Arrive without a plan

Here’s an idea: the next time you go on a trip, don’t make any plans until you arrive.

This might sound counterintuitive, but I believe the longer you delay making plans for a new place, the better your overall experience will be.

To keep it short:

1. Resist the urge to plan before you leave
2. Arrive with curiosity
3. Meet and talk with local experts to figure out things to do

A few notes:

This plan works well for solo or pair travelers. It is difficult to pull off for large groups. If you do give it a go with a large group, I’d love to hear about it.

This mostly applies traveling to cities. If you are trying to visit the Antarctica peninsula many parts likely won’t apply. There are definitely places where you need concrete plans before you arrive.

Lastly, this algorithm works better when you are traveling for at least a week and have at least a few days for each place you want to visit.

Planning at home is suboptimal

The majority of trips people go on are fully organized at home. Reservations are made, tickets are purchased, and hotels are booked all before arriving at a place.

This approach is flawed because understanding a place is really important for figuring out things you will enjoy doing. When you are physically in a place, you understand it better. You can take in the environment with all your senses and talk to local experts. No amount of guidebooks, YouTube videos, and Tiktoks¹ will accurately capture the feeling of simply being in a place.

When your entire trip is scheduled on incomplete information, you trade away valuable freedom. Retaining this freedom is the key towards discovering and doing things that you love based on your interests.

Another way to look at it, we are dealing with the classic exploration–exploitation dilemma. When it comes to traveling, most people heavily weigh exploitation to get their “money’s worth”. Exploration is reserved for before they leave. I’m arguing that a better strategy is to weigh exploration heavily with exponential decay after the first day for a better experience.

Learning too much about a place spoils the plot

Another downside of planning at home is that you end up spoiling bits of the plot. If you do enough research about a place and watch enough videos, you end up basically reading the Wikipedia summary of a movie before going to the cinema. The summary never quite captures the magic and ruins the surprises.

Many people are disappointed about travel in the internet age because they say there are no more secrets in the world to discover. Everything has been revealed on the internet. I don’t think this is accurate. The same secrets that existed before still exist in the digital age. As long as you don’t read about them then they are yours to discover.

Almost anything can be done last minute

If you don’t make any plans until you arrive, you’ll have to figure things out “last minute”. Booking at the last minute has the undeserved reputation of being difficult and stressful.

I blame this reputation on the online travel industry, which has weaponized our fears of “sold out”. How many times have you seen a countdown clock on a hotel booking website or “3 seats left” indicator on a boat tour? The entire industry is designed to pressure you into making decisions as fast and early as possible.

An open secret is that there is near zero penalty for figuring out things last minute. Having a computer in your pocket has made this easier than ever. Of course, there’s always a small chance you might not get your first choice of hotels or activities. I think the freedom to edit your plans as you travel is worth this risk.

The first day is about exploration

There is something magical about arriving at a new place with a blank schedule. Curiosity drives you forward as everything you see is something you can explore. All the doors are open.

A great way to get started is to spend time walking around and taking public transportation. It’s truly a joy to walk around with no plan and pop into things that look interesting. Try to visit at least a couple neighborhoods to build up your mental model of the city and its nuances.

Have a meal. Or two. Enjoy a drink even if it’s early. Talk to people who work in the city. Ask about things you should do. Things they’d do if they had a long weekend. Carry a notebook and write them down so you won’t forget.

With the new information and freedom in your schedule, you can now make some plans on what you want to do. If you find a part of town you love more, you can book a longer term accommodation there. Try to resist the urge to fill out your entire schedule after your first day. You still want to retain some freedom for new things you learn about.

Tap into local experts

The biggest advantage of figuring out what to do on the ground is having access to local experts.

If you are looking for a great bar in a city, the best possible person to ask is the bartender that made you your last drink. If you care about museums, the expert in the area is the person working at the front desk of a big one. The same goes for restaurants, nature, etc.

You don’t necessarily have to stick to the person’s profession. Some of the best late night meals I’ve had were from recommendations from bartenders. Who else frequently eats at 2AM in the morning after last call? There’s a lot of knowledge overlap once you start having conversations.

If you ask the right people, you will get recommendations that are up to date and in the zeitgeist.

One great sign is if someone asks me questions before firing off recommendations. Experts know that context is important to providing a great answer. I’ll trust someone much more if they try to understand me first.

One question friends have is the chicken and egg problem. How do I first find a good bar or restaurant to go to first? Two thoughts:

1. Asking people who work or live at your first accommodation (see below)
2. Using a global guidebook like Michelin, 50 Best Discovery, and Gault&Millau. These aren’t perfect but are the closest to a global expert

Things to prepare

There are a few things that benefit from planning beforehand.

• Your accommodation for the first day so you have a place to rest and drop off your bags before you explore.
• Figuring out what to pack requires some planning on activities you have in mind and the local weather. If you forget a thing or two, you can always buy it when you arrive.
• Visas if you need them.
• If you are visiting to do something that requires prior reservation, book it (e..g eating at Noma).

Embrace being a flâneur

Imagine yourself as a flâneur, a leisurely stroller exploring the urban gardens of Paris.

Claude Baudelaire on being a flâneur:

For the perfect flâneur, for the passionate spectator, it is an immense joy to set up house in the heart of the multitude, amid the ebb and flow of movement, in the midst of the fugitive and the infinite. To be away from home and yet to feel oneself everywhere at home; to see the world, to be at the centre of the world, and yet to remain hidden from the world—impartial natures which the tongue can but clumsily define.

To travel well is to observe and understand humanity in a different setting. This doesn’t happen if you have your blinders on following a strict schedule.

You need to give yourself the freedom to listen. Once you hear the music, trust your intuition and follow where it leads you. You will end up with a great tale to share.