Close this search box.

How to Plan The Most Epic Itinerary Ever

This post contains affiliate links. If you make a purchase through one of these links, I will receive a small commission at no extra cost to you. Read my affiliate policy here

Last week, I shared the six-week itinerary my BFF Leslie and I followed on our whirlwind trip across Europe. This week, I’m going to give you an in-depth look at how we planned that itinerary. Planning a trip can be a daunting task—especially if you’re traveling somewhere you might never get to see again, and you want to make sure you get the most out of your trip. However, following these steps can help simplify the planning stage and limit the stress factor significantly. Note: I’ve broken things down into the rough timeline that we used for planning, but you may have to adjust the timing based on the dates of your trip.

Six Months to a Year Out

Decide When and How Long You Want To Travel

You might not be able to pin down the exact dates of your trip at this point, but a general idea of when and how long you’ll be traveling will have a major impact on the rest of your trip planning. Some destinations are only open seasonally, or have high and low seasons that can affect pricing, availability of accommodations, and crowds. If you’re not a huge fan of drinking and revelry, for example, you might want to avoid Munich during Oktoberfest. Having a general idea of when you want to travel can also help you avoid the risk of scheduling conflicts down the road.

Start Brainstorming on Pinterest

When I first proposed the idea of a trip to Leslie, I made a secret Pinterest board and added her as a collaborator. Over the next few months, we collected pins of places we wanted to try to see on our trip. Like any good brainstorming session, this was no-holds-barred. The only rule we had was that it had to be in Europe. Other than that, everything was fair game. We collected hundreds of pins, and it was easy to get excited about what we were going to see when there were so many fabulous pictures and blogs to read. Did we go a little overboard? You betcha. But that was part of the fun, and it helped us discover things we might have missed otherwise. Using Pinterest to Plan Your Epic Adventure | Jest Kept Secret

Get Your Passport

If you don’t already have your passport, now’s a good time to think about getting it. It normally takes 4-6 weeks to process your passport application, but by that point in your timeline, you’ll also be busy putting the final touches on your plans. If you get your passport now, it’s one last thing you’ll have to worry about later. And if you need a visa (more on that in a second), you’ll have to have your passport first. Make sure you give yourself plenty of time to get all of that sorted before your departure date. To get your passport, you will need to provide a copy of form DS-11, evidence of citizenship, identification, and correct passport photos. If it’s your first time applying for a passport, you’ll have to do it in person at a passport acceptance facility. In the US, current passport fees are $110, plus more if you want it expedited (but you won’t have to rush it if you’re doing it early). Read more about the process at

Research Visa Requirements

Depending on where you’re from, where you’re going, the purpose of your trip, and how long you’ll be there, you might need a visa. (Find out if you need a visa at Some visas can be secured in just a few weeks, but others can take months—and the last thing you’ll want to deal with is having to postpone your trip because there was a delay with your visa. Make sure you take the time now to research visa requirements and timing so that you know when you’ll need to apply, and be sure to give yourself a buffer. There will also be fees associated with your visa application, so keep that in mind when you’re planning your trip budget. How to Plan the Most Epic Itinerary Ever | Jest Kept Secret

Look at Flights

Depending on where you’re going, this might be the time to start looking at booking your flights. did a major study to identify the best time to book your flights, and results ranged from 70 to 207 days in advance. Even if you don’t need to book your flights this early, you should familiarize yourself with the recommended booking dates now so that you can plan accordingly. Also, keep in mind that not all flights are available every day, and flight prices vary by airport. Leslie and I were originally planning on flying out of Germany after 4 weeks in Europe, but then we found a much cheaper flight out of Geneva two weeks later. Because the price difference was greater than the cost of staying in Europe for an extra two weeks, we decided to add two more weeks to our itinerary. Go big or go home—or go big before you go home, I guess.

Request Time Off

If you’re working for anyone but yourself, you’ll need to give your boss plenty of notice if you’re taking a lengthy trip. Every business is different in this regard, so make sure you communicate with your employer about your plans and make sure that you submit your time off request at the right time. Be courteous, professional, and flexible—your boss might know about scheduling issues down the road that you’re not yet aware of. Don’t make any concrete plans until you’ve got your time off request approved.

Three to four Months Out

Map it Out

After pinning a gazillion beautiful pins to our secret Pinterest board, we plotted them all on a map. We used Google Earth at the time, but these days, you can build private maps on Google Maps without having to download anything to your computer. To create a private map, make sure you’re logged into your Google account and pull up Google Maps. Click on the menu icon in the top left (three horizontal bars), and select My Places from the menu. Once that loads, click on Maps, and select “Create New.” That map will be secret until you decide to share the link or make it public. You can create different layers, change icons for easy viewing (we used different icons for different types of attractions to make sure we got a good mix), make notes, and map out directions between destinations. How to Plan the Most Epic Itinerary Ever | Jest Kept Secret Mapping out everything we had pinned allowed us to see what areas we were most interested in seeing. We had a lot of pins in Ireland, Portugal, and Italy, for example, so we knew we’d want to give ourselves more time in those countries. It also allowed us to identify the outliers—places we wanted to see, but were too far away from everything else on our map to make it feasible (which is why Prague is still on my bucket list). And unfortunately, some of the information on Pinterest is either outdated or downright false. We had a few pins of places that actually don’t exist beyond the realm of someone’s fabulous Photoshop skills—and I’m usually pretty good a spotting fakes. This step will help you weed out the facts from the fiction. [box title=”Pro Tip” border_width=”2″ border_color=”#7b090f” border_style=”solid” icon=”picture-o” icon_style=”bg” icon_shape=”circle” align=”center”]If you pin something exciting on Pinterest and can’t seem to find out where it really is, Google’s reverse image search might come to your rescue. Simply save a copy to your desktop (temporarily, of course—please don’t steal intellectual property), open up a Google image search, and drag the image file into the search bar. Google will find similar images, and if it’s a real place, it’ll help you identify where it is.[/box]

Play Favorites

At this point, you might still have more destinations mapped than you can possibly see in the time you have allotted. If that’s the case, take some time to figure out what you’re most interested in seeing. Leslie and I each made a Must See list, and we put special icons on our maps to identify those places. As we continued to refine our plan, some destinations had to be cut from the list, but these Must Sees were safe from elimination. For the curious, our Must See list included Blarney Castle, the Cliffs of Moher, the Globe Theatre, Alhambra Palace, the Coliseum, the Spanish Riding School of Vienna, and Neuschwanstein Castle. How to Plan the Most Epic Itinerary Ever | Jest Kept Secret

Plan Your Transportation

Once you have everything mapped out and you’ve eliminated outliers and impostors, it’s time to make sure you can actually get to where you want to go. Most parts of Europe have an extensive railway system, but there were a few destinations that required a car or bus to get there. We did end up renting a car for Ireland because their train network didn’t get us close enough to most of what we wanted to see, but opted for trains and buses for the rest of the trip. Consequently, we had to pare down our itinerary a bit more, as there were some destinations that we couldn’t reach on public transit and couldn’t justify renting a car for. For European travelers, the Eurail website and Google Maps are both extremely useful for planning transportation between destinations. Also, if you’re going to do any shorter flights between destinations, now is the time to book those.

Two Months Out

Finalize your dates

By now, you should have a pretty good idea of where you’ll be going and when. Your time off has been arranged and your in and out flights are booked. All that’s left is to finalize the schedule for between your arrival and departure dates. This is when you’ll want to figure out how long you want to stay in each location, and how long it’ll take you to get to the next.

Book Your Accomodations

Hostels are great. We really enjoyed staying in hostels (well, most of them), and they saved our budget for sure. But because they’re popular with young international travelers, they tend to fill up fairly quickly. Two months out is a great time to start booking your hostels, hotels, rental apartments, and the like. We liked HostelWorld and for finding and booking accommodation. How to Plan the Most Epic Itinerary Ever | Jest Kept Secret

One Month Out

Book Your Ground Transportation

Your dates are set, your accommodations are booked, and you have a general idea of what you’re going to see. Now is the time to start booking your train and bus travel between major destinations. Learn more about ground transportation tips and tricks in my post 18 Things They Don’t Tell You About Traveling Europe.

Leave a Copy of Your Itinerary

We never like to think about emergencies, but they do happen—and it’s far better to prepare for them before you leave. Make sure you leave a copy of your itinerary with a friend or family at home, and be sure they have a way to contact you in an emergency. You may find that your itinerary changes a bit once you actually get going, but at least your loved ones will have a general idea of where you are and where you’re headed.

Back Up Your Documents

I’ve heard personal horror stories about people being stranded when their passports and wallets get stolen. Where possible, carry backup copies, and email copies to yourself as well. Copies won’t be official, obviously, but they can be helpful for ensuring that you’re not left entirely out of luck.

Book Travel Insurance

I didn’t end up having to cash in on this, thank goodness, but it was nice to know that if anything happened while we were traveling, we’d be taken care of.

One Week Out

Last Minute Checks

About a week before you leave, make sure you check and double check all reservations, tickets, and travel documents.

Make Your Packing List

Writing out your packing list in advance can help make sure you don’t forget anything when it comes time to actually pack. Keep a copy of your packing list with you, too, as it will be helpful in identifying loss or theft and can help ensure you don’t accidentally leave anything behind when you leave your hostel.

Arrange Transportation To and From the Airport

With all the details you’ll be planning for this trip, it can be easy to overlook the little things closer to home. Make sure you have someone ready to provide transportation to and from the airport at the start and end of your trip so that you don’t have to scramble to find a ride last minute. How to Plan the Most Epic Itinerary Ever | Jest Kept Secret

Bon Voyage!

And there you go! You’re well on your way to planning an epic adventure of your own, and hopefully, it was a fun and pain-free experience. Just remember, things happen when you travel, so your itinerary might have to change once you actually get moving. But if you’ve done your homework right, even those unexpected changes should be easy to manage, and you’ll enjoy the spontaneous changes. [box title=”Tools of the Trade” border_width=”2″ border_color=”#7b090f” border_style=”solid” icon=”magic” icon_style=”bg” icon_shape=”circle” align=”center”]

Planning Your ItineraryTriposo was a useful desktop and mobile app that helps you plan out the destinations in each city you’ll visit. This tool was great for knowing how long we could expect to spend at each attraction, as well as how long it would take us to walk from one site to the next. The reviews and forums on TripAdvisor were also very helpful.

Accommodations – We booked all of our lodging through and Hostelworld.

Train Travel – We used Rail Europe to find and book our train trips across Europe. Individual countries sometimes have their own train network sites, such as WestBahn (Austria), SNCF (France), Deutsche Bahn (Germany), Trenitalia (Italy), Renfe (Spain), SBB (Switzerland), and National Rail (UK).

Flights – Expedia is a great source for cheap flights. [/box]

Are you planning an epic trip? Where are you going, and what are your tips for planning the perfect itinerary?

If you found this post helpful, please share it! Thanks!

How to Plan the Most Epic Itinerary Ever | Jest Kept Secret

Know someone who would like this post?
Please share it!

Jess Friedman
Jess is a Canadian-American who’s always ready for the next adventure. She loves all things living, always has a million creative projects in progress, and polishes her nerd badge daily. She is passionate about helping families make and preserve treasured memories that strengthen bonds across generations. You can read more posts by Jess here.

Let’s connect!

Keep Reading

Share Your Thoughts

Your email address will not be published. Required fields are marked *

Psst! Want all the best memory keeping secrets?

Join the VIP club to get a once-a-month newsletter full of resources, exclusive offers, and fun surprises. Also, no spam, because eww.

Personally, we're big fans of good ol' chocolate chip, but we do use digital cookies to improve your experience with Jest Kept Secret and help the website function smoothly. If you continue to use this site, we'll assume you're ok with this, but you can opt out at any time. For more information, please see our privacy policy.