Planning a RTW Adventure: Moving from Dream to Travel Itinerary

When you have the ‘Round the World’ travel dream, you want to make sure that you see every single place on your Living list.

There’s no room for regrets and there’s always the (sad) realization that you may not have the opportunity to return for a future visit.  That means you have to take advantage and explore every nook and cranny that you can while you’re there, right?!

Ah, no.

Exploring the places that make your heart race is the only thing you must do on your itinerary. If you try and cram a million things in – or you rush from point to point on your journey –  it will become one big blur.  Guaranteed.My first trip to Italy was that way.  I saw so many churches and cathedrals housing “Madonna and Child” statues, paintings etc.… It was enough to make my head spin. Do I remember any of them?  Not really.  Do I remember seeing the Duomo in Florence for the first time?  Oh yes.  I had dreamed of seeing the Duomo for years before I arrived.  There was no way I was going to miss out on that opportunity.  I can still feel the tears on my cheeks when I finally stood in before it in awe.

So, when looking at your living list, take a look at why you want to go to the places on your list. Going back to my example: When you think of Italy, what do you think of?  For me:

Venice means canals and gondolas. Enjoying a gondola ride under The Bridge of Sighs. Getting lost in the confusing streets and eating gelato in St. Marks Square.

Rome means being inspired by the history of Colosseum and the Forum, walking inside the wonder of St. Peters Basilica and eating great pasta in a traditional restaurant.

Florence is the Duomo, admiring Michelangelo’s David at the Academia, viewing the perfect Tuscan countryside from the top of The Boboli Gardens and window shopping the Ponte Vecchio with all its jewellery stores displaying its golden wares.

Planning a “Round the World” (RTW) adventure can be daunting. Actually doing it can be exhausting. Nevertheless, the next time I’m in Italy, I will be sure to experience every one of the aforementioned items when I venture to those cities.  If you do it right, you can fulfil every part of your Living List dream.

So, how do you move from dream to Itinerary?

1. Know WHY you want to explore the places on your list.

The key to planning a long term adventure is knowing what your dream places are and why.  What is it about those places that draws you to it in the first place?

Start with your dreams. I love Pinterest for this. I can sit and dream about all the places I want to discover.  Every time I see a place I want to learn more about, or find a destination that has insider insights, I pin it.  If you read a great article on a website, you can pin it.  Yep, it’s why I call my boards ‘dream boards’.

With Pinterest, you can save these dreams all in one place so when it comes time to plan, you know exactly where to find the information. You can sit back and look at the big picture.  As in “Wow, you’ve pinned a lot about Italy”.  That needs to be on the list for sure.  But dig in a bit deeper.  What specific  places or experiences did you pin?

Once you understand what your expectations are, you want to prioritize those to ensure each of your dream destinations are on your itinerary.

On our Pinterest page, you’ll find lots of various boards that will get you started.  I started with one board, but it was just getting too full, so I broke them up into destinations by geography.

2. …then there’s the budget.

When you are planning a full time travel adventure, finance has to be the first and foremost thing to consider.  You don’t want to travel in high season if you want to keep your budget healthy for a long term adventure.  You’ll be heading home in a month!

Keeping to a sensible budget will allow you to either travel well for a year or have you heading home earlier than you expected (or scrambling to find a job).

Here are some great realistic views from travelers who have travelled long term:

When you’re planning a long term RTW adventure, you will experience travel burnout.  No question.  You can’t expect to jump from one city to the next and expect to be sane at the end of a year.

When I planned my RTW adventure, I planned for burnout, and so scheduled spending at least a month somewhere to chill out for a while.  Maybe it will be in Croatia since it’s relatively cheap by European standards.  If not there, then another Eastern Europe. To help with determining where would be a good place to stay awhile, I found this link really helpful.

Then of course, Pinterest came to the rescue again.  I began a new board called Long Term Travel because there was so much information on cheap destinations that I couldn’t keep it all straight! This was invaluable for the travel burnout times or when I need to chill the budget out a while.

Tip:  Here’s a post I found really insightful for spending less on accommodations for long term travelers. Not everyone has friends and family all over the world.  Camping and hostels are a couple of  ways to save a few pennies.  It’s even likely that while you’re travelling, people you might along the way will offer you a spare bed (or couch!) for a night or two.

3. Best Times to Go.

I talked about this a little in our post, Planning a RTW Adventure: Planning The Route.  Once you know where you want to go and understand your budget, you need to understand when you should go.

Wow…Where do you even begin?!

Planning where to go and what time of year was the part I found most intimidating, quite honestly.

I knew I didn’t want to travel in high season because that would blow out the budget completely. Besides, I don’t really like crowds, so traveling in low or shoulder season usually works for me.

The problem was I didn’t know what the best times were to visit each country.

I mean, where do you even find that information!?! Search through every guidebook or website for each destination?  GAH!

Well, no.  There’s a website for that, of course! I actually found two that really helped.

I found this great website called The Best Time to Visit.

I found this post really helpful by MyDomaine to find the best time to go to those must see places off peak (and who doesn’t want to see the Amalfi Coast?!)


4. Itinerary Ballet!

So, I’m going to admit, when it comes to travel planning, I use Excel. Yep, I won’t lie.  I find spreadsheets to be the best planning tool for me (so far).  I do this with every trip I plan.  (A lot of other travel bloggers use this technique I’ve discovered.)

Why not use an online tool?  For the simple fact of accessibility.  You don’t always have a reliable internet connection.

Keeping all your info in Excel makes it easy to manage.  Is it a bit old school?  Maybe.  But I’ve yet to find a great planning tool that allows me to put everything I need to know in one place.

Creating the itinerary becomes a bit like a ballet.  I’ll add something, spin it off to another section, and then delete it off the stage.  Oops!  I realize that I can’t do without it so with a quick undo it floats back onto the stage and I place it somewhere else entirely.

Sometimes I’ll even print out the itinerary and write the details down in pencil, with an eraser nearby at the ready.  It takes a lot of patience and coordination to make an itinerary work.

So, what’s in that spreadsheet of mine? It’s a single workbook with a number of worksheets:

Worksheet 1:  Living List
I have each city with experiences listed out.  I add in a column for the country, then continent, the # of days to spend there and then a column for each month. With the ‘best time to go’ information, I colour code for the months recommended to go. 

Worksheet 2: Itinerary
Here I create my own calendar specifically for the days I’m travelling.  This is the high level of where I will be in a given day. I add in whether I’m travelling, exploring and generally what the plan may be.  I have a row below that shows where I’m sleeping that night.  Generally, the name of the city/town and name of the accommodation if it’s already booked.

Worksheet 3:  Estimated Costs:
This is the breakdown so I know where my money is going.  It shows me the expense type, location, the name of the experience/accommodation/airline etc… and then the estimated cost. Lastly, I add in the confirmation information for anything booked.

Worksheet 4:  What to See/Do:
This is where I put in ‘must see’ for each location.  The cost, the website link and the opening/closing times

Worksheet 5:  Packing List:
For long term travel, this is the same list no matter where I’m going.  But it helps me plan what I have and what I need to think about for later. Of course, for smaller trips, it may be more refined (i.e. A beach getaway has the sunscreen, hats, swimmers, books, etc on the list).   For packing lists that I’ve found really helpful, check out my Pinterest Packing Tips board.

5. Planning a logical route.

Since I’m visual a visual person, I have a laminated world map that I use to do route planning.  It’s great!  You use white board markers to scribble on it so you can change it up as often as you wish.

With the spreadsheet nearby, the whiteboard markers come out to draw out  a logical route…. Each year of the RTW adventure – yes I said year, I’m a travel blogger! –  has a different colour.

I’ve heard some plan their RTW trips with a map on a corkboard and use pins.   I’ve heard people use a map with post-its. I’ve heard people cutting out magazine articles and putting them into a binder.

I’ve done all these over the years and all work fine.  Experiment to find what works best for you.

So far I’ve a rough itinerary until the end of 2019 on my laminated map and I still have a long list to go.  Guess I’ll just keep on travelling…


6. Making the Itinerary happen.

It’s one thing to have your itinerary on a spreadsheet, but until you book that first airline ticket, it’s still just a dream.

So, when do you buy the ticket for that first destination?  Do you book a round the world ticket or all your flights individually?

Here’s my take on individual tickets vs. RTW tickets:

If you have limited time to travel and know you need to be in Place A, B and C at a certain time, and can work it with the ‘best time’ to travel in one direction, feel free to book a RTW ticket.

However, if you don’t have a time restriction or have flexibility in your itinerary, then I would book the first flight and your accommodation for when you arrive and leave it at that.

Yep, as a control freak, this idea made me anxious. However, planning a RTW adventure is a whole other ballgame compared to  booking a 3- week vacation.  What if you hate Venice and can’t wait to get the hell out of there?  (Believe me, Venice is divine, but it’s not everyone’s cup of tea.)

If you have your itinerary cemented, it will cost extra to change things around.  If you have flexibility in your plans, you can find a place to stay in Florence and hop a train that afternoon.

Before I book anything though, I set up flight alerts for the first destination. When the price becomes within my budget and it’s a price I’m happy with, I book it.  I’ve tried a lot of booking sights for this.  After a lot of trial and error, SkyScanner is my absolute favourite.

Believe me, once you have that first flight and accommodation booked, reality hits.  You’re going. You’re taking this adventure!

Now it’s on to planning what to take, getting travel insurance, booking your accommodation, etc…

The key to planning a long term adventure is knowing what your dream places are and why.

If You Like It, Feel Free To Share It!


Leave a Reply

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

This site uses Akismet to reduce spam. Learn how your comment data is processed.