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Packing Guide for the Perfect City Holiday

Packing Guide for the Perfect City Holiday

In the spirit of full disclosure, this article contains sponsored content and affiliate links.

Yes! Your city break is just around the corner! You’re ecstatic to let loose but you’re dreading the packing part of vacation. We’re here to tell you it doesn’t have to be stressful. Actually, we find it quite fun (way better than unpacking when vacation is over).

Start by doing these four things first:

Check the weather and seasonal temperatures.

The weather may not say that rain is in the forecast, but it’s always wise to pack a rain jacket when visiting wetter climates. Similarly, if you’re spending time in multiple cities, you may need a little more preparation.

Next, research the city and culture to get a sense of what the locals wear.
If you’re an American heading to Europe for a city holiday, you may be surprised to hear about the differences in dress depending on the region you’re visiting. We’ll share more below.

Our family uses High Sierra Backpacks for multi-city stays.

Choose your ideal suitcase. For multi-city trips and long stays, I opt for a High Sierra backpack. It’s an ideal option in Europe where cobblestone streets are rough on traditional suitcases and you may need two hands to push a stroller. Otherwise, medium-sized suitcases with 4 spinner wheels and a strong extendable handle are perfect for a city break!

Leave some space in your bag. Never overstuff your bag. It’s tough on your suitcase and it’s a bad travel practice. I also like to leave space in my bag to bring some souvenirs home.

Ready for the Essential City Packing List? Here it goes!

  1. Comfortable sandals. This is by far the most important thing to pack!

If you’re going to Europe or any metropolitan city, having a couple options for shoe wear is important. I tend to gravitate towards comfortable sandals that are easy to dress up or wear casually. There are some places that this option is a must! In Italy, for example, wearing tennis shoes or flip flops makes you stick out like a sore thumb. In cities like Washington DC, LA, New York City, or London, it’s always nice to have sandals that can fit the attire of almost any establishment you walk into at any time of day.

Take a peak at the Nigella sandals I’m wearing, sold at  andreassous.com  and  dillards.com .

Take a peak at the Nigella sandals I’m wearing, sold at andreassous.com and dillards.com.

Here’s my checklist for the perfect city shoes:

  • Plush, padded footbeds

  • All day wear to dress up or down

  • Optimal comfort

  • Traction

  • Durability

The plush padded footbeds of the Nigella sandal by Andres Assous is my go-to and the stretchy elastic makes for easy all day wear! These are available in 5 colors, but I chose the pewter because it coordinates easily with any color combo.

2. Comfortable sneakers. Evaluate your itinerary and the local activities.

Sometimes even city breaks offer a nice day hike, especially if you’re trekking up a hillside to catch a nice cityscape sunset. For this, good supportive sneaks are important! Some tourists only pack sneakers or only sandals, but I find myself more comfortable with a few shoe options, especially where the local culture is fashion forward. As a family, we’re big fans of Brooks walking shoes. They’re supportive and last forever. Don’t forget breathable socks!

Europe tip: Tennis shoes are not often worn in Italy. With white sneakers, you will stick out as a tourist!

3. Versatile, breathable, wrinkle-free dresses. Choose styles that can be dressed up or down.

This is my got-to outfit for spring, summer, or fall city breaks! I always pack 2 - 3 dresses no matter the time of year and opt for polyester, cotton, or spandex materials. Maxi dresses and skirts are great for travel! Advantages to packing dresses are that they are entire outfits and take up less space than pants. Adding accessories (like a long-drop necklace, belt, or scarf) or switching into dress shoes can turn almost any casual dress into classy evening attire.

Location tip: In some European cultures, jeans, or even shorts in general, are not the norm. In places where there is rarely air conditioning (think most of Europe, coastal California, or northeast USA), packing breathable dresses that can be worn day or night is a smart option.

4. Layered shirts. Tanks and tees, for easy, stackable layers!

Shirts with simple or plain patterns are easy to mix and match with pants and pair with sweaters. This makes packing incredibly convenient because you can switch up your outfits with few articles of clothing. I opt for items that are easy to fold and not necessary to iron. I’ve been choosing Pink Blush as my go-to maternity wear and city attire lately. I love packing bright colors, breathable material, and shirts that go with anything.

I wear my cross-body leather bag with nearly every outfit. Check out these  super comfortable shirts by Pink Blush  featured above.

I wear my cross-body leather bag with nearly every outfit. Check out these super comfortable shirts by Pink Blush featured above.

Pink Blush offers a variety of  kimonos and sweaters  perfect for layering.

Pink Blush offers a variety of kimonos and sweaters perfect for layering.

5. A shawl, sweater, or Kimono. Keeping layers in mind, this is an obvious choice.

Bulky jackets take up a ton of space in your suitcase and you may not need them. Sweaters or kimonos are perfect for cooler evenings and easy to layer. I love my new Pink Blush Navy Blue Lace Mesh Long Maternity Kimono.

Europe tip: Many cathedrals in Europe have a dress code. I quickly found if your shoulders are showing or your skirt/shorts are too short (men included) you will not be permitted to enter duomos in Italy. For a few Euro, you can purchase a not-so-fashionable poncho to wear during your visit. Or you can just pack one!

6. Light rain jacket. Check the weather!

If it’s clear skies, you may be just fine but if you’re heading on a city break in places like Ireland, Norway, or the Pacific Northwest, a light rain jacket is always a must.

Rocking my  Revolution Race jacket  in Edinburgh, Scotland.

Rocking my Revolution Race jacket in Edinburgh, Scotland.

One of my favorite rain jacket brands is Revolution Race. These jackets fold up so nicely in our packs!

Kai and I opting for fashionable neutral-color pants in Dubrovnik, Croatia.

Kai and I opting for fashionable neutral-color pants in Dubrovnik, Croatia.

7. Nice bottoms. Pack shorts, capris, and a pair of versatile dress pants.

For a one week vacation, I always pack at least three pairs of bottoms: ideally one pair of shorts, one pair of jeans, and nice capris or a skirt. Casual dress pants or a classy skirt can come in handy for those lovely evening cocktail outings. Choosing dark or natural colors are easy to mix and match.

Europe Tip: There are a few places in Europe that find jean shorts, or jeans in general, to be sloppy. Capris, light breathable dress pants, or Bermuda shorts are a nice option for hot summers in fashion forward European cities. In Scandinavia, you’ll find more people wearing jeans and shorts. Just remember, Italian and Spanish men hardly wear shorts, unless you’re near resort towns!

8. Active wear. I never go on a holiday without leggings!

Don’t forget to bring some quality comfortable active wear for planes, trains, or hikes. In the US, leggings are everywhere but I honestly didn’t see many at all during our year of travel in Europe. That’s okay though because comfort is so important on those travel days!

9. Comfortable day pack and cross-body purse. This is crucial, especially with kids, cameras, and for all-day outings.


For purses, I opt for a cross-body bag with easy access and neutral in color to match any ensemble. My husband and I always travel with a theft-proof day pack to store our camera, snacks, water bottle, maps, sunscreen, and souvenirs. We love our Blakcliff Hudson Travel Bag because it’s fashionable for both men and women and holds everything we need! Including enough space for a laptop :) We are digital nomads after all.

10. Bathing suit. Just in case.

Always pack a bathing suit. You never know if you will need it or not and it’s better to be safe. They’re so easy to just throw in your bag.

11. An Extra tote or laundry bag. This always comes in handy.

I always pack an extra bag to be used for dirty laundry, protecting my camera when I’m out in the rain, or just in case my daughter goes a little crazy at the gift shop. More often than not, I’m glad I packed one.

Thanks for reading all about the essential Packing Guide for the Perfect City Holiday! Subscribe for our upcoming city guides, packing tips, remote work opportunities, and family travel advice.

Around the World on Daddy's Shoulders

Around the World on Daddy's Shoulders