33 Travel Tips | A Man’s Guide To Traveling With Style & Being Prepared Upon Arrival

Roadmap-1(new)I LOVE to travel.

There is just something about waking up in a new setting, seeing views you’ve only read about, and finding yourself in a crowd that speaks a foreign language that helps you understand how amazing this world is.

It was during one of these trips — living with a family in Kyiv, Ukraine — that I met my wife over a decade ago.

And although I’ve slowed down since becoming a father, I have to admit I look forward to the day when my businesses are more automated and I can take my kids out to see the world.

I spent a decade hitting all 50 US states and exploring over 20 countries.

From motorcycles, to cars, to commercial planes, to military cargo hopping (Space A). I learned a lot about traveling smart.

So having said that, here is a collection of my best travel advice:

1. Dress Sharp By Default

Opportunity awaits the traveling man who dresses in style!  Seriously, they don’t offer that unexpected opening in first class to a man who looks like a bum, or even someone who looks ordinary. They want someone who is dressed to impress and will signal to others a positive feeling through their presentation.

2. Dress Comfortably

You want some room in your trousers, a shirt that stays tucked or is worn un-tucked, and nothing that pinches or rubs. I love my Lee modern series jeans as they have a tiny bit of stretch in them – which is nice when you’re about to embark on a 24 hour flight to Australia!

3. Call Your Credit Card Companies BEFORE Leaving

Have them put a travel alert on your cards (to include debit cards) so that you don’t get a unexpected denial of service. With the recent breeches of security — a lot of card companies are being more aggressive on unusual behavior in spending.

4. Slip On Footwear

Whether it be boot or monk strap dress shoes, a nice pair of slip-on footwear saves you hassle at the metal detector when taking them off and putting them back on is simple.

5. Use Your Belt As An Impromptu Shoe-Horn

I have a nice shoe horn at home, but when traveling it’s impractical to carry. Instead, I use impromptu shoehorns such as my belt end or a plastic card from my wallet – preferably a low value/non credit cad in case you damage it!

6. For Air Travel Wear As Little Metal As Possible

A belt buckle that can pop off (rather than having to take the whole belt off) is a huge time-saver. In fact I often pack my belt in my carry-on along with my collar stays and then put them on while waiting for my plane.

7. Hang Your Jacket When Seated

If driving, you should take a couple hangers with you and utilize the hooks in the back so your jacket(s) won’t be pressed and wrinkled when seated. On a plane, I usually wear my jacket to my seat and then take it off and fold it/store it right before sitting.

8. Use Quality Luggage

travel luggageA couple reasons why this is important.

1) Your luggage protects your clothing. I have a story here in which I share how my Blue Claw Garment bag protected thousands of dollars in clothing from a maple syrup spill.

Also 2) you want your luggage be able to take a beating and help you move your gear easily from point A to point B.

Finally – 3) your luggage should keep you organized and have the little things you need on the road. I recently started using a carry on from Genius Pack and love how it has compartments for all my gadgets and even my dirty clothes. It also has a charger to re-charge my phone, is durable, and looks great!

9. A Packing Checklist

Take the time to create a simple checklist — then laminate multiple copies and keep one permanently in your bag (I keep one on Google Docs as well). This will save you a lot of money when you don’t have to buy an item you left at home.

10. Use Luggage Identification

I always have business cards inside and on the outside display of my luggage. I’ve also recently started to use bright luggage identifiers – as that my bags are mostly black, this helps me spot them quickly in sea of dark bags.  Also – in the case my bags are lost I would like to believe at least one of these identifications would survive and help my bag find it’s way home 🙂

11. Carry On Your Luggage

Your luggage won’t be lost when you’re tracking it the entire trip!  Also – this save you from additional fees and when you land you can whisk through customs and get to your destination sooner.

12. Pack Light

pack enough clothing for 2 weeks consistently in one carry-on. The key is making sure everything I take is interchangeable with everything else I pack. Less clothing, more outfits, less bulk! I also wear my heaviest, bulkiest clothing and on short trips leave the workout clothing — exercise the morning you leave and upon return, a 2-3 day rest is fine for most routines!

13. Roll Your Suit Jackets

If you don’t have a hanger bag: lay them flat, folded so the shoulder seams lie one atop the other, and roll from the shoulders down to the hem to make a tube. You can slip some small items into the roll if you want. Click here to view my images on how to fold and roll a suit jacket.

14. Fold Dress Shirts In Bundles

Stack them one atop the other with the arms spread, fold the bundle in half with the collars on top, and cross the arms over each other. Pack the bundle at the top of your luggage, and shake everything out and hang it as soon as you can.

15. Pack Empty Shoes

Slip rolled-up socks into your shoes, both to save space and to keep the shoes a little firmer so the tops don’t get crushed inward.

comb16. Carry A Comb

At home I have a brush, but when traveling light I pack my Chicago Comb. A gift from Brett & Kate over at the Art of Manliness, I’ve come to love this comb as #1 it does it’s job and #2 it’s made from solid steel and is the most durable item in my bag. This comb will be in use by my great-grandson 100 years from now.

17. Buy A Shaving Soap Bar

Liquids are limited when you fly, and shaving cream is counted against your total amount.  Throw in how most of us don’t have a small travel can, and you’ll find you’re having to buy a new can of shaving cream every time you take a trip (and have to throw it out when returning!). Instead — buy a shaving soap bar that you can just lather up with and is travel safe!

18. Always Have a Change Of Clothes In Your Carry-On

If flying, don’t put all your eggs in one basket.  Assuming that you’re checking your luggage, ALWAYS have at least one day’s worth of spare clothes in your carry-on so that you’re set if your luggage is lost.

19. Bring Your Best Sunglasses

Whether driving or on the plane, quality shades make travel easier on the eyes and in my experience are one of the most common items travelers seem to leave at home. Big, dark ones (aviators certainly seem appropriate, don’t they?) work well for window glare and sleeping.

20. Wear A Hat

Panama hat

Preferably a functional and stylish piece of head-wear, one that will protect you from the sun, rain, and/or keep you warm.

21. Wear Clothing With Pockets

Never underestimate the value of pockets. One of the reasons I love my sports jacket, I always have a place to stash my tickets, my kindle, or my cellphone.

22. Take A Bottle Of Water With You To The Airport

Drink the water completely while checking-in. Not only will you be hydrated for your flight, but carry in the empty bottle and fill it up at a water fountain and save $5 on over priced water. Make sure to use the bathroom!

23. Pack Travel Food

Compact and high in nutrients is best. Dried Fruit, Chocolate Covered Nuts, dried or sealed meats. I also like to bring apples or other low-cleanup fruit. Do NOT bring items that have a STRONG SMELL unless you’re driving/traveling alone.

24. Pack A Small Package Of Wet-Wipes

Just do it, you’ll thank me later.

first aid kit25. Carry an Emergency Kit

Aspirin or Ibuprofen, needle and thread, band-aids, plastic tweezers, micro-flashlight.

26. Breath Fresheners Or Gum

I try to brush twice daily, but when traveling it’s nice to know you’re not putting of the person next you with foul breath by having a few sticks of gum available.

27. Shower Right Before A Long Flight

When leaving Australia for the US the other day, I noted my flight was in the late afternoon. Instead of opting for my normal early morning shower, I chose to shower at lunchtime. Although only a 6 hour difference, It matters when you’re in transit for 24 hours and you start to feel ripe after 3 full flights where the airplane’s AC isn’t working as well as you’d like.

28. Audio Books & Podcasts

Audible (a great online audio book store owned by Amazon) and iTunes (home to not only music but amazing free audio shows called podcasts) are great for filling your smart phone or mp3 player with audio. It’s a magical experience to be able to listen to a well-read and engaging book while you’re flying 14 hours across the Pacific Ocean.

29. Bring A Good Small Paperback Book

Although the restrictions on electronic devices has made it a lot easier to read on the plane, there are still plenty of restrictions in customs areas, on takeoff and landings, and sometimes you only have 5 minutes to wait so turning the device on would use half your available time. Paper still has a place!

30. Armrest Rules

If you’re seated by the window or on an aisle — you are entitled to your one armrest. Give the guy (or gal) in the center row two as they have no other place to put their arms – you can at least step out and move around or lean on the side of the plane.

31. Ask Your Hotel

Once on the ground, I always ask for an emergency sewing kit, extra toothpaste/other toiletries, ensure the iron and board I have is sufficient… before I need them. If they don’t have these – you know and can prepare. If they do — you have a spare/access during your trip.

32. Have A Trip Summary Document

detailed checklist

Printed it out, email a copy to yourself and your wife/the person(s) picking you up at the airport. Although we often have this info scattered in our email, on our laptop, in texts, having it all in one place makes it 1) convenient and 2) protects us from unforeseen circumstances when our computer crashes, phone is lost, or we simply need the info in seconds.

33. Give Yourself Margin

Of all the tips listed, this is the hardest to do but the most powerful in terms of how it can improve your traveling experience. Give yourself time to deal with problems, time to prepare before your conference, and time to recover after.

Over the last few months, this way of thinking has revolutionized my travel experiences — not being rushed and having time when I return is amazing. Instead of turning on my computer when I get home, I spend time with my wife and kids. A novel idea, huh 🙂

Want a quick video summary of my 11 favorite travel tips?