Explore Southern Dalmatia: From Split to Dubrovnik - 9 Days

Day 1: Arrive in Split, Explore

From the airport, it's a short (45-minute) drive to the center of Split. Depending on your arrival time, check into your hotel and settle into your accommodation before taking the rest of the afternoon to explore the ancient port city on your own.

Start at Pjaca Square for pretty views of white marble tiles, the Iron Gate (the western entrance to Diocletian's Palace), a Romanesque clock tower with the remains of a medieval sundial, and the 15th-century Town Hall. Stop for lunch at Trattoria Bajamont, just north of the Iron Gate. From there, visit the popular Voćni trg or Fruit Square—a square that got its name from centuries of selling fruit. Here you can enjoy Renaissance architecture influenced during Split's Venetian era. For a bit of shopping and a bite to eat, head to Marmont Street, though you'll want to make your way to the waterfront to catch the sunset.

In the evening, take a stroll along Split's seafront Riva to admire the views over the Adriatic before finding the off-beat Konoba Dioklecijan restaurant, just to the left of the Bronze Gate for a bite to eat, its outdoor terrace built into the walls of famed Diocletian's Palace.

Day 2: Hinterland Cycling Tour & Picnic Lunch

Today is reserved for a memorable cycling tour of the Dalmatian hinterland beyond Split. You'll meet your guide in the morning and set out to explore the rugged and wild terrain, taking in the beautiful views of the zagora as you pedal along ancient routes of this delightfully unpopulated area. You'll follow the shores of Peruča Lake and through the River Cetina Canyon to a breathtaking spring in Milasevo, the source of the Cetina River. The region is rich with archaeological finds from antiquity up to the Middle Ages, providing insight into Croatia's fascinating past.

After a full morning ride, you'll have time to enjoy a picnic lunch in peaceful environs before returning to Split in the afternoon.

Day 3: Speedboat to Hvar, Private Boat Tour of Blue Cave & Stiniva Bay

No visit to the Dalmatian coast would be complete without some quality time on the Adriatic Sea. With that said, you'll meet your skipper this morning to board your private motorboat to discover the islands of Biševo and Vis. First, you'll cruise to the east coast of Biševo Island, a popular, though often crowded, destination, to see the mesmerizing iridescent blue waters of the Modra Špilja (Blue Cave). Upon landing on the island, you'll transfer to a cave-friendly boat before floating inside the cave to discover the natural phenomena for yourself.

From Biševo, you will then cruise to nearby Vis Island, stopping to explore the hidden coves and beaches as you choose. One such beach lies on the southern coast, the stunning pebble beach of Stiniva Bay. Obscured by towering cliffs, the hidden-away beach offers excellent crystalline waters for swimming and snorkeling as well as shade for a respite from the mid-morning sun. And when it's time to eat, your skipper will direct you to a nice restaurant for lunch.

Next, you'll continue to Hvar Island, often considered to be one of the most beautiful islands in the world due to its countless days of sun and picturesque landscapes dotted with medieval stone villages set amid lavender fields, vineyards, and olive groves. Upon arriving at Stari Grad in the late afternoon, you'll debark to check into your hotel before taking the rest of the day to explore the former Greek colony, Croatia's oldest town.

Wander the narrow network of streets lined with gray stone buildings accented by colorful window boxes as you find your way to Tvrdalj. The summer residence of the 16th-century poet Peter Hektorović, Tvrdalj, is a perfect place to take an evening stroll through its lovely Renaissance garden. Join a tour of the castle followed by a contemplative visit to the turquoise fish pond and then set out for Antika to dine on squid risotto and kotlenka varbanj—a traditional Hvar seafood-type stew.

Day 4: Sea Kayaking Around Pakleni Islands

In the morning, you'll transfer the 30 minutes to the beachfront of Hvar Town for your guided kayak and snorkel trip to the Pakleni Islands. The islands are the most beautiful part of the Hvar Riviera and are a favorite retreat for locals seeking to escape the summer heat. Altogether, there are 14 wooded and rocky islets indented with hidden coves and inviting beaches, which you will get a chance to explore by kayak.

The name "Pakleni" originates from the tar-like resin that was once collected from the pine trees that blanket the islands and used in shipbuilding. Paddle and find your ideal swimming spot or find shade under the green pines. The serene beauty of these islands is intoxicating and only a stone's throw away from the hustle and bustle of Hvar Town. Though upon your return, you might like to visit a couple of the key sites, like St. Stephen's Cathedral, or climb the steps to the terrace outside of the historic Arsenal to enjoy views over the harbor and the surrounding area before returning to Stari Grad.

Day 5: Free Day on Hvar

Today, you have free range to explore Hvar at your own pace. A great way to discover much of the island is to rent a scooter in Hvar Town and drive along the coastline through olive groves, lavender fields, and vineyards, stopping along the way to lie out on a beach you happen upon. In the afternoon, switch gears and join a half-day wine tour to sample some of the region's best wines as well as learn about its 2,400-year-old history. In the early evening, bring a bottle of wine and head to Tito's Caves, just north of Stari Grad, for a picnic as you watch the sunset from these hidden-away caves.

The more athletically inclined might prefer an early morning start to trek up to the 16th-century Španjola Fortress for views over Hvar Town and the Pakleni Islands, followed by a cycling tour around Hvar to explore the inner part of the island. Alternatively, another great option is to embark on a hike from Hvar Town to visit Velo Grablje, a near-deserted 500-year-old town, and Malo Grablje, a nice hike that takes you down a canyon into the village. Here you can stop for lunch to enjoy a delicious meal at perhaps the most authentic of the island's taverns. 

One last option is to explore the nearby Pakleni Islands. You can rent a private taxi boat to tour around the islands for the day, where you might consider taking a 15-minute water taxi to Jerolim and Stipnska or continue on to other islands farther out to walk around and explore. For the more adventurous, there is the option to go on a guided full-day or half-day sailing or kayaking tour of the islands—a great way to discover the many secluded beaches and lagoons!

Day 6: Ferry to Split, Transfer to Dubrovnik via Trsteno

Get an early start this morning to ferry back to Split and continue your journey along the coast into southern Dalmatia and to Dubrovnik. En route, you'll stop in the small settlement of Trsteno just 15 miles (24 km) outside the medieval city. Famous for its arboretum, you'll have the opportunity to explore the centuries-old grounds as well as visit the 15th-century summer residence of the Gozze family responsible for erecting the botanical garden.

When you're ready, continue the drive along the coast to the historic coastal fortress city of Dubrovnik. The early evening will be at your leisure, allowing time for you to wander and explore the "Pearl of the Adriatic."

After checking into your hotel, you'll want to get out and explore. Can't-miss activities include riding the cable car up to Srđ Mountain to take in the sunset over the nearby Elafiti Islands, visiting Lovrijenac and Bokar fortresses, and walking along the smooth, limestone-paved streets of historic Old Town. And be sure to find your way to Stradun, Dubrovnik's main street, to get your bearings and to choose from a number of excellent restaurants and wine bars. Alternatively, there's Buza Bar along the water's edge and outside the city walls—another great spot to enjoy a cocktail while taking in the sunset.

Ferry time (Hvar Town to Split): 1 hour
Driving time (Split to Trsteno): 3 hours
Driving time (Trsteno to Dubrovnik): 30 minutes

Day 7: Wine Tour of the Pelješac Peninsula

Spend a luxurious full day discovering the art of winemaking as you visit some of Croatia's most respected vintners and their wineries on a private tour hosted by renowned winemaker, Mario Bartulović. Your first experience takes you to Miloš Winery in Boljenovići on the ruggedly beautiful Pelješac peninsula. Home of the charismatic poet and winemaker Frano Miloš, you'll spend time tasting varietals made of the Plavac Mali (red) grape, like the legendary Stagnum, in addition to enjoying a comprehensive explanation of the winemaking process.

Next, you'll make your way to the small village of Trstenik to sample some of Croatia's top-awarded wines at the Grgić winery. Miljenko Grgić (or Mike Grgich) studied wine-making in Zagreb, and after his success in founding the famous Grgich Hills winery in Napa Valley, he then established Grgić Vina in 1996 together with his daughter and nephew. Taste their famous white Pošip and their red Plavac Mali Dingač as you take in the dramatic views that overlook the charming Trstenik harbor.

If there's interest, you can take a break from wine and board a quick ferry (20 minutes) from Orebić to Korčula Town on the neighboring island of Korčula. Here you can spend a few hours roaming the maze of Korčula's gray stone houses, alleys, churches, and squares. You may wish to consider finding your way to St. Mark's Cathedral to admire its strange sculptures of beasts and people, as well as visit the unremarkable house thought to be the birthplace of Marco Polo.

Upon returning to the Pelješac peninsula, you'll make your way to the 500-year-old wine cellar of your guide's family for your final wine tasting, followed by a traditionally prepared meal using locally sourced ingredients and the peka, a bell-shaped lid that is covered in coal. With full bellies and warm memories, you'll transfer to your hotel in Dubrovnik.

Driving time (Dubrovnik to Boljenovići): 1 hour, 15 minutes
Driving time ( Boljenovići to Trstenik): 30 minutes
Driving time (Trstenik to Orebić): 30 minutes
Driving time (Orebić to Dubrovnik): 2 hours

Day 8: Explore Dubrovnik, the "Pearl of the Adriatic"

Spend the day as you like, exploring this ancient medieval city. Get up early to take advantage of all that Dubrovnik has to offer, starting with a visit to the quaint, open-air Gundulić Square Market for authentic Dubrovnik wares, like dried lavender, local brandies, and dried fruits. From there, take a stroll through the narrow streets of Old Town, walk atop the encircling city walls, or head to the Lovrijenac fortress and Orlando Column.

Be sure to break up your walk by sampling the local cuisine. Dubrovnik's location on the border with Bosnia and Herzegovina and Montenegro means there is some unique fusion cuisine here as well as downright wild fast food options (think octopus burgers). But you can also find good-old Italian-inspired comfort food like pasta in meat sauce, black risotto, and basic but hearty meat-and-potatoes dishes.

In the afternoon, head to Banje Beach for a swim and some relaxation on the sandy stretch of beach close to Old Town. There's also the option to join a kayak excursion to the islands facing the city. A great way to end the day is to catch the sunset from the water on a sunset dinner cruise (2.5 hours) on a replica of a traditional karaka ship or from your own private boat. Enjoy the view of Old Town from this vantage point.

Day 9: Depart Dubrovnik

Depending on when you depart, you may have time to visit one of Dubrovnik's museums, like the Franciscan Monastery and Museum. This large complex houses many treasures, including the world's third-oldest pharmacy dating from 1317.

Alternatively, for a collection of 15,000 pieces of interesting works, visit the Rector's Palace and Cultural Historical Museum. Wander this well-preserved palace-turned-museum and explore its exhibits, some detailing life in the Republic of Ragusa during medieval times.

The drive to the airport from Dubrovnik takes around 45 minutes with normal traffic.

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