Recently I saw a post on /r/solotravel on reddit asking, “How important is an itinerary?”
The top-rated comment when I last looked was something along the lines of “whatever works best for you”, and I agree with this sentiment.
TikTok is going away tomorrow. One of the main reasons I had TikTok as part of my regular rotation is that the algorithm was better than other platforms at recommending videos I was interested in. It still wasn’t great, mind you, just better than others. And at one point it siezed on the fact that I had watched a bunch of Japan videos last year before my trip there. 99% of them have the same tips (“5 things you must do when landing in Japan!”) but every now and then someone will post their absolutely bonkers Japan itinerary. Seriously: it’s planned down to the hour, with no room for problems or improvisation. So, for me, this is much too structured. I won’t even mention the 40,000+ steps a day!
At the other end of the spectrum there’s my 2019 trip to Switzerland. Before arriving I booked two nights at an Ibis in Carouge (in the Geneva metro area) near my friend Joshua. That’s it. The only event officially scheduled was my flight back home nine days later. I ended up venturing over to Chamonix and Interlaken for multiple days each, then spending the rest of the time in Geneva, all on Joshua’s recommendation. Both Chamonix and Interlaken were wonderful surprises, and this spontaneity worked out well. However, I spent multiple hours, multiple times, sitting in a bar or cafe searching up where I would go the next day, how I would get there, what hotel I would stay at, what the reviews for that looked like, second-guessing myself, and low-key stressing myself out, with the clock ticking.
Based on learnings from that trip, I decided I needed to arrive somewhere with at least a skeleton itinerary of where I would go and where I would stay, in two day chunks. And say what you will about AI and Large Language Models and ChatGPT, it turns out ChatGPT is really helpful for travel planning. For last year’s trip to northern Switzerland, I used a prompt similar to:
I’m traveling to Switzerland. I’m planning to be there 11 nights. Aim to stay in each town for two nights. The trip will start in Zurich and I want to travel down the train route toward Zermatt. After two nights in Zermatt, propose a town somewhere along the train route between Zermatt and Zurich airport. I prefer mountain towns and don’t want to stay in large cities like Zurich or Geneva. I have stayed in Interlaken before, so you can leave that off. Format the output in a table, with some key activities for each day.
Out of that I ended up with a rough itinerary of places to stay and things to see:
| Day | Location | Key Activities |
|---|---|---|
| 1 | Zurich | - Arrive in Zurich and explore Old Town (Altstadt) |
| - Visit the Swiss National Museum or take a boat ride on Lake Zurich | ||
| 2 | Zurich | - Day trip to Uetliberg Mountain for panoramic views and hiking |
| - Stroll through Bahnhofstrasse, one of the world’s most exclusive shopping streets | ||
| 3 | Lucerne | - Travel to Lucerne and visit the Chapel Bridge and Old Town |
| - Explore the Lion Monument and Glacier Garden | ||
| 4 | Lucerne | - Take a day trip to Mount Pilatus or Mount Titlis for breathtaking views and activities |
| - Enjoy a lake cruise on Lake Lucerne | ||
| 5 | Andermatt | - Travel to Andermatt, a charming mountain town |
| - Explore the Gemsstock area for hiking or scenic views | ||
| 6 | Andermatt | - Ride the Glacier Express panoramic train to nearby scenic spots |
| - Visit the Teufelsbrücke (Devil’s Bridge) and Schöllenen Gorge | ||
| 7 | Zermatt | - Travel to Zermatt, home of the Matterhorn |
| - Stroll through Zermatt village and visit the Matterhorn Museum | ||
| 8 | Zermatt | - Take the Gornergrat Railway for stunning views of the Matterhorn |
| - Enjoy hiking trails like the Five Lakes Walk | ||
| 9 | Kandersteg | - Travel to Kandersteg, a picturesque mountain village |
| - Visit the stunning Oeschinensee (Oeschinen Lake) via gondola | ||
| 10 | Kandersteg | - Explore hiking trails or take a cable car to Sunnbüel for alpine scenery |
| - Relax in the peaceful village atmosphere | ||
| 11 | Zurich Airport Area | - Travel back toward Zurich airport and stay in a nearby town like Rümlang or Kloten |
| - Prepare for your departure and enjoy a leisurely evening |
From this start, I’d continue the conversation to refine the itinerary. For example, I can tell ChatGPT that I don’t want to spend more than 3 hours in a single day on a train, and that I’ve already visited Lucerne so it should propose another stop. After some back and forth with ChatGPT, I end up with a loose itinerary, with enough time at each place so I don’t feel as though I’m always packing and moving.
The next step is to go to booking.com and search up places to stay. I read reviews, look at the map to see how far the hotel is from the train station, see if it’s in the city center or on the outskirts, see if there are restaurants around, etc. Knock on wood, I’ve had positive experiences with booking.com1, but I still take the opportunity to book directly with the hotel when possible based on a bad experience with Expedia many years ago. (Fool me once…) Key in this is to avoid non-refundable reservations. Yes, you will almost always pay more to get reservations that can be canceled without penalty, but it’s the only way to get the flexibility I’m looking for. With only a few exceptions2, I try to book the choice where I can cancel up to the night before. I’m not aiming to have all of my lodging booked before arriving, but I at least want to have the first few nights locked in so that I have a destination after long flights and little sleep.
With some actual lodging booked and ideas about where to stay the other nights, I can now pay attention to smaller details. In Switzerland, that means pricing out train trips between the proposed towns and seeing if the math on a Swiss Half Fare Card makes sense3. In Japan, that means Google Streetviewing the walk from my Asakusa subway station to my hotel. You get the idea; now we’re in to the fun part of the planning.
Once on the ground, as the trip progresses, there’s plenty of slack to adapt to changing interests or conditions. On my Japan trip, I swapped Kamakura for Osaka. On my last Switzerland trip, I opted for an overnight in Thun instead of another night in Zurich. Zero regrets about either choice.
The next solo trip I plan I’ll try to do it in the open here on the blog, and then go back and compare after the trip is done. Now… where to go?
Footnotes