How to Build the Ultimate Itinerary: Samples, Examples and Best Practices

Group Travel, Schedule / Wednesday, November 11th, 2020

Ever notice how some people are able to pull off the best trips, making it seem as simple to them as breathing? While some people might just be lucky travelers, we’re willing to bet 9 out of 10 of those people had crafted out a well-planned trip itinerary. They’re the sort of people who check the boxes ahead of time: they know where they’ll be, what they’ll see, how to get there, and more. Really, it’s no sweat off their back.

For some travelers, this sort of planning is half the fun. For the rest, though, the idea of planning a travel itinerary is time-consuming and stress-inducing, especially when you’re planning for more people than just yourself. If you’re part of the latter group, take a moment to hear us out before you resort to just ‘winging it’ as a result of overwhelm. Our travel itinerary tutorial has all the information you need to turn your dream trip into a reality—whether you’re traveling for professional purposes or just to enjoy some time away with friends. All set to start planning?

Jump ahead:

What is A Travel Itinerary?

If you’ve never made a travel itinerary before, you might not know what one entails. A travel itinerary isn’t just a list of popular things to do. Rather, a travel itinerary is a breakdown of how you (or a group of travelers) should spend their time, supported by all the essential details. Most itineraries are broken down into days, and each day is further broken down into activities or stops.

While there are many travel itinerary templates out there, the cool thing about itineraries is that they can be adapted to fit your needs. A basic itinerary will often include flight details, accommodations, travel times, sights to see, and important phone numbers, but you can certainly add more than that.

What to include within a travel itinerary really comes down to its purpose.

For example, let’s say you’re a solo traveler who wants to make the most of your time in Iceland. Your travel itinerary will likely include your flight details, car rental information, hostel or hotel accommodations, as well as sights to see along the Ring Road. Things like shopping and restaurants to try can be left unplanned, especially since it’s just you as you can explore those things as you please.

On the other hand, if you’re hosting a group of 40 people for business travel, or perhaps you want to start your own tour group company, you’re going to want to make sure each itinerary has as much information as possible for the entire trip. This includes all of the flight, airport, hotel, and transportation details, as well as their work (or activity) schedule and restaurants for breakfast, lunch and dinner.

In the best-case scenario, failing to provide adequate itineraries will have you answering A LOT of questions from 40 different people. Worst-case scenario? You probably won’t be able to find dinner reservations or attractions to visit or even accommodation on a whim with a group of that size. Don’t be that person.

4 Reasons Why Creating a Travel Itinerary is Essential

An itinerary:

  • 🙏 Prioritizes your wants.
    There’s no way to see or do everything in one place, which is why an itinerary is useful in getting your ideas on paper so you can visualize which sights/events/attractions are the most important.
  • 🕒 Maximizes your time.
    When you do your research ahead of the trip, this means you’re not spending time on your trip Googling things to do next, which is a total waste of your time away. Plus, if inclement weather occurs on a day where you had something planned outside, you can easily swap plans with another day that was more indoor-focused without missing a beat.
  • 💸 Helps you stay on budget.
    When you break down your itinerary into days, you can allot a given budget to each day. If you know that one day is particularly expensive, you can plan to dial back the spending the next day, such as going to a free park or packing your own lunch.
  • 😎 Creates smoother travel.
    Creating an itinerary helps you see and fill in all those ‘gaps’ between your stops, thereby forcing you to think about how you will get from A to B and from B to C. There’s nothing more frustrating than assuming that something looks close on the map, only to realize on the day that it’ll eat up 6 hours of travel time.

group travel

What Makes An Itinerary a Successful One?

Not all itineraries are created equal. This means that some are going to be more of a hindrance than helpful, whereas others might not provide any useful information at all. The key is to strike a happy balance with your planning. Here’s why under-planning and overplanning can hurt your travel itinerary, and how you can make yours a successful one:

How under-planning hurts your travel itinerary

The point of having a good travel itinerary is to have all your ducks in order. This means including all pertinent information. We’re talking flight details (airlines, flight numbers, flight times, passport/visas), hotel information (address, phone numbers, check-in times, distance from airport), and transportation (rental car, rail passes, ferry tickets) at the bare minimum.

Can you imagine hopping through countries on a world trip you’ve so been looking forward to for ages, only to get held up because of overlooked issues with your passport or visa?

How over-planning hurts your travel itinerary

Overplanning a trip can be just as damaging to a successful trip as under planning. Overplanning leaves little to no room for spontaneity, and you’ll likely stretch yourself too thin and wear yourself out before you know it.

The best kind of trip is when you start chatting up a local and discover some worthwhile attractions you didn’t know about prior to your departure. While well-laid travel plans are an integral component of any successful trip, don’t forget to build in some free time to go explore these local-knowledge tips or even just some downtime to reset and relax.

And remember, time changes are tough. When it comes to jet lag, a general rule is that it will take you as many days to recover as time zones you’ve crossed. Younger people tend to bounce back quicker, while it can take longer for older adults. Keep this in mind and try to not pack your days too much if you can avoid it.

How to strike the perfect balance with your itinerary planning

The big three—flights, accommodation, and local transportation—are no brainers. For any trip, no matter how big or small, make sure you have these three covered. But you really shouldn’t stop there.

Have some important numbers on hand in case of an emergency. If you’re traveling internationally, do you know if your current phone plan will work, or will you need to update it? Make sure you research things to do in the area you want to see and perhaps a few restaurants you want to try. Does the restaurant you’ve got your eye on book out months in advance? What about plays or concerts or other attractions? Do you need to purchase tickets ahead of time? Do they need to be printed or are mobile tickets OK?

Don’t be caught disappointed because you didn’t ‘know’ about something interesting nearby or you can’t experience something because of lack of planning. You’ve likely come a long way, so make it worth your time! With that being said, reserve some unplanned gaps throughout your trip for spontaneity, flexibility, downtime, or even just a solid nap.

itinerary builder

Creating Your Perfect Itinerary

The more you travel and the more you get used to creating itineraries, the easier the process will become. But if it’s your first time and you’re not sure where to start, consider using a template or an online platform to get the ball rolling. Here are some of our favorites:

Free itinerary templates

Jotform offers excellent PDF templates. Most of their templates are drag-and-drop, allowing you to easily plan the flow of your day. You can choose specific templates like a flight itinerary, for example, or you can choose an all-encompassing one that includes your flight details, daily schedules and more.

free itinerary templates

Once complete, the itinerary samples will be saved as PDFs that can be printed to have on hand as well as sent on to friends or colleagues via email. Once received via email, they can be downloaded to a mobile device, a perfect solution if wi-fi turns out to be spotty at the destination.

Free online platform for itineraries

Perhaps you want something a little more interactive when it comes to an itinerary? Allow us to introduce ourselves—we’re Guestboard, a user-friendly tool for managing schedules and events.

Guestboard can easily be used as a travel itinerary app. You can build schedules for the group online and in the app in no time. You can also create handy checklists, and there’s even a messaging board that can be used for the group to communicate. Multiple threads will keep the information organized, which is especially helpful for big groups that want to find a buddy to grab a drink before an event, split the cost of ride-sharing or check out a museum together.

itinerary software for groups

Guestboard is FREE for the first 30 guests, making it ideal for planning small business trips, yoga retreats, friends and family vacations, and more. If you have more than 30 guests, it’s just $0.50 for each additional guest, so you only pay for what you’ll use!

Paid Platform for Itineraries

Travefy is a high-end online tool for building travel itineraries, more likely to be utilized by companies than individuals (for business travel, for example), or perhaps by tour group operators. If you fall into this category, then you’ll enjoy their easy interfaces and the professional end result of the itinerary. Designing travel or flight itineraries is easy, as all you have to do is drag and drop itineraries into their customizable templates.


In order to use Travefy, users have to pay a monthly (or annual) cost.

Distributing Your Travel Itinerary

By now, you likely have some ideas forming of how you’re going to create your travel itinerary, whether it’s with an itinerary maker or online platform. But before you jump in head first, you also want to consider how you’re going to distribute the information in a way that makes sense for your trip and those involved.

Here are some possible ways to share your itinerary:

📬 Printing a complete itinerary packet and snail-mailing

  • Pros: phone signal and wi-fi can be spotty, especially in remote areas, so it’s handy to have the information you need on hand just in case, even if it feels pretty old school. And sure, while most of the world has gone digital, there are still some businesses that require printed paper copies of tickets, etc.
  • Cons: having a packet of information can feel cumbersome, especially if you’re trying to pack light. It’s also less eco-friendly.

📥 Sending itineraries via email

  • Pros: you can easily ensure that everyone has pertinent information ahead of time, all in one place. Also the more eco-friendly option.
  • Cons: depending on your signal, it can be difficult to pull up information instantly, and some information simply isn’t formatted appropriately for mobile. Do recommend to your travelers that they download ‘offline’ copies to their phone ahead of time if they can.

🌐 Posting itineraries on a static website

  • Pros: accessible and fancier, which is ideal for clients/business travel and other professional events. Some websites allow travelers/attendees to interact with one another ahead of the trip, too, which can feel welcoming.
  • Cons: guests don’t necessarily get alerted when changes occur, and the organizer might not want the itinerary as public information.

    (Like the idea of having everything online, but don’t want to pay hosting fees for a static website? This is where Guestboard can help.)

A Few More Things to Consider When Planning Your Itinerary:

Here are a few final tips before you get out your pen and paper and start planning:

  • Build-in free time. If you have the availability to pad the beginning of your trip with a free day, you should do it—especially if there’s a time change. Sure, it’s tempting to want to do it all. But it’s not so fun to do it all when you’re coming off an 8 hour time change.
  • Give yourself space. The more space your itinerary allows between activities and transportation, the better. Anyone who’s ever missed a flight, bus, train…you name it, can attest to this little nugget.
  • Take note of local holidays. If you’re the ultra-social type, using your trip to attend something like Oktoberfest can be a great way to experience a new city and meet locals. The opposite applies, too. Not a fan of overcrowded spots? Noting the local holidays is a great way to steer clear of crowds and busyness.
  • Consider both efficiency and budget when making decisions. It might be $100 cheaper to fly into a less busy airport, but if it takes you two hours of train travel to reach your final destination, is it really worth it when you figure in the time wasted (+ train fare)?

After the Trip

Wheels are down, luggage is reclaimed, everyone’s heading home, and you’ve just successfully planned and executed an amazing trip. Whether you planned itineraries for your whole team for business travel or just a fun getaway with your friends, you’ve officially been there, done that. So, now what?

There’s no reason all that hard work of planning should go to waste after the trip is over. Post-travel feedback is extremely helpful when it comes to planning future travel itineraries.

If you planned business travel, can you ask your colleagues what worked and what didn’t?

If you’re part of a tour company, can you ask your travelers what was their favorite part, and what could perhaps be swapped out in the future?

Even if you just planned a trip with your friends, try to get together with them a few weeks later once they’ve settled back into their routine and see what stands out most from the trip.


No matter your intent for travel, itineraries are a great resource to keep on hand and refer back to in the future, such as, what was the name of that great hotel again? Or that place that served the best pasta? When it comes down to it, if you’ve had a great experience, you’ll want to share your travel itinerary with friends so they can experience the same awesome trip (and count you as a travel guru, of course), or even revisit the itinerary yourself in the future. At the very least, hanging onto your travel itinerary is a great way to memorialize the experience!

Ready to start building your travel itinerary? Get yours rolling here.

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