional during this moment of crisis. They put us foreigners ahead of themselves in ensuring care and comfort. I don’t wish an earthquake on anyone, but if I’m ever to experience one again, I want it to be in Bangkok, a city that rose to the challenge.
Luggage & Accessories
With so many airports to travel through and all the walking involved, it paid big rewards to ensure everyone had high quality luggage. I noticed that mom had bad luggage on the Alaska cruise. The wheels were placed too close together and the luggage would topple over at the slightest movement. I made sure she got new luggage with good wheels for the Asia trip.
My preference is Rimowa, but I appreciate it’s expensive. The reality is any modern luggage from Samsonite or other well-known brands will be sufficient. The key is to ensure the luggage is trolly style with four wheels and that the wheels operate smoothly. Something with a coded lock is always better than keys and something without zippers is a big plus.
For other accessories, I found myself lending out my battery pack several times a day, so that’s another good one to have. I also brought an assortment of USB cables which came in handy throughout the trip as people realized they didn’t bring the right cable for their phones or mobile devices.
Finally, ensuring everyone has an eSIM or a local SIM card made things much easier upon arrival. There are moments where there’s no airport WiFi or it’s not working properly, so having the local data capability before landing helped in several situations.
These are all small things, but with a large group, they become major time savers.
Photos
Perhaps the second most important part of the trip after experiencing it was to take lots and lots of photos. I was the most annoying person during the trip because I always had a camera pointed at people, however after the trip, they’re appreciative of all the memories they now have.
To solidify the memories, I’m in the process of producing a photobook of the trip using the excellent Fundy Designer Suite. Once produced in Fundy, the photobook can be easily sent as a PDF and my preferred format, in a magazine print version. There’s nothing that can beat the tactile feeling of holding your own memories in your hands.
A photobook in a magazine style with heavyweight photo paper in China costs only US$20 per copy. It makes for a great memory for all the travellers.
Special Thank You
Throughout the trip, I was a bit worried how mom would be treated. We were staying in some chic hotels designed for a slightly younger crowd. I was worried they may make mom feel out of place. Nothing could have been further from the truth. At every chic hotel, they went above and beyond to not only make mom feel comfortable, but they treated mom like she was their mom.
I was teary eyed several times throughout the trip seeing how they made her feel at home. I want to give a special thank you to the team at Kimpton Maa-Lai in Bangkok, The Library in Koh Samui and New Punjab Club and The Henry Steakhouse in Hong Kong. Each of these teams went well beyond any expectation to make this an incredibly memorable trip for all of us, and especially mom.
Speaking of thank you, I encourage you to write emails to the senior management at any establishment that goes beyond expectations. I sent notes to each of the above establishments and the replies again brought tears to my eyes. In one case, the team took a picture together and thanked mom for visiting and welcomed her to come back again.
Great service should be acknowledged and great people should be recognized.
Conclusion
After 17-days of fun, I handed mom and my aunt over to the Air Canada staff at Hong Kong International Airport. I was relieved to have handed them over safe and sound, but I felt sadness that I hadn’t arranged a trip like this before. We had an incredible time and we now have so many funny stories to tell of the expereinces we made together.
Our earthquake experience dwarfed it all, but the special moments we had in each city will live on forever in our memories and our hearts. I appreciate it’s tough to arrange a trip with many participants, but I recommend that you push through the anxiety and challenges and find a way to make it happen.
Trust that things will work out in the end and just go for it. It’ll be worth the hassle! I hope that you’ve enjoyed this post of what it took to arrange this epic trip with mom. Let me know in the comments below if you’ve arranged a trip like this before.
What lessons did you learn from your family trips? What could I have done differently to make this trip even better? We’re already planning another trip with mom to Africa in January 2026 so your insight would be greatly appreciated 🙂
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What a beautiful family trip and a helpful guide for the rest of us! The pictures are terrific as usual. It’s also fun to see a more personal side—thanks for sharing. I especially liked your point about staying longer in fewer places; that’s such a good strategy for multigenerational travel. I took my mom on a Tauck Danube cruise last May and had a great time. You really never know how long you have…sniff.
It’s inspiring to see you get such great results from the Fuji gear—I’m tempted every time I see your photos. My own setup is in flux: I picked up a Leica D-Lux 8 instead of waiting for the X100VI, but haven’t taken it on a trip yet. It’s so compact! I’m even considering selling my A7R5 for the A1II—60MP is overkill for me, and I need something better for faster subjects.
Good luck in Africa—can’t wait to see what you come back with!
The new comments login caught me off guard! – John
Fantastic write-up, and fun to read! Thanks! Some of the issues you encountered sound familiar… (finding a place to eat, for example).
From the images, it seems that you took your GFX100SII, the GF55/1.7 and the GF110/2 plus the X100VI with you, right? I’m asking because we just had the conversation about the 55/1.7 in the other post. How did that work out with these two lenses? Did you bring other lenses with you?
Hi Simon,
This was the trip that I mentioned in our messages. I primarily used the GF55 in the four cities and loved the results. For the Asia trip with mom, I took the GFX100S II, GF32-64, GF50, GF55 and GF110. I only used the GF32-64 a handful of times, typically for the hotel interior shots. The GF55 was on the camera 80% of the time, with the remaining being the GF110. I think I used the GF50 once or twice during the trip.
Given how well the GF55 performed on the Asia trip, I decided to take only two lenses with me to Seoul during the May long weekend, the GF55 and GF110. I’ll be posting those images soon so you can be the judge, but I was very pleased with the results. I think the GF55 and GF110 is a killer combination for travel.
I think I would be perfectly happy on a trip with the X100VI and GFX100S II and GF55 combination. With 102MP and f/1.7, I could easily crop in the GF55 in the same way Fujifilm encourages cropping on the GFX100RF with its 35MM lens. Speaking of the GFX100RF, my partner purchased one and I’ve been playing with it. I need more time to form an opinion, but initial impressions are subdued. I think it needs another iteration before it becomes a must have.
Hope the above helps. Let me know if you need more info or have other questions.
Fantastic, thanks! I think I will try the same combination to Iceland, plus maybe the 20-35 to cover wide angle. Not sure if I should take a longer lens (250?), but that will make the kit even heavier.
Interesting feelings about the GFX100RF. I was also considering it briefly, but in the end decided against it. An interesting concept for which Fuji is to be applauded, but, as you say, maybe the next or the next after iteration….
I’m surprised that you travel with so many primes! I’m contemplating a GFX travel kit of GF 45-100 + GF 20-35 – have you used either?
I mirror many of your thoughts regarding the A7RV. I own an X-H2s and am considering rationalizing all lenses on that system down to a XF16-55mmF2.8 R LM WR II and calling it a day. Modern zooms are closing the gap on the primes; and ultimately it makes more sense to invest spare cash into GFX.
I’m surprised too! Sometimes I just take the GF32-65 and GF55 or GF80 and call it a day. I’ve taken the GF45-100 once or twice on trips and I always come away feeling it’s too heavy to carry all day. However, it’s wickedly sharp and if that’s the focal range you need, it’s hard to beat. For your APSC system, did you see the new Sigma f/1.8 zoom lens coming out? That looks very compelling as a one-and-done travel lens!
Thank you for a great article and story. Having visited all of these places I found it particularly interesting and your photos brought back some good memories.
I noticed you used a X100VI for some of the pictures where I would have expected your M11. I would be interested in hearing about what made you change gear and what your experiences were.
Hi Christoph, you have eagle eyes 🙂 After a long, long wait, I finally got my X100VI.
The reasons I didn’t take the M11 were: 1. I wanted ease of use and having autofocus on the X100VI is a big help; 2. I was already carrying so much camera gear with the GFX100S II, DJI Pocket 2 and DJI Neo that I wanted to save weight wherever I could; and 3. It’s easier to match colours with two Fuji cameras.
I’m in the process of writing a review for the X100VI. To really test it out, I took it on another trip after mom’s Asia visit. I took it to Seoul and loved using it there. It’s such an intimate camera because it’s so small and light, and it has the capability to focus very close. This is great for food pictures when travelling.
More to come in the review, but the X100V was already an amazing camera and I was stupid to sell it prior to the X100VI launch. I thought I was being clever to cash in on the hype at the time. Little did I know that I would be without a small camera for more than 1.5 years! The X100VI takes everything awesome about the X100V and makes it so much better thanks to the updated autofocus and addition of IBIS.
I do feel that I’m not using the M11 enough these days. I’ve recently convinced two of my close friends to go head first into photography. They’ve purchased several film cameras and are burning through cash on rolls and development 🙂 They’ve also been buying vintage lenses (the kind you need a radiation tester before using) and I’m loving the results they’re getting. I plan to pick up some vintage class for the M mount soon.
The least used camera however is not the M11. It’s surprisingly the Sony A7R5. I’ve barely used it since the GFX100S II arrived. I’m considering selling the A7R5, but it’s such a capable camera that I know I’ll need its high speed autofocus one day and will regret having let it go. Perhaps the safari I’m planning for early next year will be the perfect place to use the Sony.
Thank you for that very interesting comment. I am looking forward to your X100VI review.
Amazing story and trip for your mom. You are a GOOD son.
Thanks Henry! Mom and Dad both made a lot of sacrifices to give us a better life. I wish I had realized this earlier, but it’s never too late to start appreciating someone. I hope that we can replicate this fun in a safari in Africa targeted for January 2026.