How to plan a vacation trip in 7 steps (travel blogger style)

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.

how to plan a vacation anywhere in the world

How to plan a vacation (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, it’s not going to awesome places.

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Or eating delicious food.

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Or making cool friends along the way.

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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:

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I even include things like the weather and information for airport lounge access.

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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.

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  • 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:

    1. Recommendations
    2. Social media
    3. Friends and family

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    “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.

    Social media

    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.

    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.

    “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.

    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

    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.

    Step 2: Pick a time to travel

    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:

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    And here’s a flight two months later:

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    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 aren’t visiting a destination — typically due to weather (e.g., a ski lodge in the summer). You’ll normally find very affordable flights and accommodations during this time, but on the flip side, there’s 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 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.)

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    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:

    1. 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.
    2. Holidays. You know what’s more expensive than vacationing in New York City? Going to New York City on New Year’s Eve. And if you’re budget conscious, you’re 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, 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:

    • Call the local tourism office. Most every country, state, and city will have a tourism office that’ll be more than happy to help you with your travel plans. Simply ask them, “When’s 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 you’re 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, it’s time to…

    Step 3: Take time off of work

    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.

    This. Is. RIDICULOUS!!!

    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).

    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, 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:

    • You own a project and it might not get done while you’re gone.
    • The work might end up on your boss’s 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 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.

    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 I’ll let celebrity chef Gordon Ramsay take it from here:

    Gordon Ramsay shouts WRONG!

    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:

    1. Travel credit cards
    2. Repositioning with error fares

    Let’s take a look at both now.

    Travel credit cards

    We’ve written about travel credit cards before — but it bears repeating:

    Using travel credit cards to pay for flights is a Big Win.

    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.

    Repositioning with error fares

    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:

    • 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.
    • Scott’s Cheap Flights. A tried-and-true resource when it comes to finding error deals. Scott’s offers a free newsletter that’ll notify you whenever they find a deal along with instructions on how to book it.
    • Next Vacay. This is Naveen’s 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:


    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.

    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, you’re going to want to make sure you have a place to stay while you’re on vacation too. That brings us to…

    Step 5: Find a good place to stay

    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.”

    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!).
    • They’ve aggregated accommodations ranging from uber-luxury hotels to small mom-and-pop bed and breakfasts. Also, they’ll kick back a free night in a hotel for frequent users. Awesome.
    • Though a bit more limited in selection, i-escape gives travelers only the best accommodations at the best prices.
    • With over 35,000 hostels in over 170 countries, HostelBookers should be your first stop when trying to find a good hostel. You’ll have no trouble finding an awesome (yet budget-friendly) option here.
    • HostelWorld. Another great option to find hostels. The site’s 24/7 customer support is also at your call in case you have any questions or concerns about your bookings.

    Bonus: Want to start your dream business and never depend on a boss again? Download my FREE Charles Schwab’s 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 he’s 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.

    1. Save money for travel
    2. 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.”


    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.”

    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 won’t 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 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:

    • Create multiple income streams so 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.

    Download a FREE copy of the Ultimate Guide today by entering your name and email below — and start blowing up your net worth today.

    Yes, send me the Ultimate Guide to Making Money

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