8 Steps to Plan a Trip Somewhere You’ve Never Been

Planning a trip somewhere you’ve never been before can be a little overwhelming. Especially if you’re going alone!

I think this ends up delaying or even stopping people from pulling the trigger on booking a trip because they don’t even know how they would start to plan. But don’t worry- I got you.

There’s lots to think about beforehand when planning a trip to a destination you’ve never been and probably know nothing about.

How do you pick an area to stay in?

How do you pick a hostel or hotel?

How do you get to and from the airport?

All of this can feel like a lot to think about. Not to mention, if the place you’re going to speaks a different language and now you have a language barrier to add onto all of this uncertainty. Sheesh.

The travel anxiety can be super real. But I’m here to assure you that you can do it, it’s not that bad, you’re not gonna die. Please don’t let these things hold you back from booking your trip.

 You just need a little planning and preparation so you can be more confident on your travels, and I’m here to deliver!

Now, I’m going to share with you how I plan to go to a new place that I know nothing about.

1. Ask your friends for any information they have!

Before I go somewhere new, I post on my instagram stories asking if any of my friends have been there before, know someone who has, or if they have any recommendations for me. This has been super useful to me on previous trips.

Utilize your network! People LOVE to talk about their travels (like me-duh), so take advantage of it.

2. Do a google search of the place you’re planning on going to.

Learn some basic information about the country, what airport you would fly into, what their currency is, their native language, if there’s a visa needed to enter the country/travel requirements etc. Just look for any basic info you think you might need. 

Pro tip: have a look if there’s any local holidays during the dates you’re travelling to this destination! Lots of places are either really busy or completely shut down on certain holidays, it’s best to be aware of them and plan accordingly!

3. Search TikTok for information about travelling to this place.

This has seriously been the most useful resource when planning trips. You can watch other people talk about their experiences travelling to this place, their recommendations, do’s and don’ts, what area they stayed in, hostels or hotels they stayed in, you can get SO much information from TikTok. And it’s more fun than reading articles. Duh. (Unless they’re my articles).. If you’re not on tiktok, utilize youtube, instagram reels or whatever your grandma is on these days..

4. Figure out what area(s) you want to stay in

I usually decide this with both google and TikTok. I’ll do a google search of “best areas to stay in *insert destination here*” and read some blogs or articles. These blogs/sites will most likely also help you answer some other questions as well like which hotel/hostel you want to stay in, things to do etc. You can also search on tiktok, youtube, instagram, pinterest, and wherever else your heart desires. Utilize all of the search engines!! If you’re planning on moving around during your trip, plan out your route too.

5. Book your flights!

Yayyy this part is so fun. Once you know what area you’ll be staying in, you can have a better idea of which airport to fly into, obviously this depends on which country you’re going to. Sometimes there’s only one international airport, sometimes there’s multiple.

Once you book your flights be sure to do a little celebration dance because it’s official!! You’re finally going. *This is mandatory*

One thing about me is that I’m not a penny pinching traveller. I’m not willing to take 3 buses and a boat and spend an extra day travelling to save a buck. Totally cool if you want to do that, but I’ll be flying into the closest airport to where I’m staying. Time is money and I would rather spend more time in my destination rather than more time travelling to it.

Which brings me to my next point about flights…

I am not someone to ask about how to get the cheapest flights. Like I said, I’m not trying to do everything the cheapest way. I will not be taking the worst flights to save money. I won’t do long layovers or lots of connections if I don’t need to. I will choose the best, most direct flight with preferably a 2–4hr layover time. I don’t care if it costs a bit more or even a lot more. AND I’m in Canada so there’s really no such thing as cheap flights anyway…

At the end of the day, it’s your trip. Do it how you want.

I book almost all of my flights on Expedia. I will usually look at a few different sites before booking like sky scanner, google flights, and on the airline’s site, but I often find the pricing to be the same. I know people have some shit to say about Expedia but I’ve used them for a while now and in my experience it’s always been super easy, their customer service is great and it’s really easy to change stuff if needed.

You can browse Expedia through my affiliate link here

Last thing about flights… For my solo travellers especially, please try to plan your flights so you land at your destination during the day! This is for your own safety. I always do my best to make sure I’m arriving somewhere during daytime hours if it’s at all possible.

Please look out for yourself. See my blog on Solo Travel Safety as well.

6. Figure out where you’re actually staying. Hostel/hotel/Airbnb…

For hotels and Airbnbs, TikTok and google are great search engines and obviously my favourite… You can also read reviews on sites like Booking.com and Expedia which are super useful. For hostels, again, you can search google for articles on “best 5 hostels in *insert destination here*” From there I’ll pick a couple that seem decent and then I’ll go to Hostelworld or Booking.com and read reviews there.

If you’re really not sure if somewhere is going to be your vibe, you can always just book a couple nights to start and then possibly extend your stay or go somewhere else if you’re not loving it there. Just be mindful of how booked up places can get and if they’re in their busy season or not.

If you’re a big vibes person, like me, and the vibes of a hostel/hotel really matter to you (especially if you’re staying more than a few days) here’s something you can do: Book the place you think you will like the most, then book a backup option for 2 days after the first place. Be sure to check the cancellation policy before doing this, but if your back up place has a 24 hr cancellation policy, you can suss out the first place on day 1 and then have time to cancel the back up if you’re happy to stay there. If you don’t vibe with your first pick you can just leave and go to your second pick that you already have booked! 

Did that make sense? That was a lot of words..

Sometimes places will give you a refund if you don’t end up staying your whole stay but of course this is dependent on the property, don’t bet on that. I usually only do this with hostels since they’re cheaper anyway. I don’t mind losing out on some money to stay in a different place that I feel better at. The place you choose to stay has a big effect on your whole experience!

I use either booking.com or hostelworld to book hostels, and Expedia or booking.com for hotels!

7. Plan how you’re getting from the airport to the place you’re staying.

This will take so much stress off just knowing this before arriving. Search TikTok and google for how to get around in the area and the best way to get to and from the airport. In Bali, they have Grab which is like Uber, super easy and pretty safe. I was able to take a Grab car to my hostel from the airport super easily. In Costa Rica, they only have buses, cabs (which are mostly scammers), and private transport. I arranged a shuttle through my hostel for airport pickup in CR. In Tokyo, which I am planning for right now, the best way to get to my hotel is by public train. So I have to figure out how that works. Which I will search on TikTok. Catching on yet?

My best tip for figuring out transportation is to ask wherever you’re staying. If you’re staying at an airbnb, ask the host. If you’re staying at a hotel or hostel, ask them over email or WhatsApp. They may even have a shuttle for you from the airport.

8. The Fun Stuff!!

Plan some fun things you want to do and see! I usually compile a list in my notes app of ideas of things I want to see and do while I’m there, and places I want to eat/drink, tours I want to do etc.

I think it’s super useful to have a list of ideas, but it’s also important to go with the flow! Meet new people, be open, say yes to things that interest you, invite people to come along with you on adventures. This is where the real magic happens. I’ve met some of the most amazing people and made some lifelong friends while travelling.

Having a healthy balance of planning things you want to see and flying by the seat of your pants is optimal.

(Edit) Hot Tip: Do yourself a favour and before you even start planning a trip, have a little look at your passport. First, make sure you can find it. And then, make sure it doesn’t expire before or during your trip. Cause if you end up in the airport with an expired passport, girl, you ain’t going anywhere! (Some countries won’t let you in if you have a few months left either so be aware of when your expires).

If you’re wanting to plan a trip in the near future and you just feel really lost, I hope this helps you.

If you’re wanting to do your first solo travel adventure but you’re having anxiety about it, I hope this helps you.

If you came here maybe looking for a sign that you should book the trip, this is it.

Life is now. Let’s make the most of it.

Bailey <3

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