Top 5 Mistakes When Planning a Vacation (And How to Avoid Making Them)

Updated: Mar 3

So you’ll finally have some time off from work or school and you’re out to make the most of it—congratulations, you’re going on an adventure! If you’ve already cozied up in a coffee shop to start planning a vacation and travel itinerary, you’ve probably already been through the stages of wanderlust and heavenly Instagram photos and have now arrived at this stage: Overwhelmed.

Having planned countless international trips for both clients and myself, I know the feeling. If what you’re looking for on your trip is an authentic and meaningful cultural experience, then you’ll want to avoid the big mistakes that land so many other tourists with a frustrating, exhausting vacation.

The Top 5 Mistakes You’re Making When Planning a Vacation

1. You rely solely on ratings and reviews sites like TripAdvisor. 2. You try to see too much in too little time. 3. You assume you can’t afford the vacation you want. 4. You assume guided group tours aren’t for you. 5. You don’t get in touch with a local.

Read on for my insider bonus tip for combatting each of these travel planning mistakes!


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1. You rely solely on ratings and reviews sites like TripAdvisor. Don’t get me wrong, I’ve been known to cruise over to Tripadvisor to see what I absolutely can’t miss at my destination. But if I only relied on these sites to know what to see and do when I’m planning my travel itinerary, I would miss out on all the things that would make the trip special and unique.

Instead, I suggest finding travel blogs specifically about your destination, asking friends for recommendations, leaving time for wandering around, and picking a neighborhood to explore with no plan (rather than just making a beeline to the main tourist attractions).

Pro Tip: My favorite site for finding quirky, off-the-beaten-path places to visit and explore is Atlas Obscura. They focus specifically on hidden spots around the world, deep cultural traditions, wonders of nature, and more. This is a great resource to boost your travel itinerary with places to visit that you might never have even heard of!


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Tired-Tourist

2. You try to see too much in too little time. I get it: you don’t know the next time you’ll be back in that part of the world, so of course you want to see as much of it as you possibly can. The FOMO is real! But try to imagine the pace you’re setting for your vacation and how you’ll feel at the end of those jam-packed days.

Would you rather be rushed and exhausted, jostling with other tourists all day at a bunch of monuments? Or would you rather take a few items off your travel itinerary so you have more time to just wander around, soak in the local culture in a memorable and meaningful way, and really experience the essence of your destination?

Pro Tip: It’s so easy to get caught up in what we “should” see when planning a vacation. Take a deep breath and ask yourself, “Would visiting X be meaningful to me?” If you’re not that interested in art, maybe you don’t need to go to every museum. And if you’re short on time, it’s totally okay to not go to ANY!

If you really like the outdoors, maybe you can skip the crowded tourist area in the center of town and go on a scenic hike outside of the city walls. Make sure your trip is centered around what you enjoy, not what everyone else thinks you should do.


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3. You assume you can’t afford it. Traveling can be expensive. For many, they just don’t think they can afford that luxury no matter how they look at it. But before you rule it out or cut back on your dream vacation plans, make sure you’ve evaluated the many tools and alternative options out there.


This topic could be a thousand articles in itself (indeed, some have dedicated entire blogs to it). If you go in with the mindset that you can’t afford all the things you want to do, you won’t be as excited about your vacation or as motivated to save for it.


Pro Tip: My favorite way to save on travel costs is to pick a program on http://www.workaway.info, which is how I lived for free with locals in Italy for a month, in exchange for making artwork for them. I also recommend an app called Acorns, which rounds each credit/debit card purchase up to the nearest dollar and “squirrels” it away into a fund that is invested for you with no headaches! It’s the perfect way to save some cash for your vacation without even noticing that it’s missing. Every cent adds up!


For more tips and tricks, you should check out my “10 Easy Ways to Save Money for Travel” blog post. In it, you’ll find so many simple methods to save for your dream vacation!

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Tourist-Group-in-venice

4. You assume that guided group tours aren’t for you. I used to steer clear of guided tours on my vacations—who wants to be herded around with a bunch of people you don’t know and eat at restaurants only catering to tourists? No thanks! But in the past few years, I’ve had to reconsider my former grudge.

Some guided tour companies today (Creative Edge Travel included!) are building truly authentic travel experiences that give you access to unique cultural opportunities you otherwise couldn’t find on your own, like having a long lunch with locals in their home, or gathering chestnuts in a forest and then cooking traditional recipes using chestnut flour at an abandoned mill by a stream.

The right group tours are an amazing way to tackle new adventures, make friends from all over the world, and get a true taste of what everyday life is like in your destination. But don’t worry, if you’re still skeptical about sharing your vacation time with others, we also offer private, custom experiences!

Pro Tip: Look for guided tours that limit the number of guests to 10 at a maximum. Read the travel itineraries thoroughly and ask questions like “How much time will I have for just wandering and exploring?”, “Could I see these places and book these tours on my own, or are they really unique?,” and “Does it bring me to an area I would have trouble reaching on my own?”. If you’re looking for an immersive cultural experience on your next vacation in Italy, check out our current trips and itineraries here.


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5. You don’t get in touch with a local. I realize this can be daunting—how can you possibly connect with a stranger in a foreign country? But you’d be surprised by how much this one tiny step out of your comfort zone can change your vacation for the better.

Most people around the world are thrilled to share their culture with someone new and learn about theirs as well! For example, I connected with a language partner on Italki.com in a city I knew I’d be traveling to. A few months later, I found myself dining with her family in their gorgeous farmhouse overlooking all of Florence, which was a truly unforgettable experience! (*Don’t forget your safety precautions though. You can’t trust everyone you meet online.)

Pro Tip: You can get started on sites like Couchsurfing, Italki, Showaround, or Tours by Locals, and don’t overlook the power of asking your network if they have any connections in your destination!


Making these travel planning mistakes, among many others, can sour an otherwise great vacation. You want to make sure you have the best time you possibly can, so why risk it? Follow along with our blog for more advice on how to make the most of your next vacation with some practical travel tips, our packing list, and free guides. For a unique and authentic adventure in Italy, be sure to take a peek at our upcoming experiences in Italy!


Creative Edge Travel offers small group and custom trips to the lesser-known areas of Italy. Visit our Upcoming Trips page to see where we’re headed next!

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