Alexander Graham Bell once said, “Before anything else, preparation is the key to success.” It’s doubly true if you desire stress-free travel. It’s the little things you do beforehand that make all the difference on your journey. While I can’t guarantee you won’t hit bumps along the way if you follow this pre-travel checklist you’ll pave the way to a more relaxing holiday.
Before I jump in: I’ve put together a great trip-planning resource page with a lot of the important travel links and tips discussed below. Bookmark it and you’ll have all you need at your fingertips.
First Thing to Do For Stress-Free Travel: Research Your Destination
I’m all about serendipity and exploration but nothing is worse than returning home to find two miles from where you stayed was something amazing and you missed it. I learned this the hard way. Spending your time on little research should be one of the first steps when preparing for your trip.
In a nutshell: it’s the best way to hedge your bets.
Begin with The Classics
Ask your friends for recommendations and the tried and true Google search. Then take that list and dig a little deeper: use terms like “Most unusual experiences in [name of place]”, “Most Photogenic”, “Must-see” or “Best,” and you’ll find a list of posts with wonderful nuggets of information.
Look at the Local Tourism Board Website
For more practical info, search local tourism board websites for city or regional facts, local apps (see below), and the basics like weather during your stay, things to do, special events, and so on.
If you know the attractions you want to visit, look at their websites first. In addition to information on hours and location, you’ll often find directions via various modes of transportation, list of additional activities, unexpected restrictions, plus whether or not they offer workshops, lectures, or VIP benefits.
Let the 5-Star Hotels Point You in the Right Direction
Search the sites of 4-5 star hotels in your destination. Under headings such as “activities”, “around town” or “Things to do”. Many times you’ll find great ideas for restaurants, excursions, or non-touristy experiences you won’t find anywhere else.
Download Local Apps
Modern technology puts the world at your feet. Why not make it work for you, especially when you know you have a connection. Search the app store for the most relevant local apps based on your itinerary. Look for subway apps, stores maps, museum or airport layouts, travel guides, you name it. It takes very little time, most are free, and you’ll love having the information at your fingertips so you’re not scrambling at the last minute.
Confirm Your Hotel Has WiFi
If the realities of work and life don’t allow you to be off-the-grid, double-check your hotel has WiFi before you walk out your door. It may be the 21st century but I can’t assume my accommodation lives in it, especially in exotic developing countries. Even if it does, access may be limited, it may cost extra, or so antiquated it won’t support the files you use. Don’t find out after you’ve checked in. That’s the opposite of stress-free travel.
If You’re Going International, Double-Check Your Mobile Carrier’s Service
I came home after a trip to Kenya with a $675 mobile bill and wanted to throw up. It was my fault I didn’t research how Verizon would calculate my data plan and while I assumed it would be pricey, I was blown away by the fact that 20 minutes of 3G at the Nairobi airport waiting for my flight to JFK netted out to almost $700.
Every carrier is different and its best to assess your costs at the get-go. A trick for managing your fees is to engage airplane mode all the time. You can still access WiFi without dealing with all the roaming nonsense.
If now and then you have to dive into the great data plan vortex, knowing what you’re in will keep you sane.
Assess Your Needs at Least Two Weeks Before You Leave
When I first started traveling I packed the day before I went holiday and invariably realized I’d forgotten something I could easily have bought at home but now must spend stupid dollars in a foreign country. IF the stores have it. Definitely NOT stress-free travel.
After years of making myself crazy, I started a new tradition. Fourteen days before any major trip I go through my belongings and put aside the items I’ll pack for my journey. If there’s something I need the two-week window gives me plenty of time to order it and have it shipped directly. With Amazon Prime, shipping is free. Abuse it.
Yes, it requires a little effort but when the time comes to walk out the door it’s smooth sailing.
Invest in Travel Insurance
Don’t take a chance on losing a ton of money (or in extreme cases go into debt) when you don’t have to. Invest in travel insurance. Why? Let me tell you a couple of true stories.
- My father and stepmother were going on a big luxury vacation to Russia. A few days before they were to leave their dear friend fell critically ill and was in the hospital. They didn’t want to leave. Because they invested in travel insurance they recouped all their money. Happy days!
- Dave and Deb, two friends of mine who are professional travelers, were on an Amazon cruise when he slipped on some stairs and broke his back. If they hadn’t had travel insurance they would have paid a minimum of $50,000 to cover the costs of the two medevac units they needed to fly him out of such a remote location, the week-long stay in a Peru hospital to get him stabilized, and the air ambulance back home afterward.
At the very least, spend money on a policy that covers you for medevac expenses so if you’re in a remote or difficult destination you can be airlifted out and receive proper healthcare.
If you’re in the States, I promise you, getting hurt or falling ill in another country is NOT covered by your U.S policy. However, some premium credit cards do have travel insurance partnerships. It’s worth checking out.
If you’re not sure what insurance to use, visit Insuremytrip.com to compare and contrast different policies from the world’s best vendors.
Check for Vaccinations Requirements or Health Alerts
As a precaution, check to see if there are any vaccinations or medications required or suggested for your destination. I’ve listed them in my trip-planning resource page for easy access.
Check Your Passport’s Expiration Date
If you’re traveling internationally, check your passport expiration date and make sure you don’t need a new one. Stress-free travel only works if you’re able to enter the country you’re traveling to.
Most countries require passports to be valid at least six months prior to travel so its less about the actual expiration date as it is about the lead time you’ll need.
There are also countries that require two empty facing pages for customs’ stamps. If you’re an avid traveler and don’t have space, make sure you get a new passport.
Confirm If You”ll Need a Visa
No matter where you live, to find out if you’ll need a visa, you can do a quick check on TraVisa (or my resource page). The site will tell you whether your destination country requires a visa for American requirements based on your destination and your citizenship.
For American Citizens, another great resource is the U.S. Department of State’s website and Country information, it too provides passport requirements and visa needs plus a lot of other great information.
Check Your Prescriptions
Always include prescriptions in your travel preparations. Will you need a refill before your departure date? Will you run out before you get back? Don’t get caught on the wrong side of this scenario.
Stock Up on Basic Meds
There’s nothing worse than feeling ill on the road. Don’t make things worse by running around for meds while you’re sick. Pack a small Ziploc bag with the following over-the-counter medications.
- Products to relieve stomach upset/diarrhea/ constipation
- Aspirin or Ibuprofen for headaches and small aches and pains
- Antibacterial ointment for scrapes and cuts
- Antihistamine ointment for insect bites
- Eye drops for dry, dusty climates (If you chronically suffer from sensitive eyes like me, Systane and Zaditor are a lifesaver.)
As an extra precaution, speak to your doctor about prescribing an antibiotic you can take with you just in case. I spent an awful two days in Lima with a nasty something on my way to Machu Picchu. Thankfully, I cut the plague short by packing antibiotics for just such an emergency.
Let Your Bank Know Where You’ll Be
A few years ago, I walked into a store in Cambodia to buy knickknacks and my debit card was declined. I didn’t have another credit card with me (Tip: always bring at least two credit cards with you), and I didn’t have enough cash for the rest of my trip. Ouch.
It turns out that a scarf I’d bought the day before raised a red flag with the bank. Assuming I was at home in New York City, the bank’s computer system marked my purchase as was fraudulent and froze my account. It took me three hours I could have used sightseeing to get it sorted out. Now I notify my bank via my bank’s online portal before every trip outlining the dates, countries, and cities—including any layover city—I plan to visit. I haven’t had a problem since.
Stop Mail Delivery
If you don’t have someone to pick up your mail, have it held. Two minutes online with the United States Postal Service and you’re good to go.
Organize Your Electronics
I am a technology freak but I can be overwhelmed by the number of adapters and plugs needed to keep all my devices purring on the road. More than once I’ve looked at a pile of cords thinking I had everything only to learn too late, I didn’t.
In an effort to gauge my needs, I lay out all my gadgets—cameras, iPhone, external hard drives, etc on a table with their associated plugs and accessories. Then I figure what I need to take on the plane and what I will check, and place them into two piles. Next, I determine whether I’ll need an adapter my destination or any layover countries I’ll be flying through. I separate cords I will use more often (ie. my iPhone charger) and place them in a separate bag so they’re easier to find. I carry ALL my cords with me in my carry on bag
(Hint: if you buy a travel power strip, it makes things so much easier. You only need one adapter to charge 3 devices!).
Photography enthusiasts: Bring at least two extra batteries per camera body and a lot of memory cards. Nothing is worse than photographing something wonderful only to have your card run out unexpectedly. Be sure to reformat before each trip.
Pack a see-thru bag for carrying all the essential cords etc. that way during your trip you’ll know whether you’ve left something behind.
Leave a Detailed Itinerary With a Friend or Family Member
It’s always a good idea to leave a detailed itinerary with a friend or family member, especially if you can’t count on cell reception, and doubly so if you’re traveling solo or in a remote location. You want people to know where to find you if for some reason you go MIA or, God forbid, you’re sick or injured and cannot speak on your own behalf. It’s also critical if there’s a crisis back home and someone needs to reach you.
I give family members the following information broken down chronologically.
- Flight information
- Dates at each hotel (in order) plus contact numbers and website addresses
- Local/emergency contacts if applicable
- Your travel insurance policy number and emergency contact information
Set/Schedule Your Out of Office Email
People hate it when they think you’re around when you’re not. It leads to paranoia and thoughts you might be ghosting them.
I schedule my Out of Office messages the minute I confirm my travel dates. I also set a reminder to change my cell’s voicemail on the morning of my departure.
It’s particularly important when you’re going to remote destinations in Mongolia where technology is absent. In such cases, I leave instructions on my outgoing message detailing when I’ll return their call.
Make Copies of Your Most Important Information
Always take printed copies of your passport, credit card account numbers/emergency call numbers, itinerary and travel insurance details.
My smartphone “Notes” app is my go-to app when I travel, but I always pack a printed backup. Why? Because why risk being up poop’s creek if you lose your phone or it’s stolen? Or, as I’ve done on several occasions, realized at the worst possible moment that I accidentally let the battery run out.
What’s your favorite pre-trip advice for stress-free travel? I’d love to hear your thoughts in the comments.
More Great Trip Tips Worth Checking Out To Take the Stress Out of Travel
If you’re not sure whether you travel in a bubble, you may want to find out.
Try these tips if you dread sitting at the back of the plane.
Because I often have to work, even on my pleasure-based journeys, my laptop is always with me. But hours of looking down at the monitor had my muscles twisted in knots until I tried this remedy.
My favorite podcasts across a variety of genres including news, true-crime, great story-telling, travel, and photography.
You’ve never traveled alone but you’re itching to try it. Here’s how to begin.
If you need some essential travel items or maybe something specific for a cruise, safari or particular season, visit The Insatiable Traveler Amazon Store, it’s only products I use and love.
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