6 tips to make the most of your gap year

Travel to 10 countries, over 9 months, and learn 100 skills?


1. Have a specific learning objective (or two)

Every year is an opportunity to learn something new. Your gap year is no different. Take the attitude of heading out for your gap year with the possibility of learning 1-3 new life skills. Make them as measurable as possible. The less vague, the better. For example, don’t just say you want to become good at traveling. You’ll never really know if you’ve succeeded unless you can boil it down to something more specific.

Your goal could be,”I want to become certified in scuba diving.” Boom. Extremely specific and clear. You’ll know exactly when you’ve achieved this goal, and who knows, you might even become a professional diving instructor like one of our students!

You could also choose something like, “I want to be able to arrive at a strange, new place, and feel comfortable starting up a conversation with the first person I meet.” This is a social skill, but an invaluable life skill. You’ll be able to use it at work, in college, wherever you find yourself. These are the kinds of skills that matter most for the rest of your life.

2. Don’t stop at one location

Why confine yourself to a single place? You’ve probably already been doing that for years!

Your gap year is an opportunity to roam, to ramble, to wander the great unknown of our planet and of your own experience. If you’ve lived your whole life in a city, why not visit a few remote villages or explore a foreign ecosystem. If you’ve already traveled around Europe with your family, why not go to the places you weren’t able to see?

A multitude of locations will give you perspective far faster than any semester in college will. Not just on the differences between train stations and hostels, but also the differences in human societies, values, visions of the good life, and of course, your own fallibility.

And of course, if you want to visit 10 different countries in wildly different climates and regions, you could always do Winterline 😉

3. Have a detailed plan, but be ready to throw it out the window

Life demands flexibility. Your gap year is no different. If you’re doing it right, you won’t be in your hometown doing the same old same old.

So, get out into the world with enough to do that you won’t get bored and start doing reckless things to pass the time. But then be ready to throw that plan away if it no longer fits the situation. You may have drafted up the perfect travel itinerary back at home, and now that you’re in Costa Rica or Belize you realize that almost every single bus in your town runs once a week and you’ll have to set up camp for a while. There’s always a blessing disguised in curses like these. Take it as an opportunity to meet someone new, to develop a new plan, to explore the area, or to slow down and try to live like the locals!

4. Try something new

This goes without saying, but there are already too many people who take gap years to just travel from one beach to the next. It surely gets old after a while, but the problem is, if you do it for long enough, you run out of time to be doing the things that could have life-changing value for you. Life is better with a few challenges.

As Jeff Selingo, education writer for the Washington Post, put it:

For a gap year to have a significant impact on success in college, and later in the working world, it needs to be a transformative event, quite distinct from anything a student has experienced before — a meaningful work experience, academic preparation for college or travel that opens up the horizon to the rest of the world. It should also be designed to help students acquire the skills and attributes that colleges and employers are looking for: maturity, confidence, problem-solving, communication skills and independence.

Take the time to figure out what kinds of new things would be fun, valuable, and doable for you. Try to have a balance in your gap year. You want to make it worth it, so don’t tire yourself out with only terrifying things, or only easy things. Find the balance between the two, and then keep pushing yourself further.

5. Focus on relationships

This can’t be overstated. The people you meet on your gap year could verily change your life. You might study world history in Europe and have an amazing time like one of our students did on her Independent Study Project. Inevitably, you will learn the most about your strengths and weaknesses and what you can give to the world with the help of others around you.

“I am the people I meet, the videos I take, the coffee I drink with a dash of milk and two packets of Splenda. I am my dog’s best friend, and it’s my bed she runs to when she hears fireworks in the summer.” — Callie

The quality and quantity of friends and mentors you make during your gap year will all depend on you and what you give to those relationships.

6. Be safe

Last but certainly not least. Your gap year will be full of adventure. And adventure always comes with a dash of risk. Make sure you’re being calculated with the risks you take. If it’s a small risk and high reward, then great! If it’s a small reward and high risk then maybe you want to think of ten other amazing things you could do. You can still have plenty of fun while being safe. The key is finding the right mix of fun, safety, and learning.

So do your homework about visiting a place before you get there. Every society has their own written and unwritten rules. For your safety and for the peace of mind of your friends and family, know where you’re going, and be prepared for both the best of times and the worst. Do you know CPR? First Aid? Can you build an ad-hoc shelter if needed? Do you have a communication plan? Emergency evacuation insurance? If you’ve thought through these and more, you’re on your way toward a safe and happy return from an amazing gap year adventure.

If you’d like more resources on having a safe and successful gap year, feel free to reach out to us at admissions@winterline.com.

What It Feels Like to Get Ready for a Gap Year: Getting Comfortable Being Uncomfortable

9 months. 10 countries. 100 skills. The best gap year ever.


The phrase, “get comfortable being uncomfortable,” has shaped my actions since I was a little girl. My father has constantly instilled this idea and way of life into me through both repeating the phrase and implementing it through his active parenting style.

I’ll never forget that for three consecutive summers in a row, he told me, “This is the summer you get tough.” Looking back on it, we laugh at his endless hope that I would “get tough” each summer. But, in hindsight I think his advice has encouraged me to become the adventurous person I am today: getting ready to take a gap year with Winterline. I challenge myself each year more so than the last to take a step even further beyond my comfort zone. My gap year is naturally that next step.

So, why am I even taking a gap year?

To take a step away from school

I have been on such an academically-motivated path for most of my life that I feel as if I’m going to burn out if I don’t take a break. I think I will be more confident going into college with the experience that Winterline will provide me during my gap year.

To learn more about myself and discover who I am

Although many people tell me that I have a clear vision of my identity, I tend to constantly ask myself, “Who am I?” as I’m sure most 17-year-olds do. I want to be able to learn more about my passions, what makes me tick, what I love to do, and who I truly am at my core.

To learn skills

The main reason I chose Winterline is because of the amount of countries we will visit and the amount of skills I’ll learn. I’m hoping to not only learn skills, but to become a more marketable and independent person as a result. I don’t want these skills to just last for the trip, but for my lifetime.

To have fun

This slightly goes back to my first reason, but I need to have some fun. I have stressed myself out way too much with school, golf, work, etc. due to my self-imposed “perfectionism.” I need to take a break from those day-to-day stressors and allow myself to let loose and have more fun in new and exciting environments.

To challenge myself to become comfortable being uncomfortable

This is the year I am going to “toughen up” and challenge myself in more exhilarating ways. Each year I make progress on learning to love being out of my comfort zone, so naturally I think Winterline is my perfect next step.

anna get ready for gap year

Compared to my friends who will all be attending college in the fall, I am definitely in the minority of what I am doing to prepare for my upcoming year. There are so many differences in how we are all getting ready for our years away from home:

Dorm shopping versus gap-year shopping

While all my friends are already Snapchatting pictures of red Target carts full of bedding, appliances and new clothes, I have just received my Winterline packing list and am currently deciding which travel backpack I should purchase for all my belongings. I am definitely already a bit envious that my friends don’t have to endure the anxiety and stress that comes with bringing less than 50 lbs of stuff for an entire trimester abroad.

Searching for a roommate versus preparing to be nomadic

Aside from a few friends who have decided to go “random” with their roommate, most rising freshmen have already found their perfect match and know what to expect with the person they’ll be living with. I, on the other hand, don’t even know how to start mentally preparing to have no stable roommate. Instead, I will be living nomadically with a large group of people for one year.

Picking out college courses versus having a trip itinerary

While my friends are trying to avoid taking Microeconomics at 8 AM, I have a specific trip itinerary that will not be changing based on whether or not I want to get up early. But I definitely can say I have a better pick of classes than most of my friends, like “SCUBA 101” and “Principles of BMW Driving.”

Keeping in touch with family and friends versus trying really hard to keep in touch

Although my friends and I will both be away from home, I think we will face some different obstacles in terms of trying to stay in touch with family. While the Wi-Fi on campus may be acting up and not letting students FaceTime their parents, I’m afraid that being completely off the grid at any given time may challenge me to think of new ways to keep in touch with my family… Pigeon messengers may be making a comeback for me. 🕊

Snapchats about school versus Instagram-filled travel posts

My Instagram will be filled with exotic pictures around the world while my friends’ feeds will be pictures at parties and football games. I will be trying to live vicariously through them in some ways (except when I see them post about midterms on Snapchat), but I know they will also be jealously drooling over my feed.

In spite of some of the amusing aspects that make up the differences between my preparations for a gap year and those of my friends getting ready for college, we are all feeling pretty nervous. We all will need to “get comfortable being uncomfortable” regardless of whether we are taking a gap year or going to college in the upcoming fall.

I am confident that I will be able to not only achieve what I have set out to do with this year, but that I will also be able to make new goals for myself that will encourage me to continue to step beyond my comfort zone in the future. Life is about getting comfortable being uncomfortable and I am ecstatic to start this journey in September.



Should international students take a gap year?

Maria, an alum from the 2015-2016 cohort, is now at university in the Netherlands. Originally from Colombia, Maria submitted this interview for US News & World Report on the growing trend of international students taking gap years.

9 months. 10 countries. 100 skills. The best gap year ever.


Why did you decide to do a gap year before attending university?

I was lucky enough to attend an international school in the middle of rural India from 2013 to 2015 when I graduated. My classmates came from more than sixty different countries and all of them had a repertoire of diverse adventures and stories to tell.

Sometimes we would all sit down sipping some chai, telling anecdotes of our motherlands with pride in our hearts and tears in our faces. These evenings could go on until two or three in the morning but they taught me the lessons of a lifetime.

It was like this that I discovered that sometimes I would learn more about the world and life in those sessions than what I had learned in school for a whole semester. This is when I realized that there were other ways of learning, there were stories to discover and people to meet.

University sounded like an amazing opportunity to expand my knowledge on something that I am going to spend my whole life doing, but there was something else calling me. There was a desire of seeing those places that my peers were talking about, of experiencing those landscapes and feeling the people.

I was tired of sitting in a classroom while the world had so much more to offer. I wanted to learn, but I didn’t want to do it on their terms.

group photo gap year cohort alpha smile angkor wat cambodia-4062

Where did you go and what did you do for your gap year?

In September 2015, I found myself traveling to ten different countries, with seventeen strangers, learning 100 different skills.

I started in Central America and moved to South East Asia and lastly, Europe. I am now a certified SCUBA diver, a certified Thai Masseuse, semi fluent in French and fluent in permaculture; passionate about Ballet, Bollywood, Flamenco, and my list could go on and on.

In each country, we learned a skill that was relevant to the location that we were at. In this way, we were not only tourists but we were travelers, tasting each country as we flew in and out.

How did it help you prepare for university?

My gap year taught me how to be comfortable while feeling extremely uncomfortable.

Changing not only countries but cultures from one day to the next can be extremely exhausting for the mind. Being away from home means that the comforts that you once experienced are no longer there and not having a permanent home teaches you how to make of yourself the home you deserve.

And to be honest, isn’t that exactly what we need for university? Don’t we need to feel comfortable in a foreign place surrounded by strangers that will soon become your friends?

If you ask me, after traveling the world for nine months, university sounded like a piece of cake… and it kind of was.

Benefits of a gap year

“I believe that Winterline helped to make that possible. Even a year later, I am still benefiting from Winterline and I want to thank you for creating such an incredible opportunity. It has truly been life-changing.” — Jamie F.

Wonder why gap years are the fastest growing option after high school? Look no further. The benefits of a gap year are almost universal. With more and more students taking 5-6 years to graduate from college, taking a year between high school and college to learn more about the world, work, and yourself not only makes financial sense, but is just way more fun.

9 months. 10 countries. 100 skills. The best gap year ever.


Check out this gap year infographic below to learn more about the benefits of a gap year. You can also download it here.

Benefits of a gap year

Meet Alice: Hamilton Fan and Dog Lover Taking A Gap Year

Alice will be traveling to 10 different countries and learning 100 new skills as part of the Winterline Global Skills Gap Year program. Read on to learn why she considered taking a gap year, and the things that excite her the most about traveling the world.

Thinking about taking a gap year too?



I remember sophomore year, hearing of a student at my high school doing a gap year and it piqued my interest. For a long time I was set on being in the graduating class of ’21 and in a weird way I felt like this college graduation year defined me. Then, I realized it was more important to actually accomplish something and experience the world than it was to graduate college the same year as my high school peers.


My mom was in the foreign service as a diplomat, and has been really supportive and encouraged me.


I think one of the first questions a child is asked from an early age is “What do you want to be when you grow up?” and I’ve always had a vague answer or said something I was somewhat confident I could be decent at. But I’ve never had an answer to that question that I felt any confidence about. Winterline provides an opportunity for me to try so many different skills and provide me insight on my strengths.


It’s pretty hard to choose, each country sounds amazing. I’m pretty excited about Thailand, I really love food and it’s pretty different from the Asian countries I’ve been too.


I’m pretty excited to scuba dive, I’ve always been interested in the underwater ecosystem. I always am interested in the problem solving and negotiation learning experience. I think I’m pretty good at that and I’m a quick thinker.

Alice taking a gap year


Unrealistically, I’d live in California in a mansion with 100 dogs. But realistically maybe something in psychology or publishing. I’m not really sure though.


I’ve traveled to Beijing and Hong Kong. I was adopted from Beijing when I was four months old, and I went back when I was five when we adopted my sister. Two years ago I traveled to Hong Kong with a friend because my dad was the consul general and the government paid for my flight which was a perk. I then flew to Beijing to visit a friend who had moved there and I climbed the Great Wall of China in Birkenstocks.


I think there’s going to be a lot of self-growth and I’m interested in comparing myself from the beginning to the end of the trip.


I am extremely extroverted, but when I first meet people I’m kinda quiet. Not to toot my own horn but I think I’m pretty funny, and go with the flow. I don’t really get mad for longer than an hour and then I move on. I also managed to forget how to ride a bike.


I really like musicals, I can’t sing but I can appreciate and envy those who can. Since New York is four hours away by bus I’ve been able to go to a couple broadway shows, Ameliè and Natasha Pierre and the Great Comet of 1812. I also know Hamilton by heart.



Ready to take a gap year too?