Our Journeys

Naples to Brindisi: Secrets of Southern Italy with Sierra Club - October 2025
October 19-31, 2025

$6,556

Naples to Brindisi: Secrets of Southern Italy with Sierra Club – October 2025

You simply don’t know Italy if you haven’t experienced its deep south. Colonized by the Greeks and adorned by the Romans, Southern Italy boasts some of the oldest and greatest Greek temples outside of Greece. Wandering the streets of Naples, the one-time cultural center of the Roman Republic, capital of the Bourbon Kingdom and UNESCO World Heritage site, you’ll imagine its rich history of 27 centuries in the making. We walk along parts of Europe’s most picturesque coast, the Amalfi, and embrace inspiring views on Capri from the heights of Mt. Solaro, to the winding paths and cliffs that plunge into the sea. Our travels present us with opportunities to sample local wines, olive oils, cheese and some of Italy’s best pastas and sauces, not to mention gelato at almost every turn. Our walks include a stroll along ancient farmer paths through quiet countryside and average five miles each day, with gains of 1,000 feet at the most for a moderately easy trip.

From spectacular, lesser-known wines to hidden artistic treasures and mystical, unforgettable landscapes, Southern Italy is full of surprises. Highlights include a stroll on the crater edge of Vesuvius, a tour of Pompeii, a two-night stay on the charming island of Capri, a visit to the Greco-Roman ruins of Paestum, a fun cooking class at local farmhouse, a walk through the stone city of Matera with homes built in caves, a rural walk in verdant Puglia, and a swim in the translucent Adriatic Sea.

This tour across Campania, Basilicata, and Pulgia in our own private coach offers the best that Southern Italy has to offer. We’ll understand why the Italians call it the “Paese Felice,” or Happy Land, and appreciate why the Italians themselves vacation in this place of scenic beauty and delicious food. Register today and enjoy our unforgettable itinerary.


ITINERARY


*Please click on each day to view daily itinerary.

DAY 1 - Sunday, October 19: Naples

Arrive in Naples today and make your way to the group hotel. Those arriving in the morning can spend time exploring the historical center of Naples on their own. The grandiosity of this city’s countless royal buildings and spectacular churches is a great surprise for a first-time visitor. With the Duomo as an ideal reference point, we suggest you take in one of the local markets and ancient neighborhoods, and bask in the colorful and charming old town. We will meet as a group for the first time in the early evening for a welcome talk and dinner where we sample the authentic, world-famous Neapolitan pizza together with other local specialties. Lodging in Naples.

DAY 2 - Monday, October 20: Naples - Caserta

oday begins with a discovery hike in the spectacular Caserta’s Royal Palace Park where an expert botanist will guide the group through its beautiful gardens, fountain, and hidden corners. After returning to Naples in the afternoon, the group will visit the Archaeological Museum, which lays the historical and cultural foundation for the remainder of our trip. Its extensive collections include antiquities recovered from Pompeii and Hurculaneum. Dinner will be on your own tonight. Lodging in Naples.

DAY 3 - Tuesday, October 21: Vesuvius & Pompeii

No visit to Southern Italy would be complete without a visit to Mount Vesuvius and Pompeii. We will start the day with a refreshing hike up the ash maker itself, Mount Vesuvius. A volcanologist will teach us about his trade as we hike up and around the black sand that encircles the crater. Along the way, we will also learn how the legends of Vesuvius dominate local folklore. After lunch, we will make our way to Pompeii, the ancient Roman settlement that was destroyed in A.D. 79 by the explosion of Mt. Vesuvius and remained covered in thick protective ash until its excavation began at the end of the 1700s. Lodging in Naples.

DAY 4 - Wednesday, October 22: Capri

This morning, we will embark on a short cruise to the fabled island of Capri. After arriving, we will drive up the unforgettably winding road to Anacapri, a picturesque town of 5,000 that somehow clings to the mountainside. An easy hike brings us to Migliara, where we enjoy a view of the Punta Carena lighthouse and neighboring Ischia and Procida islands. After enjoying the breathtaking views, we will return to Anacapri with its lively little shops, and coffee bars for some free time before dinner. Those looking to hike some more can choose to ascend Monte Solaro by foot (Capri’s highest point at 1,926 feet above sea level). A chairlift option is also available (ticket not included) for those that would like to take in the views without the additional hiking. Lodging in Anacapri.

Hiking: 3 miles; elevation change: +200 feet. Distance and elevation gain will be more for those who elect to hike up to (and possible down from) Monte Solaro.

DAY 5 - Thursday, October 23: Capri

Today we will embark on a scenic hike through the heart of Capri followed by a picnic lunch. Later we will visit Villa San Michele, an 18th-century villa built by the Swedish physician and writer Axel Munthe that features some of the finest examples of Neapolitan Baroque artwork. With deliberate work and research, he aimed at creating a sanctuary where art, nature, and healing could intertwine harmoniously. The book Villa San Michele, a collection of memoirs by the author, became a best seller in the US in 1930 and has been loved by millions of readers since. The day ends with a dinner featuring local fish specialties. Lodging in Anacapri.

DAY 6 - Friday, October 24: Capri, Amalfi & Paestum

This morning, we say goodbye to Capri and head to Amalfi by boat. You will have time on your own to visit the Amalfi’s charming streets and the Catedrale di Sant’ Andrea, which is a combination of Sicilian, Arabic, and Norman architecture. Afterward, we will take a scenic hike along the coast before transferring to Paestum in the late afternoon. Tonight, in Paestum you will enjoy a dinner of traditional specialties. Lodging in Paestum.

DAY 7 - Saturday, October 25: Paestum

This morning, we will explore the ancient Greco-Roman city of Paestum, including its Temple of Hera, the goddess of family, childbirth, and women. Built in 550 B.C., it is exceptionally well preserved. In the museum, we will view unique frescoes depicted on tomb slabs that date to the 5th century B.C. (including the world-famous Tomb of the Driver). In the afternoon we will visit a local water buffalo farm to sample freshly made buffalo mozzarellas and experience a fun cooking class at a local farmhouse. Lodging in Paestum.

DAY 8 - Sunday, October 26: Altamura & Matera - Syracuse

Today we will travel to the lesser-known and incredibly beautiful Basilicata region, until recently one of the poorest regions in Italy. The region is known for its Middle Eastern appearance, making it a desired filming location for biblical-era productions. We will stop in Altamura to taste and learn the history of the region’s traditional bread that is famous throughout Italy. Next we will visit Matera, which surely be one of the highlights of our journey. Matera’s labyrinthine streets combine ancient stone structures with buildings of later eras in a fascinating blend of old and new. Our exploration in Matera will include a visit to one of the cave homes furnished exactly it was before the government mandated evaluation of the city in the 1950s. At dusk, when the city’s white stone turns pink, a quiet walk on its cobblestone streets will take you back in time. Lodging in Matera.

DAY 9 - Monday, October 27: Matera

Today we will hike through the Parco Regionale delle Chiese Rupestri, Park of the Rock Churches. Once home to ancient civilizations, this area today is a nature sanctuary that provides protection for numerous plant species. Our trail leads us through deep gorges with prehistoric caves. One of the highlights will be a visit to the stunning Crypt of the Original Sin, a fresco that was painted with astonishing colors and techniques 1,300 years ago. We will enjoy a simple yet traditional farmer’s lunch with local products and sampling of wines before returning to Matera to spend the late afternoon and evening exploring at your leisure. Dinner tonight will be on your own with abundant choices in close proximity. Lodging in Matera.

DAY 10 - Tuesday, October 28: Castel del Monte & Valle d'Itria

This morning, we will reach the renowned UNESCO Word Heritage site of Castel del Monte, where we will delve into its intriguing and mysterious history. This octagonal shaped fortress is considered a masterpiece of medieval architecture, filled with hidden symbols that have captivated scholars for centuries. Following our exploration, we will journey to the lush Valle d’Itria, a picturesque valley blanketed with vineyards and olive groves. The landscape is dotted with hundreds of trulli – the traditional dry-stone structures with conical roofs once used by Apulian farmers. We’ll enjoy a hike among the ancient olive trees, whose powerful, sinuous trunks rise majestically from the reddish soil, creating a striking open-air museum. Lodging near Alberobello.

DAY 11 - Wednesday, October 29: Alberobello & Itria Valley

Today we will explore another UNESCO World Heritage site, the village of Alberobello. This charming and picturesque town is renowned for its architecture. Home to the largest concentration of trulli, around 1,600 of these iconic hunts, the village offers a fascinating glimpse into traditional Apulian life. We’ll start with a demonstration of how these distinctive structures were built, followed by a hike along an ancient farmer’s path. The trail winds through sturdy stone walls, olive groves, and rich array of oak, cork and carob trees, providing a beautiful immersion into the valley’s countryside. Lodging near Alberobello.

DAY 12 - Thursday, October 30: Polignano a Mare - Ostuni & Locorotondo

This morning, we will explore the stunning coastline of Polignano a Mare from a unique perspective on a small boat tour along its dramatic cliffs. We’ll have the chance to enter the sea caves and marvel at the mesmerizing shades of blue in the water. There will also be the opportunity to swim directly from the boat in a few secluded coves or admire from the boat the vibrant marine life and breathtaking scenery. After some free time in the charming town of Polignano a Mare, we will visit Ostuni, known for its whitewashed walls and breathtaking views over the Adriatic Sea. If time allows, we will visit the picturesque town of Locorotondo. We’ll end the day with a simple and delightful wine tasting, followed by dinner and local music. Lodging near Alberobello.

DAY 13 - Friday, October 31: Transfer to Airport

This morning after breakfast, the group will transfer by bus to Bari airport for our flights home or to other locations. We recommend scheduling your return flight for Noon or later.



INFORMATION


What is included in the trip

  • Lodging with private bath in small hotels, villas and countryside inns
  • All meals (except three dinners)
  • On-trip transportation

What is not included

  • International airfare to and from Italy
  • Personal expenses
  • Travel Insurance
  • Tips for drivers and guides

MORE INFO