Many people panic at the thought of trying to find a place to go during their limited vacation time. Fighting for a popular time of year with other employees, cost of flights, finding accommodations and shoving their "relax" time into their companies allotted amount of PTO days. I, on the other hand, am trying to take full advantage of my position as a desk-free, remote, unchained employee and travel as much as I can. I love the freedom of flight! Sometimes I let flight searches tell me where I’m going next. As long as it takes me and my backpack from point A to B, let’s go! Thanks to the work I do every day, I have a lot of experience with booking, organizing, coordinating and planning travel; a set of skills which I recently put to good use to book a month-long trip across 8 cities in 3 countries.
How To Get Started
When booking a working vacation there are many details you’ll have to figure out, but the ones listed below are the ‘big picture’ questions that help guide me:
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Where do I want to go?
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How long do I want to be gone?
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Do I want relax, beach, adventure, explore?
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Do I want to stay in places for a while or hop around?
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How many days will I be working and how many will be non-working days?
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How much money do I want to spend?
Once you’ve answered these main questions, you’re ready to begin planning your trip.
Where Do You Want To Go?: Book Your Flights
Determining where you want to go and how long you want to be gone is important because… you must land at some point. Skyscanner.com is my go-to tool for finding the best deals on flights and has a great feature that allows you to search ‘everywhere’, an option for those of us who don’t care and just want cheap and warm. Below are some key points to follow when booking:
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Be flexible. Flights are most often the priciest part of your trip and being flexible with dates is the best way to ensure you get there the cheapest way. Skyscanner.com shows you the cheapest flights regardless of airline and the cheapest day to depart and return. Hence, the more flexible you are, the better deal you will find. (I always try to fly on weekends or hop on night fights so I don’t disrupt my workday, Fridays and Mondays are typically more expensive)
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Look for alternative airports. Sometimes it’s cheaper to fly into a different airport within your destination. For example: If you are flying to London and you can save $300 (round trip) to fly to LGW instead of LHR, I would book LGW and look for accommodations, events and things to do in that neck of the woods. That $300 is the price of a week’s hostel stay, a wild night out in the best club (Egg, cough, cough) or entry to some really cool museums/events. Totally worth rearranging my previously thought out plans to save that much money.
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I recommend booking travel as soon as possible. The reason? It’s a commitment to your trip. Most airlines charge outrageous change fees to change your flight dates or times. Call me a sadist, but it’s a painful way to force me to go, just in case I get the pre-trip jitters or make excuses that I can’t go because The Office isn’t available on Netflix outside of the US". Once your flight is booked, it’s official. Tell your friends and tell your work people so they know why you look so raggedly tired and why you recently started signing off with ‘Disfruta tu día’.
Once You’ve Committed: Plan your Trip
After I have forced my own hand to click ‘book’, my next thoughts are "What is my budget? What timezone will I be in? How will I ensure my work continues seamlessly? What the heck do I want to do when I get there? How many work days vs travel days do I have?". So many things to consider, but all equally important.
With this trip, I knew I wanted to visit those famous European nightclubs, enjoy the beautiful architecture that is older than my home country and travel through the beautiful Spanish countryside by train. I read many blogs, posts, traveler guides, books and Lonely Planet recommendations to come up with my choices. I knew with Europe being GMT, I was going to be 6-7 hours ahead of my CST timezone. I planned to explore/travel in the mornings and afternoon, work afternoon to evening and party until the morning… sleep would come as a last priority. IT’S EUROPE!
I knew it was going to be more expensive due to the Euro vs Dollar situation, so I had budgeted accordingly (I always have a running travel budget and pull out of that fund when I am ready to coddiwomple). It was important to me to stay in bigger, more progressive cities during the week (better chance of strong wifi, meeting people, access to food and parties closeby); and smaller towns during the weekends (a perfect place and time to unplug and enjoy myself).
*Never connect to a new or unknown WIFI network without having a VPN setup. You don’t want to be working in Europe while also sharing your data with the "Prince of Nigeria".
The Fun Part: Book Your Accommodation
Once I decide where I want to go, book my flights and decide what kind of trip I want to have (relax, beach, adventure, explore), I book my accommodations. I book my stays dependent upon three things: location, convenience, and cost.
1. Location dependent bookings make sense if you are exploring specific places and landmarks. For example: On my trip to London, I knew I wanted to do touristy things like Big Ben, Buckingham Palace, London Eye, etc. It doesn’t make sense to stay far from those areas, pay money to take a lyft or train over, then have to use part of your day to travel back. I wanted to be close, spend the day, take my time enjoying the architecture and stroll back to my "home" for the night.
2. Convenience bookings make sense dependent upon your trip needs. If you just landed from a 14 hour flight and want to immediately get to your abode, sleep and gather yourself, I would book using airbnb.com. It gives you private space and allows you to have a more solo experience, relax, and choose your surroundings dependent upon your mood. As a single woman traveler, I only stay in locations that have had 10 or more people already use that residence and leave good reviews.
Whereas, If you are in the mood to party and meet people, I would book a hostel. When booking my stays, I use hostelworld.com. I only book places with a rating of 8.5 or higher and always read the last 10 reviews to ensure the most recent people that stayed there had a good time and the wifi signal was strong.
3. Cost as a criteria is up to you. On my month long trip, I had a certain amount of money budgeted and I wanted to spend under 25% of my budget on accommodations. I was ok with spending less money on hostels and more money on food and going out. I only stayed in hostels this trip and loved every minute of it. For me, all I require is a clean, safe place to sleep until I am up and out exploring again.
These are rules that I, myself, abide by to keep me feeling safe and comfortable, you will come up with your own as you build your travel ledger. The order of these items is completely up to you.
(Working on this blog in the middle of the Latin Quarter in Paris. What’s that? No big deal, just the Eiffel Tower in the background).
PRO TIP #1
When traveling by train/metro between Spanish cities, some trains had wifi available on board for free or for a higher priced ticket. It was a great way to get to my next destination without missing a beat. Also, if you are lucky enough, some seats have electrical outlets by them. This lets you create a more detailed itinerary, not having to account for time away from work while you transition cities.
It’s Time: Take Off
Following these steps will help prepare you for your trip, but keep in mind that unexpected changes happen frequently whilst traveling. Dealing with these road bumps may seem difficult at the time or even insurmountable feats that require a strength you didn’t know you had. Sometimes, the outcomes are more devastating than others (I recently missed my flight to Morocco and didn’t have any idea where to go and what to do next), but going with the flow and diverting your energy towards your new plan quickly, is a skill you will perfect as you travel more. It will only make you more confident and give better stories to write about in your travel blogs.
(In the middle of the city center in Valencia, stood a colosseum. The view was incredible and the outdoor cafe provided great signal)
PRO TIP #2
Find an outdoor space when it’s nice out and remind yourself that there is a world above your computer screen! This allows you to soak up some Vitamin D, get fresh air and people-watch. Also, when you finally have to be heads down for work, working outdoors makes it feel like you are still partaking in a very local experience.
Please keep in mind that you don’t have to travel internationally to take advantage of your remote position. If you have the travel bug, just go wherever that leads you. It can be a small town in Tennessee to Sao Paulo, Brazil (which is definitely on my list), the same rules apply. I hope you now realize your potential to travel and how lucky you are to have the ability to do so. If you need help booking or have questions about how to start traveling while working, traveling as a solo female or how to pack appropriately, contact me on Instagram @kolkkat or twitter at @ChromaticHQ.
