If traveling has taught me one thing, it’s to be intentional about the places I go, the things I do and the people I see. Each year I try to carve out time for a few different kinds of trips, from spending weekends at home to going somewhere I’ve never been before.

In thinking about this topic, I realized that there are four types of trips we should all try to take each year (if circumstances allow). There are also two trips we should take at least once in our lives. I’ve illustrated what they are using my own experiences – let me know if you agree after reading through!


My sister and I lip synced and gestured as our other sister recorded us on an iPhone. We were creating music videos on the Triller app, one of many activities over three days that let our uninhibited silly sides out.

I rarely get to spend time with both of my sisters at once – Jac is a plane flight away and our visits typically revolve around larger family gatherings – so being home in Massachusetts last weekend was special. We binge watched Veep, teased each other mercilessly, took a million Snapchats, and loved on each other in a way that only sisters can.

My trips home are usually routine affairs, but it is the routine that I love and miss every time I head back to D.C.

The magic of family is the love and familiarity that will fill you up and drive you crazy in equal measure. You only get one family – whether blood or close friends – so make them a priority.

The first trip you should take every year is the one you take to see loved ones. 


The 4 Trips You Should Take Each Year

We spent an afternoon sitting at the foot of this church and watched boats pass by on the canal.

Working in a fast-paced agency environment takes its toll. It wasn’t until a couple of years ago that I gave myself permission to take two weeks off at a time, because it would take at least a week to unwind from the stress of my job.

In August I spent two weeks in France and Italy wandering cobblestone streets, biking around lakes in the Alps, peeking into old churches, tasting Italian gelato, and eating next to Venetian canals. I was flooded with so much newness that there was no room for work to creep into my thoughts. It was bliss.

Not everyone needs to escape to a faraway place for multiple weeks in order to de-stress. You know what’s best for you. But think of a place and an amount of time to spend there that will enable you to fully relax and recharge. Is it a weekend at a beach? Spending time at your cabin in the woods? Being in the company of family and friends?

Whatever it is, do that.

The second trip you should take every year is the one that resets your mind, body, and spirit.


The 4 Trips You Should Take Each Year

Prayer flags outside of the Sri Maha Bodi in Anuradhapura, Sri Lanka.

I had never been to Asia, so I decided to visit Sri Lanka to see a part of the world and a way of life that I had never been exposed to before.

Truth be told, my only encounters with anything or anyone from Sri Lanka (save for one interview assignment for work) were the labels “Made in Sri Lanka” on the inside of my clothes from J. Crew and Banana Republic.

So I went. I rode buses with Sri Lankans and talked to them. I poked around ancient ruins and learned about the island’s influential Sinhalese kingdom. I surfed with Shaggy and danced at surfside bars with the owners of the lodge where I stayed. I ate local specialties, drank from fresh coconuts, and tasted Sri Lankan liqueur.

Through it all, I gained a greater understanding of the Sri Lankan way of life. This country is so much more to me now than a tag in my shirt or what I read about the 2004 tsunami. Sri Lanka taught me a lot about life, culture, and people, which in turn will make me a more educated traveler and better global citizen.

The third trip you should take every year is the one that opens your eyes.


The 4 Trips You Should Take Each Year

Looking out at the first rays of light from the top of Old Rag.

Our alarms buzzed at 1:30 a.m., exactly two hours after we went to sleep. We went through the motions of putting on our hiking clothes and gathering our gear, all the while sipping on coffee to give us as much of a perk as our bodies would allow at that early hour.

We made our way to Old Rag, a mountain in Shenandoah National Park, with the objective of hiking to the summit by sunrise. Four hours of pitch-dark hiking lay ahead of us.

I love to hike, but I had never climbed an actual mountain before this excursion. The Appalachians aren’t the tallest or most technical mountains to climb, but it was still a big task for me, having only ever done trails of a handful of miles at a time. Four hours of inclines and rock scrambles were sure to challenge my physical and mental fitness.

I just hoped I could keep up with the group – some of the most athletic people I know.

We climbed for what seemed like forever, only stopping a couple of times for water and snacks. At one point I ran straight into a log and scraped my shoulder, leaving me with an ugly wound that I showed off the rest of the day.

With some help over the most challenging parts of the final rock scramble (where everyone needed a hand), our group stepped onto the summit as the first rays of light emerged from the horizon.

We spent an hour watching the sun slowly rise over the Virginia countryside. I silently relished in my accomplishment of climbing a mountain – a small one, but still a mountain! – and set my sights on what my next pursuit would be.

The fourth trip you should take every year is the one that challenges you in a new way.


The Two Trips You Should Take at Least Once in Your Life

The 4 Trips You Should Take Each Year

Hanging out at The Green Rooms in Weligama, Sri Lanka.

I needed to do something for my thirtieth birthday. I was having the same jittery feeling I had at 25, when I ended a relationship, moved, and changed jobs within a month. I wasn’t interested in that kind of drastic change this time around, but thirty is a big milestone. I had to do something that was more than a bar crawl.

It hit me: I should check off a bucket list trip. Machu Picchu or Guangxi, China, perhaps. But my birthday falls during the most unfortunate month of February, when Machu Picchu is being smacked by rain on the daily and Guangxi is cold and uncomfortable.

Instead, I decided I would jump on a good flight deal to somewhere in the world that had decent weather in February. One day, a very affordable roundtrip fare to Sri Lanka popped up on The Flight Deal.

As I mentioned before, I had some basic awareness of Sri Lanka through the clothes in my closet and an assignment I had completed for Lions Clubs International. Other than that, I knew nothing about the country. So, of course that was the place I should go! Bonus that I only knew one other person who had been there.

It was important to me not to follow anyone for my 30th. Wherever I went had to be my experience. A path I charted on my own. I wanted my eyes to be opened to a country, a people and a culture that I knew nothing about before. Sri Lanka would be just the place to go.

And it was. This was my first major solo trip abroad and it was transformative. It didn’t all go according to plan – I even bruised a rib surfing – but it was exactly the trip I had envisioned. More importantly, it was the trip I needed. It was fulfilling, educational, eye-opening, thrilling, scary, joyful, fun.

I returned from Sri Lanka more confident and self-assured than I’ve ever been. Friends and family have even commented that something seems different about me. I’m proud that I took the trip, and I hope that everyone will make solo travel a priority at least once in their lives.

The first trip you should take at least once in your life is the one you take for yourself.


I boarded a flight to Fort Lauderdale having told no one. That’s totally unlike me. The one thing I’m superstitious about is air travel, and I am religious about texting my parents before I take off and after I land. I also say a prayer before takeoff, and I prayed that not having told my parents about this trip wouldn’t result in the plane crashing.

I was going to Fort Lauderdale to see a boy. Someone who had been in my life for years and had only recently become more than a friend. But he lived far away, and Fort Lauderdale was a cheap place for both of us to get to.

It was exhilarating, taking a leap of faith for love or whatever it was between us. We spent the weekend lounging on the beach, eating fresh seafood dinners, and listening to live music.

The fact that the fling ended in a huge fight a few months later is immaterial. That time, I walked out of his car and into the airport and never looked back. But Fort Lauderdale will always be Fort Lauderdale. It was ours: A grand gesture, a shared experience, and forever a fond memory.

The second trip you should take at least once in your life is the one you take for love.


I have no doubt that other categories of annual and bucket-list travel will emerge as I go through life. Are there any you would add? Let me know in the comments!

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