City Break Packing List & Styling Options (with photos)
We are out and out city explorers. Urban centres, culture, food, and history is what keeps us fascinated when we visit a new destination. And we do that in style! After exploring close to 100 cities and counting in various countries, we have perfected our city break packing list to the T.
So whether you are visiting for a weekend trip or a week – this City Packing List has you covered!
City Break Packing List – Getting Ready
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When planning a city trip (or any vacation for that matter) packing light is super important. For one, flight baggage fees are rising every year, and many hotel suites & accommodations are ‘tiny’, and carrying multiple bags and suitcases is a hassle!
Trust us, stick to a carry-on – a backpack, duffel bag, or hand luggage. Use packing cubes and lightweight clothes to fit outfits for a 3 day trip or 2 weeks. In the following post, I will share how I pack my dresses, skirts, and tops (and accessories from hats, cosmetics, electronics, etc.)
For a carry-on, we trust and love our Pacsafe backpack – Pacsafe Venturesafe 45 L. This size is carry-on friendly and it easily fits our large size packing cube, cosmetics pouch, and more. What we like about this backpack is that it opens up from the side like a suitcase and makes it easy to store, and access items conveniently.
It also has nice front pockets for organization to store our charging cables, universal adaptor, notebook, and toiletries. Pacsafe is made of anti-theft and slash-proof material, and it keeps our belongings safe when we are using public transportation in cities.
Another option is the Osprey unisex-adult Farpoint 40. Just like the Pacsafe, it opens up on the side, has dedicated pockets for storage, and comes with a very comfortable strap.
For a daypack, we use Pacsafe Metrosafe 25 Liter Anti Theft Backpack, and my husband uses it to carry our camera gear, sunglasses, and water bottle.
I prefer to carry crossbody bags when I am traveling. It makes it so easy to join tours, hop from one neighborhood to another. When traveling for work, I carry a tote to store my travel essentials and a 12 inch laptop.
My favorite is my Longchamp LePliage tote bag in a small size. This bag usually comes with me on all of my trips – neatly folded in a small envelope size (to bring my souvenirs and shopping goodies back home).
Save this: All of our city itineraries and travel guide
City Break Packing List Summer Essentials
To effectively pack for a city break in a carry-on, opt for lightweight, wrinkle-free clothing – dresses, tops, skirts, trousers.
For bottoms (pants, jeans, or leggings) stick to 1-2 pieces for a week’s trip. Or wear it for a weekend getaway. Learn what to pack for a weekend away.
The same goes for outerwear. Even in the summer months, carry a cardigan, denim, or faux leather jacket for dinners or night outs. They are handy inside an aircraft and on sightseeing cruises.
Take 1-2 jackets for a week’s vacation, or wear it in-flight for a quick 2 day trip. Keep reading as I will share how I style it!
Tops & Blouses
Carry 2-3 tops with you, depending on the duration of the trip. Pack lightweight, flowy blouses that make you look pretty on camera. Pairing a top or a blouse with comfortable legging, or denim is the best way to travel in style.
Plus you can wear the same jeans, or linen pants at the bottom!
Bottoms – jeans, linen pants, leggings
For bottoms, try to maximize the leggings or denim pants that you are carrying. Opt for dark wash jeans that match well with any color of blouses.
I take my American Eagle jeggings with me everywhere, and they are very comfy to wear all day long. You can easily make a style statement with your jeans – pair it up with a designer belt, or leather boots (in late autumn/fall months).
Linen pants are also great, as long as they are wrinkle-free, and in dark colors.
For city trips, leggings are effortless too. I wear my Lululemon leggings with cute tops or oversized sweatshirts.
Dresses & jumpsuits
I love dressing up when I travel. Pick flowy, cute dresses in the summer and spring months to brighten up the photos, and stand against the urban jungle – skyrise buildings, old town centres in Europe, or shopping malls.
Dresses (maxi, or short dresses) are lightweight, and very easily packable. Buy an outfit with a good lining that is not bulky. An interesting back design is always a BONUS – so jazz up girl!
I prefer wearing long dresses, and pair them up with comfortable sneakers (black or white).
In the fall months, you can switch to a jumpsuit or earthy-tone dresses to match the weather! Style it with a denim or faux leather jacket.
Skirts
I wasn’t a skirt person until I tried pleated flowy ones – don’t they look great in photos? Plus they are very comfortable to wear, and effortless to pack. I roll them up and sneak them in, in one of the sides of my backpack.
They are wrinkle-free, so no worries about ironing. If you don’t have wrinkle-free pants, skirts are a nice and graceful alternative!
Just like pants, dark colors are always a good idea for skirts too, and for multi-use – change the top!
Comfortable walking shoes
A pair of comfortable walking shoes are a must for city breaks. From wandering old towns, concrete boardwalks to taking stairs, you will need shoes with good arch support.
My husband and I switch between lightweight sneakers or hiking shoes, and both are good for walking. For dresses and skirts, I prefer white shoes (check my VANS, and KEEN white shoes).
It is a good idea to opt for a waterproof material for your shoes. Depending on your trip and the activities, you might want to carry heels (for business, events, fancy dinners) – so try to make room for your second pair inside your luggage, and wear the sneakers.
Buy VANS or KEEN white shoes
Light Cardigan and/or Jacket
A light cardigan is handy all year round, and I carry mine in the summer, fall, and spring months. When going sightseeing, I am more of a denim jacket and a faux leather type of gal and I love how it makes me look all put together.
Both denim and leather (bomber style) jackets go well with dresses and pants. If I am on a 2-3 week trip, then I carry both and change it up when necessary.
Before traveling to a city, I always check the weather, and if it’s a destination with frequent rains and chilly temperatures, then I would pack a lightweight waterproof jacket (soft shell or rain jacket) with me.
For week-long trips, you can do something like this (perfect for rainy weather)
- Denim or leather jacket | Light cardigan | Waterproof jacket with hood
- Denim jacket | Leather jacket | Waterproof jacket with hood
Try to wear one of the jackets to save space in your luggage.
Sunglasses
One of the must include travel items are a pair of sunglasses for me (doesn’t matter what weather it is). Sunglasses not only provide protection, but they instantly light up your overall outfit!
My favorite: RayBan Erika Sunglasses. I use polarized glasses on mine, and they are fabulous, easy to wear, pack and maintain (my oldest RayBans is over 7+ years old and I still wear them!)
You can pack whichever brand works for you. Keep them inside of your day pack or crossbody bag.
Space saver: My RayBans box is sleek, but sometimes I still have to switch the cover for a microfiber pouch. I keep the cleaning cloth inside, and it works fine – to protect it, and save space inside of my crossbody bag!
Stylish accessories
I love adding 1-2 accessories to jazz up the outfit. It could be a belt on a dress or a statement piece on a pair of simple jeans. If you love watches, that is a good option too.
Over the years, I have invested in a few designer pieces (belts, a few scarves, mini bags) to accessorize my outfit. I re-use these items all the time, so the money spent was worth it! Plus they still look as good as new.
A hat or a beret is also a great accessory, and they will not break the bank. I bought this red beret I wore in Paris, and this floppy hat I wore in Victoria, Canada from Amazon. Both of these items are easily packable, and compact to store inside of the hand luggage or backpack.
Cross body bag
When you are out and about exploring on your city break, going hands-free is important (and leave your daypack and tote in the hotel). I own quite a few crossbody bags, and for travel, these are my favorites – Gucci Soho Disco bag, and Pacsafe City Safe anti-theft purse.
Inside my crossbody bag, I have a minimalist anti-theft passport wallet (for passport and credit cards), my cell phone, a mini cosmetic pouch with make-up, a coin purse (for loose change, cash in different currency), and sunglasses.
All of these day essentials fit inside my bag easily and it is super light to carry all day long!
Loungewear
Carry a pair (or two) of loungewear, nightdress, loose boyfriend shirts – whatever makes you comfy and happy at night!
Add on: Swimsuits and a pair of flip flops if you are heading to the beach on a day trip or enjoying the pool at the resort.
Here is a quick list for men and women for a city packing list for a week-long trip,
- 7 x Shirts (him)
- 2-3 tops, 3- 4 dresses (her)
- 2-3 x Bottoms – jeans, pants, shorts. Or skirts (her)
- 1-2 x Walking shoes, formal shoes for events
- 1-2 x Bomber jacket and/or Waterproof jacket
- Stylish Accessories – scarf, hat/beretm belt
- 1 x Sunglasses
- 2 x Loungewear
- 1 x daypack or crossbody purse/tote
- Toiletries: Sunscreen, moisturiser, toothpaste & toothpaste, travel size shampoo, conditioner, lotion, medications, small first aid kit, make up essentials
- Electronics: Cellphone, camera, charging cables, universal adaptor, power bank, laptop/Kindle
- Travel Documents: Passport/photo ID, visa, credit cards & cash, hotel, tour, transit passes, travel insurance
What To Pack For A Winter City Break
For a winter city break packing list, you will have to add a few warmer pieces depending on the cold temperatures. Winters in Canadian cities and in Europe are so different.
And I am talking – 30 degrees C with wind chill in Toronto, vs – 6 degrees C in Zurich – so your outerwear is the main item that needs to be considered!
Winter Parka or warm coat (waterproof)
You will need your warm coat or winter parka in most cold cities. When visiting cities in the Northern Hemisphere with extreme cold temperatures in December through February, opt for a warm parka.
This North Face parka has a removable hood, so you can cover yourself when it’s cold and windy. With deep pockets, this is great for keeping your hands warm and toasty inside.
Packable short puffer jackets are a good option too. Opt for something with bright colors to pop against the snowy backdrop (like yellow, red, blue).
If you are exploring cities with mild temperatures (up to – 7 degrees C), you can get by with a nice wool coat – the ones that come with a waterproof coating. I love my Aritzia Cocoon Coat for its style, warmth, and longevity.
Any winter outerwear you carry, ensure you wear them to save luggage space. And remember if it gets colder, you can always layer on.
Thermal tops, bottoms, leggings
Thermal wear is important so that you are warm, and comfortable while sightseeing in the winter. I use merino wool long johns and carry 1-2 depending on the trip duration and activities planned.
They won’t take a lot of space inside the luggage – you can just swap one of the summer dresses for thermals.
Buy: Merino wool top | Merino wool bottom
Sweaters or cardigans
Keep a light cardigan to use as a mid-layer. Sweaters are also handy for indoor events, or at a restaurant. I swap my denim and faux leather jacket for a light cardigan. Cardigans in black or brown are perfect as layering pieces.
This is also useful during the day when temperatures are slightly warmer.
Winter boots
Winter boots are a must for cold city destinations. Wear tall or ankle-length boots, with a warm insulated lining. Do consider the weight of the boots as well especially if you are carrying them on your flight, and not wearing it.
It is also important to check the outsole and the threading on it. The outsole in the winter boots should provide a grip when you are walking on slippery, icy surfaces in the cities.
Buy: SOREL Joan of Arctic Boots | UGG Boots | North Face Shellista Boots
Warm socks
Carry merino wool socks to keep your toes warm!
Warm Scarf
A scarf can brighten up your outfit, and keep you warm and cozy. Infinity and triangle scarves are my go to in the winters. I pair them with my plain parka.
Gloves
Warm gloves are a must for winter city trips. Get gloves with fingers that you can easily slide in and out when needed.
Also when you are out and about, you will need your fingers for clicking photos or checking your phone, these tech gloves will come in ‘handy’.
Beanie
Pack cute beanies or toques to cover your head and ears. Beanies also add a nice color to the usual/plain winter parkas or oversized sweaters.
All Winter Packing List Items: Men & Women
Here is the entire list of packing items for a winter city break for him, and her
- Long sleeve tops, shirts
- Bottoms – jeans, leggings
- Nice sweater dress for dinners out (her)
- One x Winter parka, or wool coat
- Thermal wear (merino wool)
- Sweater or cardigan (as mid layer)
- One pair x Winter boots
- Sunglasses
- Stylish accessories like a belt
- Scarf
- Gloves
- Warm socks
- Beanie
- Lounge wear
- Toiletries: Sunscreen, moisturiser, toothpaste & toothpaste, travel size shampoo, conditioner, lotion, medications, small first aid kit, make up essentials
- Electronics: Cellphone, camera, charging cables, universal adaptor, power bank, laptop/Kindle
- Travel Documents: Passport/photo ID, visa, credit cards & cash, hotel, tour, transit passes, travel insurance
Electronics – City Break Packing CheckList
Electronics are just as important as clothing, especially a universal adaptor when visiting cities in other countries, and a charging cable.
Here is our entire electronics packing list,
- Phone: Cellphone. We travel with our iPhones. This is where we store our passes, booking information, use it as a camera sometimes, and also to connect with friends and family
- Sim card: Optional
- Charger: I love multi charging cables, and I have a few at home. They are so handy to charge multiple electronics like iPhones with lightning cable, cameras with microUSB, etc. Grab yours today
- Universal Adaptor: A universal adaptor is a must, if you are visiting cities in Europe and own electronics from North America (round pins vs flat ones). You can buy yours here
- Camera: Don’t forget your camera. We carry our Sony Mirrorless Camera and Sony A7iii. The mirrorless is super lightweight, and it can be stored inside a small crossbody bag. The A7iii is super powerful (perfect for gloomy, low lighting shots). Check prices for A7iii and Sony A6000
- SD Card: To back up all the photos. Buy yours from Amazon
- Wireless Headphones
- Power Bank
- Laptop: Optional
- Kindle: We love to read books on our Kindle. Grab the new Kindle e-Reader here, and read unlimited books!
Toiletries – City Packing List
Our summer and winter cosmetics list does not vary a lot, except that the moisturizers are creamier. The good thing about traveling to cities is that you will find these amenities easily, so don’t overpack.
I prefer carrying mini sizes or have them in travel containers to save space in my transparent toiletry bag.
- Moisturisers: My number one moisturiser is this Vitamin E cream from Body Shop. I have been using it for over 10+ years, and they are so good. Carry the 50 ml size, which is also carry-on approved
- Sunscreen: For sun protection at all times of the year
- Lipstick/balm: Carry chapstick, and your favorite lipsticks, lip color
- Eye pencil: My au-natural make-up includes a foundation, and eye pencil! My favorites – IT Cosmetics | Rimmel Eyewear Exaggerate
- Perfume: Travel size perfume
- Shampoo/conditioner
- Tooth paste, tooth brush
- Hand sanitizer
- Small first aid kit
- Don’t forget your prescriptions, Advil, etc.
Other essentials + packing tips
- Packing cubes: For easy packing and organization, we use packing cubes. You can buy yours here or here (for pink ones)
- Reusable water bottle: When you are out and about exploring a new city, staying hydrated is important. Carry a reusable water bottle on your city trips. Here is my favorite bottle
City Break Packing CheckList For Documents
Travel documents will be slightly different for everyone depending on where you are traveling, visa status, and purpose of visit, but here is something to get you started,
- Carry a form of photo ID (Driver’s Licence or Passport): Ensure you carry your passport if traveling overseas. It should be valid for at least 6 months from the date of arrival in the new city. Ensure the passport is in good condition and not torn or tempered. If traveling in the same country, you can get by with a photo ID like in Canada. Do check what is required in your airport of departure.
- Visa: Check if you require a tourist visa for travel. Check them in advance (I like to do it a few weeks to a month in advance, sometimes upto 3 months depending on the visa processing time).
- Currency and Credit Cards: Don’t forget your credit cards, and currency.
- Transportation: Reserve car rentals, order city passes online for public transportation. Advance planning and booking will allow you to save money and enjoy a stress free trip
- Hotels: Confirm hotel reservations, and save your emails, or a screenshot of the booking email
- Travel Insurance: No packing lists and travel gear is complete without insurance. Super important! Get quotes from World Nomads here
We hope you found our winter and summer city break packing lists useful in planning your trip. Like we were saying, we LOVE exploring cities and we love that you do too.
Don’t forget to add a nice experience to your trip itineraries such as a cultural walking tour, food tour, or city views from above. We book our excursions with GetYourGuide!
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