How to Book a Last Minute, Super Cheap, Multi-City Break Using Minimal Annual Leave

How to Book a Last Minute, Super Cheap, Multi-City Break Using Minimal Annual Leave

Wow that’s a big title! But that’s exactly what this post is about. When I talk to my friends about my upcoming travel plans, they tend to comment on the fact that a) I seem to go on a fair few long weekend breaks despite my lack of money and annual leave; b) my destinations seem random because I’ve never expressed an interest in that place before and; c) it must be more expensive booking a trip so last minute! The first two points are sort of true, but the third definitely isn’t. So I thought I’d share with you how I go about booking a last minute, super cheap city break using minimal annual leave.

Every good lesson needs an example, so I’m going to use my trip to Poland last year as a shining one. You may have guessed from the title of this blog post that it was indeed a multi-city break! I needed to use up my remaining few days of annual leave before it reset (for once I actually had some left over!) and time had flown by meaning that I only had a couple of weeks left to do so. I ended up booking a multi-city break to Gdansk and Krakow, spending a couple of days in each destination before heading home with a new found love of pierogis.

We booked our super cheap, multi-city break to Poland incredibly last minute, confirming our flights and accommodation just 5 days before travelling, but the below advice would work just as well a year in advance!

Couple smiling at the camera with giant Gdansk word behind them - cheap city break

Choosing Your Destination

There have been so many times that I’ve had my heart set on travelling to a specific destination on a specific weekend and missed out on going anywhere because I just can’t afford a £400 weekend away. The key to a last minute, super cheap city break is flexibility and open-mindedness. My process is as follows:

  1. Get onto Skyscanner and type in my nearest departure airport, making sure to select ‘add nearby airports’ to get as many options as possible
  2. Select ‘search everywhere’ function
  3. Search a whole month rather than a specific day – you never know when you could be saving hundreds by travelling a day later or earlier!
  4. Then the fun bit: destinations will be listed in price order so start from the top and either choose the first destination or scroll until you find somewhere you like the sound of. Have a click on the icon below and see what you can find!
UK Skyscanner 120 x 60

One thing to bear in mind is the cost of living in your destination. I’ve just done a quick search from Leeds Bradford, and whilst Ireland is the cheapest option (just!), I know that Poland, Lithuania and Slovakia will be significantly cheaper when I get there. Sometimes a destination might be £50 more expensive to travel to but your hotel will be £50 less a night and the beer will be a quarter of the price, so always take this into consideration.

Flight Times

Before you choose your destination, consider the flight times. Sometimes, but by no means always, cheaper flights can mean crappy flight times. If you have to get up at 3am for your flight, you’ll spend the first day of your trip walking around like a zombie wishing it was bedtime and spending the money you’ve saved on your flight on copious amounts of caffeine. You’ll most likely need to get a taxi to the airport as it’s too early for public transport, which again negates the savings.

It’s not just about the costs though, it’s also about maximising your time which is hugely important if you have limited annual leave. My favourite time to fly is in the evening, as it means I can go to work for the day and head straight to airport when I’m done. Although this means arriving late at night, it also means waking up fresh the next morning ready to start your holiday AND not wasting a day of annual leave for travelling.

colourful buildings in Gdansk - cheap city breaks

Getting the Cheapest Flights

There are a lot of rumours out there for getting cheap flights like ‘always book on a Tuesday’, ‘make sure you delete your cookies’ etc. but I’m not sure if these are true. I do however have a few tips that have worked for me before:

  • Once you’ve used Skyscanner to find your flight, it’s occasionally cheaper to book on another comparison site such as Kayak or Travel Supermarket. This isn’t always the case, but worth a look if you have the time.
  • If you’re travelling with someone, compare the prices when booking for one passenger versus two. I have no idea why, and again it’s not always the case, but sometimes the cost can be double per person when searching for two travellers!
  • Similarly, sometimes it’s cheaper to book your outbound and return flights separately rather than as a return flight. There is a risk that you’ll book the way there and the way home will sky-rocket in price, which has happened to me before.
  • Do you have more than one airport near you? It can work out cheaper to fly out from one airport and fly back to another, for example I might fly from Leeds Bradford but fly back in to Manchester or Doncaster.

Finally, and this is where the multi-city break comes into play, is there a creative way to get a cheaper flight? Look at internal flights and see if it works out cheaper to explore more than one destination. When I booked Poland, it worked out significantly cheaper (half the price) to fly from Gdansk to Krakow and then from there back home than it would have been to fly direct. This worked out great because we got two holidays in one using only two days of annual leave, with our flights as follows:

  • Thursday night – fly Doncaster to Gdansk
  • Friday & Saturday spent exploring Gdansk
  • Saturday night – fly Gdansk to Krakow
  • Sunday & Monday spent exploring Krakow
  • Monday night – fly Krakow to Leeds
Girl smiling directly into the camera on a cheap city break in Gdansk


I’m a big fan of Air Bnb and use it almost every time I go away now. You can get some beautiful accommodation, often much cheaper than a hotel and it’s great to have a bit of extra space. If you choose somewhere with a kitchen you could also prepare your own meals to save further, but this isn’t something I usually consider as eating out is a big part of travelling for me. The option is there though!

I’ve stayed in some beautiful Air BnBs over the last couple of year, my favourites were in Cluj-Napoca where we had an underground double width jacuzzi bath with a telly in the wall, and Vilnius where we had the tiniest but most adorable studio apartment! Both were between £20 and £30 equivalent per night, that’s £10-£15 per person per night! If you haven’t used Air BnB before you can use this referral code to get up to £34 off your trip.

Girl in double width bubble bath with tv in the wall behind - cheap city breaks

One point to note is that location is important when planning a short weekend, as you don’t want to be spending time travelling in and out of the city centre when you only have a couple of days. In this case I do tend to spend slightly more to be in a central location and be able to walk straight out of my apartment onto those cobbled streets and old city squares. Bear in mind that staying outside of the centre might mean spending money on transport (especially if you’re staying out late and have to get taxis).

Money Saving Tips

If you’ve chosen a cheap city break destination such as Eastern Europe, you can probably live like a king whatever your budget! But there is always room for savings on any cheap city break. Here are a few tips to keep the pennies in check:

  • Think about what you want to spend your money on. If, like me, you’re obsessed with food then you might want to only visit the free museums because museums aren’t your priority. If you’re really into art, you might consider cooking food in your Air BnB so that you have more money for galleries.
  • Don’t spend all your money at the airport – take an empty water to the airport and refill it once you’re through security and make your own sandwiches for the plane.
  • Cash vs card. If you like to spend on a card (I certainly do!), make sure your bank doesn’t charge you for spending abroad. I use a Monzo card which is great for this and gives a good exchange rate. If you want to use cash, research the best place to change it up. I’ve found that in a lot of places it’s much, much better to take British cash with you and exchange it abroad rather than get your foreign currency before you leave.
Girl in a museum on a cheap city break in Gdansk dressed up in a crown

So, over to you. How do you go about booking your super cheap city breaks whilst conserving that precious annual leave? What are your top tips for saving money on holiday?

Nell xx

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Pinterest graphic for super cheap city break

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