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25 Lessons I’ve Learned from Traveling 100+ Days a Year

I have always loved travel. Even when I was a kid I loved watching travel shows and dreamt of exploring the world. Now that I am an adult, I travel as much as I can. Last year I traveled 113 days! I have learned a lot of dos and don’ts and tricks of the trade, and I am sharing them with you today! Here we go:

1. Always Carry Some Cash (in the local currency)

Not all cities have uber/lyft and not all taxis take cards. Keep some cash on you so that if you need to take a cab, you can.

2. Put Your Bag in the Overhead Compartment Wheels Out – Not Sideways

If you put your bag in the overhead compartment sideways, you aren’t just being inconsiderate and taking up extra space, you might make your flight late. The flight attendants are going to have to move your bag to make more room and it is going to hold up the boarding process.


3. Check-In for Flights Right Away

By checking in as soon as possible you can get in a better boarding group, select a better seat or a better spot in the upgrade list.

4. Consider Setting Up Apple Pay on Your Phone

This is convenient if you get separated from your wallet.

5. Pack a Snack

Throw a couple granola bars in your bag. They won’t take up much space, and I always end up eating them.

6. You Only Need 2-3 Pairs of Shoes

Seriously. And don’t pack those fancy heels just-in-case. You will only actually wear them if you need them for a specific event.

7. Be Loyal to an Airline

I am loyal to United because Chicago is a hub and they fly internationally. I signed up for the credit card, use it for pretty much everything, and pay it off each month. In return, I get upgraded to first class a few times a year, and I get at least enough points for a flight (or two) to Europe.

8. Be Loyal to a Hotel Chain

Earning status with a hotel chain can give you perks including room upgrades, free WiFi, complimentary breakfast, early check-in, and late checkout.

9. Choose Your Credit Card Wisely

If you are loyal to an airline or hotel chain, you may want to sign up for their credit cards. Other credit cards, like the American Express Platinum Card, give you lounge access at airports.

10. Invest in a 21” Roller Bag

This slightly smaller roller board always fits and isn’t taken away for looking too big.

11. Always Have a Change of Clothing

Bags get lost. It happens. If you are checking your bag, make sure you have a change of clothing in your carry on. Often it takes 24 hours for your bag to be recovered. When my sister’s luggage was lost recently it took 4 days before her bag made it to her.

12. Find Out If Your Luggage is Checked Through to your Final Destination

If you have a connecting flight, find out if you need to collect and re-check your bag or not. Just ask when you are checking your bag to find out.

13. Sign Up for TSA Pre

It saves me time and gives me peace of mind. Keep your TSA Pre number in your phone – sometimes my ticket isn’t marked for TSA Pre and since I have my TSA Pre number on my phone I am able to go to the counter and have my ticket updated. BUT – not all airlines participate in TSA Pre – Iberia is an example.

14. Don’t Count of Using WiFi on Your Flight

It tends to be slow, and on my last 3 flights, it hasn’t worked at all. I always plan on working on a project that doesn’t require WiFi during the flight. Older planes don’t have WiFi capability.

15. Bring Basic Over the Counter Medicines when Traveling Abroad

You have no idea how hard it is to find cough drops and Sudafed in some countries. You can read about which medicines I pack for international trips in this blog post.

16. Ask the Person with the Same Phone/Camera to Take the Photo

Asking strangers to take your photo is a pretty common occurrence when you are traveling. The photos come out better when the person taking them knows what they are doing. I ask someone else who has an iPhone to take my photos – or if there is someone with a Canon DSLR I will hand them my camera.

17. Keep Transportation Cards Loaded and Ready

If there are cities that you go to often, get reloadable cards for public transportation, and find a spot for them in your wallet. I am in New York City and London a few times a year, so I keep my metro and oyster cards in my wallet and with at least enough money for a couple rides on them in my wallet. This way I won’t loose them or forget to pack them (this was a problem in the past).

18. Keep Basic Essentials in Your Carry On at All Times

Instead of constantly packing and unpacking basic essentials, just keep them loaded in your suitcase at all times. It prevents me from forgetting things and it saves me time when I am packing. I keep a toothbrush, spare contact lenses, dental floss, pedialyte (for hangovers), makeup removing wipes, shout wipes, band-aids, a mini deodorant, and a small hairbrush in my carry on at all times.

19. Be Prepared to Bring Extra Stuff Home

It is rare to go on a trip and come home without buying anything. Sometimes I shop a lot – when I went to Morocco I planned for it.

20. If You Have an AmEx, You Have Travel Insurance

American Express credit cards’ benefits include some car insurance and travel insurance. Check to see which coverage comes with your card, but generally speaking the cards have return protection, purchase protection, baggage insurance, a global assist hotline, car rental damage, and car rental loss. (American Express hasn’t sponsored this post – I am just most familiar with their cards).

21. Apple Maps Works When You Don’t Have Service

I can’t explain this sorcery, but it is true. The trick to getting this travel hack to work is to load the map using wifi, and once it is loaded, it should keep working even after you lose the wifi connection.

22. Don’t Leave the Do Not Disturb Sign on Your Hotel Door at All Times

I realize that this is a bit of a freak example, but when we were in New York City, an air conditioning unit in the room across from ours broke. The room filled with steam and water (about 5 inches of standing water), and the hotel staff held off on going into the room because of the sign – even though water was flowing into adjacent rooms and into the rooms below. The do not disturb sign made what might have been a small problem into a really big problem – and I think it is safe to assume that the best case scenario for that hotel guest’s belongings is that they were just soaked with steam and water – but some things could have been ruined.

23. You Never Know When You Will Need a Business Card – or a Band-Aid

This rule applies to life, not just when you are traveling. You never know when you might meet someone that you want to pass a business card onto. I keep a couple cards tucked into my wallet so that I never leave home without some. There have been times when I randomly chat with someone who ends up being in a related industry and I want to give them a card. And I always want to have a card on me in case someone asks. I keep a couple band-aids in that same wallet – because it’s better to have one and not need it than to need it and not have it.

24. Wait in the Taxi Line, Don’t Take a Ride from Anyone who Approaches You

I know that taxi lines can be long, and it might tempting to take a ride from a drive that approaches you at the airport but don’t do it. Worse case scenario, it might be dangerous. Best case scenario, you might get scammed out of money.

25. Research Tipping Before Going to a Foreign Country

Each country has its own tipping practices. Some countries don’t do it at all, while in other countries you are expected to add on 10% or round up. If you are confused, ask at your hotel. The other thing to know is that outside the US, servers will likely bring a small credit card machine to your table and swipe your card right infront of you. Usually you can’t add on tip after the fact with those machines, so ask the server if they need to know the adjusted total before they swipe the card.

What do you think? Do you have any travel tips to share? Let us know in the comments!

first photo by Katie Donnelly

25 lessons learned from traveling 100 days a year

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