12 Steps for Multi-Destination Travel Planning

June 2014 • United Kingdom, France, Italy 

Planning my first trip to Europe was terribly overwhelming. There were so many places I wanted to see and I only had a limited number of vacation days to work with. By the time we had boarded the plane, though, I had fallen in love with the entire process. I find it is so empowering to know that I can set myself free from the hum drum of daily routine and embark on an incredible journey curated just for me. 

Here are the twelve high level steps that I follow to plan my itinerary. Your trip does not need to look like mine or anyone else's. I just hope that you get out there and see the world!

When you start the intensive research required to plan an international trip, you will inevitably find hundreds of articles and comments instructing you that it is impossible to see that city in a day or two, in fact you need at least TWO MONTHS! Well as much as I genuinely appreciate the feedback from the modern day travel nomad who bounces from place to place on the dime of local tourism boards, or from the experienced travelers in Europe who can travel throughout the region without the cost and time of a long haul flight, not to mention a much more generous vacation policy, I am here to tell you that it is OKAY if you want to go to Europe and see it all (or as much as you can) in the short amount of time you have.  

I was really intimidated when I started to plan this trip. Most of my friends had studied abroad in Europe, so either their itinerary was pre-planned for them by the school, or they found themselves in a sink or swim scenario where they figured it out as they went during their six to eight weeks across the pond. I remember one girl telling me that the total cost of her study abroad cost over $20,000. 

Needless to say, when I started planning out my savings for my first trip to Europe, I was prepared for the worst. I gave myself a year to plan and budgeted way more than I actually needed.

Since that first trip, I've developed a pattern for how I typically plan my trips. See below for a step by step guide to trip planning:

Step 1: Open Google Maps and plot out all of the cities I want to see.

Step 2: Pick a date range to figure out how long the trip can be.

Step 3: Start searching planes, trains and auto rates and schedules to plot out when I can logistically arrive and depart each city. Record the schedule and costs in a spreadsheet.

Step 4: After I've determined how much transportation is going to cost me, I can set a budget for food, hotels and activities. I may also start adding activities to the schedule.

Step 5: Review rough draft itinerary with travel partner who will point out all of the flaws in my plan. For example, not allowing enough time to get to the airport, or to eat or to sleep - but I mean, are those things really important??

Never Settle Travel Tip #1: Things take time, Donna!

Inevitably remove that extra country or city or hike. I am eternally optimistic, but I usually plan around a model of three countries and five+ cities over about 12 days including long haul flights.

Review updated itinerary and budget with travel partner.

Step 6: Start booking flights, starting with the long haul international flight, usually at least two months in advance.

Step 7: Start booking hotels and wish I had started earlier because these babies book up fast for the summer. 

Step 8: Book activities online if possible. 

Step 9 & 10: Start planning outfits and making sure I can fit everything into a carry-on.

Never Settle Travel Tip #2: Only bring a carry-on and a personal item on your multi-city trip

Unless you are an instagram model who is paid to bring twelve pairs of shoes and coats and dresses, bring only a carry-on for multi-city trips. It will simplify your travel, because luggage does get lost and it can be difficult to return it to you if you are constantly on the move.

Also, American's are spoiled by the amount of underseat storage and overhead compartment space on our international and domestic flights. In other countries, however, especially on their domestic carriers, these planes are retrofitted for very different guidelines. I have been on flights where my backpack HAD to go in the overhead bin, and the overhead bin would not have fit my typical rectangular carry-on. Many of these budget airlines are also very strict with their one bag carry on policy, so you have to make sure even your purse fits in your carry-on. Many future posts will discuss these experiences in more detail. 

So how do I bring only a carry-on, in fact only a backpack on my trips??

Never Settle Travel Tip #3: Pack with space saver bags. Bring Downy wrinkle release spray to deal with wrinkles which actually wont be too bad as long as you roll up each item of clothing.

I have done this for every trip and it has not failed me yet. I have managed to bring winter coats, countless dresses and even things I didn't end up wearing thanks to these bags. However, for this first trip I used another trick.

Never Settle Travel Tip #4: Plan for outfits that can be re-worn in a different style. Or just re-worn with a little TLC from the aforementioned Downy wrinkle release spray....

Step 11: Order currency from the bank, walk out with your stacks feeling like you just won Monopoly.

Never Settle Trave Tip #5: Actually, don't walk out with stacks. Ask for mostly large bills. You do not want to draw attention to yourself by pulling out a bulging wallet.

In Europe, cash is definitely king. Unless you are staying at a Marriott-like property, make sure to bring enough cash to cover your food, activities and accommodations. Some small towns, boutique properties and hostels do not always have reliable credit card machines. Some do not even take credit card, but they will most likely state this upfront on their website. Feel free to email the property ahead of time to ask these questions so you don't withdraw more than you need.

Step 12: Print out a copy of all flight itineraries, train tickets, activity vouchers, hotel confirmations and personal identification documents. 

The last step may seem like overkill in this paperless, app friendly world. However, I have seen first hand the trials of someone losing their wallet and trying to get on their flight. You have to prove your identity and so it's nice to know you have a back up, even if it is just a scanned copy. Also, some immigration counters want proof of where you are staying and when you are leaving, so it is better to be prepared.

Bonus Step: Have a major freak-out before the trip. Run around buying extra things that I don't need because "There's no Target in Europe!" and then stay up all night doing all the laundry, cleaning my place, and packing and re-packing my bag. 

And that's it!

So, take a deep breath, drink all the beer and wine, eat all the pizza and pasta, and enjoy the incredible people watching. It's so worth it!