How to Plan A Perfect Vacation Trip: 7 Easy Steps (+ budget tips)
Planning a vacation doesnt have to be a pain. Thats 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.
How to plan a vacation trip (and not hate yourself)
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, its not going to awesome places.
The backyard pool of my hotel room in Thailand.
Or eating delicious food.
Follow me on Instagram: instagram.com/ramit
Or making cool friends along the way.
Im the one on the left.
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 Im going to show you a simple system that will help make your trip MUCH easier.
How to plan your vacation in 7 easy steps
- Step 1: Decide where to go
- Step 2: Pick a time to travel
- Step 3: Take time off work
- Step 4: Find affordable flights
- Step 5: Find a great place to stay
- Step 6: Call your credit card companies
- Step 7: Budget consciously for your trip
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. Theyve dedicated themselves to helping others get the most out of their travel experiences and now they want to help you.
So without further ado…
Step 1: Decide where and how to go
Naturally, where and how you go on vacation is determined by your individual circumstances:
- Are you more crunched for time or money?
- Are you traveling alone or with friends or your family?
- Is your work flexible with when you can leave or do you have a set time frame when you can travel (e.g., a teacher)?
- Do you want to go somewhere close by where you can drive, or would you have to fly?
And depending on your situation, you might break from the suggestions in this article and thats okay! I only want to provide a framework you can work from. What you do with it is ultimately up to you.
Knowing this, youre going to want to decide where you want to go. Doing this first is important for two big reasons:
- It helps you psychologically. The mental benefits of setting a good goal are enormous. Having a goal destination in mind gives you something to work for when youre preparing for your trip.
- It determines practically every aspect of planning. No two vacation destinations are alike, which means each destination is going to change the way you tailor your budget and itinerary.
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:
- Recommendations
- Social media
- Friends and family
Recommendations
People you trust can be great sources of destination inspiration and its 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 youd love to go to.
It doesnt 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.
Social media
Your Facebook and Instagram arent 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 peoples photos, you can leverage Instagram collections like Matt and start compiling your own images from places youd like to go. For information on how to exactly do that, check out Instagrams page on it here.
Friends and family
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.
Ive been traveling more for friendships than anything else, Naveen Dittakavi of the travel deal website Next Vacay says. Its nice to bond and catch up with old friends especially as we get older.
Do you have a friend youve been meaning to visit for a while? Or maybe a family member you havent seen in a long time? Reach out to them and use the opportunity to visit them.
ACTION STEP: Decide where you want to go and get specific
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:
- Specific
- Measurable
- Attainable
- Relevant
- Time-oriented
Its the solution to vague goal setting that gets you nowhere. Like whenever anyone says, I want to get fit for their New Years 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.
Step 2: Pick a time to travel
Traveling is like a game of Twister: Its 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.
Lets say you want to take a 7-day trip to Cabo from New York City.
Heres what a flight from July 6 to July 13 costs:
And heres 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:
- Peak season. This is the time of year when most tourists will visit a location. This is often due to good weather and holidays surrounding it (e.g., the Grand Canyon or Mount Rushmore in the summer). Flights and accommodations tend to be the most expensive during this time.
- Off-peak season. This is when the majority of tourists arent visiting a destination typically due to weather (e.g., a ski lodge in the summer). Youll normally find very affordable flights and accommodations during this time, but on the flip side, theres usually a reason for it being off-peak. In some countries, off-peak can mean a monstrous monsoon happens nearly every day.
- Shoulder season. This is the time between peak and off-peak and a good time to take advantage of the benefits from both seasons.
Shoulder seasons are my favorite time to visit, Karsten says. You dont want to visit during the wrong season.
Shoulder seasons allow travelers to take advantage of good weather at a certain destination, AND theres the added benefit of lowered cost on flights and accommodations.
(Also you dont have to deal with a bunch of annoying tourists.)
ACTION STEP: Find a date to go on vacation
Pull up Google Calendar and start looking at dates that work for you.
If youre looking to save extra money on travel, consider your destinations off-season or shoulder season.
Nailing down when exactly they occur isnt difficult, though, as long as you take into account several factors. The biggest of which are:
- Weather. Summer is always going to be an incredibly busy time for common vacation destinations like cruises, beaches, and…well, anywhere where there are outdoor activities. Also the fact that school is out for the summer means families will be traveling a LOT during this time.
- Holidays. You know whats more expensive than vacationing in New York City? Going to New York City on New Years Eve. And if youre budget conscious, youre going to want to keep in mind the holidays when YOU travel. Depending on the destination, flights and hotels are going to be more expensive if it lands on a major holiday.
Bryce Conway, CEO of the travel hacking site 10xTravel.com, leverages this knowledge when he travels, saying:
One of my wifes and Is favorite thing to do each year is to go to Western Europe either over Presidents Day weekend or MLK Day weekend. Its 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:
- Call the local tourism office. Most every country, state, and city will have a tourism office thatll be more than happy to help you with your travel plans. Simply ask them, Whens your peak season months? (For a comprehensive directory of tourism offices, follow this link.)
- Compare flights and hotel prices for different dates online. If you find that the date youre trying to book is WAY more expensive than another one a few months away, you might be booking on 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, its time to…
Step 3: Take time off of work
SAD FACT OF THE DAY: The majority of Americans dont 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.
This. Is. RIDICULOUS!!!
Youre losing time and money by not taking your vacation days. These are benefits ensured to you by your employer. Use them!
And if youre on vacation, youre definitely going to want to use them (yes, even YOU remote and freelance workers).
ACTION STEP: Take time off of work
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, heres one now:
Subject: Vacation request (October 2nd through October 6th)
Hi [managers name],
Id like to request vacation time from Monday, October 2nd, through Friday, October 6th because Ill be taking a family vacation over those days.
While Im gone, Ill be reachable by phone but not email. Ill be making sure that we have coverage in the support queue while Im gone, and Ill also be distributing a playbook to my team so its clear who owns which issues.
Is this OK?
Thanks,
-Ramit
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:
- You own a project and it might not get done while youre gone.
- The work might end up on your bosss plate.
- Your boss might have to delegate YOUR tasks to other workers (which nobody likes doing).
This script addresses all of these points in the last paragraph. By showing that youve already gone the extra mile to make sure that your responsibilities will be taken care of in your absence, you allay your bosss concerns that your work wont get done.
It also maintains a friendly tone throughout the message AND you give a good reason for your absence. Youll want to send this email weeks possibly even months in advance. Its 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.
Step 4: Find affordable flights
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 Ill 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:
- Travel credit cards
- Repositioning with error fares
Lets take a look at both now.
Travel credit cards
Weve 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 were 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 youre 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 youre nervous about getting into travel hacking through credit cards, thats okay. Theres another solution thatll help you find ridiculously cheap flights.
Repositioning with error fares
Ill 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 theyd 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 youre finding flights:
- Secret Flying. This site immediately posts any errors or deals they find. You can even use their handy search function and enter your country of origin and destination so they can find a deal more suited for you.
- The Flight Deal. Another great site to find amazing deals on airfare as well as hotels, rental cars, and travel credit cards. They also give you information on flight deals happening in almost every major U.S. metro area.
- Scotts Cheap Flights. A tried-and-true resource when it comes to finding error deals. Scotts offers a free newsletter thatll notify you whenever they find a deal along with instructions on how to book it.
- Next Vacay. This is Naveens very own site that helps travelers find the best deals. Next Vacay automatically crawls through various airfare sites to find you the cheapest flight possible.
One key thing to remember when purchasing an error fare:
Youre taking advantage of their mistake. If you point out how they messed up, theyre 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 dont ignore an amazing flight deal because its departing from a different airport than the one closest to you. Remember how its 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 youre 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 dont have to fly out of your own home city. Im from Atlanta. However, when I flew out to India a few years ago I didnt 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 Scotts Cheap Flights. A quick search on Skyscanner shows you that a flight to Chicago is just $90 from Denver.
Its cheaper then to fly to Chicago and catch that amazing flight deal for $290 total.
If youre 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. Its going to take more time but the trade-off is huge for your wallet. Remember: When traveling youll often be pressed for either money or time. Choose your flights accordingly.
ACTION STEP: Start searching for error fares and reposition if you have to
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, youre going to want to make sure you have a place to stay while youre on vacation too. That brings us to
Step 5: Find a good place to stay
Finding a great place to stay that doesnt break the bank sometimes seems impossible.
However, finding a great deal on accommodations is simple IF youre 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. Its 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, thats 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 i-escape.com, suggests Naveen. They have sweet deals for hotel accommodations at different price points. Another great one is Hotels.com. 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.
ACTION STEP: Book a great place to stay
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.
- Airbnb. More than just renting spare bedrooms, you can find some really cool places at a relatively low cost if you are diligent in your search (you can even stay in a freaking castle!).
- Hotels.com. Theyve aggregated accommodations ranging from uber-luxury hotels to small mom-and-pop bed and breakfasts. Also, theyll kick back a free night in a hotel for frequent users. Awesome.
- i-escape.com. Though a bit more limited in selection, i-escape gives travelers only the best accommodations at the best prices.
- HostelBookers.com. With over 35,000 hostels in over 170 countries, HostelBookers should be your first stop when trying to find a good hostel. Youll have no trouble finding an awesome (yet budget-friendly) option here.
- HostelWorld. Another great option to find hostels. The sites 24/7 customer support is also at your call in case you have any questions or concerns about your bookings.
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Step 6: Call your credit card companies
Imagine youve finally made that trip to Paris youve always dreamed of. Youre 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 its 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.
Declined.
You dont have any other way to pay for it. Soon youre in a French gulag, breaking big rocks into smaller rocks until you can repay your debt. This is what could happen (probably) if you dont warn your credit card company about your travels.
Credit card companies get nervous when they see you make purchases you dont normally make especially when those purchases are somewhere you dont live.
Thats why its 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 dont even need you to talk to a rep its fully automated.
You just call up the company and say, travel plan at the prompt. Then theyll ask you for the countries youre going to in order of your visit, when youre going, and when youre coming back.
Then they authorize the cards to be used in each of those countries.
ACTION STEP: Tell your credit card companies about your travels but prep for the worst
Call your credit card company and tell them about your trip.
Here are the numbers for the major card companies out there to help:
- Visa: 1-800-847-2911
- Mastercard: 1-800-307-7309
- Discover: 1-800-347-2683
- American Express: 1-800-528-4800
Simply inform the representative that you plan on traveling and that youll be using your card. Theyll ask you where youre going, how long youll be gone for, and voila! Youre 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 youve warned them that youll be traveling and they still cancel your credit card when you try to make a purchase abroad.
Thats okay! Because youre an IWT reader, youve prepped for this situation by packing two alternatives:
- Cash. Its always a good idea to carry $100 – $500 in emergency cash just in case something goes wrong. I bring cash with me just in case my card doesnt work while traveling, Naveen says.
- ATM/Debit card. One of the biggest hassles when it comes to getting money while abroad is international fees especially when it comes to ATMs. However, you can circumvent that with the right cards.There are certain cards that will refund your ATM transaction fee. Charles Schwabs debit card is a great example, Naveen says. In fact, I have a friend who keeps a certain amount of money in his Schwab account so he can use it if hes abroad or in Vegas or something since the fee is refunded to your account by the bank.
Step 7: Budget consciously for the trip
There are TWO ways you can prep your vacation budget.
- Save money for travel
- Earn money for travel
Both can be simple, painless, and really fun (seriously).
How to save money before you plan a vacation
One of my favorite ways to save money for a trip is through a process called mental accounting.
Pretty much what mental accounting looks like.
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 its going towards your traveling goals.
By mentally accounting this money for travel, youre 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. Its 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.
ACTION STEP: Automate your finances
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 wont take more than one or two hours out of your day, but it will save you thousands of dollars over your lifetime.
Earning money while traveling
Saving money isnt 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.
Thats why my team and I have worked hard to create a guide to help you navigate all the systems thatll help you earn more money today: The Ultimate Guide to Making Money.
In it, Ive included my best strategies to:
- Create multiple income streamsso you always have a consistent source of revenue.
- Start your own business and escape the 9-to-5 for good.
- Increase your income by thousands of dollars a year through side hustles like freelancing.
Frequently Asked Questions About Planning A Vacation
How much money should I save for a vacation?
If youre 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 thats your budget per trip, although some trips can be more expensive! They dont all have to be the same price.
What is a perfect vacation?
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.
How much money do you need to travel for a week?
On average, people spend between $1500-$2500 for a one week vacation trip. Thats about $180-$310 a day for hotel + food, and around $400 for airfare alone. That doesnt include other travel like car expenses or attraction fees.
1 Comment
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matt
Sorry about your lounge situation. Plaza Premium leaves a lot to be desired. The Singapore Airlines lounge at SIN is excellent and travel hacking Star Alliance is pretty easy with United (or Aeroplan in Canada).