How To Pack Everything In A Carry-On Bag For A Weekend City Break

Sometimes packing for a quick weekend away can be more stressful than packing for a two-week holiday.

For city breaks especially, you can’t predict the weather, you’ll need both walking shoes – or at least shoes that won’t make you want to chop your feet off after a day of sightseeing, and ‘nice’ shoes. And unless you’re some kind of baller who doesn’t mind forking out for checked luggage, everything has to fit into a carry-on.

So, since I consider myself the queen of weekend breaks (if you need inspiration, check out my list of the best European city break destinations), here’s my guide to packing everything you need for a two-night city break into one carry-on bag – including some tips for beating the airlines’ liquid restrictions.

How to pack if you’re going carry-on only on a city break

Choosing your travel outfit

What you wear on the plane en route to your city break destination can make or break your packing strategy. You’ll want to go for comfort, obviously, but you probably don’t want to look like, homeless when you land. Oh, and you’re also going to want to wear the heaviest items of clothing you’re taking, to avoid extra luggage charges. And then there’s the hassle of stripping off at security, which means avoiding wearing anything that might set the alarms off.

Shoes

I like to start from the shoes up. Nobody wants to have to go barefoot over that gross threadbare carpet that ten million stinking toes have traipsed over at security, so opt for a ‘soft’ shoe. I usually wear my Converse trainers or – if I’m going someplace warm, my flip-flops. Depending on their weight, you might want to wear your heaviest shoes for the flight, just so you don’t have to carry them. For hiking trips, I’ve worn my much-loved Salomon boots on the flight before.

Bottoms

Anyone who professes that leggings aren’t trousers clearly hasn’t been on a long-haul flight. I’m giving you permission right here right now to wear leggings on the plane. They’re comfy, they’re lightweight and black bottoms go with everything. If people don’t look closely, they might just think you’re wearing grown-up pants. Just don’t go for those cheap, see-through Primarni ones, they give public legging wearers a bad name. Simply Be have a great selection of leggings for every shape – see here.

Up top

Your top half is the place to utilise the potential of layering. I tend to go with a plain vest top, a shirt and then layer a hoody over the top. Hoodies are cosy, you can use them as a pillow, you can pull one on under your jacket if it’s super chilly where you’re going – basically, they’re so versatile that you can’t afford to travel without one.

If a hoody will suffice, you’re golden. But if you’re going someplace freezing, or you’re off on a winter city break, you’ll need a coat. I pack one coat and one coat only for a weekend away, and bring a different scarf, faux fur stole or hat to switch my look up during the trip.

No matter what kind of climate you’re off to, it’s also wise to have a cheap waterproof mac rolled up and on-hand should you need it.

Handbag

Most airlines allow a small handbag in the cabin alongside a larger bag. This is where you should keep your cash, passport, phone, headphones, Lonely Planet guide, gum, and other small personal items. I’ve taken rucksacks, laptop cases, beach bags and all sorts – but you should check how strict the airline you’re flying with is.

My ultimate travel essential is a USB plug charger. This one has four ports, and interchangeable adaptors so you can use it with your electrics whether you’re off for a city break in Europe, the US or whatever.

If you’re travelling with camera equipment, use your camera bag as your small carry-on. The only camera I travel with is my Olympus Pen E-PL7, because it’s compact enough to fit in certain smaller bags.

And guess what guys? You can basically wear the same outfit on the journey back. Just switch your top and obviously, your underwear. I’ve just cut your luggage weight in half, right?

What to pack in your carry-on

If you’ve selected your travel outfit wisely, you can now pack your carry-on bag efficiently. Here’s what you’ll need for a two-night trip:

Six pairs of underwear, in case you pee yourself. Doesn’t matter if you haven’t done it since you were five, it’s better to be safe than sorry. Besides, knickers take up like zero room.
Four pairs of socks, in case it rains and your feet somehow get soaked.
One pair of jeans. I sway towards black skinny jeans because you can dress them up or down.
For evenings: two dresses / two ‘nice’ tops. If you have extra room, play around with skirt, culottes or short combos
Your ‘good’ shoes for evenings – there’s nothing worse than being knocked back from what you’ve heard is the bar to go to because you’re in trainers
Something to sleep in. Unless of course, it’s a dirty weekend you’re being whisked away on.

How to fit your liquids in your cabin bag allowance

First, only put your actual liquids in the plastic baggy. Here’s what should go in a separate toiletry bag that can stay inside your cabin bag:

Toothbrush
Hairbrush
Face wipes (yes I know they’re terrible for your skin but you can sacrifice your normal skincare routine for one weekend)
Eyelash curlers
Solid makeup, for example powder bronzer
Paracetamol (for the morning headache)
Blister plasters (if you’re taking new shoes or are planning to do a lot of walking)

Now, here’s what should go into your clear plastic bag (and how to beat the 10 items or less rule)

Travel-sized toothpaste. I’ll never understand why even the poshest hotels don’t have toothpaste in the rooms. You could take a full-sized 100ml tube on board but some airports are super strict about the stupid plastic baggy closing properly so it’s generally best to buy a miniature.
Full-sized roll-on deodorant or travel-sized aerosol.
Mascara, concealer, foundation, eyeliner etc if you wear it.
Lip balm (take this out to keep your lips moisturised on the flight).
Face moisturiser with SPF – I love Soap & Glory’s BB Cream for weekends away. I use it morning and night when I’m travelling, so I don’t have to carry two or three separate products.
One perfume sample. Rip it out of a magazine or ask at Duty-Free – you seriously don’t need to bring a huge glass bottle of fragrance away with you!
Mini conditioner. If I have to make a choice between bringing shampoo and conditioner, conditioner wins every time. I could wash my hair with fairy liquid and it would still look presentable and clean so long as I have my conditioner to stop it going frizzy. It’s also the thing some hotels don’t have.
Mini dry shampoo. If I’m only going on a two day trip, I’ll do everything in my power to make one blow-dry last the trip.

For shampoo and bath soap, that will be in the hotel. If not, or if you’re staying in a hostel, buy a cheap bottle at the corner shop when you land. You should also add a bath towel or travel towel to your carry-on if you’re staying at a hostel.

I’m a card-carrying skincare addict so I understand if you’re aghast that I haven’t mentioned cleanser, toner, serum etc. But seriously? You can go without for one weekend. Just do a little pampering session upon return!

And as for the carry-on case itself? There are SO many chic ones out there.

Alternatively if you’d rather carry a small backpack, I absolutely love my Osprey Sirrus 26 litre backpack. I know some travellers swear by packing cubes but I’m yet to try them.

There you have it: how to pack for a weekend break if you don’t want to drag a heavy case around or pay for checked luggage – without looking a state. Hope this helps!

What are your best packing hacks? I’d love to hear them in the comments! And are you a roller or a folder? I’m definitely a roller.

If you want to welcome more travel tips, tricks, destination guides and general banter from me into your life you can follow this blog on Facebook, Instagram, Twitter and Pinterest. I also have a Youtube channel. You can also subscribe to my newsletter for weekly updates.

Pin this

This is a collaborative post but packing tips are my own.