Friday Five: 5 Tips on How to Choose the Best Hotel

where to stay in santorini

I’ve mentioned Matt’s ability to pick hotels in a few of my travel guides (most recently here and here). It’s amazing. Personally, I struggle to pick a dinner restaurant, let alone a place to call home for a few nights. The information is down right overwhelming. Not to mention the stress of questioning your decision. So, I figured it might be helpful to hear how he chooses where we stay! After all, there’s nothing better than knowing you made the best choice, right?

Here are Matt’s tips for picking a good hotel…

Unless the extent of your travel is the neighboring city for Sunday Mass, then you know that TripAdvisor has rendered travel agents useless. This website has evolved into the very best and sole consultant when it comes to hotels, restaurants, or even things to do in specific cities. Just note that we always book the hotel through because of the great rewards. Jenna talked about that in her post on 5 tips to travel more often if you’re looking for more advice!

When Jenna and I begin trip planning, it usually goes something like this. Jenna tells me what country she wants to visit. We book the flight, then the keys are handed over to me to research, then book all hotels and restaurants throughout the duration of the trip. She plans what to see and where to shoot, I handle all the logistics. We’ve stayed in such a wide array of places from castles in Ireland to Country Inns in Asheville to boutique inns in Charleston.

At one time, this was both time consuming and overwhelming. But just like anything else, repetition eventually leads to comfort and ease. I’ve compiled a list of the five most important factors to weigh when attempting to separate the best hotel from the rest.

1. Traveler Photos

The hotel photos you find on travel websites are very similar to how you manage your personal Instagram.  It’s not exactly a breakthrough when I say that unfiltered iPhone photos are nothing like doctored, manicured and well thought out snapshots. The default photos on websites are only going to tell half the story. Back in my single days, if I really wanted to know what a girl looked like I’m not eyeing her posted photos, I’m looking at her tagged photos! I want limited makeup, bad angles, candid shots.

Hotels are no different. The Super 8 Motel in East St Louis probably looks like the Taj Mahal online, but in reality it’s most likely a half-way house. That’s why I always persuade people to browse through the “Traveler” photos on TripAdvisor. This is going to give you the best interpretation of the hotel property, views, and amenities. If you look through these and she still looks good, that’s when you know to make the commitment. One of the best examples of this was on our most recent trip to Santorini.

2. Hotel Details

I want to know all the particulars of a hotel before handing over a quarter of my monthly rent for a three night stay. Luckily for us, TripAdvisor makes this easy. You may or may not be surprised that some of the most luxurious and well regarded hotels on the globe will also nickel and dime you to death. Parking and breakfast is one thing, but internet? I expect that to be free. Be wary that sometimes the hotel details on TripAdvisor aren’t always transparent, so if something is free it will clearly stipulate.

To some it’s not a huge emphasis, but I personally love to book a hotel with free breakfast. But beware, “Breakfast Included” won’t cost you anything but “Breakfast Buffet” will. Same story with Wi-fi, if it’s truly free TripAdvisor will state Free Wi-Fi. If you’re renting a car, you’d be best suited to find a hotel with “Free Parking,” because “Parking” is going to add a $100 to your bill upon check out. So be sure to vet the “Overview” section properly, and make sure you browse through the “Hotel Details” to weigh the features most important to you.

3. TripAdvisor Awards

TripAdvisor issues two different awards: Travelers’ Choice and Certificate of Excellence. These awards are Green badges you will occasionally come across on the site.

Travelers’ Choice has been around for over 15 years, and is the highest award given on the website. It’s given to about 1% of hotel properties each year and usually encompasses the best of the best.

The Certificate of Excellence is no slouch itself and usually is given to hotels that demonstrate consistency. In order to even be considered for this certificate, it must meet this criteria: maintain an overall rating of 4 out of 5, have a minimum number of reviews, and been on TripAdvisor for over 12 months.

So when perusing through the website, keep an eye out for these badges.

4. Look Closer at the Ratings

TripAdvisor is known for its highly reputable and robust rating system. When booking your trip you should live and die by these ratings. While the 1-5 scale (and all the decimals in between) is a terrific indicator, I usually like to take a deeper dive into the data. So under that bold 4.2 there’s a percentage scale listed with five different criteria’s: Excellent, Very Good, Average, Poor, and Terrible. If you want to know if a hotel is worth that hefty price tag, it better be showing ~70% of ratings in the excellent category. And if you’re finding a questionable amount of terrible and poor ratings, steer clear like it’s the Zika Virus.

Lastly, while you’re browsing around that rating section you’ll also notice a breakdown of demographics. Filtering the “Traveler Types” can really give you a better answer depending on the purpose of your travel, i.e. business, couples, families, etc. So to summarize this bullet point, the holistic rating (example 4.2) is great and all, but before booking I would recommend looking at the numbers at a more granular level to avoid buyers remorse.

5. Best Value Filter

The last reason and probably the most important. Back in May, TripAdvisor shifted from their normal ranking system of top reviews to what they refer to as “Best Value”. This proprietary algorithm weighs ratings, pricing, popularity, location, and personal user preferences. All of those are pretty self-explanatory, with the exception of the last one. Nonetheless, I’ve found that this filter gives you hotels with the most bang for your buck. I still like to filter back to “Traveler Ranked” to compare and contrast options, but the “Best Value” system ultimately pits value against total traveler rankings, presenting the cream of the crop.

While TripAdvisor has shown they have the travel business down to a science, my opinions aren’t exactly scientific. Jenna and I aren’t travel experts, so if you have some TripAdvisor tips or vacation advice please share in the comments below! Browse more travel posts here.


11 thoughts on “Friday Five: 5 Tips on How to Choose the Best Hotel

  1. WOW! I never knew that TripAdvisor had so much information on it. Honestly, I’ve been to the site dozens of times and never realized how in-depth it could get. Thank you so much for sharing all these tips! This was insanely helpful.

  2. First of all what a beautiful hotel pictured in this post! These tips are great and will certainly be coming in handy because were about to start planning our baby moon x

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