Have you got a big trip to plan? Feeling a little overwhelmed and don’t know where to start?
Planning a trip for a lot of folks, myself included, can bring about some legit stress and anxiety. Planning a vacation is a big deal and there’s a ton that goes into it. And most importantly you want to get it right.
For most of us planning a big trip isn’t something we do all the time. Practice makes perfect right? Well, the practice is the hard part since most of us can’t plan a trip every month.
But not to worry, you’ve come to the right place. If there’s one thing we know it’s how to nail that perfect trip. Whether it’s for just a week in your neighboring state or months abroad, this ultimate travel planning guide has everything you need.
Here’s what we will be covering. You can jump ahead by clicking on any of the links below.
This is a BIG article friends so be sure to bookmark it or save it to your favorite social media (to your left) so you can reference at a later time. Let’s get to it!
Travel Planning Style
The great thing about travel is how personal it is. Travel means something different to everyone. Travel for you might be about tasting the food and culture of some distant land. Or perhaps it’s vitamin-D therapy on a tropical beach.
When it comes to planning a trip there are no doubt many different styles. Some like everything mapped out for a trip while others prefer a little spontaneity.
I’ve had some really great travel experiences with absolutely no plan other than the destination. I don’t mind landing in some foreign land without a plan. I kind of enjoy the adventure and the nervous energy of “what now?” But this style has its draw backs for sure and is not for everyone.
Have you ever gotten back from a trip to discover that you missed something really cool? Happens to us all the time. For that reason, we do like to plan and have a strategy so that we can get the most out of our trip.
How Do We Travel?
Over the past 20 years of traveling our style has definitely changed. Some of that has to do with how busy the travel scene has gotten. I remember being able to bounce around Europe no problem without having anything booked ahead of time. Today that doesn’t work so well with how busy it’s gotten.
How we plan a specific trip also depends on how busy the destination is. For a trip to Paris we would have everything booked up, yet some distant corner of Nepal we wouldn’t worry about as much.
In general, we prefer to have our accommodations mostly booked ahead of time. We typically use Booking.com since they allow free cancellations just 24 hours before the booking. This allows some flexibility should we need it. More on this later.
When it comes to meals we may do a little pre-research but we find the best restaurant beta is had once you’re there.
We also find a lot of value in researching things to do ahead of time. Your time while on vacation is a precious commodity and we prefer to not spend that time trying to figure out what to do while on vacation. Pinterest is a great platform to find things to do when traveling.
The biggest reason we like to plan ahead a bit is that it gets you stoked for where you’re going. Exploring what you’re going to get to do and see is a blast and only adds to why travel is so great.
On the other hand, leaving room for flexibility is important in your travel planning. Things are bound to go awry at some point in your travels and freaking out because your plans get messed up is no good. So taking a chill pill and rolling with the punches is an important skill while traveling.
Check out Sustainable Travel for tips for a better travel experience.
Finding The Best Travel Destinations
Our favorite part of travel planning is exploring the world for destinations. It’s a treasure map full of surprise and inspiration around every corner. Once you start you never know where you’ll end up.
Interactive Travel Planning Map
Our favorite way to plan a trip is through the interactive travel planning map at Skyscanner.com. Once there click on
Now you just pick your departure city and date and you’re off to the races. Just click and drag the map about to see what flights cost to various parts of the world. This is a really fun way to explore some new destinations and find great deals.
Pinterest Travel Destinations
If you aren’t familiar with Pinterest you’re missing out. This is a great resource for travel inspiration. Just type in your destinations or search for something like, “cheap travel destinations” or “luxury travel destinations.”
FREE Extended Layovers
Have you heard of Stopovers or Extended Layovers? Any layover more than 24 hours is called a stopover. And the best part is you can use these to leverage free travel. This is one of our favorite ways to travel.
For example, we are heading to Ireland this spring and there was an available stopover in Paris. We decided to spend 2-weeks in Paris as a stopover on our way to Ireland. The best part is it actually saved us a $100 bucks.
Research Travel Costs
Planning a vacation wouldn’t be complete without talking about the dreaded money component. It goes without saying that we aren’t made of money and travel can be costly.
So now that you have an idea of what flights cost let’s get an idea of the living costs once you’re there. For this we use a couple resources.
- To get an idea of accommodation costs we just hop on Booking.com.
Nextwe head to Budget Your Trip. Here you can punch in a destination and it will give you an idea of costs such as food, drinks, and even groceries. It’s a great tool for staying on budget. Below is a screenshot of what you’ll see.
Armed with these two pieces of the puzzle you now have a pretty good idea of what your trip is going to cost.
Planning What To Do
When it comes to finding the best things to do on a trip we often start with Google and Pinterest. These are good resources to find the mainstream touristy things to do.
At the same time it’s important to mix in some less touristy options. We enjoy getting off the beaten path as much as we can. For this we use travel forums where you can talk with folks that often live in the area you’re visiting.
How To Apply For A Passport
It’s now time to get you a passport. Obviously required for international travel but there’s also talk of them being required for domestic travel by 2020. So regardless it’s time to just get one.
You can find country specific recommended expiration timelines here. In the left column just put in your destination.
5 Steps To Apply For a US Passport
Passports will take 4-6 weeks so plan accordingly. To start the application process head to the
Do You Need A Travel Visa
A travel visa, also called an entry visa, allows you to enter into a foreign country for a specified amount of time. There are many foreign countries where no visa is required in order to visit. Some that do require an entry visa issue one automatically on your arrival.
The quickest and easiest way to see if you need one ahead of time is through iVisa.com. If one is needed you can purchase through iVisa and let them take care of the headache but they do charge a fee in addition to the cost of the Visa.
To go about it on your own here are the steps.
The next screen will highlight some general information about the country and mention if a visa is required. Scroll down and click, “Entry, Exit, and Visa Requirements.” This will give you links to the particular embassy where you can apply for a visa.
How To Stay Safe While Traveling
Our approach to staying safe while traveling is about knowing the risks before you go. Here’s an in-depth Guide to Travel Safety but I’ll cover some basics here as well.
- We start with the travel forums mentioned above to get an idea of how things are going in a particular country. If there is any sort of political or civil unrest there will be a lot of chat about it.
- The forums are a great place to learn about any common scams. Such as counterfeit currency that we got nailed with in S. America. Could have been easily avoided had we checked.
- For health-related safety such as vaccines and prophylaxis, we go to the CDC Travel website or if available head to your local travel medicine clinic.
- If you’re visiting say Machu Picchu or other high altitude locations be sure to educate yourself about Altitude Sickness and how to avoid it.
- Get yourself a basic travel first aid kit and some common over-the-counter medications to keep you safe and happy while traveling. Check out our DIY Travel First Aid Kit and recommended medications to take with you.
- We NEVER travel without travel insurance. It has saved us so many times. It’s worth it just for the trip cancellation, lost baggage, and delay coverage. But if you have any sort of medical emergency you’re going to be high and dry without it. But with that being said read How You Might Already Have Travel Insurance And Not Know It. We personally use World Nomads travel insurance and love it!
How To Find Cheap Flights
After ALL this work, it’s now time to find that cheap flight. I see a lot of people who claim to have the ultimate booking site for cheap tickets but I assure there is no single site that works well for everything.
In addition, flight prices can change for no good reason. We were recently looking at a Ryanair flight from Scotland to Greece and it was only $25 one-way for a few weeks. Then it jumped to $90. A month later we looked and got that same flight for $17!
I used to be a believer in the private/incognito mode for your web browser. The thinking here was to block the booking sites so they can’t see your browsing history as you are frantically searching flights. But we’ve tried this for years and never could see consistent results so we kind of debunked that theory.
Travel Credit Cards – A quick Rant
The only true way to travel free is with travel credit cards. Jill and I haven’t paid for a major flight in probably 15 years and we travel a lot. Flipping credit cards is the only way to go if you’re serious about travel.
All your full-time travelers fly free with credit card miles and it’s a little ironic that we are the ones that write about all these great booking sites which we rarely use.
If you’re serious about travel, have good credit, and can ALWAYS pay your bill each month, it’s time for some credit card hacking. Beginners Guide To Travel Hacking And The Best Travel Credit Card is a great place to start.
I also can’t overemphasize the importance of understanding Airline Alliances for not only credit card miles but airline mileage award programs as well. A lot of people get this wrong and end up with miles they can’t use.
Thanks for listening, rant is over….
Trusted Booking Sites
I’m going to list some of our favorite sites, why we like them, and specifically what they are good for. The most important thing to remember is to shop around. Just because booking site X was the best for your last trip doesn’t mean it’s the best for today.
Momondo is a favorite amongst frequent fliers. If I had to pick one it would be these guys or skyscanner. Momondo also searches smaller airlines that the bigger competition misses. They also have a good cheapest day to fly calendar.
Travelocity is one of the big chains and while it’s certainly worth checking it doesn’t really bring anything unique to the table.
Finding The Best Accommodations
Accommodations are very personal. Some of you will be out to save every dollar you can while others will want a little luxury. For Jill and I, we find that we never spend a lot of time in our rooms so we typically opt for something middle of the road.
Our days of splitting a bunk room in a hostel are over but we have no problem renting a private room with a shared bath. Everyone will have different preferences here.
The one thing we strongly encourage you to do is keep your accommodation bookings as flexible as possible.
I can’t tell you how many times we’ve unexpectedly fallen in love with a place and wanted to stay another night. On the flipside, you might have booked a bunch of nights in a place that’s just kind of, well blah.
Having the freedom to adapt is SO important when traveling. For this reason we primarily use Booking.com.
Booking.com lets you book a place without charging a credit card and the vast majority of places allow cancellations just 24 hours in advance. This is great for how we like to travel.
The prices are very competitive but what you do miss out on are some perks. For example, Hotels.com buy 10 nights you’ll get 1 free. That’s great but the cancellation fees are brutal should you have to make a change.
When visiting new places where we aren’t exactly sure what to expect, we really like the flexibility that Booking.com offers.
Our last bit of advice is to have a look at AirBnb. We find it especially useful when traveling with another couple. Instead of booking two hotel rooms you can usually find a great two-bedroom AirBnb rental for a lot less.
For the ultimate travel hack, here’s How We Get Free Accommodations While Traveling Abroad.
Booking.com is our favorite by far since you can cancel bookings just a day ahead of time. Their prices and selection are always on par with the other sites.
Hotels.com buy 10 get 1 free is hard to beat. Their prices are usually really good but they do have some hefty cancellation fees.
HostelWorld is the best Hostel booking site that also has great budget private rooms that we use a lot. You won’t see these places on the other booking sites.
How To Pack Light
Being flexible, spontaneous, and able to roll with the punches are crucial to successful travel. And there’s no better way to jack that all up than by having some massive suitcase.
Find more great How To Pack Light Tips so you can spend more time on travel and less on the stuff.
Download Our his & hers travel packing list
Print this packing list and throw it in your bag so you'll be good to go for your next trip.
Our Biggest Piece Of Advice…
When you land in some foreign far corner of the earth where nobody speaks English do yourself a favor and have your transport out of there figured out.
After a hellaciously long international flight, there’s nothing worse than being bombarded with aggressive taxi drivers while you try to figure out if that’s a fair price or not.
Do yourself a favor and research this before you get there so you can start your trip off on the right foot.
Or better yet catch a ride from a friendly local
Thanks for making it to the end! I hope you got something out of it. If you liked it don’t forget to share it to your favorite social media, links are to your left.
Until next time, happy travels!