How to Plan a City Trip: 7 Steps to the Perfect City Break

Decide on a Destination and Travel Dates

Whenever we plan a city trip, two questions come up immediately: where and when?

Often, one influences the other. Sometimes the destination is clear and we’re looking for a good time frame — other times the dates are fixed and that shapes the destination. That’s why we’ve combined these two decisions into one step.

No matter what you’ve decided first — or even if you haven’t made up your mind at all — here are a few tips to make the choice easier:

Tip 1: We love traveling to cities in the summer. The upside: cities are often less crowded because it’s vacation season and many locals have escaped the heat. The downside: it can get seriously warm.

Tip 2: Make sure there are no major trade fairs or events happening during your travel window. Back in his younger days, Basti once booked a flight to Dublin — without a place to stay, like you did back then — only to discover on arrival that it was St. Patrick’s Day.

Tip 3: If your dates are set but you haven’t picked a destination yet, we have some inspiration for you. We’ve listed the best travel destinations for every month — including city break options, of course.

Tip 4: We stay for at least four full days in a city. When we travel with the kids, it’s at least six.

Tip 5: Planning a city trip can get expensive fast. If you want to save money, consider going off-peak. Most tourists visit cities over long weekends, so from Sunday through Wednesday, prices are usually lower than from Thursday through Sunday.

Tip 6: To help you figure out the best time to visit and roughly how many days you need for the most popular city breaks in Europe, we’ve put together a handy overview table below.

Take Care of Your Travel Arrangements

Destination and dates are locked in — nice! Now there are two important to-dos we always tackle next. First up: sorting out how you’re getting there. We’ll break it down into three options: plane, train, and car.

Getting There by Plane

When we search for flights, we use Skyscanner and/or Google Flights. That gives us a solid first impression of which direct connections are available and what prices look like.

Tip 1: If you’re flexible, search all nearby airports — either together or one by one. For example, first all flights from one airport, then the next, and so on.

Tip 2: Comfort matters just as much as price to us. We don’t want to get up in the middle of the night or arrive late in the evening. That narrows things down — and honestly, that’s a good thing.

To keep a clear head, we jot down the best results. Which airline has good departure times and a solid price on which days and from which airport?

Once we’ve settled on an airline, we go straight to the airline’s own website. We enter our dates and, if we’re flexible, shift them by +/- two days to find the best deal. By the way, we ALWAYS book directly on the airline’s website.

Bonus tip: If you ever experience a flight delay, our article on flight delay compensation walks you through how to get your money back.

Getting There by Train

You don’t always need a flight, of course. If you’re planning a short trip to Amsterdam and you’re already based in Cologne, for example, a train or car is totally doable.

For the train, it’s worth booking your ticket in advance so prices don’t creep up on you.

Tip: Many European rail operators offer advance-purchase fares that can get you to popular destinations for surprisingly little. Check your national rail provider’s website for current deals and price lists.

Getting There by Car

Driving gives you the most flexibility when it comes to timing. Your main concern will be finding parking.

Tip 1: We’ve written dedicated guides with our best advice on parking in Amsterdam and parking in Paris. Definitely check those out if you’re heading to either city.

Tip 2: As a general rule, we’d suggest a hotel slightly outside the center with its own parking or a park-and-ride lot with a good connection to your hotel. Most cities have solid options for this — just check parking costs in advance.

Book Your Hotel

The second key to-do is finding a place to stay. To make it easy, here’s exactly what matters to us in a hotel:

• Great reviews!
• Minimalist & clean design
• Comfortable bed
• Quiet location
• Central and well-connected
• Good Wi-Fi

What doesn’t matter to us:

• Breakfast included — we always decide on-site whether we want it or not
• Extras like fitness rooms, saunas, bars, etc.
• Star ratings

For our search, we head to Booking.com, enter our destination and travel dates, and filter by maximum price per night and high review scores.

We start with hotels rated above 9. If nothing fits, we drop to above 8 — but we always aim to stay above 8.5.

Then we take a closer look at whatever’s left.

Tip 1: Check out the room options carefully. Which hotels match your expectations and which fall short?

Tip 2: Pay attention to location. For first-time visitors, we recommend staying in the center so you can walk to most things easily. There’s usually one neighborhood that works best for this. For over 80 cities, we’ve put together our hotel recommendations with the best neighborhoods to stay in.

Tip 3: Read the reviews carefully. Filter by the worst ones and scan them — which drawbacks are fine with you and which are deal-breakers? This tip alone eliminates quite a few hotels.

This way we narrow things down to a shortlist of three. At that point, it almost doesn’t matter which one we pick — all three meet our expectations and we really can’t go wrong.

We always book directly through Booking.com.

Plan Your Itinerary

The most important to-dos are done. Now we move on to the ones that take a bit more time — and the first is planning what we actually do on the ground.

We start by getting a rough overview: What are the main attractions? Which ones do we actually want to see? And do we need to sort out tickets in advance, or can we handle things spontaneously? For this part of the trip planning, we love using Google Maps, Instagram, and Google Search.

We save the most important sights to a Google Maps list, then decide which are major attractions that need more time and which are quicker visits.

Major highlights include things like the Eiffel Tower and the Louvre in Paris, or the Colosseum and the Vatican Museums in Rome. Other things to see that don’t fall into that category include:

• Neighborhoods or streets we want to wander through
• Restaurants, cafés, ice cream shops
• Markets
• Viewpoints
• Local favorites and off-the-beaten-path spots

Tip 1: Plan one major attraction per day and fill the rest of the day around it.

Here’s how we approach every city break: We pick our main highlight for Day 1 — say, the Eiffel Tower. Then we figure out how to get there — subway, metro, or boat. While researching, we also check whether we need to buy tickets in advance. Everything else for the day gets planned around that anchor point.

For example, it might look like this: We take a boat ride to the Eiffel Tower. Afterward, we pick a great nearby neighborhood — Montmartre — to stroll through, with some good restaurant picks already saved for lunch. While we’re there, we also stop by Sacré-Cœur and enjoy a beautiful panorama.

We go through each day like this — but we also stay flexible. Sometimes we can’t find a great restaurant near the main attraction and spontaneously head to a different neighborhood for lunch instead. That’s totally fine.

Tip 2: Divide the city into zones. Once you’ve picked your main attraction for the day, look for other points of interest in the same area. That keeps travel distances short and your energy levels up.

Tip 3: Try to keep each day as open-ended as possible so you can adjust on the fly if something doesn’t go to plan.

Get a City Pass

Once your itinerary is set, it’s time to think about tickets. Two options: either get a city pass or book tickets individually.

We’ll cover city passes first, then walk you through booking tickets on their own.

In large cities with lots of (pricey) attractions — like New York, London, and Paris — a city pass can be a really smart move. You get free admission to many attractions and often skip the line too.

You can buy one either for a set number of days (see as much as you want in that window) or for a set number of attractions (more flexibility, but you choose which ones carefully).

City passes make the most sense when you want to pack in a lot of sights in a short amount of time. There are usually several passes to choose from, and picking the right one isn’t always straightforward.

Tip 1: We’ve done the legwork and put together city pass comparisons for several major destinations so you can find the right pass without the headache. Our most-read guides are the city pass comparison for New York, the city pass comparison for Rome, and the city pass comparison for London.

Here you’ll find an overview of all our city pass comparisons

Tip 2: Write down all the attractions you want to visit and note the regular admission price for each. Add up the total and compare it with what the city passes cost — you’ll see very quickly whether one is worth it.

Book Your Tickets

If you’ve only planned a few paid attractions, a city pass probably isn’t worth it. In that case, booking tickets individually is the way to go.

For each attraction, we look into where to get the best tickets and which type to buy — because for some highlights, there are multiple ticket options that can make a real difference.

Tip 1: To save you the research, we’ve written ticket guides for Rome, Paris, and Barcelona — covering which attractions you should book in advance and exactly where to get them. For famous sights like the Eiffel Tower, the Colosseum, the Acropolis, and The Shard, we’ve written dedicated articles focused entirely on ticket options.

Aside from city passes, there are generally two ways to buy tickets: the official ticket shop and third-party providers like GetYourGuide and Tiqets.

Tip 2: We recommend buying individual tickets through Tiqets or GetYourGuide, two of our favorite trip planning apps. Both are available in English and you can cancel most tickets up to 24 hours in advance.

Plan Your Transfer from the Airport to the Hotel

Your city trip is almost fully planned — yes! There’s just one thing left, and it’s always our final step before departure: figuring out how to get from the airport to the hotel.

We check all the options: public transit, taxis, and private transfers.

In 90 percent of cases, we take public transit. There’s usually a solid connection into the city center that takes us right to our hotel. We research in advance what tickets are available and where the smartest place to buy them is.

In the process, we usually also figure out whether there’s a transit card or a rechargeable card — like in New York or London. That takes care of getting around during the whole trip at the same time.

In most cities, you can walk to plenty of sights. But sometimes an attraction is a bit farther out, or you just don’t feel like walking anymore — and that’s exactly when a transit card pays off.

We’ve written guides on airport transfers and metro systems for many cities. Search and see if we’ve covered the destination you’re planning a city break to.

Frequently Asked Questions About Planning a City Trip