About Us
Our Story
HoliSail started with a dream that had nothing to do with tourism.
It began with a simple desire: to live closer to the sea.
After years of exploring different paths, our founder discovered the world of sailing and the profession of a skipper. What started as a personal journey soon turned into something bigger.
While learning the ropes of nautical tourism, one thing became obvious — most sailing holidays looked exactly the same. Similar routes, similar programs, and often a complicated process for travelers who had never chartered a boat before.
HoliSail was created to rethink that experience.
Instead of selling boat rentals, we design complete sailing journeys with a clear idea behind every trip — whether it’s a wellness retreat, a culinary experience, or an adventure like our unique sailing treasure hunts.
Because sailing should feel like an experience, not a logistical puzzle.
Handpicked Destination
Our strict screening process means you’re only seeing the best quality treks.
Personalize Your Cruise
Want to make your sailing adventure truly your own? With our personalized options, simply share your vision, and we’ll do our best to make it happen, based on what we can offer.
Support When You Need It
While cruising with us, we are always available to you for any further necessities. Feel free to contact us with any questions you may have.
Our Crew
HoliSail journeys are shaped by a small crew of sea lovers, explorers, and storytellers.
From the helm to the galley, each person plays a part in turning a week at sea into something truly memorable.
Miloš Milojević
Dreamed of becoming a ship captain as a kid. Ended up creating HoliSail instead. Usually found behind the helm, searching for the next beautiful bay, or explaining why life is always better at sea.
Anđelija Anđelić
The organizational heart of HoliSail. Always coordinating, planning, and making sure everything runs the way it should. Almost always with a book nearby, and not afraid of a rope when needed.
Aleksandar Kedžić
One of the captains helping lead the HoliSail. Unofficial head of the fresh-fish-for-dinner department. Always ready to drop a fishing line. And if he catches a fish (which somehow he always does)… don’t even think about cooking it before he does.
Our Partners
Some HoliSail journeys are made possible with the help of incredible people we love working with.
Željka Zdravković
Guiding movement, breath, and moments of stillness at sea. Helping guests reconnect with themselves somewhere between sunrise yoga and sunset silence.
Milan Stojković
If you’ve heard about HoliSail, there’s a good chance Milan had something to do with it. A digital marketing strategist who has worked with tourism businesses across the world, Milan spends his time making sure the right people discover our sailing adventures.
Our Philosophy
The HoliSail Way
We believe sailing should feel simple, personal, and meaningful.
Our journeys are designed to bring people closer to the sea, to each other, and to the quiet rhythm of Mediterranean life.
Every trip we create follows a few simple principles that shape the HoliSail experience.
Simplicity
No complicated planning and no hidden costs. Our all-inclusive sailing journeys allow you to simply arrive, step aboard, and enjoy the experience.
Small & Personal
We keep our groups small and our experiences personal. No crowded boats, no mixed cabins, just a private group sharing the journey together.
Meaningful Experiences
Every HoliSail journey follows a theme, from wellness retreats to unique sailing adventures. Creating deeper and more memorable moments at sea.
I had never done a sailing holiday before and honestly didn’t know what to expect. But after the first day I understood why people fall in love with this kind of travel. The Ionian islands are perfect for sailing. Calm waters, beautiful villages and incredible scenery.
I joined the sailing trip around the Sporades with two friends, and it turned out to be the most relaxing week we’ve had in years. One afternoon we anchored near Skopelos and swam straight from the boat for hours. Later we walked through the old town and had dinner in a tiny family taverna. It felt very authentic, not like a typical tourist trip.
One of the most beautiful travel experiences I’ve ever had. Sailing through the Greek islands gives you a completely different perspective of Greece.
This was my first yoga retreat and I couldn’t have chosen a better one. Every day started with yoga and meditation, followed by sailing to another incredible island. One afternoon we practiced yoga on a secluded beach and later had dinner in a small local taverna. It felt authentic, inspiring and deeply relaxing.