A Beginner’s Guide to Planning Your Very First Trip

Sri Lanka, First Trip | Packs Light

Eventually, after one too many travel stories from friends, one too many episodes of Anthony Bourdain’s TV shows, one too many Cancun vacation Facebook posts, and one too many times crying at Eat, Pray, Love… a person just breaks. That’s it. I need to go somewhere.

And I say, Yes! 

Congratulations. Infection has set in. You have only a few moments left until you’re forever changed by the Travel Bug. R.I.P.

Now that you have the crippling insatiable urge to travel like so many of us, you may find that you have some questions, like:

“Where do I begin?” “Is travel really expensive?” “Who can I even travel with, will my friends even go with me?”,
and of course the proverbial, “Where the hell am I going to go?!”

Every traveler has been where you are at one point. Deep breaths.

Let me guide you down this rabbit hole. Hopefully the following guide will ease the transition from dreamer to traveler, and I’ll be staring in jealousy at your Facebook photos soon enough!

Why now?

Are you like me where you get cabin fever easily and you’ll just die without some sort of intermission from your daily life? Do you have a destination you’ve been dying to sink your hiking boots into? Do you have family you want to visit, but also want to make the most of the trip?

You need to decide upfront what your true travel intentions. This will help you plan accordingly and not try to do too much—or worse, get completely overwhelmed and not do nearly enough.

Sri Lanka, First Trip | Packs Light

On my last trip, with my study abroad friends in Sri Lanka! A group of 3 was PERFECT for this 5 day adventure.

Location, Location, Location

Well, where do you want to go?

If you have had a dream trip in mind for years and this is finally your chance to make your dreams a reality, perfect. You’re set. If you know you want to go to Asia but aren’t sure exactly where or what you want to do yet exactly, then you need to do some research!

You can ask your friends about trips they suggest or that they’ve been on, buy a travel book, or, my suggested method, check out social media. You can barely log on to Facebook, Twitter, Instagram, or any social media really, without seeing someone on a trip somewhere amazing to make people jealous. Take the hint!

Ask them how they went about planning, where they stayed or any money-saving tips they picked up on their trip.

Another idea, which is probably one of the most cost-effective way to travel: go somewhere that someone you know lives.

You’re dying to go somewhere in Europe and you have a second aunt that lives in London—go to London! You can use your aunt’s house as a base point to explore the surrounding areas (Blood is thick, right? Thanks Aunty!), and save money by not paying for lodging.

Personally, my Pinterest account is where I personally find and store all of my travel ideas. Check it out, or create your own, and if you see a picture that inspire you, go from there.

Who’s your crew?

Are you riding solo-dolo? Rolling deep?

When traveling solo you you should definitely consider the safety level of your destination. Don’t let that stop you from traveling alone though! I’ve traveled solo a few times and had a fantastic experience—it gives you the freedom to meet people on the road and go with the flow.

Pro-tip: My favorite travel community, Girls LOVE Travel, is my favorite place to ask for solo travel advice and meet up with random (safe, helpful, travel-centered) ladies!

But if you’re not so keen on traveling solo your first trip, you’ll have to plan a trip with a group. In that case, you need to decide if you want a smaller group (which I consider 3-5 people), medium (5-8 people), or a large group (8+ people).

Trips with smaller groups tend to be more intimate and with people you know better like close friends or family. This may influence where they want to go or the comfort level of your vacation. Larger groups are often more of a hassle to plan a trip for, but they do offer a more dynamic group of people and the opportunity to split into smaller groups if necessary. Pick your poison.

Another thing you need to consider when you’re planning a trip is literally who you’ll be with. Friends? Family? No matter their relation to you, the personality of your travel buddies is vital to your travel experience.

If you’re an adrenaline junky who lives on the edge, and you invite Lawrence whose idea of a crazy weekend is a night at a small jazz club… do you see how that might cause a conflict when you guys plan things to do? Or imagine traveling with your close family, and every time you tried to smolder at a hot Italian guy across the Trevi Fountain your grandma winks at you? Hard pass. So choose your travel buddies appropriately.

*Extra Tip*: Safety! View my other article I’m Not Neurotic, I’m Cautious! 5 Simple Ways to Stay Safe While Traveling, safety tips you should take before and while you’re traveling. They could save your wallet, or even your life!

Travel funds? …What are those?

This is a very very complex issue. Everyone’s financial situations vary, for better or worse (and trust me, as a college student, mine is literally always worse, sob). But here are some easy ideas for funding that first trip:

  • Start saving early on. Work overtime. Work a side hustle for extra income. 
  • Get a nomadic job. Recruiting, private tutoring, teaching, web-design, social media managing, journalism, blogging, professional consulting, etc. Get creative!
  • Sell your stuff! Home, car, furniture, small children (just kidding :)).
  • Travel scholarships (Google it)
  • If you’re in college, study abroad, and study abroad scholarships

However you can manage to scrounge together the money, do it. Dust off your hustle game and get to work!Trip Planning | Packs Light

Logistics. Like, really.

Whether or not you’re a first time traveler, it’s a good habit to have almost as much of your trip planned out in advance as possible so you don’t get into a sticky situation while you’re away from home.

Do you have your passport? An essential but easily procrastinated piece of the puzzle if you are traveling internationally (and yes, Canada is international).

You can go through conventional methods of getting a passport and it may take you one to three months, or you can request an expedited passport by paying a little more, and receive it within three weeks.

Make a travel schedule of what you plan to do each day. As I said, it’s devastating to overbook yourself and not enjoy your trip, and just as bad to be too tentative and be bored on your vacation because you didn’t plan ahead. Make sure you have your money, plane tickets, local travel (subway, train, bus, boats, etc) before before hand so you know the most cost effective and safest ways to travel.

And what about your home life? Just because you’re jet-setting to Paris for a week doesn’t mean your dog can suddenly feed itself. Prearrange pet care, childcare, house care, etc. at least two-weeks in advance before your trip so you don’t have to sweat while you’re in an airport.

Following this checklist should guarantee every first time traveler smooth sailing (unless where you’re going has literal rough seas. Results may vary).

By planning ahead, doing research, and with a little support and will power, you can travel. I repeat. YOU can travel!


The journey of a thousand miles begins with a single step! Do you have any advice for someone planning their own trip, or have any more questions about planning yours?
I’ll be answering questions and suggestions in the comments.

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19 Discussion to this post

  1. Rob Taylor says:

    Yes, the “who” of traveling is so important. I often forget that there is more than just me to consider. I also forget that some activities aren’t great for a pack of 8 peeps. And good call out with the travel schedule. That’s so important. I try to only book 1 or 2 activities per day, cuz you know, relaxing is important too.

  2. Tiana says:

    Great guide for a newbie and some great reminders for a seasoned traveler.

  3. Cynthia says:

    This is absolutely true! I want to travel to discover different sights and sounds and see all that this world has to offer! Really enjoyed reading your article!

  4. brianmayroam says:

    Make a copy of your passport to carry around with u. Keep the original in your hotel or wherever u staying!

  5. melody pittman says:

    Lots of laughs here, thoroughly enjoyed your post. My favorite was the part about preparing and “doesn’t mean your dog can suddenly feed itself”. Still laughing. 😉

  6. Jess says:

    Definitely a handy guide for a newbie traveller! I think everyone remembers having no clue what to expect the first time they seriously went “travelling”… I was so disorganised back then that when I unpacked my backpack in Portugal I’d flown from Australia with just one of my runners! Inconvenient to say the least!

  7. Jessica Langer says:

    This was a great guide with awesome insight! You seem to have lots of experience.

  8. justine says:

    These are all great tips and very comprehensive too!

  9. rosiescapes says:

    good points 🙂

  10. Shereen @crazytravelista says:

    Great tips, especially for someone new that just has no idea where to start. Sometimes all they need is a little push 🙂

  11. Eva Bosh says:

    I consider myself an experienced traveller, but some of these tips are always helpful. And to everyone reading this, don’t think you are crazy if you get overwhelmed – I do too, but that’s one of the beauties of the whole experience 😀

  12. Alyssa says:

    I love this! Americans really don’t travel enough. In my travels, I met British people and Australian people who travel about every 3 months, and they travel for 3 months. Everywhere else, people know how to travel! In America, I know some people in their late 30’s who have never even been on a plane. This is a great article to get people started!

  13. Girl Gone Gallic says:

    I second the comment about “who” you travel with… I made that mistake once years ago and it ruined an entire Europe trip! Safety as a female traveler is important to, just be smart.

  14. Yes many moons ago at the age of 22 I left from the UK and went alone to Greece (for 7 years off and on).

    I was very shy and got so sick of everyone telling me I would never dare to do this – This was the very best thing I ever did for myself – my confidence and self belief sky rocketed.

    I met so many amazing people and had a ball.

    My main advice any new travellers would be to be careful with your money and always plan your next step before your totally broke.

  15. Love this! A cute first time traveler nudge. 🙂

  16. Janna (@jannaonajaunt) says:

    Great checklist! I had to go through some of this when I first started traveling. 🙂

  17. Rosemary says:

    Great ideas and tips for first time travelers. Thanks for sharing!

  18. Chiera says:

    great tips! even for seasoned travellers 🙂 Thanks x

  19. Great advice! Although I am not a beginner traveler anymore this would have been an extremely helpful guide when I was! Keep up the great posts and tips! (:

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