How we plan a trip from scratch (the order we book things in)
Planning a trip is not about the perfect itinerary. It is about doing things in the right order. Here is the order we use, and the tools that come out at each step.
Most people plan a trip in the wrong order. They fall in love with a hotel, book it, then find out the flights that match are painful. Or they book a tour for a specific day and then the rest of the trip has to bend around it. Or they open ten tabs, get overwhelmed, close them all, and go back to scrolling.
Planning a trip is not really about the itinerary. It is about doing things in the right order so each decision narrows the next one instead of fighting it. Here is the order we use.
1. Pick the season, then the country
Before anywhere else. The same city is a different trip in July than it is in October. Southern Europe in August is beautiful and crushed with tourists and 38 degrees. The same places in April or September are 24 degrees, half the crowds, and lunch tables actually available.
If you already know you are travelling on fixed dates (a specific week off work, kids’ half term), the season picks the country. Northern Europe is great in June, not great in February. Marrakech is perfect in October, brutal in July. Bali is dry season May to September, wet the rest of the year.
We usually spend the first ten minutes of trip planning on this alone. It saves more money than any other single decision.
2. Lock in the flights
Once you know when and where, book the flights before anything else. Flights move in price the most, they lock in your exact dates, and everything else builds around them.
A rule of thumb we use: two to four months ahead for regular international, three to six for peak season (summer, Christmas, Easter). Any earlier and airlines have not released their cheap seats yet. Any later and what is left is either business class or a bad connection through somewhere unpleasant.
One small tip. Once you find a flight you like on a comparison site, open a second tab and check the airline’s own website for the same route on the same date. About one in three times, the airline direct is a few pounds cheaper and comes with a better cancellation policy. Worth the two minutes.
If you want the flight and hotel bundled, sometimes the package price is genuinely lower than the sum of both.
3. Book the hotel
Now you know exactly which dates and which airport. Time to work out where you will actually wake up.
The neighbourhood matters more than the hotel. A four-star in the wrong district is a worse trip than a three-star in the right one. Some rules that come up a lot:
- Stay near a metro station. Every extra ten minutes of walking to transport is an extra half hour per day gone.
- Look at where you actually plan to spend your time. If the museums and food you care about are in one district, sleep near there.
- Look at the reviews for the noise, not the decor. A pretty room next to a nightclub becomes a bad room by 2am.
Free cancellation is worth the small premium. Plans change, better prices sometimes drop, you might find a nicer stay later. Being locked in for six months on a non-refundable rate is a false economy.
4. Book the “I would cry if I missed it” activities
Now the itinerary starts to take shape. But before you plan every day, book the two or three things you know you cannot leave without doing.
- Colosseum in Rome, Doge’s Palace in Venice, Alhambra in Granada. Sell out weeks ahead in peak season, and on-the-day queues can eat three hours.
- Sagrada Familia in Barcelona, Anne Frank House in Amsterdam, the Vatican Museums. Same story.
- Big activity experiences: hot air balloons in Cappadocia, desert safaris out of Marrakech, dhow cruises in Dubai. Peak season fills up.
Book those first. Skip the rest for now.
Cross-check both. Same tour sometimes shows up on each with different prices and different cancellation windows.
5. Leave forty percent of the days blank
This is the step most people skip and most people regret.
If you plan every hour of every day, you spend the whole trip chasing your own schedule. The best moments almost never come from the plan. They come from a wrong turn, a cafe you walked past twice before going in, a shop you noticed from a bus window.
We aim for about sixty percent planned, forty percent blank. Enough structure to hit the things you came for, enough space to actually be somewhere.
6. The small things that make it work
A few extras that are worth handling before you go.
Getting around in Europe. If your trip involves more than one city, or you are hopping between countries, the train is almost always better than internal flights. Faster city centre to city centre, no airport queues, better view.
Visa paperwork. Some visa applications ask for proof of return travel before you actually book the ticket. A refundable ticket works, but a dummy reservation is usually cheaper and does the same job.
Travel insurance. Boring, always worth it. A missed connection, a stolen phone, a hospital visit. Even the cheapest policy usually pays for itself the first time something small goes wrong.
Cash and cards. Most places take card now. But some do not, and some charge extra for small transactions. Carry a bit of local cash for coffees, taxis, and tips.
The whole thing in a sentence
Season first, then country. Flights before anything else. Hotel next, and pay a bit more for cancellable rooms. Book the two or three big-name activities that sell out, skip the rest. Leave forty percent of the days blank.
Everything else works itself out.
Or, tell us where you are going
If you would rather not do all of that yourself, that is exactly what we do. Tell us about the trip you are imagining and we will build the flights, the hotels, the activities, and the small things around what you actually want. One reply, then a call if it is a fit.
Quick answers about visiting this place
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What should I book first when planning a trip?
Flights. They move in price the most and lock in your dates. Once flights are booked, everything else builds around them. If you book the hotel first and then can't get flights that match, you either lose the room or reshape the trip around it.
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How far in advance should I book flights?
For international, roughly two to four months out for economy and three to six months for peak season (summer, Christmas, Easter). Too early and airlines have not released cheap seats yet. Too late and everything left is business class or a bad connection. The middle window is where you actually save money.
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Do I need to book activities before I arrive?
Only the ones you would be genuinely sad to miss. The big-name sights (Colosseum, Doge's Palace, Alhambra, Burj Khalifa, Sagrada Familia) sell out in peak season and the on-the-day queue is often two hours. Everything else can be booked once you are there and know how you feel.
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How many days should I actually plan out in advance?
About 60 percent of them. Leave the rest blank. The best moments on any trip are almost never the ones on the schedule. If you fill every hour, you spend the trip chasing your own itinerary instead of being on the trip.
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Is it better to use one booking site or many?
Many. No single site is the cheapest for everything. Flights are usually best on a flight-focused site or the airline direct. Hotels have their own aggregators. Tours have theirs. Comparing across a few takes ten extra minutes and often saves you real money.
Let us build the route, the places, and the bookings.
Tell us where you are imagining and we will come back with a plan built around you. One reply, then a call if it is a fit. No spam, no pressure.
Start your trip