Travel: How To Book a Trip

Today I wanted to try my best and answer a question from a very nice reader, Florence, who sent me the following email:

I’m contacting you to see if you could possibly share your thoughts on the process of booking a holiday. It doesn’t’ matter if it’s a city trip, jungle trek or beach holiday. You’re obviously good at researching and finding the best spots thus I’d like to have insights about what your cues are for finding a great restaurant, the best neighbourhood to stay at, the most wonderful hotel, the best room in the hotel or even how to find a great destination. There is so many information on the net these days that I find myself a little bit overwhelmed.

I am very happy to share my thoughts on how I book a trip – from the very beginning – though I am far from an expert in this arena. What I am, is somebody who enjoys travel, and tries to do it quite often. And that itself is my first tip for booking a holiday efficiently and effectively – the more you do it, the better you will be at it! After a while, you will be a pro, for sure.

All right – now let’s start walking through my process of booking a holiday!


Hanging out with the penguins in Cape Town

1. The destination. This is where I always start. Others might start with a particular restaurant, or sight, or hotel, but I start with the place. Somewhere old, or somewhere new? I am fortunate to have a good number of friends with more travel experience (and much healthier travel budgets) than me, and I usually can find lots of inspiration from them – I hear about an awesome new holiday and add it to the list in my head. Or I read something from a book, or see a place on TV – anywhere. Believe me, once you start keeping your eyes and ears open for great destiatnions, you’ll see they are all around you!

If you’re still having trouble thinking of a cool place, go to your local bookshop! Head to the travel shelf and pick up some books. Here are a few that I suggest leafing through:


National Geographic: World’s Best Travel Experiences – my favorite!

National Geographic: Journeys of a Lifetime

Lonely Planet Best In Travel 2014 – found this one while bored at Urban Outfitters (I feel too old and crochety for 99% of the apparel section now).

2. The accommodation/neighborhood. Have you ever had a friend visit and taken them around to show them your area? Or had a friend take you around? Then you should know how important the neighborhood and accommodation are. They can make a great destination seem dreadful (unfortunately I’ve had a few experiences like this), and a so-so place charming and lovely.

Some people start with the sight they want to see when they are figuring out a neighborhood, but in my opinion, that can end up backfiring (can you imagine how happy you’d be with your trip to New York if all you did was try and find the closest hotel to say, The Statue of Liberty?).

Instead, I like to first start with a list of the hotels I like first, no matter where they are. Then, I choose the top 3-4 candidates, and map them out on Google Maps. I’ll take a look at a macro view, seeing where each of them is, and then will zoom into each of the neighborhoods. Are there lots of restaurants nearby? Good shopping, and local sights? Usually at that point, and armed with an idea of the prices, I have enough to make a decision on hotel + neighborhood.

Our villa's ocean view in Bali

Our villa’s ocean view in Bali

3. The best room in the hotel. For this, I use the hotel’s website for photos/square footage. I also read Tripadvisor “room tips” section and focus in on the specific recommendations. Finally, if I’m still unsure, I’ll email the property and specifically ask for a room recommendation/placement with the criteria I’d like: king bed, new bathroom, quiet area, away from the elevator, etc. Because of these steps, I’m usually satisfied with the rooms I’ve received at hotels of all different types of calibers (though yes, I’ve also experienced the occasional fleabag!).

Matzo ball soup in Budapest

Matzo ball soup in Budapest

4. Great food. Food is a huge component of wherever we visit. We all have to eat, right? And food is one of the best ways to experience local culture. If you’re me, that means you’re eating at least three times a snacks. For recommendations, I usually rely on three sources.

Tripadvisor: I find Tripadvisor recs to be very good at identifying bad spots – but not always necessarily the good places. This is because I feel like in certain cities, the top “recommended restaurants” tend to be those focused on tourist business. Tourist friendly and good food doesn’t always have to be mutually exclusive, but sometimes you don’t get the full “local” flavor and ambiance you might be looking for (though you’ll probably get an English menu).

Chowhound: Lots of great tips in here, but I often don’t have the patience to peruse more than a few threads (which is usually enough for my purposes).

The concierge/local travel guide: If we’ve hired a local guide for our destination, I’ll always ask them first for advice. Next, I’ll ask the concierge. I’m very specific for both, especially the concierge. I’ve found that some concierges at many hotels, including top ones, seem to direct clientele to the same places over and over again. Sometimes its laziness, sometimes its what a “typical” customer of that establishment may like, sometimes they may be even getting a kickback. To try and mitigate this, I’m always very specific: “Dinner for two with alcohol around $XX, great local foods, casual enough that I can wear a t-shirt, within X miles of this site.” I find that most concierges like a more challenging task, and find it even fun to try and find the perfect place for you!

Honorable mention: Yelp. Of course in the U.S. Yelp is great – but outside not so much. When in the U.S. and certain international cities though, check Yelp – you may be surprised!

All right, and there you have it – my high level process of booking a holiday, starting with destination, neighborhood, hotel room selection, and food. I originally was going to cover sights, but those are so personal that I figured I might tackle that topic another day. I hope this was helpful, and please share your own processes for booking holidays, I’m sure other readers (and myself) would love to hear them!

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  • Anonymous
    April 21, 2014 at 8:17 am

    Beautiful scarf!

    • Katherine
      April 21, 2014 at 9:13 am

      Thank you! 🙂

  • Ella Pretty Blog
    April 21, 2014 at 9:28 am

    Loved this post – am pinning it to my travel board…Planning trips ALWAYS stresses me out (where to go, where to stay, what to eat, what to see LOL!) I like your advice on checking the room tips section of tripadvisor & looking at chowhound to find good restaurants.

  • Tabitha
    April 21, 2014 at 9:49 am

    Loving Pingu!

    • Katherine
      April 21, 2014 at 1:01 pm

      Me too!

  • Katherine
    April 21, 2014 at 4:42 pm

    If you want some good cultural experiences, booking through is quite good. You can experience living in someone else’s apartment or home which has most of the amenities you need and local neighbourhood.

    • Katherine
      April 21, 2014 at 7:59 pm

      That’s a great point and an apartment/Air BnB stay is next on my list – I’d love to try it out one day in a city like Paris.

  • bisbee
    April 22, 2014 at 4:32 am

    All great tips – I’ve already used a lot of them when booking my trip next week to Paris and London!

    One question…we’ve had difficulties in the past with cell phone and iPad usage. Hit with high bills when we get home, etc.. We’ve been sucessful in dealing with this in the past – explaining that the particular person we dealt with didn’t fully explain to us what the hidden charges could be and what not to do, and we’ve gotten the majority of the charges taken off our bill.

    This time we went to AT&T, and we purchased International texts for both of our phones. Other than that, we won’t make calls, we’ll turn off data so we don’t inadvertantly use it (for automatic downloads, etc.), and we’ll only be able to use Wifi where it is provided – in the hotels, Starbucks or the like, etc.. So we won’t have easy access to the Internet unless Wifi is available.

    Do you have any other suggestions? Thanks!

    • Katherine
      April 22, 2014 at 9:25 am

      This is one area where I’ve been a little remiss as both of us just use our corporate phones. I do the same as you with the international texting plan – makes things so much cheaper. I use Wifi as well and rely on WeChat/iMessage for communication when I dont’ want to run up roaming charges. Other than that I haven’d had much experience but I’ll research this and post any updates I have!

  • Katie Cook
    April 24, 2014 at 8:36 am

    I just looked on Bloglovin’ and we were side by side on the travel section about how to plan a trip! How funny that we both wrote about this on the same day! I LOVE your post though:) Great ideas!! Just found your blog and can’t wait to read more:) xoxo Katie

    • Katherine
      April 24, 2014 at 10:36 am

      Hi Katie, that’s such a coincidence! Your post was fantastic!

  • jae
    April 24, 2014 at 1:16 pm

    How much does flyertalk play into your travel decisions?? I thought your hubs was really into the points game or it is location and destination first then figure out upgrading with points afterwards?

    • Katherine
      April 24, 2014 at 2:59 pm

      Hi J it’s location first definitely! And then if we can use points from our work travel we definitely will. It’s honestly probably 50% try to figure out if we can upgrade on points, if not then seeing if we can catch a fare sale, etc and trying to be flexible around dates. I won’t pay a huge amount for flights but if we can get a decent deal we’ll book. Our points levels have definitely dwindled especially as I’m flying less for work.