There’s a Scandinavian maritime saying that those who sail together share one fate. For Yasido founders Stefan Varadinov and Stefan Kalaydzhiyski, that fate began on a boat, where they met and built a partnership. “If you can spend a week on a boat working as a team,” both reflect, “you can build something together on land.”
They tell me that a decade ago, renting a yacht meant navigating tons of emails, handwritten availability notes, and uncertainty before it even began. For them, as avid sailors, that friction was more than an inconvenience and led to building a platform aimed to bring structure, trust, and automation to one of travel’s most fragmented niches.
“You’d send 10 to 15 emails just to get one booking moving,” Varadinov recalls. “Then you’d confirm the yacht, and later find out someone else booked it by phone. That was normal.”
Today, Yasido is often described as a “booking.com for yachts,” but the comparison only scratches the surface. Beneath its interface lies an operational engine built to handle the legal and logistical complexities of chartering a vessel.
For Varadinov, the path to building the platform was shaped by two parallel passions. Professionally, he spent years in the online space, focusing on e-commerce and business process automation. Personally, he grew up around boats and spent much of his life sailing, particularly in Greece. “I’ve always built systems,” he says. “But sailing was my childhood dream. Yasido is where those two worlds meet.”
The platform began not as a startup, but as a private tool. Varadinov and Kalaydzhiski, together with Maxim Krizhanovski, combined industry expertise from a lifelong captain, engineering depth from a software architect, and Kalaydzhiyski’s background in finance and automation. As fellow sailors began asking to use it, the team realized they had created something with broader potential. “People started using what we built for ourselves,” Varadinov says. “That’s when we understood this could be a real product.”
Why yachts aren’t just “Airbnb on water”
At first glance, yacht rentals seem like a natural extension of the sharing economy. Yet Varadinov argues that comparing them to apartment rentals or hotel bookings misses critical differences.
“Boats are not hotel rooms,” he explains. “You don’t travel alone. You need a group, often eight to ten people. Many are first-timers. They need guidance, not just a booking button.”
The operational complexity is significant. A yacht cannot leave port without official clearance. Crew lists must be submitted and verified by authorities. Captains must hold valid licenses for specific vessels and regions. Insurance, safety equipment, and maintenance records must be checked. Payments often involve large deposits and staged transfers. “The sea isn’t forgiving,” Varadinov says. “In a hotel, if something goes wrong, you get another room. In peak season with yachts, there may be no replacement.”
Yasido’s core value lies in managing this complexity behind the scenes, the founders tell me. For users, the experience is simple: search, compare, book. But the moment a reservation is made, a chain of processes begins. “When you click ‘reserve,’ we process multiple documents immediately,” Kalaydzhiyski explains. “Crew lists, port approvals, insurance checks, captain validation; it all starts before you even arrive.”
The platform also aims to tackle a longstanding trust problem in the industry. Historically, customers wired large sums, often €10,000 to €20,000, to unfamiliar operators. “I’ve done it myself,” Varadinov admits. “You email someone who claims to have a boat and think: is this real? You call friends to verify. It’s stressful.” Yasido aims to address this by vetting partners, monitoring maintenance status, and building long-term relationships with captains and charter companies.
Building trust and accessibility
Another misconception Yasido seeks to challenge is the cost of yacht travel. Kalaydzhiyski believes platforms like his are reshaping perceptions by aggregating supply and improving pricing transparency. “People hear ‘yacht’ and think luxury only,” he says. “But split between eight to ten people, it can cost the same as a regular vacation.” Yasido’s marketplace model allows charter companies and owners to access demand while offering travelers better conditions.
“Our paying customers are the partners,” Stefan notes. “But we carry responsibility to both sides — owners and travelers.”
“Booking is only the beginning,” he adds. “Support before and after the trip matters just as much.”
The global yacht charter (boat rental) market is estimated at over $9 billion annually as of 2024–2025. Europe dominates the market, accounting for about 69% of global charter revenue, largely driven by Mediterranean destinations such as Greece, Croatia, Italy, and France.
Despite operating globally, Yasido’s growth has been driven largely by word of mouth. Sailing, Varadinov says, creates loyalty and community.
Today, Yasido serves customers across Europe and beyond, including the United States and Japan, while aggregating tens of thousands of boats across more than a thousand destinations. Yet onboarding new vessels remains complex due to regulatory differences between markets.
“In Greece, for example, requirements are strict,” Kalaydzhiyski explains. “You may need a local company, certifications, inspections. Individual owners can’t manage this alone.” In response, Yasido increasingly helps owners navigate compliance and operational setup. “We didn’t plan to offer this,” he says. “People asked for help, so we built the capability.”
The platform supports multiple charter models, from bareboat rentals for licensed sailors to fully crewed experiences. For Varadinov, the mission remains grounded in experience rather than scale alone. “Business isn’t just about money,” he says. “It’s about building something meaningful; something that makes people feel good about what they’re doing.”
