In conversations about travel the most asked question I have received is, “How do you actually go about planning a trip?” While this question may seem simple to those that are well versed in traveling, it can be a really overwhelming task! So I’m here to share some experience and tricks that I think are pertinent to planning the perfect trip! I hope this becomes part of a series of posts where I can go into more details depending on your destination so let me know where if there’s somewhere you’d like a step by step guide!

Let’s start with some questions you will need to keep in mind upon planning a trip. Where do you want to go? What are your MUST haves? How long do you have? Are you adverse to the cold/hot? What is your budget? These are some necessary questions to ask before you embark on your journey!

I’m going to use a European trip as an example here. As for the questions above let me answer them for this sample trip:

Where do you want to go? Europe, multiple countries. What are your MUST haves? Paris Disneyland, the Colosseum. Do you prefer hotels or Airbnb? Airbnb. How long do you have? 11 days. Are your beginning/end dates flexible? No. Are you adverse to the cold/hot? Prefer not being in extreme heat. What is your budget? $2500.

Flights: Now that we have our guidelines established it’s time to find a flight! When I booked my most recent trip I found the best deal thanks to Scott’s Cheap Flights. It’s a free email newsletter with updates of super cheap flights that Scott finds. There is a paid subscription version where you get more frequent cheap flights but for the occasional traveler I think the free version works great! I’m in no way associated with the site or with Scott, I only think it’s a great service and has helped me personally save a lot of money!

If you’re wanting to go to Europe, let me tell you a secret. Flights around Europe are SO CHEAP. I’m talking like $15-60 for flights between different countries. So don’t worry about flights between all the places you want to go yet. Book your initial and last flight first. If you’re okay with flying in and out of the same location that is easiest. Find a round trip flight and at this point you are half way done! Scott recommends taking his recommendations and then plugging in your starting and end point into Google Flights. Google flights is awesome because you can see a calendar of airfares. This is especially helpful if you are flexible in your travel time. Some months are several hundreds less than others and this is an easy way to see this visually.

So you’ve now booked your initial and last flight, this means you have the most expensive flight booked and now this is really happening! Now for the fun part, to connect all your destinations. For example if you’re flying round trip in/out of London, let’s look at a map keeping this in mind. If Disneyland Paris and the Colosseum are my must-dos on this trip then I’m going to look at flights/train to Paris, France and Rome, Italy. To compare some of your options I recommend using Rome2Rio. Plug in your starting and end point to see all the options of getting there. This will help you compare price and time differences between airplane/train/bus. This will also link out to relevant website to book that mode of transportation but I always recommend double checking this with Google flights if you choose to fly. In this example I would do the following calculations for two alternate routes:

Route 1: Price from London to Paris + Price from Paris to Rome + Price from Rome to London.

Route 2: Price from London to Rome + Price from Rome to Paris + Price from Paris to London.

Is one route significantly cheaper? Let’s use that one!

Flights Part II: I personally prefer to stay in each destination longer to really get to know the city rather than rush through it. This is a decision you will have to make as you decide the specific days you want to travel between locations. Keep in mind some activities may take up an entire day (like Paris Disneyland). Once you decide how long you want to spend in each place, it’s time to book those individual flights! Keep in mind you will need to account for the price of bringing a checked bag, reserving a seat, and for some flights, even the charge for a carry on bag. Also keep in mind what size IS even allowed for what may be included. A lot of European carriers have smaller carry on bins than US carriers. I personally just ordered this small carry-on from Away that fits the guidelines for the flights I’ll be taking since I definitely do not want to pay for a checked bag (seriously racked up some big bills for this before!) So now you’ve booked your flights! You are so close to being done putting together the main structure for your trip!

Accommodations: I have to say my favorite way to travel the last few years is with Airbnb, especially on a budget. If you haven’t used Airbnb before, you can use my code for $40 off your first booking! Keep in mind if you’d rather have a whole place to yourself or if you’re open to sharing with the house/apartment owner. I’ve stayed in both situations and never had a problem, in fact sharing a space is sometimes the best way to get a real experience in the city as I’ve had many hosts recommend the best local food/drinks/experiences and sometimes they even join in! If you’re set on staying at hotels, I would check out several price comparison websites such as Booking.com and Expedia for the best deal. An important part of picking the ultimate accommodation is also making sure it’s easy to get to relative to all the activities you want to do. For example, there will probably be some outlier cheap Airbnb listings but they will be very inconveniently located relative to where you want to explore. Google maps will be your best friend for this!

Book insurance: I recommend AIG Travel Guard, it’s what I’ve insured my past few trips with and protects against pretty much anything you can foresee happening on your trip ie. lost luggage, cancelled flights, medical costs, trip cancellation etc. There’s different levels of coverage and the cost depends on how expensive your trip is, so be sure to add up your travel, baggage, and accommodation costs for the quote! If you buy insurance at least 15 days before your trip, you get extra benefits so make sure to buy ahead!

Now for planning out the trip essentials! Clothes and shoes for the right weather, adapters, chargers and more. New article coming soon to help you start your packing! Any other trip planning related articles you’d like to see next? Let us know in the comments below!

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