Exclusive Southern Italy Vacation: Sorrento, Matera, Ostuni

A 12 day trip to Italy 
5 out of 5 stars
7 reviews

Embrace the soul of Italy found in history, culture, and cuisine on your custom-tailored Italy that will take you away from the beaten path to explore rugged coastlines, pristine beaches, historical towns, and archeological treasures. Stretch your legs along the Amalfi Coast and expand your understanding of ancient heritage found along the peninsula dating back to the Greeks. Uncover brilliant Baroque architecture and charming fairytale homes, the splendor of Capri and the charm of contemporary caves. The distinctive spirit of Southern Italy takes you from the Tyrrhenian Sea to the Adriatic on an immersive scenic tour of villages, customs, and scenery.

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Most tours are customized for private travel.

General Information

Detailed Itinerary

Places Visited 

Sorrento, Capri, Herculaneum, Mount Vesuvius, Paestum, Matera, Ostuni, Bari, Polignano a Mare, Monopoli, Alberobello, Lecce, Castelmezzano

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Sorrento – Arrive in Naples and Transfer to Sorrento at Leisure

Sorrento is the perfect western gateway to the Amalfi Coast attracting 19th-century poets and authors like Lord Byron and Goethe, Dickens, and Tolstoy to enjoy the natural beauty that spans the Bay of Naples. The cobbled lanes wind along the glistening shore leading alongside palatial hotels and a network of boutique shops. The scent of the sea air fades beneath the ever-present aroma of lemons. Your flight arrives at Naples International Airport, where your private transfer greets you. Travel outside of the bustling southern city and around the bay passing the infamous peak of Mount Vesuvius. The grandeur of Sorrento is understated nestled between the staggering bordering cliffs reaching 180 feet above sea level.

The relaxed ambiance spreads across the beaches and former noble houses, as well as through the heart of the historical city center leading to Piazza Tasso. After settling into the comforts of your luxury hotel overlooking the charming waters lapping at Marina Grande, the remainder of the day is yours to bask in the welcoming charms of the city. The Basilica di Sant’Antonio has a dramatic exterior reminiscent of a brutalist office building, but the interior paints a more ethereal picture with uncovered Roman artifacts and medieval paintings reflecting dark themes. The gilded ceiling glints in the soft light embodying the extravagance of the Baroque design.  

What’s Included: airport transfer, accommodation

Day 2: Sorrento – Intrigue at Herculaneum and Mt.  Vesuvius

At breakfast, the scent of lemon permeates the dining room of your hotel at breakfast accompanied by the aroma of freshly brewed espresso and delicious pastries like rococo, which is made from almonds. Your private driver leads you around the bay once more to dive deep into the history of the region beginning at Herculaneum. The marvelous city has stepped out from Pompeii’s shadow as a unique destination of its own revealing captivating treasures from the Roman settlement preserved in the shell of magma and mud formed during Mount Vesuvius’s eruption in 79 AD.

After reemerging from the past by stepping outside of Herculaneum, you can venture to the slopes of Mount Vesuvius, the perpetrator in the destruction of the two ancient cities. The mountain is the only active volcano remaining on mainland Europe with 2019 marking the 75th anniversary of its most recent eruption. A gradual walkway leads to the summit at 4,202 feet above sea level. The panorama overtakes the entire Bay of Naples looking back toward the chaotic beauty of the eponymous city. You also have a view into the caldera dipping 1,000 feet into the mountain with a diameter of 2,000 feet. Puffs of smoke seep through the active fumaroles like a reminder of what took place two millennia ago.

For dinner, you can venture to the anticipated flavors of Caracol, one of the restaurants awarded a Michelin Star for 2019.  The restaurant overlooks the pristine water on the Tyrrhenian Sea nestled between tufa rock and in view of the Phlegrean Fields. Chef Angelo Carannante leads the kitchen’s mission in following the Mediterranean culinary traditions concentrating on the explosive flavors of each ingredient while also elevating the contemporary presentation. Many of the dishes change based upon the season with the tasting menu always reflecting the freshest ingredients sourced locally resulting in mouthwatering flavors.

What’s Included: accommodation, tour, breakfast

Day 3: Sorrento – Traverse the Splendor and Culture along the Amalfi Coast

The morning returns with the panorama sweeping across the grandeur of the seaside.  You will revel in the beauty of the water, the colorful homes, and in the returning bustle to the city streets seen from the window of your hotel dining room. Your driver will greet you in the hotel lobby after breakfast eager to lead you along the famous 25-mile stretch of road known as the Amalfi Coast. The narrow thoroughfare winds along the promontories and steep cliffs wedged against the Tyrrhenian Sea linking Positano in the west to Vietri sul Mare in the east. The drive blends the scenery of colorful coastal homes and towns climbing the ridges amidst lemon groves and winding streets with the terrifying view down steep cliffside plunging into the water.

The town of Conca dei Marini displays the charm of the Amalfi Coast without the crowds that pour through Positano or Amalfi. The shoreline has soft, quiet beaches embracing the romantic ambiance and lead to a maze of narrow lanes weaving into the pockets of the mountainside where pastel tower homes and cottages glint in the sunlight. The neighboring town of Priano is decorated with majolica tiles along the votive shrines. The town derives from a history of Greek settlements and the tower soaring above the coastline once defended the citizens from Saracen pirates during the reign of the Amalfi Republic.  

What's Included: accommodation, tour, breakfast

Day 4: Sorrento – Beauty with a Full Day on the Charismatic Island of Capri

After breakfast, you will set sail on the ferry bound for the idyllic island of Capri. In the distance, you will notice the cliffs of the island rising above the water and reaching nearly 200 feet above sea level. The gorgeous landscape acted as a background to the film It All Started in Naples, the last movie starring Clark Gable released during his lifetime. Sofia Loren co-starred as Gable’s formidable love-interest. With 2019 marking Loren’s 85th birthday, a visit to Capri brings a new perspective to the pristine landscape and unfettered charisma of the island captured in the film nominated for an Academy Award for art direction.

Ceramic plaques quoting philosophers who have visited the island over time decorate the three pathways winding through Capri Philosophical Park located at the end of the Migliera trail. The ilsand’s legendary beauty has inspired Hollywood stars like Clark Gable and Sofia Loren, as well as ancient aristocracy like Emperor Augustus. A leaf terrace near San Giacomo hosts a delicate fragrance of blossoming flowers amid a grand pergola framing the image of the Faraglioni sea stacks emerging from the elegant water.

What’s Included: accommodation, tour, breakfast

Day 5: Sorrento – Uncover Ancient History at Paestum before a Cooking Class

The region of Calabria has a remarkable history often depicted along the streets and villas of Pompeii.  However, the well of heritage runs much deeper than ancient Rome personified in the enchanting Greek temples of Paestum. The famous archeological zone contains some of three of the world’s best-preserved ancient Greek temples, as well as frescoes and ceramics dating back millennia. Greek settlers created the collection of religious sites in the 6th century BC in honor of Poseidon before the settlement fell to Rome in the 3rd century BC.

After visiting the history of Campania, you have a deeper immersion into the culture of the region with a private cooking class exploring the Cilento province. Dishes typically use local, seasonal ingredients favoring the flavors of the traditional local territory. The chef introduces you to the customary ingredients of the region including white figs, buffalo mozzarella, and Cicerale chickpeas. You start with a typical Lagane and chickpeas, which consists of strips of dough made with water and flour cooked on hot stones and combined with chickpeas, onion, celery, and bay leaf before frying the mixture in a pan. The recipe dates back the ancient Greek settlers.

What’s Included: accommodation, tour, breakfast

Day 6: Matera – Travel to the Basilicata Region and Tour Famous Matera

Matera shimmers like a Jewel in the Basilicata region with homes made of white tufa stone glinting gold in the sunlight. Settlements along the crags set deep in the Gravina Gorge date back approximately 7,000 years with more elaborate ancient and medieval structures crowning the slopes leading to the plateau. The unique allure of Matera has garnered the city the 2019 European Capital of Culture celebrating the intriguing layers of history displayed like a palimpsest beginning at the riverbanks along the gorge until reaching the central cathedral situated on the rugged spur. The city feels timeless in its preserved streets and renovated architecture set beneath the 17th-century Romanesque-style cathedral.

The rose window brings 16 rays that reflect the wheels of time and an image of archangel Michael defeating a dragon. The ancient village is located beneath the medieval streets amid the calcareous rock looking down into the Gravina Valley. A network of houses, alleyways, and stone churches twist into the gorge walls creating habitable grottoes known as sassi. Locals have reclaimed the sassi as part of their heritage turning old one-bedroom homes once shared with entire families, chickens, pigs, and donkeys into boutique shops and award-winning restaurants.

While in Matera, you can dine at Vintantonio Lombardo, a restaurant with a newly acquired Michelin Star for 2019. The chef offered his own name to the establishment to make the guest feel as though they are walking into his home during the dining experience. Each dish takes inspiration from the surrounding stone of Matera balancing strength and subtlety, hidden flavors and grand gestures. While the seasons help dictate the flavors, the menu surpasses the restrictions of the seasons with tasting menus utilizing the best ingredients available while in an elegant dining room located inside a sasso, an emblem of Matera’s soul.

What’s Included: accommodation, transfer, tour, breakfast

Day 7: Matera – Charming Villages and Gorgeous Coastline of Basilicata

In the morning, the golden light washes over Matera for a distinctive glow from the sassi facades. After breakfast, you set out into the countryside for an intimate encounter with the villages of less visited region of Basilicata. Castelmezzano climbs the slopes of the Lucanian Dolomites beneath the jagged pieces of granite boulders that protrudes from the rock face at approximately 3,231 feet above sea level. A tunnel carved into the mountain links the town to the neighboring gorge wall revealing a typical medieval historic center. A cluster of concentric houses overlooks the basin with sandstone slab rooftops. Stairways connect the various levels of town leading to spectacular views from the surrounding peaks. Life revolves around Piazza Caizzo, where the Romanesque-style façade of Santa Maria dell’Olmo acts as the centerpiece.

For an unforgettable experience over Basilicata, you partake in the Flight of the Angel. The zip-line excursion connects Castelmezzano to its sister-town of Pietrapertosa on an opposite slope of the Lucanian Dolomites. The excitement pales in comparison to the view over the fabulous landscape as the wind bites at your cheeks before you reach Pietrapertosa at 2,913 feet above sea level when traveling a distance of 4,764 feet. The ancient Saracen fortress crowning the town emerges from its camouflage as you glide over the vale nearing the streets of Pietrapertosa.

What’s Included: accommodation, tour, breakfast

Day 8: Ostuni – Venture to Puglia and Relax in the Elegant City of Ostuni 

At breakfast, the scent of fresh espresso accompanies the semi-sweet aroma of pane di Matera, a typical bread of the city with a flaky crust. Your private transfer greets you at the hotel and whisks you out of Basilicata to reach the heel of Italy’s famous boot-shaped topography. Before reaching the bright and inviting town of Ostuni, you stop at an olive orchard and mill owned by a local family of Salento province. The incredible landscape shaded with trees and sporadic rocky promontories.

Olive oil in the region is known as “yellow gold,” with traditional methods taking precedent in the production and bottling of the oil. The herbaceous scent of the trees fills the orchard as your guide leads you through the landscape and into the warehouse to view the processing equipment. Customary methods pressed the olives between heavy stone plates allowing the oil to seep out of the sides and into containers. Sampling the delicious oil brings aromas of nuttiness and citrus leading to a lingering spiced flavor on your palate.

The city of Ostuni flickers with whitewashed buildings climbing along the hillside. The Mediterranean architecture reflects the charm of the preserved medieval streets with narrow always, supportive archways, and a staircase leading to the prominent cathedral. The essential belvedere provides a panorama over the countryside brimming with olive groves leading westward to the turquoise waters of the Adriatic Sea. The hillside on which Ostuni sits was settled during the Paleolithic period with the Messapians building along the upper district of the ridge by the 1st century BC. The mixture of the cathedral’s Gothic and Romanesque design culminates with the beige color of the stone contrasting the surrounding white walls.

What’s Included: accommodation, transfer, tour, breakfast

Day 9: Ostuni – Visit Stunning Polignano a Mare and the Historic City of Bari

In the morning, you can venture out of Ostuni to reach the charming town of Polignano a Mare. The quiet streets stretch to the edge of the promontory at 79 feet above sea level. Teenagers linger on the edges of the cliffs waiting for the perfect moment to dive down into the Adriatic Sea. The old bridge at Lama Monachile north of the historical center contains traces of the former Via Traiana, the Roman road erected during the 2nd century during the reign of Emperor Trajan.

The town is also known for being the birthplace of Domenico Modugno, the writer and performer of the renowned Italian ballad, “Volare.” Embrace the past charms of the historical whitewashed walls and narrow lanes leading to terraces with panoramic views over the water.  Settle into a café and indulge in the aroma of seafood grilled on an open flame with dressed with a squeeze of sweet, tart lemon. Locals lounge on the soft sands of Blue Flag Beach, an easy walk from the heart of Piazza Vittorio Emanuele II.

Continue to Bari, the urban expanse of Puglia with grand boulevards and majestic culture dipped beneath the legendary Basilica di San Nicola, which houses the relics of Saint Nicholas. The 12th-century structure was erected to house the relics stolen from Turkey by fishermen and remains an important place of pilgrimage for Catholics and Orthodox Christians. The vaulted crypt sits beneath the elaborate 17th-century wooden ceiling decorated with flecks of gold. The scent of myrrh is said to stem from the remains of the saint.

What’s Included: accommodation, tour, breakfast

Day 10: Ostuni – Wander the Unique Ambiance of Alberobello and Monopoli

After breakfast, the whitewashed walls of Alberobello come into view during your scenic drive out of Ostuni. The sunlight glints against unique Mediterranean architecture revealing the particular stout shape of the homes topped by the distinctive conical rooftops. The original architectural design allowed the farmers and inhabitants of the province to avoid the tax collector dating back to the Spanish occupation of the 1500s by preventing a town charter. The structures are made from limestone with an intricate design peeking above the surrounding olive groves. The thick stone helps keep the interior cool in the summer and warm in the winter. Stroll around the cobblestones along the center of town where approximately 1,000 trulli homes line the streets creating a fairytale ambiance most notably along Rione Monti. The western edge of town slopes along the modern edges with several lanes offering a grand panorama of the historic conical roofs and picturesque palm trees.

After enjoying the storybook atmosphere of Alberobello, you will continue to the seaside allure of Monopoli. The quiet charisma of the medieval seaside town contains narrow streets and charming piazzas overlooking the picturesque marina. The combination of Old-World ambiance and gorgeous beaches welcome you with a refreshing sea breeze and the aromas of delicious pastries drifting out of the nearby bakery. A canon-mounted bastion adorns the promenade leading to the 16th-century Charles V Castle. Fishers tend to their nets along the shores hidden at the edge of the little harbor while their colorful boats decorate the clear turquoise water.

What’s Included: accommodation, tour, breakfast

Day 11: Ostuni – Explore the Fascinating History and Beauty of Lecce 

The history of Lecce emerges from the marvelous Baroque facades decorating the streets at the center of the city. The fascinating colors and intricate designs reflect the artistic heritage of the community often touted as the “Florence of the South.” Golden yellow limestone glints in the daylight the color of soft butter adding an extra layer of glamor to the churches and palaces. The Messapii people of the eastern Atlantic laid the foundations of the first settlement over two millennia ago before the Romans took over during the reign of Emperor Hadrian.

The Basilica of Santa Croce is the best-known architectural structure in the city due to its lavish 17th-century Baroque façade featuring a collection of magnificent rose windows with a complex series of statues depicting sheep, dodos, cherubs, and monsters. Eagles, griffons, and lions add to the regal appearance of the artistry alongside vines sprouting from the pillar capitals around profusions of fruits, trees, and leaves. The Roman Amphitheater was erected in the 2nd century AD and uncovered beneath the prevailing Piazza Sant’Oronzo.

The original edifice could hold more than 25,000 spectators while the ruins are still decorated with columns, arches, and a marble mosaic floor that remains in use during summer concerts and public performances. After learning paper-mâché is the prominent artform of Lecce, you find the work around the city with the development of the art closely aligned with religion dating back to the 17th century. While Florence had marble during the Renaissance, Lecce’s artistic awakening utilized local resources as well, with workshops and studios showcasing their art in the windows along the central streets ranging in sizes and themes from religious to daily life.

What’s Included: accommodation, tour, breakfast

Day 12: Ostuni – Transfer to Bari Airport for your Flight Home

In the morning, the view from the summit of Ostuni provides a lush blue hue deriving from the eastern horizon along the Adriatic Sea. The doors to the Pre-Classical Civic Museum of Murgia open in welcoming visitors into collections depicting Delia, a 25,000-year-old expectant mother preserved in a local cave from the Paleolithic era. The cathedral dedicated to the Assumption of the Virgin Mary was erected in the 15th century but retains a sense of grandeur from the 18th century when the art was added to the ceiling and altars. After breakfast, your private transfer greets you in the hotel ready to escort you to Bari International Airport for your flight home.

What’s Included: airport transfer, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.