Planning a vacation doesn’t have to be a pain. That’s why I want to show you a great system you can use to plan the perfect trip. As a personal finance expert, I keep a budget in my mind when planning my trip too.
Want to learn how to plan a vacation? I’ll tell you, but first: Do you know what one of my favorite parts of vacations is? No, it’s not going to awesome places.

Or eating delicious food.

Or making cool friends along the way.

One of my favorite things is planning the vacation. Nothing makes me feel better than a well-formatted calendar with flight info and dinner reservations.
Check out this itinerary I prepped for a recent trip to Singapore:
I even include things like the weather and information for airport lounge access.
It looks like a lot…and it is. However, you don’t have to go as crazy as me.
Today I’m going to show you a simple system that will help make your trip MUCH easier.
To help you even more with planning your vacation, we also talked to a few notable travel bloggers and professionals on how you can get the most out of your vacation planning. They’ve dedicated themselves to helping others get the most out of their travel experiences — and now they want to help you.
So without further ado…
Naturally, where and how you go on vacation is determined by your individual circumstances:
And depending on your situation, you might break from the suggestions in this article — and that’s okay! I only want to provide a framework you can work from. What you do with it is ultimately up to you.
Knowing this, you’re going to want to decide where you want to go. Doing this first is important for two big reasons:
It can often be hard though to decide where you want to go.
After all, you can travel anywhere in the entire world. With all of your choices, how are you going to decide?
There are three great areas you can look towards to find your next vacation spot:
People you trust can be great sources of destination inspiration — and it’s the main way Matthew Karsten, aka the Expert Vagabond, decides where to go next. Check out his website, he definitely knows how to plan a vacation.
“Word of mouth is probably my top source for recommendations,” Karsten says. “[When I hear of a good place], I keep a bucket list of destinations I want to visit in Evernote, along with details about possible activities and links to relevant online articles.”
Ask your friends and loved ones for good vacation recommendations. See what they liked about the place and what you can do there if you decide to visit.
Also, create a “bucket list” of destinations you’d love to go to.
It doesn’t have to be on Evernote either. It can also be in a Google Doc, Excel sheet, the Notes app on your phone, or in your middle school diary. Every time a friend recommends a place to go, write it down. You can refer to this later when deciding where you want to go.
Your Facebook and Instagram aren’t just for getting likes, you can also use them to find awesome vacation destinations.
I use Instagram’s ‘collections’ feature to save other people’s photos based on location,” says Karsten.
He continues, “Instagram changed travel a lot. All of a sudden, destinations that never saw too many tourists are getting swamped with people trying to copy popular photos they saw on Instagram.”
Though you might not want to copy other people’s photos, you can leverage Instagram collections like Matt and start compiling your own images from places you’d like to go. For information on how to exactly do that, check out Instagram’s page on it here.
Sometimes the best vacation destinations are where your friends and family are. Not only can they help you save money on accommodations but they can also fill you in on things to do there.
“I’ve been traveling more for friendships than anything else,” Naveen Dittakavi of the travel deal website Next Vacay says. “It’s nice to bond and catch up with old friends — especially as we get older.”
Do you have a friend you’ve been meaning to visit for a while? Or maybe a family member you haven’t seen in a long time? Reach out to them and use the opportunity to visit them.
Once you decide where you want to go, I want you to get specific with it. It can be anywhere. Say you decide, “I want to go to London!” I want you to get even more specific with it.
A good example: “By July, I want to go to London for a week with my boyfriend.”
If you want to take it a step further, set a SMART objective for your vacation plans.
SMART stands for:
It’s the solution to vague goal setting that gets you nowhere. Like whenever anyone says, “I want to get fit” for their New Year’s Resolution or “I want to travel in the future.”
The way it works is it niches down these big vague goals and gets precise with them. This leads to better focus when you set out to accomplish your goals.
Check out my article on how to set SMART objectives to learn how to craft one yourself.
Traveling is like a game of Twister: It’s best to stay flexible.
When you travel is just as important as where you travel. In fact, your timing can mean the difference of hundreds, possibly thousands of dollars in airfare.
Let’s say you want to take a 7-day trip to Cabo from New York City.
Here’s what a flight from July 6 to July 13 costs:
And here’s a flight two months later:
Time matters! Which is why you should be flexible with your travels.
“Flexibility is the most important thing in finding a cheap flight,” travel blogger and entrepreneur Nomadic Matt says. “You need to be flexible in your date. If you have to go to Paris on a specific date, then you have to pay the fare. There’s no magic bullet to make the price go down.”
He continues, “But by changing your date by a day or two, you might be able to drop the price.”
If you want to find the best time to travel to a destination, consider these three things about the location:
“Shoulder seasons are my favorite time to visit,” Karsten says. “You don’t want to visit during the wrong season.”
Shoulder seasons allow travelers to take advantage of good weather at a certain destination, AND there’s the added benefit of lowered cost on flights and accommodations.
(Also you don’t have to deal with a bunch of annoying tourists.)
Pull up Google Calendar and start looking at dates that work for you.
If you’re looking to save extra money on travel, consider your destination’s off-season or shoulder season.
Nailing down when exactly they occur isn’t difficult, though, as long as you take into account several factors. The biggest of which are:
Bryce Conway, CEO of the travel hacking site, leverages this knowledge when he travels, saying:
“One of my wife’s and I’s favorite thing to do each year is to go to Western Europe either over President’s Day weekend or MLK Day weekend. It’s not a holiday over there. The weather is not as nice as it is in America, but everything is half price and you can walk straight in.”
A few other ways you can find an area’s peak season:
Remember: Not all destinations are alike. That means their peak, off-peak, and shoulder seasons will be different.
Once you know where and when you want to travel, it’s time to…
SAD FACT OF THE DAY: The majority of Americans don’t use all of their vacation days.
A 2018 study conducted by the U.S. Travel Association discovered that over half of Americans leave vacation days on the table due to pressures at work.
You’re losing time and money by not taking your vacation days. These are benefits ensured to you by your employer. Use them!
And if you’re on vacation, you’re definitely going to want to use them (yes, even YOU remote and freelance workers).
The difficulty of requesting vacation days varies from job to job. However, you can make the process simple for you and your company by using some good old-fashioned scripts.
Oh look, here’s one now:
Subject: Vacation request (October 2nd through October 6th)
Hi [manager’s name],
I’d like to request vacation time from Monday, October 2nd, through Friday, October 6th because I’ll be taking a family vacation over those days.
While I’m gone, I’ll be reachable by phone but not email. I’ll be making sure that we have coverage in the support queue while I’m gone, and I’ll also be distributing a playbook to my team so it’s clear who owns which issues.
Is this OK?
This is a great script to use even if your vacation is during a “busy time” for your company.
Why? First, consider why your boss might want to deny you vacation time:
This script addresses all of these points in the last paragraph. By showing that you’ve already gone the extra mile to make sure that your responsibilities will be taken care of in your absence, you allay your boss’s concerns that your work won’t get done.
It also maintains a friendly tone throughout the message AND you give a good reason for your absence. You’ll want to send this email weeks — possibly even months — in advance. It’s far easier for your boss to say “yes” when the company has time to plan for your absence.
For more information on requesting time off, see my article on how to ask for vacation days.
One of the most common misconceptions about traveling is the idea that flying (especially international) has to be expensive.
I have my thoughts on this…but I’ll let celebrity chef Gordon Ramsay take it from here:
In fact, flying can be one of the most affordable parts of the trip if you know how to leverage the right tools.
Two of the most effective tools to find affordable flights are:
Let’s take a look at both now.
We’ve written about travel credit cards before — but it bears repeating:
Say a round-trip flight from New York to Paris costs $500.
If you book using the card we’re about to suggest, you could get that same flight for FREE.
In fact, you can save THOUSANDS each year if you leverage reward points. And the more time you have to plan, the more points you can amass — many cards even give you sign up bonuses.
But with so many options out there, which one should you get?
For more information on travel credit cards as well as how you can maximize them, be sure to check out our article on the subject.
NOTE: If you’re in credit card debt DO NOT sign up for a travel credit card…or any other credit card for that matter. Instead, check out my article on how to get out of debt fast.
If you’re nervous about getting into travel hacking through credit cards, that’s okay. There’s another solution that’ll help you find ridiculously cheap flights.
I’ll give it to you straight: Airlines really mess up sometimes.
Sometimes their mishaps lead to some great deals for you through “error fares.” Error fares are airline tickets that are, temporarily, a WAY lower price than they’d normally be (typically through technical or human error). These fares often mean travelers can get tickets from mainland U.S. to places like Europe and Asia for a few hundred dollars or less.
To find these errors and deals, there are a number of websites that are dedicated to hunting them out.
Here are a few that I suggest you leverage the next time you’re finding flights:
One key thing to remember when purchasing an error fare:
You’re taking advantage of their mistake. If you point out how they messed up, they’re going to realize it and not let you have the deal. Stick to booking through the sites above or through third-party sites like Skyscanner instead.
Also don’t ignore an amazing flight deal because it’s departing from a different airport than the one closest to you. Remember how it’s important to be flexible on when you leave? Same goes for where you leave.
This is key to a process called “repositioning.”
Repositioning simply means that you’re willing to depart from an airport that might not be close to you. Also, you might be arriving at a destination that might not be your final one.
From Naveen:
“You don’t have to fly out of your own home city. I’m from Atlanta. However, when I flew out to India a few years ago I didn’t fly out of Atlanta. I booked a few different tickets that took me from Baltimore, then back to Atlanta, then to Paris, then to Bombay. I ended up coming back through my home airport — but it was cheaper than trying to find a flight from Atlanta to India!”
Say you live in Denver and want to fly to London. All the flights from your airport are crazy expensive ($900+).
However, you find a flight going out of Chicago to London for $200 on Scott’s Cheap Flights. A quick search on Skyscanner shows you that a flight to Chicago is just $90 from Denver.
It’s cheaper then to fly to Chicago and catch that amazing flight deal for $290 total.
“If you’re willing to go to a different airport, you can save a TON of money,” Naveen says. “If you want to go to say Paris, but there other cities in Europe on sale like Dublin, you can then take a flight to there and hop on over to where you want to go in Europe via train or plane.”
By repositioning your origin point and destination, you can save a ton of money on airfare. It’s going to take more time but the trade-off is huge for your wallet. Remember: When traveling you’ll often be pressed for either money or time. Choose your flights accordingly.
Sign up and start following the sites we mentioned above to find great deals on flights through error fares.
You might even get lucky and find an error fare through an airport near you!
Once you have your flight, you’re going to want to make sure you have a place to stay while you’re on vacation too. That brings us to…
Finding a great place to stay that doesn’t break the bank sometimes seems impossible.
However, finding a great deal on accommodations is simple IF you’re willing to break the mold.
“[My wife and I] were in Switzerland a couple of years ago and we stayed at a hostel in a private room,” recalls Naveen. “There are no budget hotels in a place like Switzerland. It’s either a hostel or ultra-glamorous hotel. The hostel we stayed at was still very comfortable and affordable for us though.”
Along with hostels, travelers can also find great, affordable places to stay through home sharing sites like Airbnb or Couchsurfing.
“If you really want to save money on accommodations, backpacker hostels are the way to go,” Karsten says. “I once spent a month living in a Nicaraguan hostel for $5 a night!”
If you really prefer to stay in a hotel though, that’s okay! You can book awesome deals on hotels using travel credit cards since they often allow you to spend points on hotel rooms.
There are even awesome cards like the Starwood Preferred Guest Credit Card that allow you to maximize your points for hotel stays.
Many websites also exist to help you get the most out of your hotel bookings.
“One site I really like is,” suggests Naveen. “They have sweet deals for hotel accommodations at different price points. Another great one is They have a program that holds 10% of your spend with them, and eventually they give you a free night. So every 10 nights or so, you can get a free night in a hotel.”
By being flexible and a bit judicious with your accommodation search, you can find an awesome place to stay during your vacation and not break the bank.
Use the tools below to help you find some of the best deals on places to stay.
Imagine you’ve finally made that trip to Paris you’ve always dreamed of. You’re taking in the sights, the sounds, and the people. You LOVE it. So you decide to buy yourself a nice meal to celebrate your first night — and it’s amazing.
Then comes time to pay for your check. You hand your credit card over. Your waiter scans it…and scans it…and scans it again.
He hands it back to you and shakes his head.
You don’t have any other way to pay for it. Soon you’re in a French gulag, breaking big rocks into smaller rocks until you can repay your debt. This is what could happen (probably) if you don’t warn your credit card company about your travels.
Credit card companies get nervous when they see you make purchases you don’t normally make — especially when those purchases are somewhere you don’t live.
That’s why it’s important to give them a heads up before you go.
From Naveen:
“I call my card companies beforehand in order to tell them about our travel plans. Most of these companies don’t even need you to talk to a rep — it’s fully automated.
You just call up the company and say, ‘travel plan’ at the prompt. Then they’ll ask you for the countries you’re going to in order of your visit, when you’re going, and when you’re coming back.
Then they authorize the cards to be used in each of those countries.”
Call your credit card company and tell them about your trip.
Here are the numbers for the major card companies out there to help:
Simply inform the representative that you plan on traveling and that you’ll be using your card. They’ll ask you where you’re going, how long you’ll be gone for, and voila! You’re prepped for travel. Not getting stranded abroad is definitely a key step in how to plan a vacation.
Much like airlines, credit card companies often screw up even when you give them the heads up.
You might find yourself in a situation where you’ve warned them that you’ll be traveling and they still cancel your credit card when you try to make a purchase abroad.
That’s okay! Because you’re an IWT reader, you’ve prepped for this situation by packing two alternatives:
There are TWO ways you can prep your vacation budget.
Both can be simple, painless, and really fun (seriously).
One of my favorite ways to save money for a trip is through a process called “mental accounting.”
Mental accounting is a psychological technique wherein people treat money differently depending on how they got it and plan on spending it.
A great example of this: Using a sub-savings account.
Most banks allow you to create a sub-savings account along with your normal savings account (you can even name them too!). You can put money into this account each month and know that it’s going towards your traveling goals.
By mentally accounting this money for travel, you’re leveraging a powerful psychological trick of focusing your savings goals.
You can even couple the sub-savings account with another great system I love: Automated finances.
Automating your finances is a system wherein your money works passively for you. It’s the ultimate cure to never knowing how much you have in your checking account and how much you can spend.
When you receive your paycheck, your money is funneled to exactly where it needs to go — whether that be your utilities, rent, Roth IRA, 401k, or your savings account.
“I always have a budget for travel,” Naveen says. “That includes saving a couple hundred dollars a month towards a travel fund. This is the money that I saved through the IWT system. I use for hotels and restaurants.”
If you want to learn more about how to automate your finances, check out this 12-minute video of me explaining the exact process I use below. Setting everything up won’t take more than one or two hours out of your day, but it will save you thousands of dollars over your lifetime.

Saving money isn’t the only way you can hold onto cash during your travels. There are actually a variety of ways you can earn money while abroad too.
That’s why my team and I have worked hard to create a guide to help you navigate all the systems that’ll help you earn more money today: The Ultimate Guide to Making Money.
In it, I’ve included my best strategies to:
If you’re thinking of an ideal budget for a vacation, a good rule is to spend around 15% of your gross income for vacations for the year. So divide that amongst the amount of trips you want to take and that’s your budget per trip, although some trips can be more expensive! They don’t all have to be the same price.
It depends on you! A perfect vacation is on that might include the perfect place with the perfect people, plan, & nothing goes wrong – or it does. There are things out of your control to consider like weather, mood, activity times, and other things that help or hurt your plans.
On average, people spend between $1500-$2500 for a one week vacation trip. That’s about $180-$310 a day for hotel + food, and around $400 for airfare alone. That doesn’t include other travel like car expenses or attraction fees.

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