Two one-hour, lively, educational “I Used to be Somebody” sessions are included in the tour to make your trip complete. (Check with your tax advisor regarding the possibility of a tax deduction for this educational experience.)
Two one-hour, lively, educational “I Used to be Somebody” sessions are included in the tour to make your trip complete. (Check with your tax advisor regarding the possibility of a tax deduction for this educational experience.)This comprehensive Croatian vacation (limited to just 20) will have you visiting remarkable wineries, using local ingredients for our private cooking class focused on traditional cuisine, delighting in wine-paired meals and a vineyard picnic, relaxing by the sea, exploring several historic cities and towns, and basking in luxurious hotels each night.
Hand-Picked Experiences
- We’ll visit the best of Croatia, including walled cities and tiny villages — Split, Dubrovnik, Korčula, Hvar, Ston, Putnikovići, Smokvica, Čara, and more
- Tour and taste a wide variety of Croatian wineries (including boutique, family-owed) and enjoy wine-paired lunches and picnics
- Take a private cooking class to learn all about traditional Croatian cuisine
- Visit UNESCO sites and historic places
About Your Hosts

Carl and Diana are hosts of the popular I Used to be Somebody podcast and newsletter, inspiring 50+ professionals on how to build their (Un)Retirement good life. They are also co-authors of the Amazon best-seller Pickleball for Dummies.
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Croatia Wine & Food Tour Details
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- Tour Dates: April 26 – May 3, 2026
- Trip Price Per Person: $5,600
- Single Supplement: $900
- Guide: Local Guide
- Group Size: Limited to 20 people
- Meals: All meals except one lunch
- General Tour FAQs
Tour Itinerary
DAY 1:
Welcome to Croatia! We will meet you in the afternoon after lunch in the waterfront city of Split surrounded by the sparkling Adriatic Sea. After you check into the hotel we’ll come together as a group for introductions, getting to know fellow travelers who will be sharing this incredible journey. We will then head out for a walking tour of Split’s historic city center. We’ll discover the marvels of the 1,700-year-old Diocletian’s Palace, a UNESCO World Heritage site, and delve into the enchanting landmarks of the Old Town.
As the sun begins to set, we’ll head to one of our favorite local restaurants, a gem beloved by locals and visitors alike. Here, we’ll indulge in authentic Croatian cuisine, perhaps starting with freshly caught seafood, Dalmatian prosciutto, or a glass of crisp Pošip wine. We’ll celebrate the first evening of this unforgettable adventure surrounded by the charm and warmth that Croatia is known for. Cheers!
DAY 2:
After enjoying breakfast in the hotel at your leisure, we’ll head out for Marjan Hill. We’ll stroll through its serene paths to discover breathtaking viewpoints with panoramic vistas of the town and surrounding areas. You’ll see a 16th-century Jewish cemetery, charming medieval churches, and more. It’s the perfect blend of history, culture, and natural beauty. Those interested can walk up the hill to get some exercise rather than take the shuttle.
We’ll find a lunch spot where you can do lunch on your own. In the afternoon there is an archeological site we can explore, beaches to visit, or head back into central Split. Tonight, we dine at another local restaurant and spend the night in Split.
DAY 3:
After breakfast, we’ll check out of the hotel and depart via catamaran for the dreamy island of Hvar.
The day begins with a scenic drive to small family wineries along the northern shore of Hvar Island, with incredible views of the Adriatic. The first stop is Vrboska, often called “Little Venice” for its charming network of stone bridges and canals. Next is Jelsa, a quaint fishing town with a laid-back vibe. Then it’s on to Stari Grad, one of Europe’s oldest towns. We’ll also venture into the heart of the island with a drive through Pitve, a charming village with panoramic views of the island’s rolling hills; Vrisnik, where locals still press olive oil using traditional methods; and Vrbanj, the island’s largest village.
After we sip our way around, we’ll rest at lunch surrounded by vineyards, enjoying local Dalmatian dishes, wines, and olive oil.
We’ll check into our hotel in Hvar. A town whose streets are alive with energy, from the chatter of visitors and locals in open-air cafes and the sound of waves lapping at the marina’s edge. Before dinner, we’ll take a guided general climb to the Fortica Fortress, perched high above the town. The fortress offers unparalleled views of the Pakleni Islands and the shimmering Adriatic, a perfect spot for sunset photos.
We’ll conclude the day with a delicious dinner together.
DAY 4:
After breakfast, we will check out of our hotel, jump on a catamaran for Korčula Island and explore the old town. Korčula, also known as “Little Dubrovnik,” is a stunning medieval town known for its picturesque architecture, narrow streets, and rich history. The most famous sights are St. Mark’s Cathedral, Marco Polo house, and the town walls and towers.
Next, we check into our island hotel for free time to settle in, relax on the pebble beach, explore the lovely town, or grab a drink at a cobblestone cafe.
Later in the afternoon, you will have an option. One option is to jump on a bike and do a little bike tour of the area roads – a great way to see the island. The second is to drive to the village of Lumbarda, surrounded by sandy beaches and lush vineyards. Here, we visit local wineries and taste their finest creations while learning about Grk, a unique indigenous white wine variety. It has a fascinating history and distinct flavor, making it one of Croatia’s most treasured wines.
With full minds and happy bellies, we head back to the town of Korčula and spend the night.
DAY 5:
This morning, we have built in a bit of free time to allow you to explore the incredible streets of Korčula or perhaps relax by enjoying morning coffee by the water.
We’ll reconvene in the afternoon and head to a family agricultural estate in the island’s lush hinterland for a hands-on cooking class. Upon arrival, you’ll be treated with a warm welcome and refreshing local juices before rolling up your sleeves to make Žrnovski makaruni, a traditional hand-rolled pasta. As we cook, we’ll sip on exceptional local wines. A meal is not complete without dessert! We’ll finish off with a traditional Korčulan dessert cake, Lumblija.
Before returning to the hotel, we’ll stop at two family-run wineries in the idyllic villages of Smokvica and Čara. We’ll learn about the winemaking process and taste local varieties, including Pošip, a rich, bold white wine native to Korčula.
The day will conclude back in Korčula with another meal and a wonderful evening.
DAY 6:
We begin the day with a scenic boat transfer from Korčula Island to the Pelješac Peninsula, which is often called the “Napa Valley of Croatia” and stretches into the Adriatic Sea dotted with picturesque vineyards, rugged mountains, and charming coastal villages.
The day begins with a visit to the famous wineries of Pelješac, including the Grgić Winery, founded by the legendary Miljenko “Mike” Grgich. Known for his groundbreaking winemaking in Napa Valley, where his wines triumphed over French classics in 1976, Grgich brought his expertise back to Croatia to create exceptional wines like the celebrated Dingač. We’ll enjoy a tour of the winery and taste some of their finest vintages while soaking in breathtaking views of the Adriatic.
Afterward, we’ll dive deeper into the peninsula’s winemaking heritage with a stop at the Museum of Viticulture and Winemaking in the village of Putnikovići and showcases the artistry behind Pelješac’s iconic wines.
A must-see is the historic town of Ston, famed for its medieval architecture and ancient saltworks. We’ll visit the Solana Ston saltworks, one of Europe’s oldest and best-preserved saltworks, with a history spanning over 4,000 years. We’ll have a private tour, learn how this “white gold” shaped the region’s economy, and enjoy a walk among the salt pans. An optional hike along the Walls of Ston is a must for the adventurous. These medieval fortifications, stretching over 5 kilometers, are the longest in Europe.
The day will wrap up with a picturesque transfer to Dubrovnik, the “Pearl of the Adriatic,” where we’ll have a meal and settle in for an overnight stay, ready to explore this historic city the following day.
DAY 7:
Welcome to Dubrovnik! Step through the grand Pile Gate into a UNESCO World Heritage Site brimming with history, charm, breathtaking architecture, and Game of Thrones inspiration.
The morning will start with a guided walking tour of old town, including Rector’s Palace, Sponza Palace, and the elegant Church of St. Blaise, all showcasing the city’s rich blend of Gothic, Renaissance, and Baroque styles. We’ll also walk the city walls, one of Dubrovnik’s most famous features. These well-preserved medieval fortifications stretch nearly 2 kilometers and offer views of the Adriatic Sea, Lokrum Island, and the red-tiled rooftops of the Old Town.
In the afternoon you will have a choice. Those looking for exercise can do a three-hour to four-hike up Mt Srd, the hill that overlooks Dubrovnik. It is an easy path but steep up to the top. Alternatively, you will have a free afternoon for you to explore the alleyways of the old town, relax at a cliff bar with the local lemon beer, or pick up final souvenirs.
Tonight, we’ll share a final meal, open our favorite bottle of Croatian wine, and cheers to old friends, new friends and memories we shared!
“Croatia has been glorious – it’s so beautiful, and I want to go back as often as I can”
Tour Accommodations
The hotels below are subject to change based on availability. You will stay in a hotel that is equally nice or nicer.
Nights 1 & 2 > Hotel Marvie > Split
A modern hotel with a pool and spacious rooms overlooking the sea. The Hotel Marvie is located right outside Old Town and offers an excellent location for sightseeing, with easy access to the local port and coastline.
Night 3 > Amfora Hvar Grand Beach Resort > Hvar
Tucked away in a tranquil bay, surrounded by a lush pine grove, and only a short ten-minute walk from the historic and charming city of Hvar. This 4-star resort is the perfect getaway after a wonderful day of exploring.
Nights 4 & 5 > Aminess Younique Liburna > Korčula
Aminess Younique Liburna Hotel occupies a small peninsula on the southeastern edge of Korčula town, about a 5-minute walk from the old city. The secluded location guarantees perfect peace and relaxation
Nights 6 & 7 > Hotel Ivka > Dubrovnik
Hotel Ivka is located just outside the Old City. It’s a wonderful, small, family-owned hotel situated on the Lapad peninsula. It’s a charming place in a great location and a perfect way to finish our trip.
What is Included
- All local ground transportation
- Double occupancy lodging
- All meals expect one lunch
- One complimentary drink per meal
- All scheduled activities
- Wine during organized tastings and most meals
- Professional tour guide
Not Included: Travel to and from destination/meeting point, personal expenses, and optional gratuities to your guide and drivers. Travel insurance is also not included, though we highly recommend it. Check out our Travel Insurance page for more information.
While the general trip itinerary will remain the same, the actual restaurants, hotels, and activities listed are subject to modifications. Changes that are out of our control are common — restaurants close or lose their amazing chef, a winery changes their visiting hours, a hotel gets remodeled, etc. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance.
Arrival & Departure
We meet you just after lunch on the first day of the trip in the city of Split, Croatia, at a designated meeting point in the town of Split. Our trip ends on the morning of the last day in the city of Dubrovnik.
You should make your flight to arrive in Split (airport code SPU) and depart from Dubrovnik (airport code DBV).

