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⛵️ It’s a Monday afternoon in Kotor, Montenegro, and a gentle breeze carries the smallest of sailors across the bay.

Mini white sailing boats are guided by little hands with a steadying grip on the tiller. This is the sailing extracurricular activity (ECA) with Boundless Life – where sailing is a pathway to experiencing local Kotor culture and an opportunity for profound personal growth.

We recently spoke with Ragan Jolly, a Boundless Life parent, after watching her 7-year-old son complete his final sailing session on the bay. With her insights – along with some wisdom from Boundless Life’s own John Stampoulidis, a former sailing instructor in our Syros cohort – we set out to explore the ins and outs of a weekly sailing ECA in Kotor.

📸 A big thanks to Ragan for sharing her experience and photos with us to help create this post!

‍➡️ Read our complete Boundless Life travel guide on Kotor Montenegro.

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Sailing a UNESCO World Heritage Fjord

For our spring cohort in Kotor, Boundless Life introduced sailing as a brand-new ECA. Ragan was eager for her son to embrace this unique opportunity. After all, how exciting to learn sailing in a UNESCO World Heritage fjord!

On the first day of the sailing ECA, a mix of excitement and nerves rippled through the group. For Ragan’s son – who before Kotor had only minimal ocean experience – the idea of handling a sailboat was as exciting as it was daunting.

“My son can pick his way down a black diamond ski run at home in Wyoming, but sailing is living outside his comfort zone, he’s learning something brand new!”

Boundless Life partnered with a local sailing club in the Bay of Kotor to run this program. Reassuringly any parent concerns or worries were quickly put at ease, as the local Montenegrin instructors met the cohort with an expert confidence.

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Learning the Ropes

There are six children in the Monday class, aged 7 to 12, and on Tuesday it's the Trailblazer Program sailing session. Each week, parents are encouraged to drop their children off and then leave, this style of coaching fosters a sense of independence and self-reliance. Ragan explains her routine: “I pile the kids in and drive them eight minutes down the road, then drive home. Later, I fetch them on foot, and we walk home together.”

The children began by learning essential sailing vocabulary. On the first day, they were dry docked, as instruction was on learning the names of things, how to tack and dodging the boom. Ragan noted how impressed she was by how quickly her son took to these new concepts: “This is my kid who isn't even a proficient swimmer and now he can explain tacking… It just gives him a whole new vocabulary.”.

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Setting Sail in Kotor

Then, after mastering the basics during the first session, the children were ready to set sail in the second. Out on the bay, each child took turns steering the sailboat, which was perfectly sized for young sailors. Wearing snug life jackets and closely monitored by instructors from a motorized raft, which gently pulled the sailboat along, each child had the chance to experience firsthand the thrill and responsibility of steering their own vessel.

To gain further insight into the long-term impact of sailing, we spoke with John Stampoulidis, a Boundless Life team member and former sailing instructor in Syros, Greece.

“Sailing brings kids into direct contact with nature,” John explains. “It teaches them respect for the sea, the environment, and forces bigger than themselves. I’ve seen kids transform within the first five lessons, learning how to work as part of a team, but also to rely on themselves.” He adds, “There’s a famous saying: ‘A skillful sailor adjusts the sails when the wind changes’ – it’s a powerful life lesson about resilience and adaptability.”

John’s insights resonated strongly in Kotor, as the young sailors quickly grew comfortable on the water. Ragan recalls her son's excitement clearly: “When I dropped them at the sailing club last Monday, my son asked the instructor, ‘Can we capsize the boats today?’ because that's what they did the week before – learning to right a capsized boat.”

Clearly, these lessons are creating moments of courage, confidence, and curiosity that these young sailors will carry with them long beyond Kotor's shores.

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A Tradition Anchored in Culture

Today, Kotor is best known for its medieval fortifications and cruise ship tourism. While sailing isn't immediately associated with Kotor’s modern tourism, the bay itself holds a rich maritime heritage. Across the bay in Tivat, modern marinas with sleek yachts showcase a thriving sailing culture, while Kotor quietly preserves its seafaring past.

Sailing is deeply woven into the identity of places like Syros, Greece and Kotor, Montenegro. Historically, these communities flourished through their connection to the sea, relying on it for trade, prosperity, and everyday life. Generations of locals built their livelihoods as sailors, fishermen, and traders.

Participating in this sailing ECA allows Boundless families to tap into this meaningful local tradition. Partnering with a respected community sailing club means that the children experience sailing not as tourists but as part of Kotor’s enduring heritage.

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Reflections on the Water

As our sailing ECA wrapped up in Kotor, families reflected on the growth and memorable experiences gained. What began as a simple weekly activity became a defining part of their Montenegro stay, deepening connections to the local community and creating core memories for the kids.

Ragan sums it up beautifully: “By no means does [my son] have mastery of the sport yet, but he has some confidence. And I think that is a wonderful gift to give to a 7-year-old.”

This sentiment echoes the observations of John who has seen firsthand the deeper value it offers: “Sailing is so much more than a sport; it teaches skills for life,” he explains. “One of the most beautiful things about sailing is that you never fully ‘master’ it; just like in life, you’re constantly learning, adjusting, and growing.”

He further emphasizes that sailing connects families deeply with their surroundings. Whether in Syros or Kotor, sailing helps build a lasting respect and appreciation for the sea and local culture, something families carry with them long after their time at Boundless ends. “Even if they don’t sail regularly afterward, they develop a deep respect and love for the sea that stays with them forever. Once you build that bond with the water, you carry it everywhere.”

Ready to Set Sail in Syros?

The sailing ECA returns to Kotor this fall and now excitingly, it also returns to our Syros cohort, bringing back a beloved opportunity. Preparations are underway – boats ready, sails waiting!

If our Kotor sailing journey sparks your curiosity, then get in touch to find out more.  Or maybe it’s surfing that grabs your interest instead?  If that’s the case read our article on surfing in La Barra for more information.

Sailing provides children with unique opportunities to build confidence, learn essential life skills, and genuinely connect with vibrant local traditions. If you're ready to experience this magic, get in touch, then consider joining us in Kotor or Syros – your next unforgettable family adventure awaits.

⛵️ Book a Call & Get Started with Boundless!

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