My planning process for the Perfect Itinerary

How do you put together the perfect itinerary?

The perfect itinerary is not made by a travel agent that doesn’t know the intimate details of who you are, but by the traveler, passionate about making the experience exquisitely theirs.

When I started traveling, I made a ton of mistakes. I hated being on large group bus tours. Quickly, I learned “my way” of travel was not going to be done with a cookie-cutter-style tour group. I enjoyed unique experiences where I was able to really get to know the culture and the people. So, little by little, trip by trip, I ventured out and learned the easiest way to create the perfect itinerary.

Not everyone wants to invest time and energy into putting together their next vacation. When done, it shows in the perfect itinerary, reflecting the uniqueness of the traveler’s desires. Before I lay out the process and give some tips, there is no shame in copying the travels of others with whom you share similar travel values. As you travel with us, we will show you our itinerary, and give you the MUST DOs along the way. So feel free to copy us step by step if it works for your desires in travel. Imitation is undoubtedly the best form of flattery! If you want to do it on your own use my easy-to-follow planning process. I find breaking the process up over days or weeks makes for a much more enjoyable process. Take this time to dream about the destination!

STEP 1: Pick the location to build the perfect itinerary in

We have bucket lists and try to make them happen as opportunities arise (great flight prices or just a gap in time we can make the trip work), but sometimes even we are inspired by ideas regarding destinations that we would have never thought of. Either way (if we know where we want to go or need inspiration), my first step is watching an insane amount of travel videos with a notepad in hand to create a recommended list. I aim to figure out what we must see/do/eat/buy at the destination. Wolter’s World, Mark Wiens, and Kara & Nate are current favorites. I have several travel bloggers I watch on YouTube these days, but Rick Steves was my go-to a decade ago! Boy, have times changed from the days of checking out his DVDs in the library!

STEP 2: Create a Trip Advisor Trip

Now it’s time to see what the reviews look like from our recommended list. First, look up the city and see the list of sights highly recommended by TripAdvisor reviewers and compare it with what our bloggers recommend. Next, use this step to see how long you need in a place or if it has enough highly rated items of interest to make it worth the trip. Create a trip and mark your favorite things and then click to see the ways to see the place. Finally, mark favorite tours of interest that might provide a unique experience for the perfect itinerary, along with some go-to types of experiences. Click on day trips if the category exists for the destination to see if there are nearby places of interest that you can include in your perfect itinerary.

STEP 3: Create an Airbnb experience wish list

Airbnb has some really unique ways to see places and I always scour what is available. I search without dates and just look at all the things that a place may offer. You can request dates later if the calendar is not available. Don’t forget to look at nearby cities that could be wonderful day trips! I save my favorites to a wish list and ask any questions of the providers if needed. Airbnb offers a unique way to work with everyday people and avoid big corporation tours. These can also sometimes be found on Tripadvisor as well as Viator. Working with locals helps to ensure the perfect itinerary.

STEP 4: More research

If I need more experiences to consider, I also research Getmyguide, Toursbylocals, & Eatwith. All of these sites offer real options and inspiration on how to make it an unforgettable and perfect itinerary for your trip! I may also do an internet search on unique ways to see ____.

STEP 5: Narrowing the perfect itinerary down

I make a list of my top types of experiences and must-see sites. Now, I am ready to plan the layout of our days! Next, I decide which sites I want to do just on my own and look at how they lay out on the Tripadvisor trip map of my favorites. I decide which sights to see on those OMO (on my own) days to make them easier and more enjoyable. If some experiences or sights are only offered on certain days of the week, I make note of it. Most sites have their hours listed on Trip Advisor. With all of this complete, I am off to the races with the perfect itinerary in reach!

STEP 6: Choose the dates

I decide how many days we need at each destination. Next, I decide if there is a best time to see the place, considering the weather, crowds, local holidays, and the flexibility of our calendars. Once this is done, airplane tickets are booked and our Airbnb’s or hotels are locked in. After that, our perfect itinerary is filled to the brim!

STEP 7: You gotta eat as part of the perfect itinerary

I spend some time researching the best restaurants on Trip Advisor. I usually add restaurants to my Trip Advisor trip and list them near other things we will see on the map. This way, I have easy access when at my destination. I minimize the chance of eating a bad meal or spending time looking for a local restaurant that has great reviews. Additionally, you must purchase some tickets in advance. Finally, some sights are better with a tour guide to skip the line or gain special access. Finding out these details in advance helps to avoid disappointment and ensure you enjoy the perfect itinerary.

STEP 8: Build the perfect itinerary

Start booking! I use the app Tripit and forward the confirmation emails I receive to the app, which then creates a beautiful itinerary that you can share with others in your group. It also keeps all of the needed information in one place if you need to make changes. Now you not only have the perfect itinerary, but a wonderful way to keep track of it all in the palm of your hand.

Step 9: Be flexible if everything doesn’t go as planned.

Maximize your time and enjoyment in a destination, but don’t be completely inflexible. Even the perfect itinerary may end up including sights that you find you want to spend more or less time in. The most important thing to do is ENJOY seeing the world. The perfect itinerary should not box you in but allow you to see it in a unique way that immerses you into what most reflects the destination, all the while allowing you to maximize your time by deciding what most interests you before you go.

Pro Tip: Dream of your travels into the future

If you are dreaming of the next place to go, what is stopping you from the background research? Several times, I have researched a location and have not been able to go or had to change part of the trip to exclude that destination. I keep all my trips on TripAdvisor and wish lists on Airbnb and frequently recycle them if that destination reoccurs. Completing reviews on the places I have seen on Tripadvisor reminds me of places I may want to go back and see again. I also keep wish lists of Airbnb rentals and hotels for future use. If you are saving up for the perfect trip, why not daydream about when you will see it by researching it while you wait?

Pro Tip: Avoid large tour groups if at all possible

I highly advise against large tours (unless you have mobility issues and then sometimes bus panoramic tours are all that will work for you). The tour sweet spot is 6-12. This size of tour allows you easy access to the tour guide while still allowing you to experience the destination with others. Cruising? Book a private tour guide and meet other cruisers to split the cost and join your group (many times you will save up to 70% of what the cruise line charges and avoid the cruise large group tour atmosphere). If your group is 4, 6, or more, a private tour is usually quite economical and can even save money from small or large group tours. Read my guide on how to pick the best tour guide for more help.

Pro Tip: Know your audience

When I travel with Tracey, I book our days to the brim as that is how we like it, but when I take my family, a 3-5 hour historical/informational tour must be coupled with something fun, like an E-bike tour. My husband especially is a ½ day tour guy, BUT even he is fine if I fill the other part of the day with something fun like a ride around the country on an ATV. Additionally, if we have relatively hectic days, I will give break days in between, where we can just explore the city on our own. I usually have a list of options of things to see, but these are the low-key items that I will not miss horribly if we decide to do something else on the free day (s) of our perfect itinerary.