Most men travel. Few men travel well.
The difference is not money. It is intention. The man who travels well has thought about where he is going, why he is going, what he needs to bring, and how he is going to move through the experience with the same standard he applies to everything else in his life.
Here is how to do it.
Pack Less Than You Think You Need
Every man overpacks his first hundred trips. The cure is simple — lay out everything you think you need, then put half of it back.
A carry on is always enough. Always. The man who checks a bag is the man who waits at baggage claim while everyone else is already in a taxi.
The Carry On Rule:
- Three days of clothing minimum, seven days maximum regardless of trip length
- One pair of shoes on your feet, one pair in the bag
- One jacket that works for everything
- Toiletries in a proper leather dopp kit — not a plastic sandwich bag
What to carry it in: TUMI Alpha 3 or Away The Carry-On. Both are built correctly, look correct, and last correctly.
Dress for the Journey
The man who boards a twelve hour flight in sweatpants has given up before he arrived. You do not have to wear a suit. You have to look like someone who takes himself seriously.
Dark slim trousers, a clean fitted t-shirt, a light merino sweater, clean sneakers or loafers. Comfortable without being careless. You will feel better when you land. You will be treated better when you land.
The Upgrade
Business class is not a luxury. It is a productivity decision. An eight hour flight in business class means you arrive rested, sharp, and ready. An eight hour flight in economy means you arrive diminished.
How to get there without paying full price:
Credit card points — The Amex Platinum and Chase Sapphire Reserve exist specifically for this. The annual fee pays for itself in travel benefits before you book your first flight.
Status — Fly one airline consistently. Status comes faster than most men think and the benefits compound.
Upgrade at the gate — Arrive early, dress well, be polite. It works more often than airlines admit.
The Hotel
Stay somewhere worth staying. Not the most expensive place in the city. The most interesting place in the city that fits your budget.
Boutique hotels over chains when possible. A 40 room hotel with a real identity beats a 400 room Marriott every time. Aman, Rosewood, and Auberge Resorts if budget allows. A well chosen boutique if it does not.
Always request a high floor. Always request a quiet room. Always tip housekeeping daily — not at checkout, daily. The room gets better.
The Itinerary — Have One But Hold It Loosely
Know where you are going. Know what you want to see. Have one non-negotiable experience per day and leave the rest open.
The best things that happen on any trip were not planned. The restaurant you found by walking past it. The neighborhood you ended up in because you took the wrong turn. The conversation with someone you would never have met if you had followed the itinerary.
Plan enough to have direction. Leave enough space to get lost.
The Gear
Noise canceling headphones — Bose QuietComfort or Sony WH-1000XM5. Non-negotiable for any flight over two hours. The single biggest improvement to the travel experience available for under $400.
A proper travel wallet — Bellroy Travel Wallet or TUMI Nassau. Passport, cards, currency, boarding passes. Organized and accessible. Never a ziplock bag.
A quality dopp kit — Leather, structured, with proper organization. Filson or TUMI. The man whose toiletries are in a proper kit is always more organized than the man whose are not.
A universal power adapter — One good one covers every country. Buy once.
A portable battery — Anker PowerCore. Your phone dies in airports. This solves that.
The Mindset
Travel is not a reward for working hard. It is part of working hard. It changes how you think, how you see problems, and what you understand about the world and your place in it.
The man who has been to Tokyo and Buenos Aires and Cape Town and Lisbon sees his own city differently when he comes home. He sees his own problems differently. He sees himself differently.
Go more places. Stay longer. Spend less time in the hotel and more time in the city. Eat where the locals eat. Drink what the region drinks. Learn three words in every language you encounter — hello, thank you, excuse me. It costs nothing and changes everything.
The world is larger than your comfort zone and considerably more interesting.
Go find out.
There Goes That Man. The search is over.