Naples to Brindisi: Secrets of Southern Italy

Sierra Club Outings Trip # 14760A, International


  • Walk through the ancient Roman settlement of Pompeii and across the black-sand ridge atop Mt. Vesuvius 
  • Enjoy a cruise to the Isle of Capri, with a hike or chairlift to the top of Mt. Solaro
  • Learn how to cook southern Italian dishes in a countryside villa


  • All gratuities and entrances to museums and attractions
  • All meals except one dinner (accommodates vegetarian and vegan)
  • Double-room lodging in villas and country inns


DatesSep 28–Oct 9, 2014
Price$3,595 (12–15)
$4,145 (or fewer)
StaffStu Delacastro

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Trip Overview

The Trip

This tour across Campania, Basilicata, and Pulgia introduces you to the “mezzogiorno,” or happy land, where the Italians themselves vacation because of the beauty of the land and delicious food.

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. We will walk along parts of Europe’s most picturesque coast, the Amalfi, winding around the cliffs that stretch into the sea, with opportunities to talk to the locals about their farming methods and vineyards as we sample some of Italy’s best pastas and sauces. Capri and Naples offer the most inspiring views of all, and they are also known for their tasty pizza and gelato. Our rambles follow ancient farmers’ paths through quiet countryside and cover three to five miles each day, with gains of 1,000 feet at the most -- a moderately easy trip.

From spectacular, but lesser known, wine to hidden artistic treasures and mystical, unforgettable landscapes, Southern Italy is full of surprises. Highlights include a stroll on the edge of Vesuvius, a meandering walk high above the Bay of Sorrento, a visit to the gardens of Ravello (where the locals believe the devil tempted Christ), a visit to the Greek/Roman ruins of Paestum, an adventure in the stone city of Matera with homes built in caves, rural walks in verdant Puglia, a swim in the translucent Adriatic Sea, and two nights in Lecce -– the “Florence of Southern Italy.”


This is our planned itinerary and sequence of events, but it could change due to weather conditions or circumstances beyond our control. We might change our daily plan to another day to take advantage of an opportunity to see a local festival or special celebration.

Day 1: We begin our tour of Naples mid-morning, walking through the centro storico and the greatest avenues of Naples with an experienced and entertaining local guide. The grandiosity of this city’s countless royal buildings and spectacular churches is a great surprise to the first-time visitor. The Duomo is the spiritual centerpiece of Naples. We will also venture deep into the underside of Naples, visit local markets and ancient neighborhoods, and hear some of the magical tales of Naples' historical characters. We will sample some of the local specialties of Neapolitan cuisine at our welcome dinner. Sleep in Naples.

Day 2: (Vesuvius and 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 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 AD 79 by the explosion of Mt. Vesuvius and remained covered in thick protective ash until its excavation began at the end of the 1700s. Sleep in Sant’ Agata.

Day 3: (Capri) This morning we will enjoy a short cruise to the fabled island of Capri, where we will drive up the unforgettably winding road to Anacapri, a picturesque town of 5,000 that somehow clings to the mountainside. A short walk brings us to Migliara, where we enjoy a view of the Punta Carena lighthouse and neighboring Ischia and Procida islands. Those who want to hike further can climb to Capri’s highest point, Monte Solaro (1,926 feet above sea level). But don’t worry, there is a chairlift option as well! After enjoying this world-class view, we will return to Anacapri with its fascinating boutiques to enjoy free time and lunch. Later we visit San Michele, an 18th-century villa built by Axel Munthe with some of the finest examples of Neapolitan Baroque artwork. Sleep in Sant’Agata.

Day 4: (Ravello and Amalfi) A scenic drive along the coast takes us to Ravello, a town that is known for its ravishing gardens and stupendous views. We will tour Villa Cimbrone, an original 19th-century estate which boasts lifelike statues, the viewpoint "Belvedere of Infinity," and exquisite gardens that hang over the sea. We will then depart on foot along an ancient mule path to the tiny village of Pontone, where we can chat with locals about their ancient farming techniques and their belief that these methods will resist the steamroller of globalization. We end our walk in Amalfi, with time to enjoy a gelato or tour the Catedrale di Sant’ Andrea, which is a combination of Sicilian, Arabic, and Norman architecture on the outside and pure baroque on the inside. Sleep in Paestum.

Day 5: (Paestum and Agropoli) This morning we will tour the Greco-Roman city of Paestum. Here, the ancient temple of Hera, built in 550 BC, has been painstakingly preserved through the ages. In the museum we will view unique frescoes depicted on tomb slabs that date to the 5th century BC -- including the world famous "Tomb of the Diver.” In the afternoon -- time permitting -- we will visit Agropoli and its imposing Angevin-Aragonese castle. Next we'll visit the famous water buffalo farm, where they produce the best mozzarella buffalo cheese, with an opportunity to taste the cheeses. Sleep in Paestum.

Day 6: (Matera) Today we will reach the lesser-known, but incredibly beautiful, Basicilata region. In the recent past, this was one of the poorest areas in Italy -- but it's also one of the most beautiful. Its Middle Eastern appearance secured it as the setting for Mel Gibson’s movie “The Passion” and many other biblical-era productions -- and its capital city of Matera will surely be one of the highlights of your journey. The labyrinthine streets combine ancient stone structures with buildings of later eras -– a fascinating blend of old and new, which will take your breath away...especially at sunset. We can tour one of the cave homes furnished exactly as it was before the people were moved out by the government in the 1950s. The UNESCO World Heritage central city is being re-done artistically, all while keeping the historic architecture of the buildings. At dusk the city's white stone turns to pink, and a quiet walk on its cobblestone streets will take you back in time. Sleep in Matera.

Day 7: (Matera) Today we will hike into 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 to more than 923 plant species, including rare orchids and wild herbs. Our trail leads us through deep gorges with prehistoric caves. We will also visit the incredible Crypt of the Original Sin, a fresco that was painted with unbelievable colors and technique 1,300 years ago. In the afternoon, we will have some time in Matera to explore further this magical city before dinner in one of the unique restaurants carved in the rock. Sleep in Matera.

Day 8: (Valle d’Itria and Alberobello) We will travel into the famed trulli area of Apulia and the lush Valle d’Itria. Blanketed with vineyards and olive groves, this valley is dotted with hundreds of trulli, traditional dry stone structures with conical roofs that were used by Apulian farmers. After a demonstration of how these trulli were built, we will walk on an ancient farmer’s path along sturdy stone walls through olive trees and an abundance of oak, cork, and carob trees. We will then take a tour of the UNESCO World Heritage village of Alberobello -- very picturesque with all of its trulli -- and get settled in our special hotel for the next two nights. This is our opportunity to learn to cook a southern Italian meal. Buon appetito! Sleep near Alberobello.

Day 9: (Ostuni and the seaside) Known for its whitewashed walls, Ostuni overlooks the Adriatic and features a dramatic 15th-century cathedral in its medieval center. We will explore Ostuni before heading to the coast for a great walk on a beautiful beach and a chance to swim in the brilliant turquoise water. Sleep near Alberobello.

Day 10: (Olive oil tasting and Lecce) We will enjoy an unforgettable olive oil tasting on our way to Lecce, the Florence of the south. It is a baroque town full of surprises -- a church dizzyingly decorated with asparagus column tops, decorative dodos and cavorting gremlins, inspiring someone to say the façade made him think a lunatic was having a nightmare.  We will observe the Spanish influence as we tour the world famous Church of the Holy Cross and then continue to visit the monuments and buildings that make Lecce one of the most appealing cities in Italy. An outdoor veranda near the main square is the location for a delicious luncheon of many varieties of antipasti. Sleep near Lecce.

Day 11: (Otranto and Lecce) This morning we will make our way to Otranto on the Adriatic coast. Otranto is a lovely city with a small harbor, a castle, an incredibly well-preserved medieval city center, and a beautiful cathedral that hosts one of the most famous mosaic floors of the South, depicting a stupendous Tree of Life. Tonight we will return to Lecce, where we will feast on a farewell dinner of seafood and local specialties. Sleep near Lecce.

Day 12: (Transfer to airport) This morning after breakfast, we transfer by bus to Brindisi Airport for your flight home or to other locations for more tours and adventures.



Getting There

Flights from the United States are often direct to larger cities -- Amsterdam, London, Frankfurt, Milan, Rome. From there, you can purchase a shorter flight directly to Naples. It is also easy to take a train from Rome to Naples, where we will meet mid-morning on September 28. If you are flying from the west coast of the USA, you will lose a day in flight, so you must leave one day earlier than the day that you want to arrive. If you experience jet lag ("fuso orario" in Italian), the trip leader suggests arriving a day or two before the trip starts to adjust to the time change. Please do not make non-refundable travel arrangements until notified to do so by the trip leader.

Accommodations and Food

We will be staying in six different small hotels, villas, and countryside inns. These are peaceful home bases for exploring nearby regions. They are usually family-run accommodations and provide breakfasts each day. They have garden grounds and ideal terraces with views -- the perfect setting for comfortable relaxation after a walk or tour. Rooms are double-occupancy; a roommate will be provided for solo travelers. In all rooms, there will be a bathroom. All meals will be provided in the trip price except for one dinner, so you can sample a café, restaurant, or trattoria of your choice. The cooking lesson will be our opportunity to prepare some regional specialties with a chef for our "cena" dinner. Many restaurants offer some vegetarian dishes and will attempt to satisfy special dietary needs. We can buy corn or rice pasta and bring it to the restaurant for the chef to cook. There may be an occasion when vegan or a special dietary meal is not available. Please inform the leader of dietary preferences when completing your application. The foods of Southern Italy are usually the foods that most participants really enjoy. 

Trip Difficulty

This trip is easy to moderate and suitable for the active and those seeking a more relaxed vacation. It is open to all adults, as long as you are in reasonably good health, get regular exercise, enjoy nature, and want to learn about Italian culture and history. We are transported by private minibus to towns, historic sites, and trailheads for walks. Our walks or hikes will be one to six miles at a leisurely pace on established trails and paths. However, the trails may be narrow and there are sometimes irregular steps to climb. Streets in historic towns are made of cobblestones and are often uneven. It is essential to have comfortable and supportive shoes. As always, the better physical shape you are in, the more you will enjoy the trip. Before the trip, plan some walks and hikes on paths and pavement going up and down hills. 

Equipment and Clothing

The climate in Southern Italy in September and October is usually pleasant, with temperatures in the 70s during the day. Dress will be casual and comfortable. Raingear or an umbrella is always a good idea. A small day pack for water, camera, and a light jacket is handy. If you find it difficult to walk on an uneven surface, a walking stick or trekking poles might be helpful. Your leader will provide additional pre-trip information, including a comprehensive packing list, to registered participants. 


Books about Southern Italy:

  • Astarita, Tommaso, Between Salt Water and Holy Water: A History of Southern Italy.
  • Morton, H. V., Traveler in Southern Italy.
  • Richards, Charles, The New Italians.

Videos and DVDs:

  • "Cinema Paradiso," directed by Giuseppe Tornatore
  • "Johnny Stecchino," directed by Roberto Benigni 
  • "Zampogna: The Soul of Southern Italy," directed by David Marker


Sierra Club is an environmentally focused entity. We are concerned about conservation and sustainability of resources, both locally and globally. Our work is accomplished by volunteers and aided by a salaried staff, encouraging grassroots involvement. Our outings seek to empower participants toward environmental understanding and parallel concerns at home and abroad. Environmental topics on this outing are observing alternative, clean energy sources, preserving natural lands, and recycling. We can observe the practice of "0 kilometer cibo," which is practiced everywhere in Southern Italy -- using food grown locally means delicious and fresh foods. The small nearby growers deliver produce daily to the restaurants. They do not use pesticides, GMO foods, or hormones for animals. We will observe alternative energy sources: wind turbines and solar panels. By bringing our Sierra Club groups to Italy nature reserves, we encourage the Italians to see the value of preserving natural areas of beauty and enlarging parks. We have donated money on past trips to bird sanctuaries so that they can develop more programs that teach students about saving habitat for birds. Our presence has made a difference as we see more trails built, more land put into reserves, reserve areas connected with natural corridors, and new national parks being developed in the areas we visit. 



Stu DeLaCastro has been leading Sierra Club trips for several years. A lifelong backpacker, Stu has hiked in the mountains of Colorado, Wyoming, Montana, Idaho, and Utah. He has also spent time trekking in the Italian Dolomites and in the jungles and mountains of Nepal. Stu enjoys introducing people to adventure and looks forward to sharing his infectious love of the wilds. He is certified in wilderness first aid. Stu lives in the Omaha area with his wife and two daughters.

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