How To Reserve Your Flights & Hotels

Airlines, Airlines and more Airlines!

When it comes to flying, you have almost as many options as you do on the CheeseCake Factory menu (if you’ve never been, then booking your flight shouldn’t be your number one concern right now). Going through several airline websites to check prices and times could get a bit annoying which is why I like to use one of these: or Expedia is my favourite due to their 24-hour free cancellation feature and because I think the website is very user-friendly and just feels more professional. Why am I giving you two different options then? Well that is because not all airlines appear on Expedia, so it is worth checking Momondo too. If you have any other preferred websites, please share them in the comments section below.

These websites will check most of your airline options and list them down according to price, duration, take-off time, etc. They also have a number of useful filters that you can use. If money is not an issue for you (although, I think it always should be no matter how much of it you have, check the Guide to Budgeting post for why I think so!), then direct flights should be your go-to since they are the most time efficient. However, if you are on a budget then you’ll need to optimize between flight duration and price. Moreover, do not forget to check luggage policies, some airlines will charge extra for your carry on and checked in bags.

Tip: 1) Do not just go for the cheapest option, take the flight duration into account because time is money too! What I do is, I calculate how much my hour is worth (based on how much your job pays you) and then account for that. For example, lets say you get paid $50 an hour and you have two flight options: 6-hours for $400 and 12-hours for $300. The 6 wasted hours of your time are worth $300 (6×50) which means the first option is actually cheaper (I do realize that this went from a travel blog to a math exam real quick).

2) If you’re flying within the United States and do not want to pay for your luggage, Southwest Airlines actually gives you the first two bags for free, and their prices are pretty decent. 

From Hiltons to Hostels:

Booking the right hotel, in my opinion, is the most important step in the planning process, it can either make or break the trip. And I don’t mean that in a ‘omg its not a 5 star hotel’ kinda way, I mean it in a ‘it’ll take us 2 hours to get to the city center, and we need to stop by a pharmacy because I think I’ve got bed bugs and lice’ kinda way. So, here is how you make sure that does not happen to you on your next trip.

Booking & Airbnb… you’re welcome. I know a few people that use Expedia too but I haven’t. The only country I have ever visited that was not on any of these sites is *drumroll* Cuba. Yes, Cuba is stunning, beautiful and a cultural phenomena; but booking a hotel there is a downright nightmare (it is expensive but just save yourself the effort and book at the Meliá Cohiba Hotel). Back to all the other countries, here are a few things that you wanna keep in mind when booking a room, apartment or bed on and Airbnb:

1) Location, location, location. This is the most critical factor. When searching for a hotel in a certain city on, you have the option to open up a map which shows you all the hotels’ locations. In most cities, there will be a cluster of hotels right around the touristic spots, so just make sure that the hotel you choose is within the cluster or as close as possible to it. Do not depend solely on the reviews and ‘location’ score because they’re pretty relative; someone might think a 25 minute metro ride to the city center is an 8, I prefer a 5 minute walk. Some cities like San Francisco, Singapore and Istanbul will have two clusters; this usually means that there are two main touristic spots like an old city and a new city, or shopping district and wharf. A Google search will easily show you what each cluster represents and you can choose according to your preference. Other cities like Dubai and Los Angeles will have many clusters and scattered hotels. In that case, I recommend you postpone the hotel booking until after you’ve prepared your itinerary to pick a strategic location.

2) When booking on Airbnb, open up anyway and look for the cluster as you’ll not find it as easily on Airbnb.

3) Choose an accommodation based on the intention of your travels. If you are escaping to a secluded beach to relax and destress, then it is worth investing in a luxury 5* hotel. On the other hand, if you are going somewhere for non-stop sightseeing, hiking, adventures, etc. then save money on accommodation and spend it elsewhere. Remember that you won’t be spending much time in your room, you only need a bed to pass out on at the end of the day! Hostels are great if you are looking to meet other people and make new travel friends (if you’re willing to share a bathroom…).

4) Pay a little extra for free cancellation, it really comes in handy when plans change or visas get rejected (God forbid!)

5) Do not always jump onto the ‘Awesome Free Breakfast’ choices, if you have an early tour or driving out early that morning, you might not even be there for the meal.

Keep in mind, this is just the method I like to use. Some of those ‘No no’ hotels might be awesome but I prefer something closer to the cluster

Good job! By booking your flights and hotels, you’ve taken a big step towards solidifying your travel plans. Now it’s time to get excited, hyped, thrilled and onto MS Office Excel (yea, I’m calling you out on the ‘strong MS Office skills’ you added to your CV) for a sick itinerary!


4 thoughts on “How To Reserve Your Flights & Hotels

Add yours

  1. Although I’m already pretty fantastic when it comes to planning my itinerary – You have highlighted some very useful trips… and for that i owe you a big thanks!

    Looking forward to part 4!


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