College is an ideal time to seek out memorable experiences, meet like-minded people, and expand your entrepreneurial mindset.


We're here to help you discover opportunities that will propel you towards your own version of success.


During a week in beautiful Costa Rica, we offer a healthy, productive, and inspiring alternative to the traditional spring break, for students who want to do something more meaningful.

Who's this trip for? 

If you've made it this far, there's a good chance this trip is for you. We are looking for students with an entrepreneurial-mindset - this doesn't mean you have to own a company. It means you seek ownership over your entire journey. You want to find balance and meaning in all of it - work, school, relationships, passion projects, etc.

This is a rare opportunity for you to express and discover your personal and professional goals authentically, in a safe and inspiring place, surrounded by like-minded peers and experienced mentors to support you every step of the way.

"This trip was perfect in every sense of the word. I had the experience of a lifetime!"

—  Karan Kishorepuria, Northeastern University

We've been joined by students from 30+ universities, including:


Workshops & Coaching.

Participate in group discussions facilitated by your on-site mentors, tailored specifically to you and your fellow travelers, and designed to foster personal and professional development. 

In the beginning of the week, you'll be paired with a coach to work with one-on-one during

Island Office Hours throughout the week.


During that time you'll work with your coach to dive deeper into personal, professional, and entrepreneurial goals. You'll leave the trip with a plan of action, and a new mentor to hold you accountable.

"The overall theme of achieving our dreams and creating our own success was a huge topic — and one that was greatly appreciated and valued among the group. It is not often that you come across people who understand where you are at personally AND professionally who can share their similar successes and failures in order to guide you in the right direction."

- Allison Carey, University of Kansas

Gain a global perspective.

Experience a day in the life of a Costa Rican high school student during this profoundly powerful cultural-exchange day


You'll dance, play sports, work on a local school/community project, and connect deeply with a group of truly inspiring students, who will teach you the true meaning of Pura Vida.

You'll also have the chance to visit a local nearby town to shop, eat, and explore.

From local chocolate and coffee shops, to pop-up carnivals, rodeos, and live concerts, there are always pleasant surprises that shed a beautiful light on the Tico lifestyle.

"While there are so many differences between a Costa Rican and an American high school, I couldn’t help but notice how similar we all are. The students laughed with us, bonded with us over sports, played instruments for us, and took selfies just as we do. Despite the differences in language, weather, socio-economic strata and curriculum, we found each other to be fundamentally the same."

- Saalik Lokhandwala, Bentley University

Tap into your leadership energy.

The Power of the Herd is something you need to experience to believe. But in short, horses are tremendously powerful animals for what they can teach you about leadership, herd and team dynamics, and your own ability to access confidence and strength you never knew you had.

Cultivate your creativity.

Exercise your idea muscle during a fun, high-energy and albeit, kind of crazy improv pitch-competition. With your team, you'll come up with an impact-driven idea and pitch it to our team of judges. This event is both meaningful, and quite entertaining.


Just a heads up, you may find yourself pitching in a not-so-traditional environment.

"Startup Island exists at the intersection of passion and community. The question isn’t will you transform, but rather how much will you transform, and in what direction. The first full day of SI shattered the glass ceiling I didn’t realize I had on my own expectation surrounding my

growth and maturation."

- Conner Krollman, University of North Carolina-Asheville

Rest, relax and have FUN.

From paddle boarding around Lake Arenal with beautiful volcano views, and ziplining over waterfalls, to enjoying a spa day and hot springs at a beautiful destination resort, you have plenty of options to feed both your chill and adventure sides. There are also several jungle trails for your hiking pleasure at our retreat property, Leaves and Lizards.

Part of sharpening your entrepreneurial-mindset is being intentional about how you care for your mind, body, and spirit. Each morning you'll have the opportunity to begin the day with a refreshing and invigorating yoga session, followed by a guided meditation from one of our instructors.

There's more...but we like to maintain some level of mystery.

"We focused on our breath through our movements, then we took a step back and remembered to breathe as we sat in guided meditation. We allowed for our thoughts to flow freely, we would sit back and “watch” our thoughts go before us, not judging them but just recognizing them as information. There was no way we could mess this up, this was our time, to just be."

- Nico Repollè, University of Delaware

Our home for the week: Leaves & Lizards, Costa Rica

Toucans, monkeys, sloths and an infinity pool overlooking Arenal Volcano would have been enough, but Leaves & Lizards is abundantly more than that. 

Ranked within the top 1% of all hotels & eco-lodges in the world, it's not just the immense beauty, DELICIOUS food, and quality of accommodations that make our Spring Break HQ so special. It's the people, their energy, their commitment to the local community, and our shared passion for experiential learning and development.

For us, Leaves and Lizards truly is a home away from home, and we can't wait to share it with you.

Ready to take the leap?

Applications will be accepted and reviewed on a rolling basis. Once we review your application, we will notify you whether or not you have been accepted into the program.

Other frequently asked questions:


  • Round-trip flight (from within the U.S. to Costa Rica)

  • All transportation within Costa Rica


  • Retreat accommodations for seven days


  • Personal and professional development workshops & facilitated discussions

  • Adventure activities  in the jungle 

  • 1:1 "Island Office Hours" with an intentionally paired mentor

  • Daily guided yoga & meditation

  • Three meals per day, snacks and drinks

  • SI T-Shirt, Water Bottle, Journal & Extras


  • Local guides on staff 24/7


  • Lifetime membership in alumni community & online channels: in addition to the meaningful friendships created on your trip, you will have opportunities to connect with the entire SI Community, consisting of founders, creatives, techies, investors, digital nomads, personal development nerds, and more, from all over the world.

  • Gain access to the Startup Island global mentor network, consisting of 40+ mentors and coaches.

  • Access to curated job opportunities, business & passion-project collaborations, and book/podcast recommendations-galore.

  • Invitation to alumni meetups and events: frequent gatherings include dinners, salsa nights, group workouts, study breaks, and workshops, as well as #sifam-only retreats and camping trips.


  • Passion & Cause Groups: an initiative where SI alumni meet monthly to discuss and drive impact around passions & causes near and dear to them. Groups include Climate Change & Environmental Innovation, Technology's Impact on Society, and Transforming Education.

  • Opportunity to become a contributing writer for our Medium Publication, The Business of Being Happy & Healthy.

  • Access to additional online channels including our Community Connector, Gratitude List, #SIfam Slack Channel and more!

What are some takeaways that will affect my life post-Startup Island?


Your Spring Break trip is just the beginning. Once you travel with us, you become part of our growing alumni network of entrepreneurial minds from all over the world. The community is available as a resource to you for life.

Other takeaways our travelers experience include:

Refined goals that are consistent with your core values, and an action plan to achieve those goals


New business ideas, partnerships, and collaboration opportunities


Leveling up side-projects


Increased self-awareness, confidence, perspective, and empathy


Energy and stress-management techniques


Tools to flex the idea muscle and become a creative machine


A healthier relationship with technology​


What should I pack?

We send out a packing list one month before each of our trips, to ensure that you have enough time to prepare. In the meantime, think minimalism.​


Will I have cell phone service?

There is WiFi available in certain areas of the retreat property, so that you can check in with the outside world during free time, if you’d like. That said, we aim to create a space that’s healthily disconnected from technology, where you don't need or want to use your devices. During your spring break trip, you will explore one full afternoon of digital detox, including a discussion on our relationship with technology. Students leave with a strengthened connection to nature, their peers, and themselves, plus a healthier relationship with their devices.


What's the rooming situation like?

You will be sleeping in big, beautiful cabins with 2-4 travelers per room. Everyone will have their own bed and private space for clothing and personal items. All cabins have filtered water, nice bathrooms, and a patio area for hangin’ during free time.


How's the food?

No joke, it's out of this world. Expect delicious meals served for breakfast, lunch, dinner, and dessert, along with vegetarian, vegan, and gluten-free options. If you have any restrictions or allergies, you will have a chance to let us know on your pre-trip questionnaire, which you will receive after you are accepted into the program and your spot is secured.


How do I pay for the trip?

After you apply, we will be in touch with next steps. If accepted into the program, you will receive a deposit form to lock in your spot. We're also happy to offer payment plans to spread the cost of the trip out over several months -- we will gladly work with you to make your trip a reality.


Okay, I want in. What should I do now?

Awesome! Click here to apply and tell us about yourself. We'll then be in touch with next steps.