Vacation Dreams + Tips to Make it Happen

May 14, 2015

Today’s Instagram featured a #TBT from hands-down one of the best trips I’ve ever taken, surf camp in Costa Rica with my bestie. While scrolling through my vacation pictures it reminded me how much I love to travel and how I want to do it as much as possible. On the flip side, I love routine and being home and relaxing. Sometimes while out of town, I’m just counting down until I can get back to my own apartment. It takes a very special trip to make me feel content and settled while away from home.

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I was thinking recently that I want to take one big, amazing trip each year, something aligned with what Costa Rica was. Because of money and limited vacation days, this might not be realistic but I’m going to keep it in mind and hopefully make it happen. 

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Aside from huge trips, I have a bunch of exciting travel plans on the horizon. A lot of it involves visiting new babies, attending weddings, celebrating birthdays and competing in big races. People always ask me how I have the vacation days and money to take all of these trips and if you plan it right, you can make it happen. Since traveling is a priority for me, I work hard to make sure I can take all of the trips I want while still holding down my full time job.

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Here’s how I make it happen:

Side Hustle: In addition to my regular paycheck, I have a lovely spare stream of money flowing in from teaching cycling classes. I’ve been teaching for 9 years (before cycling was the empire that it is today) and I’ve always viewed this as my fun money. I still get my normal paycheck but then every other week I get extra funds that I don’t feel bad about spending freely. If you can figure out a way to make some side money, do it and use it without the guilt you might feel about money you need to put into savings.

Not Ideal Flight Times: To make trips work while staying within my allotted vacation time, I’m a redeye and early morning flight pro. I never waste vacation days for travel days. If I’m flying home from the west coast I will always choose the redeye, landing and going straight into the office. I get an extra day in LA and I don’t waste a vacation day spent on a plane. For other trips, I’ll opt for a 6am flight home so I can still get to work that morning (although maybe a tad late). Which leads me to…

Being Tired: I’m completely exhausted after a redeye or early morning flight but I don’t care. Load me up with caffeine and I’ll make it through. Every time I take a redeye (especially that time I took 2 a week apart) I question my sanity in the morning…but then I will always schedule another one. I’d rather go on a great vacation and enjoy my time, returning exhausted, than missing out on a day away.

Prioritizing: You can’t go on every vacation and some trips won’t be as long as you want, but take a look at your year and see what’s most important to you. With limited vacation days, if you think ahead you can make them work for you and you won’t feel like you’re missing out on big events. If you have a trip that isn’t high on your priority list, you can say no. If you are able to roll over vacation days, keep this in mind and maybe save some days for a huge trip next year if it’s not in the stars for 2015. 

Be Strategic: If you want to plan a bigger trip, figure out when holidays fall and schedule around them. Tack on to days when the office is closed to take a longer trip than you might have originally thought possible. 

Find What’s Close: If you’re used to hopping on a plane for your getaways, take a closer look at what’s nearby. If you need a city escape or short weekend refresh, you may find that there is something perfect a short drive away. For my New Yorkers, I’ve done a night or two away in Warwick, Bear Mountain and The Lodge at Woodloch. All of these trips have given me a feeling of getting away from it all without breaking the bank on flights.

I just went through my remaining vacations days with my calendar handy to figure out which trips I can take. For 2015…

On the Schedule: Boston (x2), Maine, Philadelphia, New Hampshire, Michigan (x2), Los Angeles, Chicago, Maryland, Savannah

Wish list: A big trip…location TBD

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My wish list is quite small as the year is already very packed with travel, mostly to places I’ve already been, but this time around for exciting events. For my one wish list big epic trip, do you have any recommendations? I’d love a relaxing tropical vacation or to visit a European city I haven’t been to.

Hope these travel tips help you get away this summer!

[*all photos from 2014 trip to Costa Rica]

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