Italian Journey: Naples, Matera, Puglia and Sicily

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  • Ideal Length:
    12 Days
  • Best Time To Go:
    April - May, September - October
  • Flight Time:
    LAX 15 Hours 45 Minutes, CHI 12 Hours 40 Minutes, NYC-All Airports 11 Hours 40 Minutes
  • AVERAGE COST PER PERSON (Single occupancy; Airfare not included):


Naples, Italy
Naples1 Day
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  • Stay in chic, cutting-edge hotel located in the heart of Naples.
  • Explore Naples attractions, including an Underground Tour.
Matera, Italy
Matera2 Days
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  • Tour Pompeii and go wine tasting near Mount Vesuvius National Park.
  • Visit a UNESCO World Heritage Site to explore its 9,000-year-old caves.
  • Enjoy the unique luxury of sleeping in a cave at Sextantio Grotte dell Civita.
Puglia, Italy
Puglia3 Days
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  • Watch women demonstrate how to make traditional pasta in Bari.
  • Be adventurous and explore the Castellana Grotto at night.
  • Visit the Itria Valley for an eye-opening olive oil tasting experience.
  • Take a private catamaran tour on the Adriatic Sea to see historic cities.
Toarmina, Italy
Taormina3 Days
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  • Explore historical landmarks and go cannoli tasting in Taormina.
  • Embark on a walking tour of the first Greek settlement in Sicily.
  • Sample local wines at a vineyard located in the foothills of Mount Etna.
Aeolian Islands, Italy
Aeolian Islands3 Days
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  • Take an immersive private boat tour of the Aeolian Islands.
  • Unwind and relax at a luxurious resort and spa on Vulcano.
  • Spend your final full-day as you wish to end your fabulous trip.
Naples Day 1
Matera Day 2-3
Puglia Day 4-6
Taormina Day 7-9
Aeolian Islands Day 10-12
Naples Day 1
Naples, Italy
Start your Italian vacation in Naples, a coastal city in southern Italy dating back to the 2nd millennium B.C. This UNESCO World Heritage Site is the birthplace of Neapolitan cuisine and home to sites such as the lavish Royal Palace and 13th century Castel Nuovo.
Woman with suitcase in an airport
Private Luxury Transfer to Hotel
Upon your arrival to the airport in Naples, a porter will collect your luggage and you will be escorted by a personal assistant to your driver and luxury vehicle for transportation to the Romeo Hotel. Full luggage assistance provided.
Romeo Hotel in Naples
Stay at the Romeo Hotel
Cutting-edge design meets chic style at this iconic hotel located amid Naples renowned historical sites. Relax in the salt sauna, take a swim in the rooftop pool, play a round of virtual golf in the games lounge (Il Salotto dei Giochi), indulge in caviar in the Beluga Sky Bar, and sample Michelin-starred cuisine at the onsite restaurant, Il Commandante.
Historical Site in Naples
Explore the Sights in Naples
Take a four-hour orientation tour of Naples with a private chauffer and guide to see Castel Nuovo, Piazza del Plebiscito, the Royal Bourbon Palace, San Carlo Opera House, Galleria Umberto and city views, including Mount Vesuvius. After lunch, take a guided tour of Naples Underground to discover more the 2,400 years of the city’s history.
Matera Day 2-3
Matera, Italy
This 9,000-year-old city of about 60,000 people is located a 3-hour drive (via transfer from Naples. Matera became a UNESCO World Heritage site in 1993. This jewel of the Basilicata region was recognized as the 2019 European Capital of Culture.
Pompeii, Italy
Pompeii Guided Tour & Wine Tasting
Take a private luxury transfer to Matera (a 3-hour drive east of Naples) with a stop for a 2-hour guided tour of Pompeii, al-fresco lunch at Cantine del Vusuvio, and a wine tasting guided by the owner of an organic winery set in the foothills of Mount Vesuvius National Park.
Sextantio Grotte della Civita Hotel in Matera, Italy
Unique Luxury Hotel Experience
Sleep in a cave! Stay at the Sextantio Grotte della Civita that features 29 spacious rooms, located in the oldest part of Sassi – la Civita – and facing the dramatic scenery of Alta Murgia National Park.
Caves in Matera, Italy
Explore Matera and Its Caves
With an English-speaking guide, see the natural caves where people lived approximately 7,000 years ago. Visit the landmarks above and below Old Matera, including the House Cave Museum. Lunch is recommended at Osteria L’ Arco, a well-known cavernous restaurant in Matera.
Puglia Day 4-6
Puglia, Italy
A visit to Puglia should also include stops in notable destinations such as Bari, Alberobello and Lecce. Learn how to make pasta, explore Greco-Roman history in small towns, embark on Michelin-starred culinary experiences, and take catamaran tour on the Adriatic Sea.
Man making home-made pasta
Old Bari & Pasta-Making Demonstration
En route to Puglia from Matera, take a guided walking tour of Bari to visit its old fish market on the seafront, Piazza Ferrarese, the Basilica of San Nicola, and the Norman Swabian Castle. At the end of the tour, see how local women – lined up outside their homes on Orecchiette Lane – show you how to make a local variety of pasta.
Luxe beachfront hotel near Puglia, Italy
Luxurious Hotels Near Puglia
Consider staying at one of three recommended hotels: the luxurious Borgo Egnazia resort in Egnazia, the 5-star Masseria Torre Coccaro in Savelletri, or the peacefully elegant Hotel La Peschiera in Capitolo. Located on the coast of the Adriatic Sea, all three hotels also feature an endless list of high-end amenities.
Itria Valley Tour, Italy
Itria Valley Tour
Visit Ostuni – known for its white walls and white-painted architecture. Go olive oil tasting at Masseria Brancati and see how organic extra virgin olive oil is produced. Proceed to Alberobello, a UNESCO World Heritage Site, for an amazing walking tour. Wrap up the 8-hour tour with a stop in Zona dei Trulli to see the town’s 1,500 beehive-shaped houses with white tips – dating back to the 14th century.
Castellana Grotto, Puglia, Italy
See Castellana Grotto at Night
A Speleological guide leads you on an exclusive, small group tour after Grotte di Castellana has been closed to the public. The Grave, Caverna della Lupa and Grotta Bianca are just a few stops along the way. Conclude your tour with a dinner at the Michelin-starred Il Pasha in Conversano.
Baroque City of Lecce, Italy
Discover the Baroque City of Lecce
More than 2,000 years old, Lecce is known as the “Florence of the South” because of the rich Baroque architectural monuments and affinity for Greek culture found in the city. Discover its hidden gems including a firsthand encounter with local artisans working with papier mache in their private studios.
Pasticciotti Leccese
Taste the famous Pasticciotti Leccese
This unique culinary experience will introduce you to the real flavors and traditions of Salento. Depending on the region, they are filled with either ricotta cheese or egg custard. Andrea Ascalone – a chef in the town of Galatina in Lecce – is credited for inventing pasticciotti.
Catamaran boat
Catamaran Full-Day Tour
Embark on a private guided boat tour along the coast to see Polignano, Monopoli, the Castle of Santo Stefano and Capitolo. There’s a stop to swim and an aperitivo of local snacks and a chilled bottle of Prosecco or Spritz will be served on board.
Taormina Day 7-9
Taormina, Italy
An Italy travel specialist can arrange your transfer to Bari Airport and your flight to Taormina – a hilltop town on the east coast of Sicily – known for the Teatro Antico di Taormina, an ancient Greco-Roman theater.
Belmond Grand Hotel Timeo, Toarmina, Italy
Stay at the Belmond Grand Hotel Timeo
With Mount Etna as its dramatic backdrop, this hotel has long been the destination of choice for European and Hollywood celebrities. It is surrounded by a six-acre park, with magnificent gardens encircling a panoramic pool. It is known for its Literary Terrace, a popular meeting place for distinguished guests.
Woman walking on cobblestone street in Toarmina, Italy
Taormina Private Guided Tour
Take a three-hour guided walking tour that includes historical sites including the city’s highest vantage point, the Greco-Roman Teatro Antico di Taormina; a small museum where many of Sicily’s ancient artifacts are kept; and a cannoli tasting with Italian coffee.
Siracusa, Italy
Explore Syracuse & Noto
Explore Syracuse Ortigia – the first Greek settlement of Sicily – to discover its ancient past and how it influenced the island’s history. Then after a 45-minute transfer ride, continue your journey to explore Noto’s charm and baroque architecture, including sites like Palazzo Villadorata. End your full-day tour with a delicious Sicilian lunch at Dolceria Costanzo, where you will find the best granita (semi-frozen dessert) in town.
Mount Etna Vineyard
Mount Etna & Gambino Winery Tour
A private driver will take you to the lovely Gambino Winery, located on the foothills of Mount Etna. Enjoy a traditional lunch in addition to an opportunity to sample some of the local wines. After lunch, your driver will make the trek up the tallest active volcano in Europe for unforgettable breath-taking panoramic views.
Aeolian Islands Day 10-12
Aeolian Islands, Italy
Explore the Aeolian Islands, an idyllic volcanic archipelago in the Tyrrhenian Sea. Take a full-day private boat tour to visit a couple of the islands to sample local wines, see the indigenous wildlife and to take a pore-cleansing dip in a natural mud pool.
Aeolian Islands Private Boat Tour
Aeolian Islands Private Boat Tour
This full-day, private boat excursion will include a stop in Lipari to explore its old town and to sample Malvasia wine. In Vulcano, you’ll discover the island’s wildlife and its fumaroles, where water of the sea, black sand and mud become the center for health and beauty. Gelso’s black beaches, Pools of Venus, The Arc of Pietralunga, Cala Fico and the Canneto are a few places you’ll see along the way.
Therasia Resort Sea and Spa in Italy
Stay at Therasia Resort Sea and Spa
On Vulcano, Therasia Resort is a quiet refuge with spectacular views of the Aeolian Islands. This is a fabulous base to discover the island’s hot springs, natural mud pools and black sand beaches. The resort features two gourmet restaurants that serve Sicilian cuisine and a spa with several unique treatments.
Catania Port in Italy
Private Transfer to Cantania Airport
It’s recommended that visitors on Vulcano spend an extra day of leisure before arranging a private yacht from the Therasia Resort Sea and Spa to the Catania Port, and then a private luxury sedan will transport you to the Catania Airport to end your wonderful Italy vacation.

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