This blog is coming to ya from Stephanie- the Queen of Trip Planning. You’ll never meet anyone with a more detailed travel itinerary than me, that I am positive of. What my husband Zach brings to the table is the acceptance of going anywhere and doing anything I plan. He’s very good at that. Lucky for me, I call the shots when it comes to our vacations. That’s how I like it.

I’ll be honest, it is no easy feat. When I sit down to plan a trip, I spend easily over a hundred hours researching and typing up my travel guide. I have steps I follow to plan each and every trip to the best of my abilities; because who knows if we’ll ever make it back to that city! In an effort to make your life easier, I have condensed those steps and simplified them.

Today we are going to teach you the steps to planning a vacation. The thirteen steps below will 100% prepare you for your next trip and make it a trip of a lifetime instead of a flat-out failure. Pretty soon you will be the best trip planner in the country (besides me of course).

So keep reading. You don’t want to skip over anything.

13 Easy Steps to Planning an awesome Vacation

Planning a trip: Step one

The first step to planning a vacation is deciding where to go.

About 5-6 months ahead of time, begin brainstorming locations for your next trip. I have a bucket list of cities I want to see, so I pull that list out and consider things like weather and distance.

We also use our ancestry to guide our travels sometimes. Some people may have a less precise way of choosing a destination like blindly pointing their finger on a map.

However in my mind, what’s the point in going to a destination when it’s the worst time of the year to go and it is miserably hot? Instead, be strategic with the destination you choose so your trip can be as enjoyable as possible.

I use AccuWeather to search weather for specific months. Once you’ve made up your mind on the location, move onto step two. (See Related: Our Travel Bucket List)

PS- Going somewhere international? Don’t forget to check your passport expiration date and order a new one if needed! A good trip planner never lets a passport ruin their vacation!

Planning a trip: step two

Now that you know where you want to go, it’s time to set those vacation dates in stone.

Maybe you only have a certain date range you can travel within due to work or school, so you’ve gotta go then. However if your dates are more flexible, keep a few things in mind.

First off, how many days do you want to spend there? If it’s an international trip, subtract days you will lose from the long flight and time changes. Next, can you fly during the week?

Flights are cheaper during the week than on the weekend. Third, do you want to be at the destination over a weekend for some reason? Maybe you enjoy the Friday nightlife scene or maybe there’s an event or festival you want to attend.

Planning a trip: step three

This next step to planning a vacation may or not apply to you; it relates to budget.

If you’re like us, we don’t set a specific monetary limit on our travel expenses. We simply make the most budget-friendly decisions for everything, but we don’t keep tally of it and let it limit us.

We usually go on one nice trip a year and we work our butts off all year to earn that. So we enjoy every minute of traveling without the stress of sticking to a budget!

With that said, some people have the need to set a budget for a trip. If that’s you, good for you! Now is the time to set a total budget for your trip and possibly a daily budget.

This way, you can decide how luxurious you’re going to make your trip and how to afford your trip. From backpacking to couchsurfing to apartment rentals to average hotels to luxury…there are options for every budget.

Set a budget now so that decisions you must make in step eight (below) come easier. For some ideas on low cost travel, here are some great tips from Endlessly Wanderlust.

Planning a trip: step four

This step is my favorite step: research!

This can range from a few hours to over a hundred hours like me! I guess it depends on how detail-oriented you are. For me, I really enjoy reading and learning about history and sites to see. So as the master trip planner, this is not a burden at all. First, I go to amazon and buy a used but recent travel book from Fodor, Lonely Planet, or Frommer’s for the location we are visiting. Then I read that from start to finish. (PS- if you don’t want to do all this research, see I’ve already written a travel itinerary for the city you are visiting here)

Planning a trip: step five

Once you have done plenty of reading, it is time to narrow things down and start your own travel guide.

I would never go on a trip without having my own guide printed. Why? If I just brought the travel book I bought, I would be overwhelmed and unable to make decisions on the spot.

Those books are amazing….but they have way too much! Unless you’re spending months in a city, there is no possible way you’d need or want to do everything in that book. Most of us do 1-2 week trips. So write your own mini-guide and make your life easier.

Open up a document and start typing the top things you want to do. Let’s keep this list general for now (we will go into more detail in step seven). Eliminate the things that don’t interest you, that are too expensive, or that are inconvenient. If you’re going to more than one city, separate those things to do by city.

When you have completed your basic bucket list for this trip, it’s time to allocate your time. If you’re staying in the same city the entire trip, skip down to step six.

If you’re jumping around to two or more cities, then ask yourself this: how many days will you spend in each city? Let your list guide you. For example, for our Spain trip I had about 40 things listed under Barcelona, 10 under Valencia, and 20 under Madrid.

So we spent the majority of our time in Barcelona and the least of our time in Valencia. Make a decision regarding which days you will spend in which cities. Discuss this with your travel mates to get their input. You won’t be able to move on any further until this decision is made…no pressure.

Planning a trip: step six

It’s time to make a trip schedule!

Can you tell this is my second favorite step to planning a vacation? That’s because I live by the minute and I’m not ashamed to admit that.

Open your travel guide document, type out each day you’ll be on vacation, and start allocating the things you want to do under each day. This may sound straight-forward, but I encourage you to use your imagination and truly think it through. This is what distinguishes you from an average trip planner to an excellent one.

This is the time where I put my imaginary walking shoes on and walk through each day in my mind. Let me share an example so you can try it too.

First, I think about the week as a whole. Say we are going to Barcelona for one week. I would imagine myself walking miles and miles per day, being a busy-bee, and seeing 4-5 sites a day.

Most likely, after a few days of a busy schedule, the beach will be calling our names. So I would schedule a beachy relaxation day mid-week for some time to unwind.

Then, I think about each day individually. Barcelona is such a big city so it would be annoying and expensive to schedule things on the same day that are on opposite sides of the city. Instead, I would schedule all the sightseeing things in the El Born neighborhood for one day and everything in the Eixample neighborhood for another day.

Are you starting to understand my walking shoes journey now? Schedule sites based on location, convenience, and whatever is going to make your life easier. It is vacation, right? The less stress, the better.

Getting back to your travel guide document, complete each day with everything you want to do and possibly restaurants you want to go to.

Then make any bookings you think you need to make before arriving. I like to book tours ahead of time because the popular sightseeing places often have a limit on how many people can visit per day. So pre-book the hot items and secure your spot with the best tours in town.

Below is an example of my broad day-by-day schedule for just a portion of our Spain trip. You can see the relaxation times in blue and the booked tickets in red.​


Sunday May 14 | BARCELONA

Formula One Race: take the 8:31am train, tickets booked

El Born neighborhood: church, market, passeig, dinner at bacoa, and drinks at juanra

Monday May 15 | BARCELONA

Las Ramblas neighborhood: walk North to South, teatre, shop

El Raval neighborhood: hospital, church

Eixample neighborhood: 545pm Casa Batllo tickets booked, 9pm Casa Mila/La Pedrera tickets booked

Tuesday May 16 | BARCELONA

Montjuic neighborhood: cable car to the castle

Barceloneta neighborhood: walk the beach, walk the parks, romantic nice dinner on the beach

Planning a trip: step seven

This step can be skipped if you’d like. However, it’s a necessity for me because I don’t like when things go wrong. This step is all about the details.

Now that you have your travel guide typed, let’s fill in the blanks. What I mean is, research details about every site.

The details you should research and type alongside each site are:

  • Hours of operation
  • Address or Neighborhood
  • Reservation or Tickets required ahead of time
  • Tips from online reviews

If you skip this step, you may show up to a site and realize it’s closed that day. Which may be fine, unless it’s your last day there. If you skip this step, you may arrive at a site and learn they let you in with tickets purchased online ahead of time only.

So once again, maybe you could move this to the next day, but if you’re leaving the next day, you’re screwed. So my opinion? Spend the extra hour or two and find out the details.

Once you’ve typed up the details, your travel guide is almost done. But there’s a few key things we need still like your flight and hotel info, right? Keep reading.

Planning a trip: step eight

At least three months out, you’ll need to book your transportation and accommodations. I prefer to do this closer to 4-5 months out to be safe.

For transportation, you’ll need to book your main method to arriving to your destination which may be by rental car, by train, or by plane. Book that first. Then think about how you will travel from the airport or the train station to where you’re checking in. Will you book a ride ahead of time? Will you catch a taxi or Uber?

Next up, how will you get around during the week? Will you walk, ride a bike, taxi, subway, rent a car, or uber? Lastly, if you’re visiting more than one city on your trip, how will you get from city to city?

If you’re going to Europe, trains are the way to go and you’ll want to book your train ahead of time online.

For accommodations, you’ll need to book where you want to stay. This could be couchsurfing, hostels, hotels, apartment rentals, or house rentals. Our favorite is using AirBnB.

We can often find an apartment in the middle of the city which allows us to walk everywhere and not have to spend as much money on taxi’s.

The Airbnb’s are also great because you get a kitchen with a fridge to use.

The only downfalls compared to hotels? No gym, no fresh towels every night, and no concierge. If you like those amenities, then try our favorite hotel booking site Booking.com.

Be sure to do your research before booking anything. Use websites like SkyScanner or Google Flights for notifications on when flight prices drop. Use websites like TravelZoo or Groupon for hotel/flight combo deals. For flight reservations, I typically use Booking.com.

Most of you probably think step eight should have come much sooner. But I have my reasons. If you book your flight before you even start researching cities, how will you know where you want to fly in/out of? Or how many days you’ll want to spend in each city? I think it’s important you have your mind made up about which cities first before you book a flight and get stuck with it.

Changing flights is an expensive headache. Lucky for you, you started planning your trip far in advance, so you still have plenty of time to book your flight and stay. (Side note: If you are going to one city only, you could definitely complete step eight after step three instead)

Planning a trip: step nine

Step nine is easy. Add your transportation and accommodation details into your travel guide, including confirmation numbers.

Use our Organized Travel Essentials document to keep these facts organized. Then look over your guide one last time, and make sure you are happy with the schedule. Finally, print that beautiful guide out! Also, save a copy on your phone/iPad as backup in case you lose it.

In addition, I recommend you print out some maps to keep on you. I like to print a one-page map of each city we’re going to to reference when we’re walking around. I mark significant landmarks and sites on it. Why? Because I put my phone on airplane mode when we leave the country to avoid extra charges, so I don’t have the convenience of typing an address into Maps.

Planning a trip: step ten

This step is only necessary if you’re leaving the country. You’ll need to research the country you’re going to. See if there are any steps you must take to enter the country.

Do they require or recommend any vaccines? Do you need a visa if it’s a longer trip? Should you get travel insurance?
For information on vaccine requirements, go here: wwwnc.cdc.gov/travel/destinations/list​

What about currency? What currency do they use? Should you get some money exchanged prior to arriving? Research and take the necessary actions ahead of time.

Planning a trip: step eleven

One week before your trip, confirm things are still on track.

Did your flight change at all? Have any tours or bookings been changed or cancelled? If you’re using Airbnb, communicate with your host to set-up the time and place to meet them for check-ins.

You’ll also need to notify your bank about your travels so they don’t freeze your cards.

Lastly, if you’re going on a trip longer than a week, consider putting your mail on hold with the USPS.

Planning a trip: step twelve

The week before your trip, you should not only start feeling super duper excited, you should also begin packing for your trip.

If you’re worried about forgetting something important, have no fear: the Greatest Packing List of All Time is here! Definitely check-out my list because there’s probably things on there you need to bring but didn’t think of.

Planning a trip: step thirteen

You’re almost there!! The last step is final preparations for your trip.

The day before your trip, be sure to check into your flight (if you’re flying). Make sure your packing is complete, luggage doesn’t weigh too much, and your travel guide is packed. Get the kitchen cleaned up, trash taken out, and guess what? By golly, I think you’re ready!

We hope this helps you feel more confident with vacation planning and helps you plan the best trip ever!