When people think about planning an extended trip, they imagine they’ll need to book flights and accommodation. There’s a little more to it than that.

There is always something that will go wrong, every time. Here are some simple things you can do before you go to make sure you’re covered.

chase sapphire reserve & chase sapphire preferred are both essential for travelers

Check your credit card perks

Before you book any flights, make sure you’re doing it on the right card.

First we got the Chase Sapphire Preferred. Then we got the Chase Sapphire Reserve.

The Reserve is the clear winner if you’re on the road often. Just be aware that they’ve recently reduced the sign-up bonus, so some of the information you’re seeing out there might be out of date. These aren’t affiliate links, by the way (I wish they were!).

Travelers are getting VIP airport lounge access, reimbursement for trusted traveler program fees, convertible points, lost/delayed luggage reimbursement, hotel and rental car upgrades, and concierge services. Make sure you have the best travel credit card for you before you go.

When we’re choosing a credit card, we’re looking for:

  • No foreign transaction fees
  • Cash back
  • Rental car insurance
  • Roadside assistance
  • Trip cancellation insurance
  • Trip delay insurance
  • Emergency medical and dental
  • Travel accident insurance
  • Purchase protection
  • Zero liability for unauthorized charges

There’s no need to buy separate insurance if you’re already covered through your credit card. Between the amount of traveling we do and the number of apartments we’ve renovated in the past few years, the cash back adds up.

It’s embarrassing to admit, but the rental car insurance came in handy when I scratched our car in Croatia. We used the trip cancellation insurance when a trip to the doctor’s office meant scrapping our plans to go to Europe. I’ve also used their warranty extension when big ticket items have broken right after the warranty expires, as they’re wont to do. When promised refunds aren’t made or stores fail to deliver, Chase makes it right.

The right travel card can save you thousands of dollars when things go wrong.

One last thing — regardless of what credit card you have, you’ll still want cash sometimes. Make sure your debit card will work wherever you’re going. This is especially important if your card doesn’t have a chip.


Go paperless

There’s no need to have someone collect mail for you while you’re away. Almost every bill can be sent to you through email.

Be sure to set up automatic payments. I check my bills regularly to make sure there’s nothing fishy going on, but I have no idea what day any of my bills are actually due.

Make sure your clients are ready to pay you electronically. It’s so simple, but some clients require serious hand holding to get this set up. I’ve had a startup founder insist on mailing me US paper cheques (luckily, Ally will let you make online deposits of up to $50k).

Upload everything to the cloud

I have copies of all my files on an external hard drive, but I don’t carry it around with me. Day-to-day, I keep all of my files on Google Drive. It’s an inexpensive, reliable, and convenient way to make sure I have access to all of my files, no matter where I am.

As an Android user, I have Google Photos set to back up all of my photos. While their facial recognition and search tools aren’t always as great as I’d like them to be, they do save me a lot of time. Remember the days of having to organize your photo files? Those days are over.

Get a library card

Nothing can replace the experience of curling up with a beautifully bound book. However, carrying around books is a real drag. Digital books means I can carry a dozen books without any extra weight. No wifi? No problem.

If you read as much as I do, buying books all the time really adds up. Casey has a Kindle and an Audible subscription and loves it. I have library cards at the New York Public Library and the Toronto Public Library, which give me access to thousands of audio and ebooks on OverDrive.

This is also the time to make sure you have an external battery, just in case.

Take care of things at home

Unless you’re selling everything you own (or were already living in your parent’s basement) you’ll be leaving a home behind.

If you’re traveling with Home Exchange, you’ll have someone at home to make sure your plants are watered and your pets are getting the attention they need. If not, you’ll have to make other arrangements.

Trying to coordinate repairs at home while you’re abroad is a nightmare. You’ll want to do routine maintenance before you go and look carefully for anything that might be in need of an upgrade.

  • When was the last time you replaced the pipes under your sink or the workings of your toilet?
  • Are any appliances on their last legs?
  • Is that light burnt out or broken?

Make sure you have someone you trust who can be your man on the ground in case of an emergency and give them a set of keys.

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