How I Plan My Solo Trips – And How You Can Too
Planning a solo trip can feel overwhelming, whether you’re a first-time solo traveler or a seasoned adventurer. Over the years, I’ve refined my approach to planning, and I’m sharing my process here to help make your trip planning easier.
This post contains affiliate links. If you book through these links, I may earn a small commission at no extra cost to you. Thank you for your support!
Step 1: Choosing a Destination
I usually start by picking a destination based on the weather – I prefer warm places, but I do make exceptions if there are mountains to climb. I’ve even ended up in the Australian Alps (yes, they’re a thing – who knew?) when I felt like an alpine adventure.
Once I know where I’m going, I figure out the best area to stay. I use Booking.com to compare accommodation options, from hotels to apartments, depending on how long I’ll be in one place.
Step 2: Booking Flights & Getting There
Once I know where I’m going, the next step is sorting out flights. If I can find a direct flight, I’ll usually take it – hopping between multiple connections isn’t my idea of fun, even if it sometimes saves money. Expedia UK has a great flight comparison tool that makes it easy to weigh up the best options based on budget, duration, and airline preference.
When I arrive somewhere new, I like to have my transport sorted in advance, especially if I’m landing late at night. I often book a private car through Booking.com, particularly in places like Ho Chi Minh City, where airport taxi scams can be an issue. Knowing I have a safe, pre-arranged ride waiting for me takes a lot of the stress out of arriving in an unfamiliar place.
Step 3: Transportation & Car Rentals
Most of the time, I walk, take taxis, or rent a bike to get around. But sometimes, you need a car.
If you’re planning to rent a car on your trip, always check the details before booking – trust me on this one.
When I rented a car in Vienna, I didn’t pay much attention to the details. I picked up the keys, got into the car, and immediately thought, “Oh no – it’s an automatic. I don’t know how to drive an automatic.” But there I was, in an underground car park in the middle of Vienna, with no choice but to figure it out. Somehow, I made it out alive (barely) and onto the motorway – only to realise I was fighting the steering wheel the entire time. Turns out, the car was in self-drive mode, and I’d been wrestling with it since I left the garage.
Moral of the story? Always check whether your rental car is manual or automatic, and whether it has any sneaky features like self-drive, before you hit the road. If you’re looking for a reliable rental, Enjoy Travel lets you compare deals easily – so you can choose the right car for your adventure (and avoid fighting with the steering wheel like I did).
Step 4: Booking Attractions & Activities
Once I arrive, I take a day to plan my activities. Collect leaflets, look at what’s available, and then decide what I want to do. I usually book my tours and activities through Booking.com, since they often have better prices than booking in person.
Once I broke my own rule in Koh Lanta when I took up a local tuk-tuk driver’s offer to take me to some attractions. I arranged to meet him the next morning, and he wasn’t exactly where I expected, but I found him. He then drove me through the middle of nowhere, handed me a stick to fight off monkeys, pointed toward the jungle, and said, Go that way. I’ll be here in two hours. I spent the entire time hoping I wouldn’t get attacked by monkeys (seriously, why did he give me a monkey stick?!), and then panicking that he wouldn’t actually be there when I got back. Thankfully, he was, but lesson learned – I’d rather book an organised tour!
Step 5: Handling Unexpected Issues
Travel isn’t always smooth sailing, and sometimes things go wrong. Like when I had a Jetstar flight from Melbourne to Hobart canceled due to fog. Instead of queuing at the help desk like everyone else, I just rebooked my flight through the airline app for free. Then the second flight got canceled too. At that point, I rebooked for the next morning, went on Booking.com, grabbed a hotel room for the night, and left the airport. Meanwhile, everyone who had queued for hours was still trying to find accommodation when I was already checked in. 🚨Pro tip: Always handle changes online when possible – it’s faster than queuing at the counter!
Start Planning Your Own Adventure
If you’re ready to start planning your solo trip, check out the best hotel and activity deals on Booking.com, flights on Expedia UK, and rental cars on Enjoy Travel to make your journey smoother.
Before You Go…
If you’re planning your own solo trip my Solo Travel Lifeline might come in handy. It’s like having a travel buddy in your pocket – without the awkward small talk.
Need a ready-made plan? Check out my 3-day travel itineraries for popular destinations—they’re packed with tips and can save you a lot of guesswork. If you want something more personalised, I also offer custom itinerary planning to make sure your trip goes smoothly.
Need a place to stay? I’ve got some handy affiliate links for Booking.com and Expedia to make planning a bit easier. If you book through them, I may earn a small commision – at no extra cost to you – so you’d be helping a fellow traveller out.
And if you want real time action, follow me on Instagram, TikToK or join the Sisterhood of Solo Travellers on Facebook for tips, stories, and the occasional travel mishap.
If you’re interested in Southeast Asia, you might enjoy my posts about Koh Lanta and Siem Reap.
Planning a solo trip? It can feel overwhelming at first, but I’ve got a guide to help – Best Solo Travel Accommodation!
Want to stay in the loop? Subscribe below for the latest from Sisters Uncharted – straight to your inbox!
