How to Plan a Trip: Step-by-Step Guide

No more "I can't" or "I don't know how"... OR "You're so lucky- I wish I could do that!" Here is your user-friendly, step-by-step guide to planning your first trip!

There seems to be a dearth of information on the how-to of trip planning. Those of us who have spent some time a-wanderin' and choose to write about it, seem to often overlook this topic. To us it comes "naturally" -- when something is easy to you, its easy to kinda forget that it might not be easy to someone else, or they haven't had the same level of experience with whatevertopic. Until now, it had never really occurred to me that there may be people who don't have the know-how or the trip-planning savvy.

How the fruit do i plan a trip?!

How the fruit do i plan a trip?!

One low-grade gripe I hear from some my traveler pals is that there is this weird "I wish I could do that" reaction from friends, family, and colleagues when they announce a new trip. We shirk it off as a jab or a meaningless comment because they don't care to hear any more about our upcoming trips. We think, "Yeah, it's not that hard..." -- mainly because we've done it countless times before and forget that there is a whole category of people who have never even been to an airport. I think sometimes we forget that we were once novice trip planners, and had to go through a learning process to get to our current "pro" status.

(1) Pick a destination.

There are a few different ways to come to your destination decision. First you have to narrow down the list:

  • By interest
  • By budget
  • By activity

Which filter you put on your search largely depends on your life circumstance at that moment. If it's a "I don't care where I go, I just need to go somewhere" trip- then think about how much you want to spend and see where you can fly within that budget. Then look at your options and weed out locations that you're not super interested in visiting. Look at the remaining locations and see what you can do there.

Alternately, if you're looking for a cool new spot to go white water rafting, throw "world's best rafting destinations" and see what pops. If you prioritize temples over nature reserves, take the remaining temple-laden rafting locales and see which one works for your budget.

I highly recommend using Kayak Explore to narrow your search. It's an extremely user-friendly tool that gives you a great visual of price and location.

You've got your destination, now lets figure out how to get there.

(2) Buying tickets

Everyone has a different set of rules for how they book their tickets. Some will only buy the cheapest, some go for the most direct, and some go for whatever happens to be the easiest to book.

Though I use Kayak to creep on prices, I've never actually used it to book a ticket. I'm a big fan of SkyScanner because I feel that I've always seen the lowest prices on that site. HOWEVER: I always check the airline site to see if they offer the same price. If its the same, or within a few dollars, I always book directly through the airline. When booking through a third-party you give up a little flexibility with cancellation and making changes, so unless the price difference is dramatic, search with a search engine and then book with the airline.

PRO TIP: Always search and book in your browser's private mode (I use Chrome's "Incognito"). Some sites track how many times you've visited (and search parameters, too I think), and prices rise a bit with each visit.

You've booked a ticket! Yay! Feels good, don't it?!

(3) Now you need a place to stay

Believe it or not, the hardest parts are done. Yes, there are a lot of small details to straighten out, but finding a spot and figuring out how to get there are the most anxiety-educing.

When searching for accommodations, I will always prioritize value above all. I never go for the (exclusively) cheapest option- I search with few factors in mind:

  • Is breakfast included?
  • Free wifi?
  • Is it centrally located? On a transit line?
  • What do the reviews say?
  • Do they offer activities or excursions?

Breakfast is my #1 must-have, with location being the next strongest contributing factor. If I have a couple places that meet all my standards, I sort by price AND (superficial, I know) by pictures. Once all (or majority) of my must-haves have been met, pictures have been seen, reviews have been scanned, I then look at price.

PRO TIP: Always read the fine print. Knowing the cancellation policy beforehand is really helpful. Also, like booking flights, if the price is the same on the direct site of the hostel/hotel/whatever, then book directly. Certain third-party sites force you to make all changes through the site (so if you call the hostel to cancel, you may be met with a "Sorry, we can't help you - please contact Shmooking.kom directly." And beware of the sites that take a "deposit" -- odds are that that amount you're paying is not going to reduce your amount due to the hotel-- it's likely that sum is the commission for the third-party site. 

Dude, you're going! You know how you're getting there... you know where you're staying. Now onto the small details!

(4) Odds & Ends: Things to consider

Let's do this rapid-fire style:

  • Does your destination require a visa for your nationality? My go-to site is VisaHQ.
  • How much can you spend on food without going broke? Are there farmers markets (mmmsamples!)
  • How about local activities/culture sites?
  • What can you do for free?
  • You may want to buy a day- or week-pass for the metro/transit 
  • Peruse TripAdvisor to see what other travelers have said about the tourist-spots in town
  • Pinterest is a huge resource - with loads of articles from travelers who have been there already! (shameless self-plug)
  • Do you need to learn a few key phrase in another language?
  • Or maybe you need to learn about the local culture, so you can make sure to be as respectful and responsible as possible.
  • Take stock of where you're going and what you want to get out of it- create your own pre-trip mental checklist of sorts.

Last PRO TIP: If you're booking your first trip because you have a friend that is a frequent traveler and you've been dreaming of being able to book your own excursion; don't compare your trip to theirs. Trip planning takes practice, and though I think I covered the spread pretty well- things will arise that you hadn't through about. For example, you may accidentally wear all the metal you own to the airport...... or book a hike and forget your snack. Just because you've forgotten a few things, just means that you'll be all that much more prepared the next time. 

Welcome to your new addiction, friends!
Feel free to ask any questions in the comment section- no question is too silly!


Alright travel-veterans, time to share YOUR tips and trips for the booking process!

  • What was your silliest mistake when booking your first few trips?
  • Where did you go on your first trip? How about first SOLO trip?
  • What booking filters do you use? Budget first? Activities first?