Perfect Three-Week Italy Vacation: Southern Italy & Sicily

The lively city of Bari encapsulates the marvels of Italy’s southern region of Puglia with lavish architecture, colorful fishing boats, and grand boulevards that bring traditions to modern life. Bari is a shining example of Southern Italy’s lavish past and contemporary vibrancy overlooks the shimmering turquoise waters of the Adriatic Sea. The scent of grilled calamari and shrimp topped with salt and a squeeze of lemon citrus drifts down the cobbled lanes, and you will immediately feel welcomed and comfortable.

Your flight will land at Karol Wojtyla Airport, where your private transfer will greet you upon arrival. Your two nights in the fascinating city will begin with settling into the comforts of your luxury hotel. You can step out and explore the charms of the captivating streets as fresh fish are brought into the marina by active fishers alongside the stunning Norman design of the Basilica di San Nicola. The structure was erected in the 12th century as a place to house the relics of Saint Nicolas, also known as Santa Clause, which were stolen from Turkey in the 11th century. The interior bursts with the scent of myrrh, which is said to emanate from the remains of the saint and contain special powers. The wooden ceiling glints with gilded details added in the 7th century, for a lot of beauty to take in.

Outside of Bari, your private driver will lead you around the marvelous Pugliese countryside to visit the Castle del Monte, a dramatic depiction of 13th-century medieval architecture with Gothic cornice towers, Romanic lines, and a unique octagonal design. The mysterious project utilized the number eight to create dynamic symmetries during the winter solstice and summer equinox accentuated by the limestone and quartz façade. The interior retains counter-clockwise staircases rising to the top of the towers, as well as broken pieces of marble and mosaic once decorating the grand halls.

Visiting a local olive orchard outside of Bari will introduce you to the fantastic flavors and specific, treasured production of olive oils in the region that accounts for approximately 40% of Italy’s olive production. The dry soil and shading leaves provide herbaceous aromas as you explore the variety of olives around the orchard, which possess different depths of flavors. The orchard retains their heavy plates from which they produced olive oil before mechanization, offering you a demonstration on how they would stuff the olives between the stacked plates and press down, harvesting the oil running down the sides. In the tasting room, your guide can explain the differences between the levels of oils, the best-known of which consists of “extra virgin.” You can sample the olive oil and find peppery notes with a slight bitterness stemming from the natural antioxidants.

Before reaching the town of Lecce the next morning, you can wander the incredible depths of Grotte di Castellana, the longest network of caves in Italy. The staggering stalactite and stalagmite formations create unique images scattered across the 9,842-foot long subterranean system. The deepest cavern known as La Grave contains a natural skylight that provides a ribbon of visible sky to create a majestic glistening effect. Walking through the network of caves, you will notice the temperature drop to a consistent 64 degrees Fahrenheit.

The city of Lecce will capture your imagination as you wander through the regal streets dating back to the 17th century. The scent of almonds flour and espresso will drift out of the pasticcerie as you explore the city with your guide and visit the remarkable architecture and artistry beginning with the Basilica di Santa Croce. The stonemasonry offers a lavish representation of history with the facade adorned with allegorical images, sheep, dodos, cherubs, and beasts. The interior has a more conventional Baroque design accentuated by hints of frankincense and myrrh.

Using the Baroque city of Lecce as a base for exploring the surrounding splendor of Puglia, you will find comfort in the fairytale charms of Alberobello. The cobbled lanes wind along the rolling hills and resemble a settlement for gnomes with approximately 1,500 beehive-shaped houses shaped by whitewashed walls and conical roofs made from pebbles or slim bricks. The traditional limestone homes date back to the 14th century, and from a distance resemble a hilltop village dusted with snow-cover. However, the warm Mediterranean sunlight of Southern Italy keeps the snow far from town where you can enjoy the panoramic view from Belvedere Trulli, which offers a picturesque image of Alberobello and distinctive rooftops of the trulli homes.

The coastline of Italy’s heel will become one of your favorite views at Otranto, a seaside city that overlooks the Adriatic and the Ionian seas. The crystal-clear azure waters contrast with the whitewashed walls of the historical buildings and cobbled lanes. The life of the city emanates from the charming cafes and charming restaurants that overlook the water and lead to the popular powdery white sands of Alimini Beach before fading into the crystalline turquoise and green sea.

The city of Matera symbolizes the captivating history and unique perseverance of the region during centuries of struggle. This is captured best in the cave dwellings known as sassi. Grottos cut into the walls of the gorge date back 7,000 years, while the city topping the summit above the ravine contains dramatic medieval architecture that emanates from the central 13th-century Romanesque Cathedral. The distinctive history of the city comes from the cave-dwellings that were utilized as homes and shops in the town up until the mid-20th century and account for the Sotterranea, the Underground City.

The ancient settlement is carved into the calcareous rock along the edges of the gorge. You can see into the abandoned caves where families once lived while also finding renovated caves from innovative locals who have utilized the historical space for luxury restaurants, hotels, and boutique shops. Cas Noha demonstrates life for the Noha family during their time in the home with the main gallery emulating the place where people once slept, ate, and kept their animals.

With another night in the Basilicata region, you can explore beyond the caves of Matera to visit the often-overlooked ancient history at Metaponto and soothing waters in the thermal springs of Latronico. Visiting the town of Potenza defines the classic ambiance of the region within its capital city as well as the distinctive architecture defined by the altitude, accounting for the highest town in Basilicata at 8,815 feet above sea level.

The old center crowns the top of the hill with winding cobbled lanes and a series of stunning buildings that date back to the 12th-century, with many rebuilt during the 18th century after a series of earthquakes. Boutique shops and quiet cafes open their doors to the streets absent of cars but filled with foot traffic. The ancient city gates run along the former ports of entry at Porta Santa Luca and Porta Santo Giovanni to shape the edges of the antique city and offer archeologists a sense of where the old walls once stood.

The gorgeous town of Tropea rises above the Tyrrhenian Sea approximately 230 feet on a natural terrace. The historical walls remain standing while the antique towers and gates provide a tempting romantic ambiance set against the backdrop of the sparkling blue waters. The medieval center perches on the cliffs with gray stone to contrast with the elegant white sands that spread across the shoreline. The sunlight washes over the water and glints against the shores where locals and visitors relax on comfortable lounge chairs beneath colorful umbrellas. The winding lanes of old town create an enticing maze lined with crumbling facades and lavishly preserved baroque designs leading to the headland, where you can bask in the marvelous view of the large rocky outcrop jutting out into the sea.

With another night in Tropea, you can dive deep into the beauty around Calabria by visiting traditional seaside towns like Pizzo. The majestic architecture rises atop a sea cliff and beckons to visitors from around Italy with the sweet dessert known as tartufo, a type of chocolate bon-bon stuffed with ice cream. The Piazza della Repubblica opens at the heart of the city and looks out onto the stunning waters of the Tyrrhenian Sea. Nearby, the Chiesetta di Piedigrotta stands outside of town on the road that winds down the coastline, carved into a seaside cliff with statues resembling stalagmites that date back to the 17th century. The narrow lanes of the historical city capture the essence of daily Calabrian life, boasting lively music, jovial locals, and delicious aromas emanating from the plethora of restaurants and celebrated gelaterie.

On the way to Reggio Calabria, you will pass the town of Scilla, known for its cream, ochre, and earthy houses that decorate a jagged promontory at the edge of the Tyrrhenian Sea. A dramatic castle crowns the hillside above the whitewashed walls of the Maria Immacolata church. Nearby, the fishing district shines with colorful boats and a welcoming jovial ambiance spreading to the boutique hotels and coastal restaurants where you can hear the water lapping against the sand. You will reach Reggio Calabria with your private transfer and settle into the luxuries of your hotel that overlook the movement on the Strait of Messina.

The city has an eclectic mixture of architectural aesthetic that represents the resurrection of the local spirit after a massive earthquake and giant tsunami in the early 20th century. From the esplanade along the Strait, you can have a sensational view to Mount Etna’s fuming peak in the distance. The most notable attraction in the city, apart from the beautiful beaches, is the Museo Archeologico Nazionale di Reggio Calabria. The collection displays the history of the region back to the Neolithic and Paleolithic times, as well as a breathtaking collection of artifacts from the Hellenistic period. Your guide will lead you through the gallery and introduce you to the Riace Bronzes, a pair of bronze statues standing over six feet tall depicting 5th-century BC bearded warriors.

The gorgeous town of Taormina stands on the rocky terrace above the Ionian Sea and embraces the best views across Sicily, including a sensational panorama of the smoldering summit of Mount Etna. The charming townscape has cobblestone streets lined with elegant stacked buildings that open to marvelous terraced-views. Byzantine rock-graves populate the outskirts of town and the cafes along Piazza Vittorio Emanuele bring the scent of orange citrus and freshly baked pastries.

Culture abounds in the celebrated sea-cliff town emanating from the Teatro Greco. The fabled Greek theater dates back to the 3rd century BC and was renovated a century later during the Roman occupation. The remarkable design utilized the natural grading of the mountainside to create the stadium seating for a 358-foot wide diameter. From the top row of the theater, you can bask in the panoramic view that sweeps across the countryside and is crowned by Mount Etna in the background with the preserved Doric columns in the foreground.

With four nights in Taormina, you can explore the captivating countryside and legendary beaches along Sicily’s east coast. Take time to visit the slopes of Mount Etna and even traverse the captivating craters that adorn the mountain’s summit. The protected landscape of Mount Etna National Park encompasses 193 square miles with more than 20 towns emerging from dense woods, snow-topped mountains, and deserts of glinting black lava rock. Venture to the summit at Silvestri Craters near Rifugio Sapienza reaching 6,233 feet above sea level and the fumaroles puff with smoke as you trek around the barren high-altitude landscape.

Visiting a vineyard on the slopes of the mountain will reveal the fabulous flavors of the mineral-rich volcanic soils. The winery grows thriving varietals such as Nero d’Avola, Syrah, and Cabernet Sauvignon. In the tasting room, your guide can offer information on the history of the vineyard, as well as the wines grown across Sicily. You can sample the favored wine made with the Nero d’Avola grape and resulting in aromas of black cherry and white pepper with a medium body that pairs perfectly with gamy meats and rich dishes like osso bucco.

The captivating culture of Sicily will emerge during your three nights spent in Syracuse where you can discover the fascinating history of one of Italy’s oldest cities. You can also explore the impressive preserved architecture of Magna Graecia, the coastal area colonized by Greek city-states between the 8th to the 5th centuries BC. The ancient city of Agrigento embodies Greek life and devotion in the ruins at the Valley of the Temples, a five-square-mile archeological park. Follow your guide to the enchanting columns of the Tempio della Concordia, which was constructed in the 5th century BC. The Doric design represents the best-preserved style of architecture in Sicily spanning 129.3 square feet by 55.5 feet and standing nearly 30 feet tall. The massive Doric structure acts as a reminder of the dramatic designs and remarkable feats of architectural engineering of the ancient world.

The city of Syracuse shimmers with gold against a backdrop of turquoise water. The ancient and contemporary ambiance stems from over 2,000 years of occupation dating back to the eighth century BC and growing larger than Athens and Corinth at its peak. Baroque piazzas create dazzling effects that lead to medieval lanes doused in honey-colored stone. The Greek theater in the Neapolis Archeological Park was built in 470 BC becoming one of the largest theaters of the ancient Greek world with 61 rows and a diameter of 452 feet. Peel back the layers of the city to find the ancient Miqwe located 65 feet below Alla Giudecca hotel. The ritual Jewish bath is considered the oldest in Europe and connected an old synagogue built in the 15th century AD. Three deep pools with fresh water once allowed members of the community to totally immerse themselves for ritual cleansing.

After breakfast, your private transfer will greet you in your hotel lobby and escort you Catania. The fish market brims with activity throughout the day as vendors offer glimpses of freshly caught marlin, mussels, octopus, as well as delicate sea urchin. You will have time to explore the Baroque architecture and welcoming atmosphere before continuing to Catania-Fontanarossa Airport for your flight home.