Planning a Trip: The Step-by-Step Guide
If you’ve never done it before — and even if you have — planning a trip can be overwhelming. There are endless moving parts. How much planning is too much? And worse still, what if it’s not enough?
Fear not, I’ve planned enough trips to know what actually works and what doesn’t, and you can skip the figuring it out phase. The biggest hack? Leave yourself a lot of wiggle room. Remember that travel is supposed to be fun!
By the end, you’ll have a flexible plan, a realistic route, and one reference doc to help you avoid the chaos. So, take a deep breath and let’s begin!
Phase 1: Dream list
This stage is all about your dream trip, no logistics, no cost, no geography. We’ll have time for that later, right now we’re building the bucket list.
Open up TikTok, Instagram, Pinterest, or wherever you like to find inspiration, search for the destination you’re planning to visit, and start saving. Landscapes, itineraries, restaurants, hikes, you name it. Anything that makes you excited about the destination or catches your eye, save it for later!
Phase 2: Make it real
Phase 2 Example:
- Amalfi coast
see more than just Amalfi Town
vietri sul mare
known for ceramics
grab a bite at il fornaio (fresh baked focaccia, pastries)
salerno
port town with cheaper, accessible accommodations
lunch @ Nonna Maria’s near historic centre (great caprese)
day trip to pompeii??
Now that we’ve started dreaming, it’s time to find a little more information. From here, I open my Google Doc (accessible from your laptop, phone, and even offline, which is perfect for travel), and add all the spots I saved to a list.
From here, I start Googling. Flesh it out, turn those saves into a real list. Find locations, costs, transportation to and from, historical facts, and anything that will save you time in the future. Simply having “Amalfi Coast” is no longer enough here, get specific.
Once you have all of the info laid out, you’re ready for the next step, narrowing it down.
I use Google Docs to keep everything organized — you can copy my template for free here. Open the doc, select “file” and “make a copy” to begin planning your trip!
Phase 3: Map it
Alright, once you’ve built a list of all of these incredible places, it’s time to narrow it down to what you can logically fit into a single trip. This stage is all about what’s realistic based on time, geography, and all the realities of life.
How much time do you have? Is it going to be a beach vacation or a city break? If you only have a week and you’re hoping to stay in Auckland, a hike near Queenstown might not be in the cards.
During this stage, I open Google Maps and start adding the destinations from my list to visualize things on the map. If you’re planning a multi-destination or road trip adventure, this is one of the most important parts.
From here, group destinations by location. Collect everything in the same city together, then by neighbourhood to create “blocks” which can be moved around as you get more concrete plans. This is where the details start to matter.
Start removing points of interest that are too far out of the way — or at least put them at the bottom of the list under a “save for next time” note!
If something isn’t high-priority, but you’d still enjoy it, consider keeping it on the list with an asterisk to note that it’s a maybe. You never know if you’ll end up with a few hours to kill.
Phase 4: Budget check
After you’ve mapped it, budgeting will determine any final cuts. Some items on your list might be “splurges” that are worth it. Others? Maybe you save those for the next visit.
Now is when you decide what kind of trip you want to have: are you planning to backpack and stay in hostels? Do you want to fly first class and eat at Michelin-star restaurants? Everyone has different expectations when travelling, and establishing those expectations will only make life easier later on.
Communicate with the people you’re travelling with, make sure you’re like-minded when it comes to these things, or someone will leave disappointed (or broke).
If you’re travelling with someone you don’t share finances with, consider downloading a budget tracking app (Splitwise or something similar) to make settling up easier later on!
Phase 5: Book the big stuff
This is where we start thinking about the big cost items. I’m talking flights and accommodations. Whether you actually commit yet depends on current prices, but regardless, it’s important to begin thinking about them early.
For booking flights, use a flight scanner — Google Flights, Hopper and Skyscanner are some of my favourites. Set your travel dates (bonus points for flexible dates), departure and arrival locations, turn on notifications, then sit back and relax until the scanner tells you it’s time to book. I book based on a mix of what these sites recommend and good ol’ fashioned gut instinct. Essentially if the price feels good enough, book instead of risking price hikes later.
When it comes to accommodations, consider all of your options — hotels, apartments, hostels — sometimes you’ll find a great deal in a high-end hotel, or get lucky with a fully equipped private room in a hostel. You’ll only know if you look. Check a variety of platforms (booking.com, hostelworld, etc.) Sometimes sites even offer exclusive discounts for mobile bookings. I couldn’t tell you why, but I’m not complaining!
Phase 6: Build a flexible itinerary
I’m a traveller who likes to go with the flow in a lot of scenarios, but I also don’t like missing out because of poor planning. So here’s how I go about creating an “itinerary” that still allows freedom and flexibility:
Figure out what needs to be booked in advance. Most major attractions have limited availability. Things like Machu Picchu, the Colosseum, Versailles, and more will require planning if you want to guarantee entrance and/or avoid paying 3× as much for a last-minute third-party ticket. Book these ahead. The earlier the better.
Decide on your “must-sees”. These are the places you would happily make the detour for and would feel like the trip was a bust if you missed it. These will be your top priority stops when you’re there.
Fill in the rest on the actual day. Earlier, we grouped items by location in blocks. Now that you’ve taken care of what needs to be booked in advance and decided on the can’t-miss stops, the rest is just icing on the cake! When you’re in the city, pull out your doc and choose which block of activities suits your mood that day. This style of planning leaves space for local recommendations, spontaneity, and lingering when you’re really enjoying where you are.
With this planning hierarchy in mind, you won’t feel rushed from A to B. Enjoy the free time, wander aimlessly, stumble upon some unexpected and incredible places. And isn’t that what travel is all about?
Phase 7: Arrival plan
Take a moment to research what you should expect when you arrive abroad so your trip doesn’t start with chaos.
Consider how you plan to get from the airport to your accommodations. Most major airports have reliable shuttle services, but sometimes they’re a little difficult to locate if you don’t know what to look for. Find out the location (typically a gate number/terminal/something similar to guide you), cost and route ahead of time and include it with your travel docs for quick reference later.
In this phase, also consider how you’ll be getting around. Renting a car? Make sure you have your international driver’s license. Travelling by train? Familiarize yourself with the details of train travel in the country you’re visiting. Thinking of hiring a driver? See if you can connect with one before arrival so there’s no “day-of” panic. Using public transport? Verify if contactless payment methods are available or if you’ll need to buy tickets.
These kinds of questions can usually be answered with a quick Google Search and will make your life so much easier when you arrive. Copy any useful links to your travel planning doc so you can refer to them when you need!
Phase 8: The admin stuff
Now it’s time to think about the technicalities that are important on all trips. This phase includes things like health insurance, phone plans, packing, travel documents, etc.
I’m keeping this post planning-only, but I have posts on these subjects coming soon!
