How I Travel “So Much”

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It’s rare that I’ll see someone for the first time in a while without them inquiring about my next travel destination. It’s even more rare that I’ll come back from a trip and people don’t ask how it is exactly that I can travel so much. While I think I don’t travel enough, I’ve been accused on several occasions of being a member of the CIA. This has come from different people. While I’m not denying this, I highly doubt that if I were actually a member of one of those three letter, top secret, government agencies you would even know when I was out of town, let alone the country. The truth of the matter is that what I do is not important and irrelevant in all ways. I’ve always said that if I go broke or into debt, it will be from travel before anything else. While traveling has yet to break the bank for me, I believe that even if I were a cashier at your retail store of choice, my extra money would go toward plane tickets and airbnb’s. I plan to explain in detail at a later date how I travel for cheap, but right now all that matters is how I travel often…or what others think is often.6ade1-1412697946094

It isn’t the only way, but it helps that I’m 1. single, and 2. have no children. Now, couples and families travel every single day, but I think it works in my favor that it’s just little old me. Even when I was in relationships I had to make sure my partner could go on vacation the same days I was available. They may not have a job where they can take off in two weeks for an entire week, or even a few days. When it comes to children, unless you travel during their break, you have to worry about pulling them out of school or deciding if it’s even a good time for them to be missing school. If you opt to leave them home, you have to arrange baby sitters and such on a 24 hour basis. That can easily get to be too much stress and money. So, if you are willing to travel without your partner (which I recommend doing at least once before you decide you hate it), and you have no kids that can’t take care of themselves while you’re away, then my tips may not work for you, at least not always.


I have to get technical and say that I don’t actually find flights, they literally come to me. I like to think I was smart enough to join a social network community of travelers where one of the perks is that I get flight deals and glitch feeds sent straight to my phone. Even then I don’t have to go looking because they pop up right on my home screen in real time. Pretty neat, huh? Now if you aren’t a member of one of these fancy new millennial networks (mine is paid, fyi) then it still doesn’t take much effort to go to your favorite cheap flight website(s) and sign up for emails. Some sites allow you to follow one fare for certain dates, and others let you track flights to a destination. When my notifications pop up they are for cheaper than normal flights to various destinations (it’s categorized by the departure city) and the dates are usually very particular, ranging from the current month to 10+ months from now. Now for the good stuff…

Let’s say a flight for Dubrovnik, Croatia popped up on my phone right now. I use this example because it’s at the top of my travel list. (Yes, I have a physical, paper list with my Travel Bucket List written on it.) So, Croatia pops up for a price between $500 and $650. I would first look at the dates for this flight. For that price, if I needed to travel within two months I would probably pass. When it comes to last minute travel I have a rule of never paying over $300 for a flight. I think I can be picky because I’ve paid $124 for a round trip flight to Santo Domingo, Dominican Republic and about $260 RT to Trinidad & Tobago. I usually spend about $600 on a flight when I’m splurging for my birthday trip in September. SO, if this Croatia flight is available for around $600 and I can be in Croatia on my actual birthday, then without hesitation I’m booking. It’s as simple as that for me. $300 or less for somewhere that I actually wanted to go or am willing to explore, and $600 for a birthday destination that’s fit for a Goddess. Now, things can get a little tricky with perhaps a $150 flight to Iceland during the dead of winter. That would have me rethinking some things. Yes, I want to visit Iceland, but most European destinations are at the bottom of my travel list when I’m already experiencing the winter where I am. Think about it, and if you’re willing to tough it out, more power to ya.


For this past birthday I decided the Amalfi Coast would be my destination of choice. I had been wanting to visit Positano specifically for years but the flights were always upwards of $1000 whenever I would check. Being able to fly to so many places for a fraction of that price meant that Positano kept getting bumped down my list. However, this particular flight was $600, half the price of what I normally see them going for, so I didn’t waste too much time comparing. I double checked a few flight comparison sights and saw the same airline offering the flights for $600. Without hesitation and all while sitting at my desk at work, I typed in my credit card information and clicked BOOK. Eek! There’s nothing like booking the trip you’ve been dreaming about.


I always book first and worry about the “how” later. Most sites offer free cancelling within the first 24 hours of booking, so you literally have a full day to change your mind and rethink the situation. What I recommend for the human who likes to adult on a regular basis is immediately requesting vacation time off. Hopefully your boss will say yay or nay and you will immediately know if you can move on to step three.

I’m lucky to work for a private company that gives me 25 days vacation time alone per year. Our headquarters, where I work, is in New York and our sister HR is based in Zurich. We adopted their european vacation practices and give our U.S. employees, new or tenured, 25 days vacation in addition to sick time. Now some may look at that number and be in awe, but I only recently became a permanent employee and have been making it work without that number of days. Even when I was working at companies where I was only given 10 days (2 weeks) of vacation time, it was enough for me. I always plan vacations around weekends and/or holidays. So if I wanted to be in Italy for five days, I could fly out on a Wednesday after work and come back Monday night, and would have only used three vacation days. Make it work however you can.


Hopefully you make it to step four because you 1. found the perfect flight, 2. said flight was the best price when compared to others, and 3. your vacation time off was approved! The fourth and final step is always the last on my mind, but not everyone is as lax as me. I prefer staying in airbnb’s as opposed to hotels because I want a more authentic experience when I travel. I don’t plan to be a tourist, I want to be one of the locals. Therefore, after booking a flight I’ll check airbnb to get a feel of how much my stay will cost. Unless I find a place that’s so gorgeous and cheap and I can’t sleep without having booked, I’ll usually wait until about two months, usually just one, before my arrival and try to lock down a place. If you prefer hotels I recommend booking as early as you can afford. Make sure to look around for promo codes, discounts, and anything similar. I’m against paying full price for anything, so I support any and all frugality. Do your homework! It’ll all fall into place.

So there you have it. Find the flight, compare the price, put in your vacation requests, and book your stay. Lather, rinse, repeat and do it as often as you can. VOILA!

p.s. I want to give you $20 off your airbnb booking so be sure to use the links throughout this post or here (my promo code is mwise107) and book your stay!

If you have any questions about this post or need more details about one of the sections, please comment down below. You never know, it could apply to everyone. If you want to speak privately, don’t hesitate to hit up the contact section of the website. xoxo Ciao!


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