The BEST Shoes for Traveling

I love being prepared, lately that means two things: emergency preparedness (long history there, I might cover it in the future), and shoes. I need to have a shoe for every occasion. I don’t see it as a problem, I see it as always being prepared! It really helps on press trips when they say there will be a “hike” and I have my hiking shoes when nobody else thought to bring proper shoes. (To be fair, people on press trips may be nomadic, so fair enough!)

In addition to loving it when I’m prepared I love talking about it! So, welcome to my happy place.

How many shoes do you need for traveling?

Jessica lakeside in Vilnius

I’d say you should travel with at least 2 pairs of shoes. The type of shoe will vary depending on where you are and the weather.

For example, if you’re city hopping, then some good walking shoes and a nice pair of shoes for any lovely dinners out would be a great idea. If you’re headed to a beachy area then take those sandals or flip flops along with some other shoe (depending where you are, you may want a water hiking shoe or a nice pair of shoes if you’re at a resort for dinner).

Having two pairs of shoes is important because if one starts hurting your feet, you have another option that will fit a bit differently. Yes, that includes blisters. I swear by these blister bandages. I’ve used them and I’ll never travel without them ever again! They seem to be easy to find in Europe, but I’m not sure about the US, so here’s a link for my American readers!

What are the best shoes for traveling?

Jessica in Mt Etna Crater

Everyday shoes

These are your dailies. It’s what you’ll run around in when nothing special is planned. They are perfect for sightseeing, walks in the park, and climbing the inevitable stairs to get some great views. My favorite brands are Keen, Clarks, and New Balance.

Everyone’s feet are different so you have to find what’s best for you. But these should be flats with cushioned support. Hopefully you’ll be able to walk all day long with these babies. I’ve had problems in the past with shoes being too narrow, so I suggest being thoughtful of the fitting!

Beachy shoes

I’m putting 3 different kinds of shoes under this category. You might only need one kind or all three…I’ve definitely travelled with all three before. These also depend on what kind of beach or pool you’re heading to.

For many places, water sandals or flip-flops are perfect! No fuss, one and done kind of situation. Sometimes you just need something to put on your feet so you aren’t walking on hot sand or to get from the water to your room. Water shoes are perfect for unknown water holes, slippery areas, pebbly or muddy beaches. These are now always in my bag if I’m going anywhere with water!

Standing on Prinsengracht

Hiking shoes

There are two different kinds of shoes I suggest here. You have your hiking boots in whatever fashion you need them. I have a general waterproof boot that’s great for a nice hike, when walking on a glacier in Iceland, or walking on frozen canals in Amsterdam (picture above). And then there are hiking shoes for the more jungle-vibe kind of places that are made to get wet. They are sandals with a good sole and some foot protection.

Some great brands to check out for hiking boots are Merrell & Keen. For the water hiking sandals, Keen is a great place to start and Teva had great ones as well. These are the ones I have and I love them because of the toe protection. I don’t know about you, but I stub my toe at home enough that I’m not taking my chances with hiking!

Jessica with Giethoorn house

Dressy shoes

Not everyone is going to care about this part but I like dressing up just a bit…just enough where I need a different pair of shoes. My two go-tos are cute flats and a pair of cute sandals. For the flats, I love these Toms ones and have them in 2 colors (I’d get all the colors if I could)! For the sandals, I love the flat, brown and simple look. They go with everything! Originally, I had a pair of Toms for this, too. But I’m not about brand loyalty just because every type of shoe is different. So, I ended up getting these from Teva because they are cute with support. The Toms sandals were just too flat! Walking around any European city was not comfortable. But if you’re interested, these were my original dressy sandals.

Best travel shoes tip


Break in your shoes before traveling! This is obvious to some people, but I’ve learned that you don’t know what you don’t know, so I’ll say it here. Walk around your home, around your block, or even to the stores for a few days before wearing them to a new place where you don’t have the luxury of your other shoes at home.

Travel with a shoe bag like this one to keep everything else in your bag clean. And stuff the shoe with other things to make the most of your space. My favorites are bottles (if you’re checking a bag), socks, deodorant and really anything that’ll fit but you don’t mind if they smell a little like shoes.

I like to be comfortable and, at least slightly, stylish. Ok, at least, not completely touristy looking. Honestly, though, that’s inevitable and there’s nothing wrong with it. I just like to blend in a little, but that’s just not always the case.

You be you and do what’s comfortable and best for you. This is how I pack and I LOVE learning how other people do it. I love reading the thought-process behind it all. I’ll keep sharing packing tips, so if you’re curious, like me, you can get your fix 😉

Thanks for reading and wishing you joy and travels.

Jessica Cutrufello wearing a green floral dress, glasses and pink lipstick

Hi! I’m Jessica, an American who made Amsterdam her home in 2014. I share European gems through food and memorable experiences. Want to know more? Head to my about page or check out my YouTube channel.