2025 Dalmatian Islands Flotilla
There are several wonderful charter locations in the Mediterranean, but our favorite is Croatia’s Dalmatian Islands.
Cecilia and I sailed the Dalmatian Coast twice before, in 2006 and 2016. We loved those trips and had promised ourselves we’d get back. And we did in September 2025.
Croatia has a significant history, from being used by Homer as a setting for sections of Odyssey where Odysseus is seduced and trapped in a cave by sirens, to the more recent and bloody Balkans War. It is a central melting pot of European and Near Eastern culture. Its coastline starts at the Italian border and stretches hundreds of miles to Montenegro with dozens of islands looking like they are stretched between the two ends. Mostly long and thin, lying parallel to Croatia’s mainland coast, these islands each have their own personalities and towns within them are quite different from each other.
We chose a ‘one way’ charter option, which comes with extra expense, but allowed us to spend more time on each island we visited. We sailed from Trogir, near Split, in the north west part of the country, to Dubrovnik, near the south east border. Three of our boats sailed further south to the Bay of Kotor Montenegro before returning to Dubrovnik.
Our six-boat flotilla was a nice mix of old OCSC Sailing flotilla veterans and some sailors new to international chartering. We all bonded nicely in the parties leading up to the trip which, as always, made the trip that much more special. We did have a rookie skipper on our Moorings 4500: my wife, Cecilia! She steeled her nerves, put us safely in a variety of tight berths, and navigated us safely throughout the charter. It was strange to be in a first mate role for the first time in decades, but it sure was fun watching my wife earn her wings as skipper.
Navigation was easy with modern instruments and with the well-maintained boats of Moorings and Sunsail. Breeze ranged from 5 knots to 27 knots, but mainly hung around 10-15 knots. We had three big rainstorms, only one of which was during the charter, which was bookended by two squally storms: one in Trogir the day before the charter and the other in Dubrovnik the day after the charter ended!
All along the way, we had meal after meal that seemed to out-perform its predecessor. Croatia is known for its konobas, or family restaurants. In many anchorages, konobas offer free mooring, electricity, and water so long as the crew dine there. The food and service at these family-run restaurants was invariably wonderful.
Itinerary
We visited the ‘heart of the Dalmatian Islands destinations’ and also stepped out on a few new adventures.
First Anchorage Drvenik Veli
Our yacht visited a small seldom visited island, Drvenik Veli, on Day One. We had a wonderful crew meal ashore at a fantastic restaurant.
Starigrad, Hvar Island
Then on to Hvar, first overnighting in Starigrad (which means ‘old town’) on the north coast, where we strolled the promenade and found another spectacular restaurant. Starigrad is a gorgeous, quaint, and classic old European village with a great, protected harbor.
Hvar Town, Hvar Island
Then, on to Hvar Town, the Mykonos of the Dalmatians: fun, bustling, beautiful and very exciting and vibrant after dark. (Pro tip: tour, dine and even party in Hvar Town, but berth your yacht in Palmizana, 15 minutes water taxi from Hvar Town’s noisy, busy, bumpy harbor.) Shopping, dining, and vistas from the incredible overlook at the Citadel, high above the town itself, made this a highlight of our charter.
Vis Town on Vis Island
Now, on to Vis, our favorite island in Croatia. Small enough to be quaint and easily navigable, but large enough to intrigue, with shops, vistas, restaurants, and bars, Vis also has one of the largest and most protected harbors in Europe with over two miles of quay space and dozens of conveniently located mooring balls. And, after a small hike, you can visit a WWII Submarine hideout!
Korcula Town, Korcula
After Vis, we had a longer and very exciting 20-27 knot close reach sail to Korcula, an incredibly photogenic walled town, which combines incredible charm with scores of shops and restaurants with one of the steepest and tallest maritime cliffs in Europe as a magnificent backdrop while we enjoyed cocktails at the edge of town.
Mljet
Mljet is home to several great harbors, a national park that boasts an inland lake, a beautiful swimming hole, and a magnificent monastery on an island in that lake, only accessible by ferry. Roads and paths are great for biking and hiking, and scooters and e-bikes are on offer. We tied up to a restaurant quay, had a marvelous dinner, and spent the next day swimming, e-biking and taking the ferry to the monastery. Memorable!
Bay of Kotor, Montenegro
Bay of Kotor is just SE of Dubrovnik, a day’s sail away. You have to clear customs and immigration in both countries both ways, but that was actually fairly simple and quick.
The Bay of Kotor was magnificent, with steep, granite mountains thousands of feet high dropping straight into the sea. Old Town Kotor, itself, was one of the most romantic and exotic walled cities I’ve seen. The town sits at the head of the Bay of Kotor and is a labyrinth of narrow, cobbled pedestrian walkways stuffed with bars, restaurants, shops and music. We luxuriated in the great tapas-like dishes and drinks from very talented mixologists! And, the shopping! Wow.
Marina Frapa Dubrovnik
This was a super find. Located near Old Town Dubrovnik and outside the walled city—a 30-minute walk away—it sported a swimming pool AND a pool bar. The slips were easy and staff wonderful. Moorings made arrangements for us to turn the fleet back in here at Marina Frapa after our Montenegro visit!
The crew of our boat, Soggy Dollar, had a final dinner ashore at a nearby restaurant, enjoying another delicious meal and reminiscing our two weeks aboard.
After the charter, several crews retired to the walled city of Dubrovnik to tour, reflect, and people watch from the myriad cafes and konobas inside the walls. Our crew even went to a bar overlooking the Adriatic just outside the massive city walls and divided our time between fancy cocktails and diving off rocks into the water. As I write this, I’m not sure that was the right combination of activities, but nobody got hurt!
After the charter, some headed home, others to Montenegro again, and Cecilia and I to Spain and Portugal. Croatia delivered again for us, cementing its status as our favorite European charter destination. I hope you add it to your list if you haven’t already!