How to plan a city break: a step-by-step guide & checklist for beginner travellers
- 1 day ago
- 8 min read
No idea where to begin? You're in the right place!
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Not everyone has the privilege to travel regularly, and we want to help out those of you who are heading away on your first city break, and feeling a little bit out of your depth. We’ve put together a step by step guide of exactly how to plan a city break.
Whether it’s your first time travelling, or you’re used to using travel agents or package holidays, and having most things planned & booked for you.
Or maybe you normally just opt for a relaxing all inclusive holiday option where no planning is required.
Whatever your circumstances are, this guide to how to plan the best city break in advance, leaving all your time when you’re in the destination free to explore and enjoy!
Some of the steps might seem obvious, but honestly it’s so easy to forget one, so you can use our city break planning checklist even if you’re used to travelling and planning everything yourself. It will save that panicky feeling the week before thinking you’ve forgotten something really important!
1. Choose your destination for your city break
It might seem like a simple question - where do you want to go? But choosing where you’d like to visit for a city break can be tricky and depends on so many factors.
If you already have a set place in mind you’re sorted, you can skip this step and move on. If you’re not sure, don’t worry, we have some inspiration and ideas for you, as well as tips on how to decide.
We may be biased, but we’d suggest checking out our inspiration posts if you really have no ideas, they’re short summary posts describing places we’ve been to give you an idea of what they’re like, and lots of information that you’ll need as a first time visitor. Have a scroll through, and see what you fancy.
Or, one of our favourite ways to find a destination is simply look for flights around the time you’re going, and filter for “cheapest”, “direct” and “everywhere”. You might just find a new place you’ve never heard of that will be your new favourite!!
When deciding, make sure to check and see what’s on at the time of year you’re visiting, what the weather will be like, accommodation prices, visa requirements, currency and average prices of things like meals out, excursions, etc.
2. Get yourself some travel insurance
We can’t personally recommend a particular provider, as (touch wood) we’ve never had to use our insurance, so can't really comment on how good they would be. But you should definitely have a plan that provides full coverage for accidents, cancellation and luggage loss. If you're taking expensive devices that don't have their own insurance, you can include that too. Make sure to take a good read of the terms before you go through to purchase.
Don’t just go for the trip insurance that’s recommended with your flights or accommodation provider either, it’s normally a higher price than you can get with an independent provider that covers you for the whole year.
Use comparison sites to find the best deal. It’s best to get some travel insurance before you book anything just to make sure you’re completely covered. Every policy varies.
3. Check accommodation availability for the dates you want, before you fully plan your city break
When we’re helping people plan a holiday or city break, we do say always book your transport there and back first - which we stand by. There’s no point having a hotel booked and then realising flight prices have gone up 10x and you now have no way to get there.
But it's worth checking accommodation prices first, just quickly, on a site like booking.com.
That’s because, if there's a big event or just a very busy time, prices can be extremely high or there can be next to no availability. (We’ve learnt this from making the mistake ourselves). Have a quick look to be sure, then move on to book your transport afterwards.
4. Finally, now you can book your transport!!
If you’re flying, be sure to use a good flight search tool like trip.com to find the best dates, prices and times.
We have a full post about how to find and book cheap flights, so make sure to take a read of that too.
For trains, we recommend booking through a trusted provider like Omio or direct with the rail company.
Or maybe you want to drive yourself in a rental car, travel by coach, taxi, ferry. Whatever your transport option, get it booked now!
5. Now the plan for your city break is on the way, start your accomodation search
This can be the part of booking a city break that takes forever.
Different destinations have different platforms for booking accommodation that are the most popular, but booking.com is a really solid one that has options for full holiday homes and rental units, as well as hotels (independent and international chains).
We mainly love it for the filters. You can search for exactly how many bedrooms and bathrooms, price per night, how far from the centre you’re willing to be, or which neighbourhood you want. All the way down to specific facilities such as breakfast included, free wifi, and even things as specific as having a hairdryer in the room!
You can use our accommodation search below, powered by booking.com to find something that suits your group size, and your budget.
6. Do you need any additional transport for your city break to run smoothly?
Okay, your major parts of the booking process are done - congrats! Now you need to see if there’s any additional transport you need.
Do you need airport parking, transfers on the way to the airport or to your accommodation on the other side? Maybe you even want to book airport parking plus a hotel stay for the night before or after. HolidayExtras is brilliant for all of the above, and we have a discount liink that gives you up to 25% off, so make sure to take a look here.
You also might want to look into public transport options, car hire, or planned excursions.
Maybe you’re doing a multi-city trip, and need transport between cities?
If all of this is starting to sound a bit too complicated to sit, research, plan and figure out, no stress. You can always hand your planning over to an expert, then just book the actual events yourself.
No middle man, no commission or booking fee, just a flat rate for your itinerary carefully planned to your travel style. You can more about our personalised travel planning service here.
7. Research things to know about the destination before visiting
Before you start looking into all the fun stuff like sightseeing, excursions, and food and drink to try, have a quick look into things you need to know about your destination before visiting.
For example, you should always check the government travel advice for the country, to see if you need visas, vaccinations, or any important information. You also need to check if there are any specific local laws that differ from your home country to be aware of (like jawalking or vaping being illegal).
Then look into culture and norms such as dress, food and drinks to try, eating times, and just general customs that it’s good to be aware of.
Our Travel Toolkits or personalised travel plans give you all of this information about a destination, plus all your sightseeing, bar, restaurant and cafe ideas.
(An example of one of our Travel Toolkits, the perfect guide to help you plan your holiday or city break)
8. Now, the fun part! Create a plan for what you want to do within each day of your city break, how you'll get there, and all the delicious food and drinks you'll try
This part of planning your city break really depends on your personality type and style.
Some people like to just turn up to their destination with no plan at all, wander and see what you fancy doing day to day. We love this style of travel, but you can end up coming back and finding out about something that would've been, a must on your trip, and wishing you went there.
Make sure at the very least you have a few things noted down in your phone that you want to do, see, eat or drink while you’re there.
Some people like a fully planned itinerary of exactly what to do and when, which is especially good if you’re travelling with a larger group. Walking up and down streets when you’re starving, trying to decide on a restaurant and everyone is either saying “I don’t mind” or “No because…” is an absolute nightmare when travelling. It’s better to have as much planned before you go as possible!
We’re happy to plan your group trip for you, based on your preferences and travel style. You’ll still be able to book everything yourself, we’ll just take the research off your hands and provide our extensive travel knowledge and advice too. Talk to us about our personalised travel planning service, or see if your destination is covered in one of our Travel Toolkits.
The best way to start for all travellers is by just making a few lists. Look into things to do in your destination, and write down all your 100% musts, then another list of maybes.
You can either just keep checking this while you’re there and try to fit it in as you go, or assign things to a day based on their location, opening hours, and the best days of the week to visit. Again, if that’s sounding like an awful lot to look into, don’t hesitate to contact us to help you plan.
Make sure to take a look at excursions and experiences near your destination too. The most memorable part of any trip is the unique experiences you have there.
For example, the highlight of our trip to Bruges was the chocolate truffle making class. One of our favourite moments in Malta was the guided food and drink walking tour of Valletta.
Seville wouldn’t have been the same without a trip to see a traditional Flamenco performance. The list could go on and on. GetYourGuide is a great place to start your search for unique experiences.
Let us handle the search for you, so all you have to do is press book and go! See if your destination is covered in our Travel Toolkits selection, or contact us to let us know if there’s somewhere else you’d like to see us write about.
Your checklist for how to plan a perfect city break:
Choose your destination
Check weather conditions at the time of year you're visiting
Check what's on during your visit
Get travel insurance
Book your transport to and from the city you're visiting
Book your accommodation in the city you're visiting
See if you need any additional transport (car hire, airport parking, transfers, trains between cities)
Research things to know about the city or country before you go
Check government travel advice for the country to ensure you know all you need about visa requirements, vaccinations and local laws
Check to see if there is a Travel Toolkit about your destination
Either plan your itinerary yourself, or complete our quick consultation about your travel style and let us plan it for you!
Make sure you have a list of things you want to see, do, eat and drink in the city
Book some excursions and experiences in the city
Pack, and away you go!
