How To Plan A Trip Like A Pro: The Ultimate 8-Step Guide

how-to-plan-a-trip

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15 min read

how-to-plan-a-trip 

Travel planning can seem daunting at first. But over many years of planning trips for my family, I’ve found the best processes and methods to plan a trip efficiently. Follow along on my ultimate 8-step guide and learn how to plan a trip like a–dare I say–*gasp* professional travel agent! 

I’ve been traveling ever since I can remember, and I feel so blessed that I have had the opportunity to. When I was younger, my family and I had a group of family friends who would go on organized tours; the kind where you feel like you’re herded like a flock of sheep. Gradually, my own daddykins took on the role as the designated travel planner, and organized our trips for us. From sorting out visas to booking hotels and flights–he did this all. And if you’ve ever planned a trip before, you’d know that this is no easy feat, especially planning a fully-comprehensive vacation for a large group. While juggling a full-time job, no less.

Once I was old enough, I took over the reigns and started planning our family trips. Since then, my style of travel planning has evolved. I’ve learned the best ways to accomplish certain travel-related tasks, like the best sites and processes to find cheap flights, or how to plan a day-to-day itinerary. I often get asked for my travel itineraries and travel advice, so I hope this guide will help you learn how to plan a trip, and realise that it isn’t as difficult as it looks!

Alright, let’s begin!

As you go through this guide, you might want to use my printable Ultimate Planning Guide as a checklist and fill in the blanks as you go! Just enter your e-mail below and you’ll get access sent to your inbox.

 

 

STEP ONE: Pick A Destination

The first step is the easy one. Maybe you already have a destination in mind, or you just have a long weekend break that you’d like to get out of the country but have no idea where to go. Inspiration is everywhere, and these are my favorite sites to scour and narrow my search down to a few places of interest.

Instagram. Nowadays, it’s so easy to find travel inspo on Instagram, especially if you follow a lot of travel accounts. A good one to start with is @NatGeoTravel.

⇢ Next, I hop on to one of my favorite travel planning tools: Google Flights. I love it’s Explore feature because I can just input my departure city, and put in flexible dates and it’ll churn out recommended destinations! I can even be as vague as I want, for example, I can say I’m looking for a 1-week trip sometime in the month of May, and my interests being the beach, and then you’ll get a list of cities you can fly to!

In deciding on where to go, you should ask yourself the following questions:

How much time do I have?

If you only have a 4-day weekend, you wouldn’t want to be taking an 8-hour flight somewhere and wasting almost an entire day flying. But if you have more time to spare, you can consider an overseas destination that’s further away.

What are my interests?

You need to know what interests you because you wouldn’t want to be stuck in a foreign country doing things you hate! If you don’t enjoy city life, then maybe Tokyo or New York isn’t a good idea. If you enjoy the beach, then you wouldn’t choose a land-locked country like Germany.

Also, determine what type of trip you want this to be. Do you want to be actively exploring the city, or do you just want to lay by the pool with a book all day? Or maybe a mixture of both?

Do I need a visa?

You’ll need to check visa requirements with your local consulate as some visa applications take a long time to process.

When to go?

It’s important to check the time of year you plan to be visiting for a few reasons: Weather, events and crowds.

Weather

I admit that I’ve overlooked this point on a few trips, but it really is crucial. I once went to Myanmar during the dead of Summer, with humid heat reaching up to 40ºC. Safe to say we weren’t so keen on doing much sightseeing in this heat… 

Events

Before you decide on your destination, be sure to check what events, holidays or festivals are going on around your planned destination period. For example, during the Lunar New Year, businesses in China shut down for a few weeks, so almost all activity ceases during that time of the year. On the flip side, you might want to plan your trip to coincide with a specific event, such as Japan’s cherry blossom season. So you’ll have to refer to the cherry blossom forecast and plan your trip accordingly.

Crowds

Planning your trip around high and low seasons can be a big budget saver. Prices for flights, hotels and tours usually go up during high season, which is obvious if you think of the economics of supply and demand! So if you can, try to visit in low season. You’ll also enjoy the city all to yourself without having to contend with other tourists. 

Keep in mind though that there is never really a perfect world… In some cities, such as Dubrovnik, which thrives on Summer tourists, ceases almost all activity in low season. You won’t bump into many tourists but that’s because most shops are closed and some tour companies don’t operate, so you need to be okay with that.

STEP TWO: Decide the Length of your Trip

So you’ve found your dream vacation, but what exactly is there to do there and how many days will you need to budget for your trip? This is how I determine that:

⇢ You might think Google would be the first go-to, and it could very well be, but my personal favorite is Pinterest! Pinterest is a visual search engine similar to Google but is much more visually pleasing. Instead of seeing results in plain text, you’ll see them as images and you can pick the ones that catch your eye! You’ll usually find really quality travel articles and itineraries on Pinterest. Plus, you get to save/pin your favorites to your own board and compile them for your upcoming destination. Way to stay organized!

⇢ Next, I’ll look up the city on Tripadvisor and look for their Top 10 Things to Do. This will give you a general feel of what’s popular in the city. So if they interest you, then you’ve hit the jackpot!

⇢ Lastly, I’ll type “how many days in [insert destination]” into Google search and that’ll give me a rough idea on how long most people spend in that city.

STEP THREE: Book Your Flights

So you’ve found your perfect destination, and you’ve decided the length of your trip. Now it’s time to get those credit cards out and turn all that research into reality! A few preliminary questions to ask yourself:

How much time do I have to spare traveling?

If you’re short on time, you might want to book a direct flight as opposed to a flight with a layover. However, if you have more time to spare, you could even spend a little bit of time in your layover city and get two holidays in one!

Who do I want to fly with?

If it’s a long-haul flight, and your budget allows for it, it might be wise to be traveling in comfort and choosing a premium airline as opposed to a budget one.

Also, I suffer from flight anxiety so I only go with airlines in Skytrax’s Top 10 Airline List, just to be safe. Some of my favorite and trusted airlines are EVA AirQatar Airways, Etihad Airways and Singapore Airlines.

Searching for flights

So this is where my inner perfectionist kicks in… and I honestly sift through soooo many websites to find the best prices. After years of doing this, I’ve found the ones that consistently find the lowest prices and are trustworthy. I will go into more detail on finding the best prices on flights in a later post, but here is my usual process:

Google Flights is still my #1 stop, so I’ll know the best dates to travel, and on which airline and exact timings.

⇢ To confirm, I use ITA Matrix: This one is amazing because I can actually input a few different departure cities and arrival cities, and it’ll all produce a matrix of options that are cheapest. This is great if your itinerary is still quite flexible and you’d like to know which airports are cheaper. Sometimes traveling to an airport a little further from you might save you a few hundred bucks!

⇢ Once I’m set on all the nitty-gritty details, I’ll go on to a booking site. My favorites are Skyscanner, Expedia, and Kayak

⇢ Lastly, I’ll check the prices on the actual airline website to see if there are any price differences. 

⇢ If you want to check average prices for your flight, I usually use CheapFlights.com. I love that it collects statistical data on price trends like best months to travel, prices changes over time, best months to purchase ticekts, etc.

⇢ So there is this whole fuel-dumping, “hidden-city ticketing” trend that is oh-so-complex and worthy of a post of its own that I probably couldn’t explain… but basically there are websites like Skiplagged that take advantage of loopholes in airline ticketing systems. It might be worth checking and you might be surprised at the savings you can get! 

Transportation Planning Spreadsheet
I’m a huge fan of spreadsheets. Also rainbows, as pictured here. Here’s an example of my transportation spreadsheet that I compiled for my trip through Spain and Portugal.

STEP FOUR: Book Your Accommodation

I’m gonna be real with you here. I will literally open like 50 tabs of apartments and hotels, compare them down to the tiniest details, and then filter them out. It’s a really extensive process but you don’t have to do that… I hate to admit it but it’s just symptoms of being Type A. Any other Type A’s in the house?!

⇢ I always start my search on Airbnb because I love the homes here. You usually get cooking and washing facilities in most apartments which is a huge bonus. Plus, you can usually get an entire apartment for almost the same price as a hotel room! (I go into detail about this here.) Airbnb is my preferred option when booking with my family, as we usually need multiple rooms. If traveling as a couple, I’m quite happy to stay in a hotel. 

⇢ My second favorite site is Booking.com because they have a really good interface for looking up apartments as well! So it’s pretty much like Airbnb, except without the Airbnb fee. Yay! You can also get 10% off your booking via my special link here!

⇢ Once I find a hotel or apartment I like, I’ll look it up on a hotel aggregator like HotelsCombined.com and Trivago to see if there are any better prices out there.

⇢ Sometimes if I’m booking last minute and my favorite choices are no longer available, I’ll expand my search to some of these other sites I love:

Agoda
Hotels.com
Wimdu
VRBO
FlipKey by Tripadvisor
HomeAway

⇢ To find out more about booking on Airbnb, check out my guide on Everything You Need To Know When Booking On Airbnb (Even If It’s Not Your First Time!)

Accommodation Planning Spreadsheet
Here’s a sample of my accommodation spreadsheet, with all the information I need at my fingertips.

STEP FIVE: Plan Your Itinerary

Now, this is where it gets fun!

⇢ I usually start off with Tripadvisor and check the Top Things to Do in that city, and then write it down in a spreadsheet, along with opening times, suggested visiting durations, costs, whether tickets need to be booked in advance, etc.

⇢ Another trick I have is to check out Free Walking Tours in the city I’m visiting. If you’ve been reading my other itineraries, you’ll know how much I love them Free Walking Tours. They are a great money-saver as you get to learn about the history and culture of a city, all for a price that you deem fit! Okay, so the trick is to go on to that Free Walking Tour group’s website and check out the locations they will be hitting on their tour. So you’ll know for sure that they are must-sees! If you prefer to take a more laidback approach to planning your itinerary, then you can just schedule a Free Walking Tour on the first day of your trip, and then ask the guide for tips on where to go! On the day of the tour, the guide will usually take you to all the must-see spots in the city, but only on the exterior. So if you like a certain attraction, you can always head back on your own time.

⇢ If there are day trips that you need to do from your destination city, then research tour companies that can take you there. I usually look for the smaller tour groups so you don’t feel like you are herded like cattle.. and I use Tripadvisor to find the top ones. Reviews don’t lie! Alternatively, you can find tours on Viator and GetYourGuide.

⇢ If you plan to visit a popular attraction like the Alhambra in Granada or Universal Studios in Japan, make sure you are booking your tickets well in advance, as they are usually sold out weeks or months before.

⇢ Save locations to Google Maps as you find them. This will give you a feel for where everything is. This way you can lump attractions that are close together on the same day, so this helps in your day-to-day planning.

STEP SIX: Purchase Travel Insurance

Murphy’s Law states that “Anything that can go wrong will go wrong.” and this is so applicable, especially when you are traveling hundreds of miles to another country (or even in your own country!).

A lot of people ignore this aspect of travel planning because it’s so boring. So unsexy.

But this is the real world, and shit happens. You never know if your flight might get canceled, or your luggage goes “missing”, or you leave your passport in a bathroom stall (#truestory).

Travel insurance will cover you in case of any unexpected mishaps during your trip. And what better travel insurance than one that was created by travelers for travelers? World Nomads Travel Insurance is exactly that and covers residents in over 150 countries.

With World Nomads, you can purchase your travel insurance online 24/7, even if you’re already started traveling and forgot to purchase it prior!

STEP SEVEN: Planning Your Arrival

So you’ve got your flights and swanky hotel booked, travel insurance bought, bags packed, and now all you’ve got to do is put on your noise-canceling earphones and jet set off to your holiday destination. 

But wait, you wouldn’t want to arrive at the airport not knowing the address of your hotel, which bus to take and not knowing a single word of the local language??? No bueno!

Make sure you get the following in check before leaving home!

⇢ Bookmark your hotel address on your phone. Google Maps has an offline option where you can download maps for a specific city, so you can still get access to it without data.

⇢ Find out how you can get to the hotel. There are so many ways you could get to your hotel, depending on your budget and preference; be it a bus, train or taxi. Nowadays, with ride-sharing apps, I prefer to get an Uber from the airport. In highly connected cities like Japan, taking the train may be a quicker option as you avoid all traffic on the road. Bear in mind your arrival time though. If you are arriving after midnight or really early in the morning, check to see if public transportation is still running at that hour. Alternatively, if you want to travel in style, you can always pre-arrange a private driver to pick you up at the airport.

⇢ Check-in to your flight. Make sure to double-check and triple-check your flight times and check-in early! I can’t believe how many times I’ve heard of people misreading their departure times and completely missing their flights. Check-in online early and if the airline permits, select your preferred seat!

STEP EIGHT: Enjoy Your Trip!

Now you’re ready to plan your own trip! Fly, pretty bird, spread your wings and fly! No, but seriously. I hope this has helped you to plan your own little vacation and realize that travel planning isn’t as tough as it seems. And it can be a whole lot of fun!

Was this guide useful? You can now put it to the test along with my printable travel planner specially hand-crafted by me!

 

I still can’t do this…

If self-planning still isn’t your thing, that’s okay too! There are plenty of group tours that can help you plan all that so you can have a stress-free vacation 🙂

Here are some reputable tour companies:

Contiki Travel: For the youngins. Group travel for 18-35 year old’s. They have a YOLO way of life, called #NOREGRETS.

G Adventures: Small group travel focused on adventures like safaris and expeditions. 

Intrepid Travel: Small group tours focused on traveling like a local. 


If you know someone who could use some tips on planning their own little vacation, share this with them! I’d love to know how you went with this, and also, please let me know if you have any other travel tips to add in the comments below!!

Til then, happy traveling! xo

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11 Comments

  1. Nice post! Thanks for sharing awesome tips. I also love the style of your site. Are you using Ashe Pro? It looks like another version of the one I’m using 🙂

  2. Some great tips here, especially your spreadsheets, I use Excel to plan EVERYTHING in my everyday life but hadn’t even considered using them for planning travel too. Probably going to give it a try this afternoon for our next trip to the South of France as there’s so much I’d like to see! Thanks for sharing. Shan xoxo

    1. Excel is SUCH a lifesaver when trying to get everything sorted out for travel. If you’re already using it for everything else, I promise you’re gonna love it for your travel planning 🙂 South of France sounds like bliss! I’m gonna have to make a trip there someday soon. Have a blast there! xo

    1. Yep, everyone has their own way of planning. I usually like to confirm what activities are there to do before I book my flights so I know the exact dates I need for the trip 🙂

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