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9-Day Southern Italy Tour Winter Itinerary

The Southern Italy Tour winter itinerary is an affordable way to travel through Southern Italy’s highlights.

The tour begins in Bari. The tour ends in Naples. Sightseeing includes three southern Italian regions: Puglia, Basilicata, and Campania. Sightseeing highlights include Bari, Lecce, Naples, Pompeii, and the Sassi house in Matera.

There is an optional tour to Alberobello to see the Trulli houses. And another to Otranto, located all the way south at the heal of Italy’s boot.

For more information and for the price of the Southern Italy tour winter itinerary with air from your home city submitt he form or call 800.227.1577.


  • Historical walking tour of the revitalized narrow lanes of Bari’s Old City (Bari Vecchia)
  • Lunch at a Masseria (local farmhouse) featuring regional specialties and wine
  • Stroll along 300-year old cobblestone streets in Lecce named the “Florence of the South”
  • Taste and learn the secrets of Apulian Extra Virgin Olive Oil
  • Tour Matera’s mysterious Sassi (ancient stone dwellings), a UNESCO World Heritage Site
  • Visit the archaeological site of Pompeii, a 2,000-year old city that was frozen in time
  • Tour the historic center of Naples

Optional Activites

Alberobello & its Trulli

Discover the delightful town of Alberobello, a UNESCO World Heritage Site, which introduces the Apulian traditional dry stone huts known as Trulli. In existence since the 14th century, these unusual structures featuring pyramidal, domed, or conical roofs are remarkable examples of mortarless, drywall construction, a prehistoric building technique used in this region. Enjoy time to walk through the charming and quaint town before returning to Bari.

Full Day Salento & Otranto with Lunch

A full day tour will take you all the way to Santa Maria di Leuca, the end of the tip of the Italian heel, where the Adriatic Sea meets the Ionian Sea. Rocky coastline, beaches, fishing villages, watchtowers are waiting to be experienced in the most remote area of Puglia region. Enjoy a lunch of local delicacies, before continuing along the coast to reach Otranto, the Easternmost Italian town. Stroll through the historical town center surrounded by its ancient walls, check out the tiny shops or savor a gelato in an outdoor café, before returning to Lecce.

Approximate tour duration is 8 hours.


2 nights Bari – Grande Albergo delle Nazioni, Bari

This superior first class hotel has spectacular views of the sea.

2 nights Lecce – Hotel President, Lecce

This first class hotel is located in the heart of Lecce.

1 night Matera – UNA Hotels MH Matera, Matera

This first class hotel is a ten minute drive away from the city center of Matera.

2 nights Naples – Hotel Royal Continental, Naples

This first class hotel is a historic establishment that is located right on the Neapolitan waterfront.

Similar Southern Italy Tours

Southern Italy Tour Winter Daily Activites

The southern Italy tour winter tour visits the southern Italy sightseeing highlights during the off season. Enjoy less crowds on this all inclusive southern Italy tour.

DAY 1, Thursday – Depart for Italy

Depart for Italy

DAY 2, Friday – Arrive in Bari

Welcome to Puglia, a spectacular expanse of land that juts out into the turquoise Adriatic and Ionian Seas. Arrive in the energetic port city of Bari and transfer to your hotel. The rest of the day is at leisure. Your tour will begin with an orientation meeting with your Tour Manager at approximately 6 PM, followed by dinner. We recommend you to select flights that arrive no later than 4 PM
Overnight: Bari
Meals: Dinner

DAY 3, Saturday – Bari’s Old City

The exploration of Bari starts in the revitalized narrow streets of the Old City (Bari Vecchia). View Bari Cathedral and the stunning Romanesque Basilica of San Nicola, housing the relics of St. Nicholas, known as Father Christmas. Next, your historical walking tour reveals 12th century Castello Normanno-Svevo, built by the Normans.

Afterward, linger on your own, explore Bari’s pretty squares, admire the architecture, or just sip an espresso at an outdoor café. Perhaps take the optional tour to the delightful town of Alberobello, a UNESCO World Heritage Site, which introduces the Apulian traditional dry stone huts known as Trulli. Tonight, dinner is on your own, so feel free to explore one of the piazzas buzzing with trendy restaurants and cafés and try traditional Pugliese food
Optional: Alberobello and its Trulli (PM)
Overnight: Bari
Meals: Breakfast

DAY 4, Sunday – Masseria Lunch, Lecce

Begin your day with a visit to a beautiful local farmhouse Masseria to savor lunch with regional specialties including local wine. Afterward, in Lecce, stroll along 300-year old cobblestone streets past exquisite Baroque architecture. You’ll understand why Lecce is fondly named the “Florence of the South”. View Piazza del Duomo and the Roman amphitheater dating back to the 2nd century BC. Then admire the masterpiece of Southern Baroque in the Basilica of Santa Croce. Time to wander on your own and perhaps dine at one of the quaint trattorias in the city center
Overnight: Lecce
Meals: Breakfast, Lunch

DAY 5, Monday – Full Day in Lecce

Today, spend the day at leisure to explore Lecce on your own or choose to participate in the optional tour through the Salento Peninsula. A picturesque drive will take you all the way to the tip of the Italian heel, where the Adriatic Sea meets the Ionian Sea. Rocky coastline, beaches, fishing villages, and watchtowers are waiting to be experienced in the most remote area of the Puglia region. After your lunch featuring local products and dishes, continue along the coast to Otranto, the easternmost Italian town. Walk the historic center surrounded by its ancient walls at your own pace, and why not savor a gelato while sitting in an outdoor café before returning to Lecce
Optional: Full Day Salento & Otranto with Lunch
Overnight: Lecce
Meals: Breakfast

DAY 6, Tuesday – Matera

Today learn the secrets of extra virgin olive oil, the “green gold” that enhances the flavor of almost any Mediterranean dish, as you travel to fascinating Matera. Here, learn about Matera’s roots connecting to the Paleolithic Age as you explore this UNESCO World Heritage Site. The mysterious Sassi (ancient stone dwellings carved into rock) are believed to be the first human settlements in Italy. Over the centuries, the Sassi were adapted into family homes. Tonight, dinner is at your hotel in Matera
Overnight: Matera
Meals: Breakfast, Dinner

DAY 7, Wednesday – Mt. Vesuvius and Pompeii en route to Naples

A morning drive takes you to the remarkable archaeological site of Pompeii at the base of Mount Vesuvius, a city that was frozen in time under a thick carpet of volcanic ash almost 2,000 years ago. Walk through the original sloping streets of Pompeii and view tragic fossils of people attempting to escape beside their children and dogs, along with the preserved ruins of the Temples of Apollo and Jupiter, and the Forum. Continue to Naples and enjoy some free time
Overnight: Naples
Meals: Breakfast

DAY 8, Thursday – Naples Historic Center

Start the day with a panoramic tour of the city to discover its beauty. The city overlooks the bay of Naples, extending from the Sorrento Peninsula to the Volcanic area of the Campi Flegrei, and its skyline is dominated by the majestic Mount Vesuvius. Continue to explore the historic center with its buzzling narrow streets and beautiful piazzas. The afternoon is at leisure to tour the city at your own pace, should you wish to see the Naples National Archaeological Museum, the underground city, or take a stroll on the seaside promenade. Tonight during dinner, bid farewell to your Tour Manager
Overnight: Naples
Meals: Breakfast, Dinner

DAY 9, Friday – Depart Italy

Transfer to the airport for your departure flight
Meals: Breakfast

* When all-inclusive Italy vacation prices are quoted to include airfare the price includes fuel surcharges, airport taxes, Italy airport transfers and fees. All prices are per person based on twin occupancy. Italy tours with air & land tour prices apply from the gateway airport. Prices will vary from alternative gateway airports or cities and may be higher. The total price will be emailed to you prior to any deposit being required. Airline baggage fees may apply. Please review all terms and conditions before booking.