After so many questions about how I actually plan my trips, I thought it was time for another Ask Phoebe. This time, I’m taking you behind the scenes of how I go from seeing a destination online to actually booking a flight and building an itinerary.
From finding cheap flights and choosing where to stay to planning what I want to see and leaving room for the unexpected, this is pretty much how I travel in real life. And honestly, it’s probably a little less organised than you might think!
How do you actually go about researching a destination before you decide it’s worth booking?
Usually, if a destination is on my radar, it’s because I’ve spoken to another traveller who loved and recommended it or I’ve seen it online and thought, “Woah! I have to experience that!”
From there, I’ll start looking into the costs involved, including flights, accommodation and activities. I’ll scope out videos online and reach out to friends who may have been to see if they recommend it.
There’s always a balance between research and instinct. If I start researching and the destination isn’t making me feel energised and excited, or I find myself hesitating to book it, I don’t. But if I find myself moving towards it full of joy, I go for it!
When you arrive somewhere new, how do you choose where to stay?
I use a few different apps like Agoda, Booking.com, Trip.com and Airbnb. Which one I go with really depends on what I feel like I need from the trip.
If I’ve spent too much time in hotels and need that feeling of home, I’ll book an Airbnb. If I want to be around other travellers and have a more social stay, I’ll book a private room in a hostel. And if I want something in between, with great facilities and friendly staff, I’ll go for a hotel.
I don’t really have one type of accommodation that I always choose. It depends on the destination, the trip and, honestly, my mood!
Can you walk us through your exact process for booking flights? Which sites do you use, and how do you handle things like visas?
I’m usually booking my flights on Skyscanner. I love their ‘Everywhere’ feature because I can put in my departure location and see cheap flights to destinations all over the world. I often find it inspires adventures I wasn’t even thinking about!
I have a lot of flexibility in my travel life, which allows me to find the cheapest and easiest routes when booking flights. I can wait a few days to get a better rate or choose an unusual flight time if it means saving money.
I’ll usually spend a few days charting and exploring different routes, looking at what works best for timing and budget. Then I’ll let it sit in my mind for a day or two before finally going for it and booking.
When it comes to visas, I like to sort those out when I book the flights so everything is organised from the beginning. One thing people don’t always see is just how last-minute some of my plans are. I’ll often book a flight to a completely different part of the world a day or two before I go!
How do you build your itineraries from scratch when you’re planning a new trip?
I’m always building itineraries, even when I don’t have a trip booked yet! If I’m scrolling TikTok or Reels and see something I want to do somewhere in the world, I’ll save it to a folder labelled with the country name.
That way, when I finally decide to visit, I already have a long list of things I want to see and do.
I’ll jot everything down into a list in my Notes app and then go into Google Maps and mark all the places. From there, I can start forming an itinerary based on where everything is located.
I do love to leave room for organic exploration, though. That’s really important to me. The best things are often the ones you didn’t plan for.
How do you figure out which attractions are actually worth your time in a new destination?
Sometimes you just have to go and find out!
You can read reviews, watch videos on social media or talk to other travellers, but sometimes you really need to show up in person and experience something for yourself.
Not everything is going to be amazing, and that’s okay. Part of travelling is figuring out what you love and what you don’t.
What’s your process for avoiding tourist traps and overly commercialised experiences?
I don’t always avoid them!
Sometimes a touristy experience is popular for a reason. Other times, you’ll get there and realise it sucks! It’s all part of the experience.
I think it’s more important to have an open mindset and go into it knowing you’re probably going to encounter some touristy things. You’re about to have a fun adventure figuring out whether you actually like them.
I’d rather experience something for myself than completely avoid it because someone online told me it wasn’t worth doing.
What apps, tools or systems do you personally rely on every time you plan a trip?
My Notes app is essential! It sounds odd, but that’s where I keep all my lists of things I want to do, restaurant recommendations and random travel ideas.
I also depend on eSIM apps like Airalo, Simify, Saily and Holafly. For accommodation, I love Agoda and Booking.com, while TripIt helps me stay organised. You just forward all your itineraries and booking confirmations to it, and it puts everything together into one itinerary.
I also often use Klook for airport transfers and activities, as well as Uber, Lyft and Grab for getting around.
So while I like to think I travel pretty instinctively, I definitely have a whole collection of apps quietly keeping me organised in the background!
I hope this gave you a better idea of what actually goes on behind the scenes when I’m planning a trip. I don’t have a perfectly organised system, and I definitely don’t have every detail planned months in advance. A lot of my travel comes down to a mixture of research, flexibility, and simply trusting my gut.
If you’re planning your own adventure, don’t feel like you need to have everything figured out before you go. Do your research, find a few things you’re excited about and leave some space for the unexpected. Sometimes those unplanned moments end up being the best part of the trip.
For more travel tips, behind-the-scenes stories and plenty of adventures around the world, follow my blog Travel For Phoebe and subscribe to my YouTube channel. And if you have a question you’d like me to answer in the next Ask Phoebe, send it my way!
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