Travel is magic.
It will make you more independent, resourceful, creative, and resilient. But travel also demands blood, sweat, and tears.
My guiding principle for deciding on topics to write about is “pick flowers, not weeds”. But I feel it’s also important to get a balanced perspective on a topic as important and transformational as travel.
I’m not trying to discourage you from getting on a plane – quite the opposite. I want you to return to your home after the trip with a broader perspective of the world, a more open mind, and a feeling of increased connectivity. Not limping, broke, and dejected.
A big part of travel is risk management – looking to the future to identify things that can go wrong, and taking appropriate action to avoid unnecessary suffering.
In saying that, it’s impossible to avoid every inconvenience or apparent negative experience. And in my life, I’ve sometimes found that what appeared negative at the time, became the fertilizer for significant personal growth later.
But if I can help make your road a little smoother, then I will.
I want you to have a wonderful travel experience because it will change your life, and others around you, for the better. So here are my first-hand tips for how to prevent the worst travel problems before they happen.
1. Get Travel Insurance
When tackling a large number of potential travel problems, it pays to start with the biggest ones first. Travel insurance can literally save your life. You hope you’ll never need it, but if that unfortunate day comes, you’ll be glad you’ve got it.
I have used Safety Wing for years, and heartily recommend it. It’s a travel medical insurance designed for long-term travellers, but anyone can apply for it – even if you’ve already started your trip, or your trip only lasts 1 week. There’s no need to tell Safety Wing about your itinerary in advance, which gives you more flexibility. Be sure to read the terms and get familiar with all inclusions and exclusions, so there are no surprises later. And keep your travel insurance info within easy reach in case you need to make a claim. Signing up online only takes a few minutes, and is super easy.
2. Ensure Your Passport is Ready
Most countries will require at least 6 months remaining on your passport (and at least 1 blank page – yes, that’s a real problem for frequent travellers!). It can take days or weeks to renew your passport, so sort that out at home and give yourself plenty of time. Don’t leave it to the last minute.
3. Know Visa Requirements
Speaking of passports, check the visa requirements for the countries you want to visit, and how long those visas are valid for. For example, if you’re only allowed to stay in Thailand for 30 days, don’t plan a 6-week holiday there. I know it sounds like common sense, but I’m still shocked at how many times I hear travellers getting into hot water because either they didn’t know or didn’t pay attention. Almost all immigration departments will count the day you enter and leave as a “whole” day, so don’t count the usual way.
4. Research Everything
This is where the rubber hits the road. Become the all-knowing, all-powerful guru of (enter your desired city or country name/s here). Gather all the information you need, so you know what to expect from your destination, and can make a clear game plan (at the next step). It’s all on the Internet at your fingertips, and you know how to use Google, so there’s no need to pick up a physical travel guidebook anymore.
The devil’s in the details. Research topics like accommodation, transport, attractions, tours, and food. And then research some more. Some common topics to get you started:
- What area of the city will be most suitable for accommodation (closest to attractions, restaurants, public transport, etc)?
- What are the must-see attractions, as well as some off-the-beaten-path attractions? Which attractions require bookings ahead of time?
- What are the essential foods to try?
- What transport options are available, and fit best for the upcoming trip – buses, trains, car rental, rideshare, e-scooters, etc?
- Relevant seasonal information – is the location only open certain months each year, or are there seasonal storms or floods? What’s the weather like?
- What airlines fly to the destination, and when are the cheapest flights?
My suggested benchmark for beginners is 1 day of research and planning for every 1 day of intense travelling. The time you invest now will pay dividends when you’re calmly and confidently strolling around a city, rather than rolling into a fetal position on the side of the road.
5. Plan Like You’ve Never Planned Before
It’s one thing to know what you want to do, it’s another thing to have a clear, easy-to-follow itinerary. This is where the majority of travel problems are nipped in the bud. Take all the information you’ve gathered at the previous point, and start painting a beautiful picture with it.
Make sure everything in your travel plan fits together, so there’s no ambiguity. For example, what’s the nearest metro station from your hotel, and how far is the walk? Get all the details for bus and train routes, what times they run. What attractions and restaurants are located close to each other? Group these together so you’re not wasting a single moment of your precious trip.
Remember to check the opening hours of restaurants ahead of time – ahem, I’m writing this sentence for myself more than anyone else.
Find out how to get from the airport to your hotel – train, shuttle bus, public bus, rental car or taxi? And how long will it take? Remember, if you arrive late at night, the available options might be fewer.
If I had a dollar for every time someone said I’m so lucky when my travel plans work out smoothly, then I’d retire. Listen up, people! It’s called “planning”! Luck has nothing to do with it.
Repeat after me… Josh says “Plan like a MOFO until you eliminate FOMO”.
How do you know when your plan is complete? You’ll be able to explain it to a stranger who’s never been to that city, and they’ll have all the information they need.
Inspiration: How to plan a trip to Europe (includes a free spreadsheet!).
6. Make a Plan B and C
Even the best plans can be thrown into chaos when something unexpected happens. So have sufficient backup plans in place. For example, I always research more restaurants and attractions than I’ll need, in case of an unexpected closure (like a certain Parisian vegan patisserie that closes for 1 month over summer each year, cough cough).
A tightly-packed travel plan will be at risk of the dreaded domino effect – one single delay can flow on to cause more delays in subsequent days (or weeks). For example, last year, an airport strike in Italy meant there was no way I could fly to London as scheduled, and future flights were all booked up (since it was summer), so I had to get creative, think on my feet, and find a new flight from Bari, 4 hours away by train. I lost one day in London from a 4-day stay, and had to squash my plan into 3 days. Fortunately, this wasn’t a nightmare because I built a little flexibility in my itinerary by prioritising specific attractions, tours, and food experiences as “A”, “B” or “C” priority. Instantly I could tell what items were less important and drop those from the plan without sacrificing the more important ones. No sweat.
7. Compare Reviews
Before you book a hotel, tour, or tourist discount card, look for blog posts that shed light on the experiences of other travellers. There is (sometimes) wisdom in the masses. Pay attention to common highlights and pain points, so you better know what to expect, and can decide if that’s the right fit for you.
8. Read Between The Lines
In contradiction to the previous point, sometimes it pays to ignore, or even better, decipher the real meaning behind reviews. Not all reviews are created equal, especially on user-generated content (UGC) sources like TripAdvisor, Booking.com, and Google Maps. It’s easy for inexperienced, uneducated individuals to write whatever they want, which results in conflicting viewpoints and widespread confusion. This is where you have to put a detective hat on, and learn when it’s the right time to listen to other people’s experiences or ignore the noise. For example, I read a Booking.com review about a hotel in Zakynthos, Greece, that complained about being too close to the nightlife hub with lots of noise, but that is exactly what I wanted (and I’m a heavy sleeper too), so I ignored that complaint.
9. Have A Clear Fixed Budget
Set a very firm budget and stick to it. You don’t want to run out of money in a foreign country. That means for all major trip elements (flights, buses/trains, car rental, accommodation, food, tours, attractions, entertainment), decide how much to spend, either overall or per day/week. And then simply don’t go over that limit, regardless of how tempting it might be. If you go over 1 element, make up for it by saving in another.
Regardless of how much money you save up, ensure you have enough set aside for flights back home (if you didn’t book them in advance). And if you’re planning to travel for an extended period, you really need at least 3 months’ worth of expenses saved in advance, so there’s a buffer in case of a sudden change in income (eg. you lose your remote job or the stock market takes a dive).
I am bamboozled by travellers who run out of money because of a lack of planning.
If you need help making a budget, check out my step-by-step process (and a free spreadsheet) in this article.
10. Pack With a List
Forgetting something back home after you’ve already landed in a new destination creates a murky sinking feeling in your gut. So, visualise everything you will need on your trip weeks before departure, and write it all down. I find that throughout the course of the day, I’ll think of something new and keep adding to the list. That way, the night before departure, when the empty suitcase comes out, I don’t have to wrack my brain. If you’re travelling with a friend or partner, share the list so you’re on the same page and avoid doubling up.
11. Pack Most Important Items in Carry-on
Here’s an important question… if the airline loses your luggage, can you live without it for a few days? All your important documents, medication, valuables, and electronics should be packed in your carry-on bag, not a checked-in suitcase.
12. Weigh Your Luggage
Aim to be at least 0.5kgs below your allowance, as most airports skew the scales in their favour. Nasty but true. You don’t want to waste your hard-earned money on excess baggage fees when you could use it for cocktails by the beach. If your carry-on or checked luggage might be overweight, keep a mental plan for ways to reduce the load. Recently, I got stopped by a young, overzealous ground crew at Kuala Lumpur International Airport, and rather than paying extra fees, I took out my jacket and loaded the pockets with the heaviest items in my bag. Then relished the deflated expression on their face when they realised my bag was now within the limit, and I won the game. I walked away, around the corner, opened my carry-on bag, and emptied my pockets back into it. One point to Josh.
Bonus tip: Leave at least 1kg of spare weight in your suitcase if you’re planning to buy souvenirs.
Another bonus tip: If you don’t have a dedicated luggage hand scale (which are pretty cheap on Amazon), just use a bathroom scale and stand on it with and without your bag. Do the math, and you’ve got the luggage weight. Presto!
13. Maintain Your Inventory
Take photos of everything in your suitcase, especially the more valuable items. And then create a spreadsheet that includes the item name, date purchased, value, and serial number (for electronics). This means if any item gets stolen or damaged you’ll have the required info handy to make a quick insurance claim. I also kept a folder of photos for receipts of all expensive items – preferably in a cloud storage service like Dropbox or Google Drive.
14. Check and Re-Check Your Flights
Check your flight status a couple of days in advance, and before you leave for the airport. This ensures you’re aware of any cancellations or delays. Allow sufficient time for transport to the airport – especially when relying on a taxi. And if travelling by road, keep in mind traffic jams during peak hours. I prefer to leave a decent buffer of time so I’m not cutting things too fine.
Tip: Search Google for “flight status (your flight number)” and many times it will give you the live status. However, this isn’t available for every airline.
15. Understand Airline Policies
Airline policies vary greatly, and compensation programs also vary between countries/regions. It’s important to know the small print before you get into a pickle, so you can stand your ground and demand your rights. How many changes are you allowed (if any), and what is the fee if you need to change your flight (or is that even possible)? Some airlines now include 1 free change if you test positive for COVID-19.
I was in a situation last year when an airline cancelled my flight, so I had to re-book an entirely new route, and I clarified with them that this wouldn’t use my “1 free change”, to which they agreed. The day before departure, I had a positive COVID test and had to reschedule that same flight. They claimed I used up my “1 free change”, but I stood my ground and had to stay on the phone for hours (even while I was sick) but managed to eventually speak to someone who recognised the airline’s mistake and allowed me to re-book for free.
16. Keep Important Contact Details Handy
Write down phone numbers for travel insurance, bank fraud hotline, local emergency services, tourist police, your hotel, and your embassy. In the unlikely event that you’ll urgently need these, you’ll be glad that they are within easy reach so you’re not scrambling around like a mad chicken. Keep a digital copy in Google Keep and printed copies in multiple bags.
17. Be Realistic With Your Time
It will usually take longer than you anticipate to get between locations via public transport, or through a particular tourist attraction. Give yourself a little breathing room – you’re meant to enjoy a vacation! Allow sufficient time to recover from jetlag for west-east flights longer than 4 hours. And on longer trips (over 2 weeks), give yourself some “down days” to rest your body and mind.
18. Be Realistic With Your Fitness
Do you have the stamina to walk 25,000 steps per day for a week straight with no rest days? If so, great. If not, don’t ruin your vacation. During the planning stage, if you recognise you’ll be doing a lot more walking than you’re used to, start a daily fitness routine today.
19. Be Mindful of Security Threats
Bag snatching or pickpocketing is more common in larger cities. Don’t flash your cash, and don’t look too glam. Be aware of your surroundings and stay alert. Don’t share your hotel details (especially room number) with strangers – even taxi drivers. On my most recent trip to Europe, I wore shorts with theft-resistant zippered pockets.
20. Wear Sunscreen
This isn’t just a line from a catchy 1990’s Baz Luhrmann song. If you’re heading to a summer destination (or snow as well), slap some high-SPF sunscreen every day and re-apply every 2-3 hours. It’s not fun having a sore everything, preventing you from enjoying your much-needed vacation.
21. Consider Foodborne Illness Risks
I’m a fan of trying local foods at every new destination. It’s part of the cultural identity, after all. Some destinations are riskier than others. But when in doubt, I highly recommend Travelan, a little tablet that prevents most cases of travellers’ diarrhoea. It’s not fun ruining a holiday by puking your guts out for days, or even ending up in a foreign hospital.
22. Bring Backup Food
Bring a couple of easily portable meals (such as instant noodles) for those moments when you just don’t have the energy to leave the hotel room, and working out the most popular food delivery app in a foreign language does not inspire thoughts of joy. This happened to me in southern Thailand, and I had to ask the hotel front desk staff for assistance in ordering through a local app written entirely in Thai.
23. Build a First Aid Kit
Bring (or buy) inspect repellent if you’re travelling to a location with mosquitos. Also, pack a basic first aid kit with a bandage, adhesive bandages, antiseptic cream/gel, paracetamol, allergy medication, and anti-nausea meds. I take this wherever I go, and a few times it saved the day.
24. Break Down Language Barriers
It’s easy to get frustrated when you’re in a new country and can’t speak or read the language. I’ve experienced this more times than I can count. But now I download offline languages for the Google Translate app (iOS, Android). This helped me in Turkey recently when the landlord couldn’t speak a word of English, so I turned on “conversation mode”… it saved the day.
25. Get Your Debit/Credit Card Ready
Ensure your preferred card is activated for offline payments and overseas transactions. Depending on your bank, this may be controlled via the online banking mobile app or you may need to call them. Some banks also prefer to know in advance if you’re travelling overseas.
I got stuck once at a car rental agency when my bank at the time blocked my credit card because they thought the transaction was suspicious. My internet connection was too slow to make a VoIP call and get the card unblocked. A nightmare!
The Wise debit card does a great job of cross-border transactions with low conversion fees. Highly recommended.
26. Use Virtual Debit Cards for Risky Transactions
Some destinations present a higher risk of fraud than others. One solution is to make contactless payments in-person with Google Pay, Apple Pay, or Samsung Pay. These services generate a unique card number for every transaction, whenever you tap your NFC-enabled phone on a payment terminal, lowering your risk of card skimming. In addition, online payments can be made using a “virtual” card if your bank supports it – Wise does. The less often you use your physical bank card, the better.
Losing access to a bank card mid-trip can be a disaster. So have at least 1 backup card available.
27. Bring Enough Cash
Have enough cash on hand for the length of time you’ll spend in a destination. It’s easy to go cash-free in places like London, but many other parts of the world still work on the concept that cash is king. You don’t want to be stuck somewhere without enough cash to get you out or put a roof above your head. This tip goes hand-in-hand with the previous 2 points about managing risks related to your payment cards. Keep your cash in safe places, and never unattended. If your hotel has a safety deposit box, then use it. And only bring enough cash with you for each day when sightseeing – reducing the potential damage from pickpocketing.
28. Keep Your Phone Backed Up
Use cloud-based apps for your most important data and photos, like Dropbox or Google Drive. So, if your phone is damaged or stolen, your most important data is not completely lost.
29. Take a Powerbank Wherever You Go
I rely heavily on my smartphone for everything. A flat phone battery can create a lot of frustration and throw your travel plans out the window. Make a habit of charging your powerbank every evening before going to sleep.
30. Don’t Use Unsecured Public WiFi
It’s simply not safe. Hackers prey on unsuspecting tourists who are desperately drawn to public WiFi networks like moths to a flame. It’s better to use an international eSIM or VPN service, or both. I learned this the hard way, when I connected to a public WiFi network in a hospital, and within minutes, hackers got into my Instagram account, and poof… 160,000+ followers disappeared. Ouch!
Tip: I recommend aloSIM for great value travel-friendly prepaid eSIM plans.
31. Compare Accommodation Pictures to Real Life
When using Booking.com, Agoda, Flatio and similar platforms, keep your booking details handy (make screenshots for offline use, if needed).
I had an issue in Turkey where the landlord owned multiple apartments in the same building and gave me one that didn’t look anything like the pictures on Booking.com. I had to stand my ground and argue with them (through Google Translate), and finally, they agreed to give me the apartment I was expecting.
32. Dress Appropriately
Clothing customs might be different in your destination country than at home, so research these before packing your suitcase. Don’t draw unwanted attention when in public. Avoid wearing flashy jewellery or expensive designer clothes. Otherwise, you’ll be a highly visible beacon for thieves.
And ensure you pack appropriate clothing for the weather. I took a road trip in Australia to an area that experienced 70km/hr winds off the Southern Ocean. Let’s just say a tank top didn’t cut it. Brrrrrr!
33. Understand Cultural Norms
These can range greatly depending on your destination. And a little background research can avoid all sorts of dramas. For example, it’s common in Europe to charge for toilets. So don’t walk into a Parisian café and use their toilet without asking or purchasing anything, unless you enjoy getting yelled at in French.
34. Avoid Relationship Stress and Breakdown
Travel can cause stress and frustration. There’s a popular saying “You don’t really know someone until you travel with them”. Take your friend or travel partner out of their comfort zone and familiar surroundings, and watch how they adapt and adjust (or don’t). Lack of communication is central to most relationship breakdowns, so don’t be afraid to be brutally honest with your friend or partner. Be flexible with your plans, but don’t compromise your happiness.
The Bottom Line
Travel is all about the inner journey that will bring forth the best in you. It will create new dizzying highs, and hopefully, by following my tips, you can dodge the lowest lows.
I’ve discovered transformative travel is made of 3 entwined components – preparation, positivity, and flexibility.
My approach to organising travel is to “plan for the worst, but expect the best”. Once you’ve covered all the bases as well as you can, dedicate yourself to choosing an optimistic perspective. A positive mindset tends to attract more positive experiences and people – it’s the nature of the universe.
And after you’ve followed all of the above, just go with the flow and be flexible. There are some things that will happen, no matter how hard you try to avoid them. And the more you put energy into avoiding, the more inevitable it becomes. This might seem contradictory to my advice on optimism, but that’s how life goes.
So, take a deep, slow breath and find calm and peace in the easy times, as well as the hard times. Remember that steel is forged in fire, as is your character. So, any challenge you face and learn from will only make you stronger and wiser. When you master the ability to cultivate joy in every circumstance, then you’ll become invincible.
Oh, and remember… don’t take yourself too seriously.
Life is short. Enjoy it.