How I Plan City Trips

In this blog I will share how I plan city trips, arguably my favourite form of travel. The main reason why I love city trips is because there is a clear start and finish. This creates simplicity when planning trips and allows me more time to dig deeper into where I am staying. While I enjoy the occasional road trip and month long backpacking stint across Asia, deep down I love just going to one city at a time. I’m lucky to have been to over 100 cities by this point, so this blog is based on many years of travel experience.

Season

When you want to visit has the biggest impact, and should be one of the primary decisions for you to make. Visiting New York in July will give you a vastly different experience compared to January. I’ve been in both, and you couldn’t pay me to go back in January… unless it’s for moody winter photography. Some cities are better in the winter, some are better in the summer, and some are best visited in the spring or autumn. Figuring out when you want to go will filter a huge number of places out.

Goal

The second decision you need to make is figuring out the purpose of the trip. If it’s for street photography, then I would pick London or Istanbul. If it’s for slow life by the beach travel photography, then anywhere in Andalusia will be great. If it’s for a quiet getaway where photography isn’t a priority, then Ljubljana would be my pick. Once you know the goal of the trip, it becomes much easier to narrow down the location.

Duration

The duration matters a lot, however it can also play tricks on you. Four years ago I spent just over 3 weeks in Istanbul. Last month I went back to that city for 10 days. I would say that on the second trip, I saw more of the place and got better photos than on the first trip. When I was there for 3 weeks, half of those days were spent being lazy in coffee shops. On the most recent trip, it was go, go, go.

There’s a well-known quote which says something along the lines of “a task will take as long as you have”. I know I have ruined it, but the idea is that whether you have 1 week or 3, the task will take that long. Meaning if you only have 1 week, you will get things done. If you know you have 3, you will be operating at 50%.

Typically I find that 1-2 weeks is the sweet spot for most cities. Some places like Tokyo demand slightly more time to fully immerse yourself. Other locations like Cambridge only need 3-5 days at most. While I can’t tell you exactly how much time you need, I would recommend adding 1-2 days on top of what you think you need. In 5 years of travelling full time, only once did I feel I overstayed in one spot, and that was doing a month in Venice.

Research

You’ve picked the city, now it’s time to start researching, and there are three key sources of information. ChatGPT can give you a rough framework, but I wouldn’t 100% rely on everything it says. Blogs are probably the best way to learn about a place, and luckily there are plenty of them online. If you have any sort of social media presence, asking people who follow you for suggestions has always been one of the best ways to plan.

If you don’t have time, of course you can buy a pre-made plan from a tour operator, but I would probably just use ChatGPT at that point. If you have time, blogs and YouTube are the best tools you have, because the information is coming from real people who were physically there.

Hotel

When it comes to picking a hotel, I only really care about 4 things: cleanliness, light, space, and location. I’ve stayed in plenty of dirty, dark, cramped hotels in the middle of nowhere to know that these 4 things are important. Having solid Wi-Fi in the room is nice, but not essential. I also don’t mind heavily used hotels, as long as they are clean.

Location is critical, because it can make or break your trip. I like to be as central as possible, ideally in an area with good connections and one that is walkable. When I stay in Dubai, I only stay in the Marina because you can walk everywhere, it has all the amenities, and you can jump on the metro to take you downtown or even to Deira while avoiding all the traffic. I try my best to avoid apartments, as I generally find hotels safer and more comfortable.

Essentials

Once the hotel is booked, I search for all the essentials in the area. Supermarket, laundrette, coffee shop, workspace, etc. Ideally I would have done this already in the previous step, but now I can search in more detail and read reviews.

Key areas

The next step is to research neighbourhoods and areas. I would first search for which places to avoid. I am not into danger tourism, so I don’t want to find myself in some ghetto or on a drug trafficking street. I would then research different areas and what they offer, just so I can have a rough idea. For example, in London, The City is where you go to see all the historic buildings and a clean old-school finance aesthetic. Down the road in Brick Lane is where you see a grittier side of London. Head over to South Bank for the best summer evening vibe. Once you have mapped out all the key areas, the rest is easy.

Must-see locations

I am not a fan of ticking off locations, however depending on where I am, some spots must be ticked off. For example, in Tokyo, Shibuya Sky is a must in my opinion. With these spots, I suggest less is more. Pick a handful of must-see locations and let the rest come to you as a surprise.

Routes

If the city you are visiting is walkable, and you like getting the steps in, see if you can plot some routes around the city. For example, in Lisbon, I love walking from Alfama to Belém. In London, from Old Street to Piccadilly. In NYC, from Central Park to the Staten Island Ferry.

Day trips

If you happen to have a bit more time, I highly recommend looking up what day trips you can do from the city. Day trips are a fantastic way to change things up and see somewhere totally different without the hassle of travelling to the next spot. From London you can go to Brighton, Seven Sisters, Margate, Cambridge, Deal, and a ton of other amazing spots. From Lisbon you have Cascais, Sintra, or even Nazaré at a push. I love day trips, and I feel they are a critical part of visiting a city.

Bonus tip

This is touristy and cheesy, but it’s also one of the best research tools at your disposal on the first day of your arrival. Jump on one of those open-top buses and do a couple of laps of the city. You will get a high-level overview and can make notes on where to come back to on foot.