Trip Planning Tips: How To Make Every Itinerary Epic

May 25, 2019

I’ve said this before, but while I don’t brag about much, I *do* have a knack for planning EPIC TRIPS. The actual process of planning travel itineraries, figuring out how to fit the pieces together and what is feasible without overscheduling is not only super fun, but something I seem to have a natural talent for.

So I’ve been in the process of sharing the behind-the-scenes details of how I plan trips, the tools I use, how I evaluate different elements, and now we’re going to talk about the actual building of an itinerary.

This is part of a series on how to plan epic trips. I’ve linked to the others throughout this post, and you can also sign up for my email list to download my free e-book for dozens more trip planning tips on flights, housing, itinerary, and more! Or you can purchase it on Amazon if you prefer 🙂

So first, let’s catch up with the steps that have to come before this, because we’re kind of jumping into the middle of a story…

I’ve shared a list of key questions that can help you get started and inspired when you’re not sure how or where. my general trip planning process, which tends to start with inspiration, then a ton of research where you “data dump” everything into a massive Word doc, and then begin filtering down based on the reality of your budget, number of days, etc.

Then I went into in-depth posts on how to find the right flight for you every time (if flying is indeed what you need), then how to find (and choose) the best hotel or rental for your trip.

Okay, you’re caught up now. These are important because an epic itinerary doesn’t come out of nowhere, and it’s very “chicken and the egg”. Sometimes there’s something you KNOW you want to do and you build your itinerary (flights, housing, etc.) around it—case in point, @farewhispers and I knew we wanted to do a Northern Lights trip.

Other times, you catch a great flight or you choose a destination, and then are figuring out how to build your itinerary—like the time we caught a cheap flight to Gothenburg but had no idea what to do (and ended up renting a sailboat on Airbnb…and the rest is history).

What this post covers:

Figuring out your itinerary must-haves, then pairing with nearby options
Determining one or two majorly splurge-worthy moments
Understanding your transportation options
Playing around with a few scenarios to find the best one

How to make every itinerary a little epic

Now we throw back to that massive Word doc that you’ve created, and bring back our old friend TripAdvisor as well. You may have a solid idea of where you’ll be staying and how you’re getting there—now it’s time to shade in the rest of your schedule.

Figure out your “must-haves” & pair with other sights close by

Starting with your “must have” list of sights, do some research and start to put similar pieces together.

Look at the official websites to figure out opening days and times, when they’re closed for holidays, what time of day is best to visit, and roughly how long it will take to visit. For instance, if you were visiting Istanbul, you’d discover that most mosques are closed on Fridays so you should plan around that in a 3-day itinerary.
Read the TripAdvisor reviews for a landmark, tour, or experience—look at both recent reviews as well as filter by time of year (July reviews of a fjord cruise won’t be as helpful if you’re visiting in December).
Look on Google Maps to see how far apart different things are and how long it will take you to walk between (or if public transportation is faster), or drive times if you’re on a road trip. Within your Word doc, start to group sights that are close together next to each other and make notes on how long you’d stay or what order you’d do them in.
Pore over the TripAdvisor forums and read about other people’s planned itineraries as well as their trip reports. You’ll get a feel for what has worked and what hasn’t, as well as what you’d enjoy.
Post your own planned itinerary on TripAdvisor a few times (you’ll make revisions over time, I promise) with as much detail on your likes and dislikes as you can provide, to get much more detailed advice from the destination experts (who either live there, or travel there frequently).

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Look for one or two splurge-worthy moments

I’m a HUGE believer in knowing when to save and when to splurge, and this is one of the things that can elevate a great trip to “epic” status. Planning epic travel itineraries will almost ALWAYS involve a splurge of some sort.

As you go through your research, you’re certain to come across cool, almost unbelievable, experiences, restaurants, or tours. Pinterest and travel blogs are your allies here, highlighting off-the-beaten-path ideas or a custom tour that you can seek out.

From skydiving in New Zealand to dog sledding in Norway to a delicious fancy afternoon tea in London, these have been some of my favorite travel memories. Or, consider a unique accommodation, like staying a centuries-old winery in Portugal or renting a sailboat in Sweden.

You might also like: 10 Things You Have to Do Before Every Trip

Whenever it makes sense, I also try to plan at least one active or outdoors-y activity on each trip. Partly because it’s a great way to experience a destination, and partly because you’re probably eating terribly and a little bit of exercise won’t hurt!

In Croatia we went out of our way to visit the Plitvice Lakes National Park, but it is still one of the things my mom raves about out of all our trips. In Scotland we (only partially-successfully) hiked the Quiraing.

If you’re visiting Barcelona, consider a bicycle tour as a great way to get some exercise and see the city. Seek out a hike, a sail, or some other way to get out into nature.

You might also like: 11 of My Best Travel Tips for ANY Trip

Make sure not to forget other transportation

Whether it’s train tickets, the bus, or a rental car, make sure you have a good understanding of how you’ll get from place to place, how much it will cost, and whether you need to book ahead. For instance, train tickets between countries in Europe should be treated similar to a plane ticket and booked ahead, as they go up significantly in price as you get nearer.

But within a country it depends, and you should ask the TripAdvisor forums for guidance. In Italy I could typically get tickets a day or two ahead of time for many routes (to give me flexibility), but sometimes popular routes and times would be sold out. In Jordan we just showed up, bought our bus tickets, and got on.

You might also like: Travel FAQ: How To Pay For Things While Traveling

Whether or not to get a rental car is another major question. If you’re doing a road trip (like in Scotland or New Zealand), it’s a necessity. But if you’ll be visiting major cities definitely consider carefully, because driving in many cities is insane and parking is a nightmare (an expensive one, generally).

Don’t forget that you can also rent a car for just a day if there’s a place a bit further out that you really want to visit. And public transportation is your friend!

You might also like: 15+ Of The Best Tips For Avoiding (& Surviving) Air Travel Woes

Create a few different scenarios to see what works

Most trips are going to take some trial and error, and since I like to fit in as much as possible I create a schedule like the one below to make sure I’ve thought through travel times, know which day we’re doing what, and that I haven’t overcommitted myself.

Some trips are more complex (Israel and Jordan), others less so (I didn’t even make a schedule for my Mexico all-inclusive, just printed my flight info). This isn’t meant to be a limiting timetable where every minute is planned out and there’s no room for spontaneity—think of it more like a skeleton framework and way to keep everything organized.

But especially if you have multiples people, multiple places, and moving pieces, this Excel spreadsheet is an invaluable planning tool. Here’s an example of a fairly detailed (partial) itinerary for Switzerland.

Hopefully this helps give you some more ideas for planning epic travel itineraries of your own! I’d love to hear your own tips or answer any questions…hit me up in the comments!

Other resources for epic trip planning:

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