With Karen’s Travel LLC
May 29 – June 8, 2026
Wonderful small-group tour of Calabria at an easy pace! This fabulous itinerary is for travelers who want to have a great time visiting castles and villages, enjoying spectacular vistas, and dining on exquisite local cuisine paired with excellent Calabrian wines. Join Karen Haid, award-winning author of Calabria: The Other Italy, on this exclusive tour of a beautiful Southern Italian region!
Castles and Wines of Calabria Tour Itinerary
11-day land tour
Day 1 – Arrival Lamezia Terme – Scilla – Strait of Messina
Transfer from the international airport or train station in Lamezia Terme to our costal accommodation. On our drive south, will make a stop in Scilla, a picturesque village named for the sea monster of Homer’s Odyssey. Today, Ruffo castle sits atop the legendary promontory, domicile of said creature and destroyer of ships traversing the Straits. Just a few kilometers further and we will arrive at to our lovely 18th-century castle property with modern, luxury hotel accommodations that offer a breathtaking panorama of the Strait of Messina. Recuperate from your journey with a walk in the garden or a dip in the pool before our first dinner and overnight.
Day 2 – Reggio Calabria
Our exploration of ancient wonders begins at Reggio’s National Archeological Museum, home to the famous Riace Bronzes, 2,500-year-old statues unique in the world. The city’s waterfront is considered one of the loveliest in Italy – stroll at your own pace along the sea or the elegant pedestrian-only shopping street. Following lunch in the city center, we will enjoy a private, open-air bus tour, where we’ll view Reggio’s Aragon castle, amongst other architectural gems. 
Day 3 – Gallicianò and Palizzi Marina
Our excursion takes us to Gallicianò in the Aspromonte Mountains, where the inhabitants still speak the ancient Greek language of their ancestors. We will visit the village and enjoy a hearty, rustic lunch of local products. In the afternoon, we continue to the southernmost point of the Italian peninsula for a wine tasting at a winery dedicated to indigenous grapes – ancient roots with a modern vision.
Day 4 – Fiumefreddo Bruzio
We check out and drive north along the Tyrrhenian Sea, Calabria’s dramatic western coastline. Along the way, we visit Fiumefreddo Bruzio, one of the Borghi più belli d’Italia (Italy’s Most Beautiful Villages), for a typical lunch and tour of the historic center, highlighted by romantic castle ruins and unexpected contemporary art. We continue our scenic drive, turning inland to our tranquil accommodations, a castle-hotel in the heart of the Calabrian countryside. 
Day 5 – Pollino Foothills
Luxuriate in a relaxing day on the estate, exploring the 16th-century castle and its 21st-century agricultural enterprise, both out on the farm and dining in the castle restaurant, savoring a cuisine “a chilometro zero,” literally, farm-to-table.
Day 6 – San Nicola Arcella and Santa Maria del Cedro
A morning drive through the Pollino Mountains brings us to the northwest coast of Calabria where we will have the opportunity to circumnavigate Dino Island on a boat ride that features azure water, grottos, a majestic natural arch known as Arco Magno, and a coastal tower named for the American writer Francis Marion Crawford. Our beach-side lunch will feature local seafood, and as we’re spending the day on Calabria’s Citron Riviera, we will visit the Citron Museum in Santa Maria del Cedro to learn all about this special citrus fruit. 
Day 7 – Sybaris and Rocca Imperiale
Today, we visit two monumental locations, ancient and medieval. Lost for thousands of years, Sybaris, the Greek city-state renowned for the self-indulgent behavior of its inhabitants that gave rise to the word “sybaritic,” can now be explored through its fascinating archeological park and museum. In contrast, Rocca Imperiale has stood like an “imperial stronghold” from the time of Holy Roman Emperor Frederick II, who built the castle, Calabria’s largest, on the top of a hill overlooking the sea. The medieval village, one of Italy’s più belli, gracefully unfolds along the slope and is known for its special variety of lemons.
Day 8 – Corigliano Calabro and Cirò
We check out and depart for Calabria’s east coast. Our first stop as we drive south along the Ionian Sea will be the magnificent ducal castle in Corigliano Calabro, an Italian national monument for almost 100 years! We will learn its history as we admire the beautifully restored interior. In the afternoon, we will visit a Cirò winery and discover the merits of Calabria’s best-known wine region that received DOC status in 1969. We will then continue down the coast to our beachfront accommodations in the Province of Crotone.
Castle ballroom in Corigliano Calabro
Day 9 – Crotone
Today, we will explore modern Crotone, a city that has been favored with excellent wine from before the time of Pythagoras, their most famous citizen! On our tour of the old town, we will visit its bustling food market, its imposing castle and small archeological museum, full of precious artifacts, perhaps once held by the important philosopher himself…
Day 10 – Le Castella
A morning of leisure at our beachside hotel, walk the red-sand beach, take a dip in the sea or lounge under an umbrella by the pool. We will raise our glasses throughout the day, toasting our time together, savoring our final meals and experiences. The spectacular image of the imposing Aragon Castle of Le Castella surrounded by the sparkling waters of the Ionian Sea will crown our journey, full of exquisite moments, from the gorgeous landscapes immersed in history to the warm, calabrese people with their exquisite culinary traditions.
Day 11 – After breakfast, we will depart for Lamezia Terme, the airport and train station, and say a final arrivederci to Calabria.
Karen’s Travel LLC
Castles and Wines of Calabria Tour basics:
$5,000 USD per person double occupancy, $500 single supplement
Comprehensive Small Group-Tour accompanied by Karen Haid, author of Calabria: The Other Italy, together with local guides
Maximum 15 participants
7 nights at select castle properties, 3 nights at 4* beach hotel
All meals, Calabrian wine/water included with lunch and dinner, 3 wine tastings
All excursions and tours, surface transportation and airport transfers as outlined on the itinerary
See many photos and description of a past tour on my post Castles and Wines of Calabria Tour, Inaugural Journey and my short Castles & Wines of Calabria Tour Video. To sign up for the Castles and Wines of Calabria Tour or for more information, please use the Contact Page – looking forward to hearing from you and welcoming you to Calabria!
Check out the detailed itineraries for my other programs on these links:
Calabria Cultural Tour
Traditions and Food of Calabria Tour
And don’t forget Calabria’s northern neighbor with the Basilicata Cultural Tour!