Avoid These 5 Embarrassingly Stupid Travel Mistakes This Fall
Fall is such a magical time to travel. The crowds have thinned out, the air is crisp, and the landscapes are bursting with vibrant colors. It’s the perfect season to hit the road, book a spontaneous getaway, or even splurge on that bucket list trip. But don’t let the beauty of the season lull you into making some very avoidable travel blunders. Whether you’re a seasoned jet-setter or just getting started, here are five really stupid travel mistakes you need to dodge this fall. Because let’s face it, nobody wants their vacation ruined by an “Oops!” moment.
1. Booking Flights Without Comparing Prices on Skyscanner
We’ve all done it at some point — gotten a little too excited about booking a trip and snapped up the first flight deal that popped up. But rushing into a flight purchase without comparing prices is a classic rookie mistake. Skyscanner should be your go-to for finding the best deals on flights anywhere. This tool searches thousands of airlines and online travel agencies, helping you find the lowest fares and most flexible options.
For example, last fall, I was planning a spontaneous trip to Boston to catch the fall foliage at its peak. I almost booked a roundtrip ticket for $350, thinking it was a decent price. But a quick search on Skyscanner showed me a better fare with a different airline for just $220! That extra $130 I saved went towards a stay in a charming boutique hotel in the city.
Don’t be that person who overpays for flights just because you didn’t take a few extra minutes to check Skyscanner. It’s a no-brainer that can free up a surprising amount of cash for other travel splurges, like a fancy meal or an upgrade to business class.
2. Packing for Summer When It’s Clearly Fall Weather
Fall can be unpredictable, with temperatures varying significantly between morning, afternoon, and night. A lot of people make the mistake of packing like they’re still in summer mode — shorts, tank tops, sandals, and not much else. While you might get away with this in a place like Southern California, fall in New England or Europe is a different story.
On a trip to Berlin a few years ago, I foolishly packed only light layers, thinking I’d be fine. I spent the better part of my trip shivering as temperatures dipped to the low 40s (around 5°C), and I ended up splurging on an overpriced coat because I simply wasn’t prepared. Learn from my mistake: always check the forecast and pack layers. Throw in a good scarf, a sweater, and a lightweight but warm jacket. You’ll thank yourself later when you’re cozy and comfortable instead of freezing and running up your credit card buying last-minute gear.
Speaking of credit cards, if you’re looking for a travel card that can help you earn miles and points towards free flights, look no further than the American Express Gold Card. You can get 90,000 miles as a welcome bonus when you sign up through my exclusive link. Make it your go-to card for everyday purchases, and you’ll be flying for free in no time.
3. Forgetting to Purchase Nomad Health Insurance
Health insurance is one of those things you don’t think about until you need it. And trust me, the last place you want to realize you don’t have coverage is when you’re in a foreign country trying to figure out how to say “emergency room” in the local language. Fall travel often includes outdoor activities like hiking, exploring historic sites, or renting a bike to cruise around a new city — all things that come with their own set of risks.
Invest in Nomad Health Insurance by SafetyWing for comprehensive coverage that protects you abroad. It’s one of the best choices for digital nomads, frequent travelers, or even just occasional wanderlusters. Their policies cover a variety of situations, including medical emergencies and travel disruptions, and the price is unbeatable for what you get.
On a recent trip to Costa Rica, I was enjoying a hike in the cloud forests when I twisted my ankle. The last thing I needed was to be hit with a massive medical bill. Luckily, my Nomad insurance had me covered, so I could focus on getting back on my feet — literally — without financial stress.
4. Not Using the Ultimate Travel Guide for Your Destination
Planning an amazing trip involves more than just booking flights and packing your bags. Not having a plan, or at least a rough itinerary can leave you wandering aimlessly or missing out on the best experiences. It’s not enough to just show up in a city and figure it out as you go — that’s a great way to end up at overcrowded tourist traps or eating at overpriced, mediocre restaurants.
The Ultimate Travel Guide is your answer for seamless travel planning. These guides give you a done-for-you itinerary that covers the best places to eat, sleep, and explore without any stress. Whether it’s finding hidden gems off the beaten path, knowing the best times to visit top attractions, or having all your transportation mapped out, these guides take the guesswork out of travel. Plus, if you prefer even more help, we can plan the entire vacation for you, down to the last detail. That way, you can spend your fall trip soaking in the scenery instead of stressing over logistics.
I remember a fall trip to Rome where I winged it, thinking I didn’t need a detailed plan. Big mistake. I wasted precious hours in line for major attractions and ended up missing out on several cool spots that I didn’t know about until it was too late. Lesson learned: travel smarter, not harder.
5. Skipping Viator Tours and DIY-ing Everything
We all love the idea of saving money, but sometimes, trying to do everything on your own can cost you more — in both time and missed experiences. Viator offers incredible guided tours and activities that can take your trip to the next level. From private walking tours of historic cities to unique cultural experiences like pasta-making classes in Tuscany or a Northern Lights chase in Norway, Viator’s got you covered.
On a fall trip to Kyoto, I initially planned to just walk around and see where the day took me. But after struggling to navigate the city’s winding streets and trying (and failing) to find a hidden temple, I quickly realized I was missing out. I booked a last-minute guided tour through Viator and got to see everything I wanted, plus some hidden gems I wouldn’t have found on my own.
A guided tour can add so much depth to your travel experience, and with Viator, you can find tours that fit any budget. So, skip the DIY approach for a few activities and let an expert guide show you the ropes — it’ll be worth it.
Traveling this fall? Don’t make these five really stupid mistakes. With a bit of smart planning, you can enjoy an amazing trip without any unnecessary headaches. Whether you’re exploring charming fall destinations, catching festivals, or enjoying outdoor adventures, remember to compare flight deals on Skyscanner, pack smart, grab travel insurance from Nomad Health Insurance, use the Ultimate Travel Guide for a worry-free itinerary, and book some awesome experiences with Viator. Oh, and if you haven’t yet, it’s high time to get your hands on the American Express Gold Card for those 90K bonus miles. Trust me, it’s a game-changer for affordable luxury travel.
Until next time here’s to smooth skies, good company, a journey full of happy memories. I’m your Travel Hack Guide to affordable luxury tips. Catch you later. Peace
Travel Hack Guy
