On January 17th, 2016, I decided to take a leap of faith. I wasn’t sure how I was going to do it, or how I was going to save up for it, but I just felt it was time.
Then came the hard part…how on earth was I going to plan a complicated backpacking trip that had been in the making for 25 years?
My friend, Roxy, asked me this question today. She’s planning a separate trip for her kids and wanted some tips on how she should begin. I’ll write about my preparation up until the week I leave, so this will be in several parts. I hope someone else out there will find this useful, but this is mainly for you, Roxy!
If you’re the kind of traveler who likes to throw the map into the wind and just get lost…you’ll probably scoff at how unadventurous and nerdy all my lists and spreadsheets are.
But I am my O.C. mother’s daughter and I like making plans, knowing exactly what I’m supposed to do so I can relax, and not worry or waste precious time. And if you’re someone who appreciates a tight itinerary, this is for you.
Before you begin, I urge you to get a travel journal. My sister had given me a beautiful lined book with a House Targaryen “dragon skin” cover for Christmas, and it was perfect for planning my own trip across the narrow sea! It’s also cool to see how your trip evolves from rough ideas to concrete plans.
Part 1: What Do You Want?
1. Where do you want to go?
Europe. That was easy. But WHERE exactly??? Italy, most definitely. But I wanted to explore more than one country since it’s easy to get around by train. I took out a map and decided that I wanted to start in Rome (which is closer to Dubai) and then travel by train northwest across Italy, all the way to the Netherlands. That was the very first decision I made.
At first, I wanted to go to 5 or 6 different countries. But with only 23 days of holiday leave, I knew I’d have to choose 2 or 3 instead, and enjoy more time in fewer places. I had initially chosen Italy, Austria, Switzerland, France, and Netherlands, but narrowed it down to 3: Italy, France, and Netherlands.
Don’t know where to go? Check out Route Perfect. This site helped me a lot!
2. What kind of trip do you want?
Do you want to travel in style? 5-star hotels? AirBnB? Staying with friends? Would you prefer to rough it? Would you like to be on your own or in a tour group? Would you like to meet and mingle with locals? Do you want to party? Enjoy nature? Catch a show? Do something extreme?
There are so many options, and every single one of your friends and family will have an opinion. Decide what’s right for YOU. That’s the beauty of a solo trip!
I knew I wanted a low-budget, culture, art, and history focused backpacking trip. I wanted to bring one piece of luggage, spend as little as possible on accommodation, but splurge on food and skip-the-line group tours because I HATE standing in a queue (such a waste of time)…and because I love to eat.
3. What would you do if you could do everything you wanted?
And I mean EVERYTHING. Pretend for a moment that you don’t have a budget (and you don’t yet, not at the moment!). Allow yourself to dream. Do some research on these places. What are the must-sees? Which cities and towns are really worth staying in or visiting? I am a huge nerd, so most of my list was made up of historical sites and art museums.
I wanted to throw in a town that I knew nothing about, and found several blogs about Cinque Terre. I fell in love with the stories about hiking through the five fishing villages and just knew I had to do it. I also knew that I’d need a nature respite from the bustling cities.
This was my original dream list:

4. How much time do you want to spend in each place?
After completing this list, you can gauge the length of time by the number of things you want to see in each city or town. With mine, I knew I’d be spending majority of my time in Italy.
Come up with a rough itinerary. This was mine:

This table evolved for weeks as I moved plans around, and only settled once I had booked my stays.
Consider travel times between cities. Allow some time for rest and relaxation after long train rides! Route Perfect will also help you estimate travel times between destinations.
5. How much money can you spend?
Do you have a travel fund? How much of your monthly income can you possibly spare until the day of your trip?
I’m a firm believer in debt-free living so I had to reassess my monthly budget. I’d already been slowly building up my travel fund, but it was nowhere near enough to cover an entire trip. (I’ve had to sacrifice a lot of luxuries over the past 7 months, but I know it’ll be worth it!)
Calculate how much you’ll have if you follow a set amount to save every payday.
6. Are you ready for a reality check?
Okay, this is the least fun part. Considering your choices in steps 2, 4, and 5, how much of step 3 can you actually do? This might break your heart a little bit, but it will also get you to choose the best things on that list.
Is your initial budget requiring you to cut something that you are absolutely dying to do? Can you still shuffle numbers around your budget so you can save more? Should you spend less time in one city so you can do what you really want to do in another? Should you choose a simpler travel style?
This is where you start bringing your dreams into the real world.
Start looking at airfare estimates, accommodation prices, group tour packages and make decisions accordingly. I started this spreadsheet the day I started planning the trip:

Of course this is a lot more detailed now, since I only have 19 days left until my trip, but it began with just estimated amounts for my airfare, hotels, and visa, fleshing it out as I went on with my planning over the next few months.
If there are things you still want to do, but aren’t sure if you can afford, put them on the list anyway. You never know if a good deal will pop up later on!
At this point, I knew where I was going, what I wanted to do, how I wanted to do it, and how much I needed (approximately). In my next post, I’ll talk about the finer details. I’ll also post links so you can download my spreadsheet templates if you want to!
Link to Part 2
