How Do I Plan For A Trip?

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I get the question a lot about how I prepare for trips and methods I use in putting together my itineraries. And while it can be a little laborious, planning your own trip is one of those things that I’ve found makes me more excited for upcoming adventures, because by planning your own trip you’re making it something that you want it to be. Spending a few days in Tokyo? Spend some time trying to find a free walking tour for one of the days you’re in town. In the Caribbean and wanting to learn how to scuba dive? Cruise through some travel forums to find a scuba academy recommended by other travelers. Have a spare afternoon in northern California where you wouldn’t mind kicking back at a winery? There are plenty of places to find that information, too.

And while I’ve said it before that traveling solo is nice in that it allows you to do what you want to do, planning your own trips allows you that same luxury. Not to mention, hiring a travel agent to plan your trip or even purchasing a trip package with its own pre-set itinerary is expensive. And are the excursions you’re purchasing in those packages what you even wanted to do in the first place?

Use that money for your actual travel expenses or save it altogether for your next trip.

Here are some of the ways I make the trips I’ve always dreamed of a reality.

Plan For the Weather

The worst heartbreak is when you’ve planned a trip out in its entirety, only to realize that the country you had spent all that time creating an itinerary for will be in its rainy season during the time of your trip. Or if it’s like my Belize trip, the absolute hottest month of the year. Before you even start looking into the specifics of traveling to another country, look to see what the weather is going to be and when the best times to travel there are. Simple searches such as, “what are the best times of year to travel to Australia,” or, “what’s the average weather in South Africa in April?” are good places to start if you want to get a good idea of what to expect. Also look to see when peak tourist times are. Oftentimes the parts of year with the best weather are the busiest for tourists.

And if you become really good at traveling, you can make the most of a trip during seasons that aren’t the most ideal weather-wise, but which have the least amount of tourists. Leaves all those sights a lot less crowded and more easily enjoyed if you’re willing to sacrifice more ideal weather.

Estimate Flight Costs

After you’ve decided where you want to travel and ensured that the weather will be decent enough to allow you to enjoy the trip, next comes everyone’s least favorite part -- booking flights. And while it’s generally the more expensive part of your trip, if you plan far enough out you can generally get lower prices. If you use Google Flights as I often do, you can actually set it to give you notifications when flights to a destination you’ve been eyeing either increase or decrease in price. I’ll generally begin looking into flights two or three months in advance, mainly because my work schedule doesn’t allow me to plan much further out than that. For others who have PTO approved months in advance, you can purchase a lot earlier and likely at much cheaper prices.

However, I’ve come to find that purchasing a flight too early can come back to complicate my trip. Wait until you have your entire itinerary created and that you’re absolutely sure about where it is that you want to travel before purchasing those tickets. It’s a costly mistake to purchase a flight before planning your total trip, only to realize after planning further that you may not want to go there after all.

Surf Through Travel Forums

This is my favorite part of the entire planning process, because it gives me the opportunity to put together a trip tailored solely to what I want to see and do. I’ll generally start off with basic Google searches, such as, “must-see things in Argentina,” or, “top 10 list of places to visit in Santiago.” Based on what I find, I’ll create a broad list from the things I read and then research those results a little more. Because what some people may find to be “top 10” may be completely opposite of what I want to do or something I’d never dream of doing altogether.

So with my list of ten to twenty possible excursions, I’ll use websites like The Crazy Tourist and Lonely Planet to research those places a little more and to weed out those options I may not be so interested in. They’re websites that give you pretty unbiased opinions of places in addition to other possible excursion options of varying price ranges. It’s all depending on what you’re looking for.

I think what I like most about each of the websites is that, in addition to giving you straightforward information on those places you’re already considering, they also give you ideas for destinations that are a little more backroad and off the beaten path than what you would maybe find in more mainstream travel websites.

After spending plenty of time researching and having consolidated my list of things to do in each city to a reasonable number, I’ll start looking into finding different excursion companies that’ll help make those plans come to life. I’ll use travel forums to see what others have say about those various companies I come across. Take with a grain of salt some of the things you read, but if you’re consistently reading a positive or negative review about a particular excursion or company, chances of it being true are likely.

Also keep in mind that if you stay at hostels as I often do, most of the time they’ll help you with setting up your excursions with companies you would’ve never heard of through online research. And sometimes those are the best kind of companies to go with and can oftentimes be booked the day ahead of time rather than weeks or months in advance.

If after reading what others have to say you think it’s still an excursion you want to do, throw it on your official itinerary! You’re that much closer to a trip tailored to what you want!

Don’t Rush to Book Your Lodging

Call me crazy, but I typically don’t reserve lodging for where I’m traveling to next until a day or two beforehand. That’s because I generally keep my itinerary fairly open to changes. By booking everything in advance, you run the risk of being caged in by your own itinerary. What happens if you like a place a little more than you thought you would and want to stay a day or two longer? You’d either have to eat the cost you already spent on lodging in another city to stay longer, or end an amazing experience you were having sooner than it needed to be.

That being said, I’m allowed the added flexibility of booking only days in advance because I typically only ever stay in hostels, many of which will have spare room whenever you choose to stay. Just another added reason to give them a try...

Put It All Together

After all has been said and done and you have your flights booked, your dates set, and an idea of what you want to do each day of your adventure, put it all together! I’m a HUGE fan of Google Sheets with planning my trips. You can find an example of how I put everything together here. It gives me a place to put all of my plans in one place, which I’ll download for my trip so that I can access it offline wherever I’m at on the road.

If you spend enough time in planning your trips, it’ll actually quickly become a hobby. I find myself creating itineraries for places I have no concrete plan of visiting anytime soon, but which give me a chance to read up on a place and get to know a little more about it from afar. Not to mention, it gives yourself another chance to see just how big this world really is and how much there is to see and do.

What about you? What are some of the ways that you plan for your own trips? Would love to hear your suggestions in the comment section!

Until next time!