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For the next hour, our group weaves through cobbled side streets and shady alleyways as Dobric brings the layered history into vivid focus. She punctuates tales of Dubrovnik’s maritime dominance — this it owed to its powerful merchant fleet and strategic position on the Adriatic — with personal anecdotes that make me feel like I’m hanging out with a friend.

We pass the apartment where her parents still live, and swing by her stately-looking high school, dramatically located atop the Jesuit Stairs (which served as the setting for Cersei’s Walk of Shame in “Game of Thrones”). Then we pause in front of the Franciscan Monastery, where she lets us in on a local beauty secret: a 700-year-old pharmacy, one of Europe’s oldest, is hidden within its Romanesque-Gothic walls.

“Most people miss it,” she says. “But if you buy anything while you’re in town, make it the pharmacy’s rose facial cream, made with ingredients from the monastery’s garden.”

It’s the first day of our weeklong cruise along the Dalmatian Coast, and we’re already off to a memorable start. While cruising is not my usual travel style — I prefer taking charge of my own itinerary — I’m beginning to see the virtues of letting someone else steer the way, especially when it means gaining this level of insider intel.

Our itinerary will take us from Dubrovnik to Split aboard the M.S. My Wish, a yacht-like vessel operated by that can accommodate up to 36 guests. Owned by a Croatian family and constructed on the Dalmatian islands, the boat is crewed entirely by Croatian sailors, as are all the ships in the company’s fleet.

My fellow passengers include a multi-generational American family, a honeymooning couple from England and an Australian celebrating his 50th birthday. Over communal meals and offshore excursions, we agree that the real luxury of the trip has little to do with our ship, and everything to do with the ease of exploring Croatia’s rugged coastline.

Most travellers to Croatia attempt to cobble together an itinerary of their own, hopping between ferries, chartering private boats, and white-knuckling behind the wheel of a rental car along mountainous coastal roads, in pursuit of the country’s 10 UNESCO-listed sites.

But on our weeklong voyage, we visit a half-dozen of these heritage sites, without having to manage any logistics. That leaves plenty of time for scenic sailing and invigorating swims in hidden coves. And while yacht-style travel may sound extravagant, 2026 departures on this itinerary start at $2,595 U.S. per person — within the range of typical pricing for Mediterranean cruises.

In the , we dock a 10-minute walk from the famed Palace of Diocletian, built as a sprawling seaside retirement complex for its namesake Roman emperor. Our local guide, Hrvoje Sarun, who works weekdays as a teacher, leads us through the gates of the fortified compound, highlighting its pastiche of architectural styles — a 3,000-year-old Egyptian sphinx here, 4th-century Roman mosaics there — while sharing historical tidbits that would captivate even hard-to-impress high-schoolers.

“Diocletian was a ruthless leader and widely unpopular,” he explains animatedly, and we all draw near. “In the end, even his wife and children left him, trading their life of luxury for this,” he adds, gesturing dramatically toward the streets.

Thanks to our ship’s small size, we are able to reach places most travellers skip altogether, like the postcard-perfect island of Korcula and the sleepy village of Mali Ston on the Peljesac Peninsula, where we visit a family-owned farm, Bota Sare, cultivating award-winning European flat oysters.

Even in , one of Dalmatia’s busiest ports, we veer away from the crowds, devoting the morning to the island’s northwestern side. We drive past the UNESCO-listed Stari Grad Plain, where vineyards and olive groves have been cultivated since the 4th century B.C. It’s considered one of the best-preserved examples of ancient Greek agricultural planning in the Mediterranean, with its dry-stone walls and chora (field layout) still intact.

Afterwards, we visit the island’s family-owned Tomic Winery to sample the fruits of that terroir. Learning about the island’s agricultural legacy makes our dinner back in Hvar town that night all the more satisfying.

The next day, as we approach the port of Pucisca on the island of Brac, our cruise director invites us to gather on the top deck. We’re passing one of Brac’s seven main quarries, which have produced a luminous, marble-like limestone for over 2,000 years. This same stone was used to build many landmarks we’d seen on the trip, including the Palace of Diocletian and the UNESCO-listed Cathedral of St. James in Sibenik.

After docking, we walk along the waterfront to the island’s Klesarska Skola stonemasonry school, where 17-year-old student Leon Gogic welcomes us into his classroom. Showing us how to use traditional tools like chisels and mallets, he shares his ambition of becoming a professional mason.

The school isn’t on UNESCO’s list, and it certainly wouldn’t have been on my self-guided itinerary. But standing in that bright, dusty classroom, watching Gogic bring milky slabs of Brac stone to life with centuries-old hand tools, I’m reminded of something Dobric suggested at the start of our time in Croatia: Most people miss the best parts. I’m glad I haven’t.

Siobhan Reid travelled as a guest of Cruise Croatia, which did not review or approve this article.