I love packing. Seriously. It is a weird thing that most people don’t enjoy. My friend recently rolled his eyes and said, “I have to go home and pack,” and I looked at him and said, “I love packing.” He looked at me like I had just grown a second head.
I have traveled for months at a time and have figured out what is actually needed, what is not, and what small things make a big difference. If you want to travel easier, lighter, and with way less stress, this is how you do it.
Start With a Good Bag
If 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 every trip smoother.
I use a Nomatic 40L bag that has been on multiple long trips and still looks brand new. It is comfortable, durable, and actually looks good. That matters more than people think. When something feels good to carry, your whole travel day feels easier.
If you prefer a roller bag, the same rule applies. Cheap wheels and weak construction will catch up to you at the worst time. Airports, cobblestone streets, long walks to your hotel. Spend the money once so you are not dealing with a broken bag in a new city.
Pack for the Trip You Are Actually Taking
This is where most people overpack. They pack for a fantasy version of their trip instead of their real one.
Are you really going to a fancy dinner every night? Probably not. Most trips include one or two nicer meals at most. The rest of the time you will be in casual restaurants, walking around, exploring, and just living in the place you are visiting.
Bring clothes that can do both. You should be able to walk around all day and then go straight to dinner without needing to change. That alone will cut your packing in half.
And let’s talk about swimsuits. You do not need five. I bring two. I call them gay and gayer. That is more than enough. No one is keeping track of your outfits at the pool.
If you are unsure about something, you probably do not need it. Let go of the what if mindset and focus on what you will actually use.
Leave Space in Your Bag
Always leave extra room. At least half a shoe box worth of space, if not more.
You will pick something up along the way. Even if you are not a big shopper, things add up. Maybe it is something you forgot. Maybe it is something you discover. Either way, you will want that space.
Packing your bag to the absolute limit on day one is a mistake. Give yourself room to move.
Use Packing Cubes and Stay Organized
I used to think packing cubes were unnecessary. Then I tried them and never went back.
They keep everything organized and easy to find. No digging through your bag. No mess. I use three: tops, bottoms, and underwear. If it is in the cube, it is clean. If it is not, it is dirty.
They also help maximize space, which matters when you are trying to travel light.
Are they life changing? No. But they make traveling a lot easier.
A Simple Packing List for a 10 Day Trip
For a ten day trip like our Sober Gay Adventures experiences in Crete or Italy, here is a simple, realistic packing list:
8 shirts in neutral colors that mix and match easily
1 to 2 pairs of pants
3 to 4 pairs of shorts
1 slightly nicer outfit if you want it
2 pairs of shoes total
2 swimsuits
Workout clothes if you plan to use them
Flip flops
A small day pack
Travel size toiletries
Sunscreen
Passport
Portable charger
Reusable water bottle
Any necessary medication
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