Top 5 Mistakes When Planning a Vacation

Updated: Sep 3, 2020

So you finally have some time off 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 your trip, you’ve probably been through the stages of wanderlust and heavenly Instagram photos and have arrived at stage overwhelm.

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

Top 5 Mistakes You’re Making When Planning a Vacation 1. You rely solely on rating sites like Tripadvisor. 2. You try to see too much in too little time. 3. Assume you can’t afford it. 4. Assume group tours aren’t for you. 5. You don’t get in touch with a local.


1. You rely solely on rating sites like Tripadvisor. Don’t get me wrong, I’ve been known to cruise over to Tripadvisor to see what I can’t miss. But if I only rely on rating sites to know what to see and do, I would miss out on the things that make the trip special and unique. I suggest finding blogs about the destination, asking friends for recommendations, leaving time for wandering, and picking a neighborhood to explore with no plan- (rather than just making a beeline to sites).

Tip: My favorite site for finding quirky, off-the-beaten-path places is


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 and you want to see as much of it as you can. The FOMO is real. But try to visualize the pace you are setting for your trip and how you’ll feel at the end of those jam-packed days. Would you rather be rushed and exhausted or would you rather take a few destinations off the list so you have time to just wander and take in the details of the culture in a memorable and meaningful way?

Tip: It’s easy to get caught up in what we “should” see. Take a deep breath and ask yourself, “Would visiting X be meaningful to me?”


3. Assume you can’t afford it. Traveling can be expensive. For many, they just can’t afford that luxury no matter how they look at it. But before you rule it out, make sure you’ve evaluated the many tools and alternative options out there. This topic could be a thousand articles in itself (and indeed some have dedicated entire blogs to it).

Tip: My favorite way to save on travel costs is to pick a program on, which is how I lived for free with locals in Italy for a month in exchange for making some artwork for them. I also recently learned about an app called Acorns which rounds each credit card purchase up to the nearest dollar and “squirrels” it away into a fund that is invested for you with no headaches. Easy way to save!


4. You assume group tours aren’t for you. I used to steer clear of tours- who wants to be herded around with a bunch of people you don’t know and eat at restaurants catering to tourists? Gag me! But in the past few years, I’ve had to reconsider my former grudge. Some tour companies today are building authentic experiences that give you access to unique cultural opportunities that you otherwise couldn’t find on your own- like having a long lunch with locals in their home or dancing the night away at an ancient tower-turned-club in a field in the middle of nowhere.

Tip: Look for tours that limit the number of guests to 10 at a maximum. Read itineraries thoroughly and ask questions like “How much time will I have for wandering?”, “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?”. Check out our current trips here.


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 step out of your comfort zone can change your trip 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 found a language partner on in a city I knew I’d be traveling to and found myself a few months later dining with her family in their gorgeous farmhouse overlooking all of Florence- an unforgettable experience!

Tip: You can get started on sites like Couchsurfing, Italki, Showaround, toursbylocals, Viator, and don’t overlook the power of asking your network if they have any connections.

Making any of these mistakes, among many others, can pretty much waste a good vacation.

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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