Over the years, I have traveled through Europe for weeks and sometimes months at a time. I have overpacked. I have underpacked. I have helped drag broken luggage down cobblestone streets helping people.
I have learned the hard way and seen others learn the hard way.
Now, especially when I am leading Sober Gay Adventures trips in Italy and Crete, I live out of one backpack for a month or more. Space matters. Quality matters. And what you bring can either make your trip easier or way more complicated than it needs to be.
These are my five must have travel items. The ones I do not leave home without.
1. The Perfect Backpack
I am a backpack guy.
I understand not everyone can travel with one due to injuries, age, or preference. But if you are traveling through Europe, I always suggest a backpack if you can manage it.
European streets are old. Cobblestones look romantic in photos, but they are brutal on rolling suitcases. I cannot tell you how many times I have watched people struggle to drag luggage across a piazza or down a narrow street.
A backpack makes getting around so much easier.
When buying one, do not go cheap. I made that mistake on my first long trip across Europe and the seams on the straps were starting to burst by the end. A quality backpack will carry you through countries, airports, ferries, trains, and everything in between.
My current bag is a Nomatic 40L pack. I have taken it across Europe three different times for months at a time. It has been to 12 countries and more than 30 cities, and it still holds up like new. It has scrapes and scratches, sure. But it is strong, reliable, and worth every dollar.
If you plan to travel Europe for an extended trip, your backpack matters more than you think.
2. The Neutral Dark ShirtÂ
When I pack, I keep it simple. Four t shirts. Three polos. Two button ups. One hoodie.
All neutral colors. Mostly grey, navy, and black.
This is not because I dislike color. It is because darker neutral clothing hides spills, sweat, and whatever you accidentally brush up against while exploring a city.
They are easy to wash in a sink. Easy to wipe down with a damp cloth. You do not have to hunt down a laundromat every few days.
This is what I pack whether I am gone for one week, two weeks, or four months. I have traveled all over Europe with these nine shirts and been completely fine.
They work for a nicer dinner. They work hiking hills in Santorini. They work wandering through Rome or grabbing coffee in Florence.
Most people look great in dark neutrals. They mix and match easily. And no one notices if you repeat outfits.
Packing light is freedom. The less you carry, the more you enjoy the trip.
3. The Collapsible Day Pack
When I travel for long periods of time, space in my main backpack is everything.
One of the best travel items I have discovered over the years is a collapsible day pack. It rolls up or flattens and takes up almost no room in your main bag.
But once you are out exploring, it becomes essential.
I keep my portable charger, water bottle, sunglasses, and snacks in there for long days walking through cities or exploring islands. It keeps everything organized without carrying your full travel pack everywhere.
The first time I spent a month in Athens, I used the city as a home base and explored different Greek islands on weekends. I would leave my large backpack at my Airbnb and take only my collapsible day pack. Because I packed smart with neutral clothing, I never needed much.
The Navigator Collapsible Backpack by Nomatic gives you flexibility without bulk. It is probably my favorite travel accessory.
5. A Portable Charger That Actually Works
Your phone is your map, camera, translator, boarding pass, and connection to everyone you are traveling with.
If your phone dies in a foreign country, it is not fun. It is stressful.
I learned that lesson early on while trying to navigate train schedules with a dying battery. Since then, a portable charger has been non negotiable.
Not a tiny one that gives you half a charge. A real one that can fully charge your phone at least once or twice.
When I leading Sober Gay Adventures tours in Italy or Crete, we are out all day. Photos. Directions. Group messages. Restaurant reservations. I cannot have my phone dying at 3 pm. I also will carry an extra for those who may have forgot theirs.
It lives in my day pack and gives me peace of mind every single day.
I recently order this Nimble Champ 10k Wireless Portable Charger after using my friends the other day. I love it and can’t wait to use it while traveling.
5. A Really Good Pair of Walking Shoes
You walk a lot in Europe.
You are walking through Rome. Climbing hills in Santorini. Getting lost on purpose in Florence. If your shoes are wrong, your trip feels wrong.
I have made the mistake of bringing shoes that looked great but were not built for miles. By day three, I was thinking about my feet instead of the view.
Now I bring one solid pair of broken in, reliable walking shoes. Not brand new. Not fashion only. Real hiking shoes.
You do not need five pairs. You need one great pair. That you can dress up and dress down.
When your feet feel good, everything feels easier. You stay out longer. You say yes to one more street, one more hill, one more sunset.
And that is what travel is about. Being able to be out as long as you can enjoying your time.
Travel does not have to be complicated. The right gear gives you freedom. It lets you move easily, pack lighter, and focus on the experience instead of your stuff. These five items have carried me through months in Europe and will again when running Sober Gay Adventures trips, and they have never let me down. If you have a must have travel item you swear by, leave a comment below. I am always looking to upgrade my list.
Yasss. Great guide! I was traveling in West Africa though and I felt like a wheeled suitcase was just fine because you can drag it over anything lol
Traveling through Italy with my mom and rolling her suitcase was a personal form of hell. LOL
[…] you take one thing seriously when packing, make it your bag. A good bag was in my top 5 things you should have for traveling. Do not go cheap on luggage or a backpack. A solid, well made bag will last you for years and make […]