Days 1 & 2 — Depart the U.S. for Sicily, Italy

Depart the U.S. and arrive in Catania, located on Italy’s autonomous island of Sicily. Transfer by motorcoach to Taormina and settle into your hotel overlooking the Ionian Sea. Tonight, gather for a welcome dinner at a local restaurant. (D)

Day 3 — Taormina

Take a walking tour of this delightful medieval town, including the spectacular ancient Greek Theater dating to the 3rd century B.C., the 13th-century cathedral, and grand Piazza Vittorio Emanuele. During an afternoon and evening at leisure, relax by the hotel pool, visit a lovely Taormina beach, or stroll past boutiques and restaurants on the Corso Umberto. (B)

Day 4 — Agrigento and Taormina

Set out on a full-day excursion to the Valley of the Temples, situated in the architectural zone of Agrigento, a World Heritage site where the vestiges of a once-great Greek city remain in impressive Doric temples and sanctuaries. Explore the stunning Temple of Concordia, built in the 5th century and still largely intact, and learn the history of these ancient ruins on a visit to the Archaeological Museum.  Return to Taormina late this afternoon and gather for dinner together. (B,L,D)

Day 5 — Mount Etna and Taormina

Just beyond Taormina looms legendary Mount Etna, an active volcano considered by the ancient Greeks to represent Vulcan, the god of fire. Thousands of years of flowing lava has transformed the mountain into a fertile landscape where citrus trees and vineyards flourish. Visit a family-run working farm on Etna’s slopes for a lunch set among lemon tree groves, and learn to make cannoli, a traditional Sicilian dessert. Arrive back in Taormina in the mid-afternoon and take the rest of the day to enjoy the town on your own. (B,L)

Day 6 — Matera

Take the ferry from Sicily to Calabria, the toe of Italy’s “boot,” and continue by road to the rugged landscapes of Basilicata. Late this afternoon, arrive in Matera, a limestone tufa town whose troglodyte churches and dwellings, known as sassi, have been designated a World Heritage site. Your home for the next two nights is a renovated cave dwelling in the city’s historic district. (B,D)

Day 7 — Matera

Delve into this enchanting village on a walking tour today, venturing into ancient caves where humans lived as far back as the Paleolithic era. Discover the unique urban plan established centuries ago and still very much intact and learn how Matera was transformed from “the shame of Italy” into a World Heritage site during the late 20th century. With more than 100 churches built from local rock, Matera is often compared to Jerusalem’s Old City. After lunch on your own, take the rest of the afternoon to explore Matera as you wish. Meet up for dinner tonight at a restaurant in town. (B,D)

Day 8 — Alberobello and Lecce

Journey to the province of Apulia, making a first stop in Alberobello, known for its trulli—hundreds of whitewashed cottages topped with conical stone roofs. Explore this fairy-tale like scene on foot, venturing into narrow alleyways and visiting artisan’s workshops and recreation of an inhabited trulli. Following lunch at a local restaurant, continue into Italy’s “heel” to Lecce, arriving in time for dinner at the hotel.

Day 9 — Lecce

Immerse yourself in the “Florence of the South,” so named for its harmonious golden-stone architecture—and its unique, ornate style known as barocco leccese. Admire the intricately carved façades, adorned with cherubs and monsters, fruits and flowers. Visit the 15th-century Palazzo Vescovile and the elaborately decorated church of Santa Croce, and stroll through a lovely piazza to the Duomo. Lecce is known for its papier-mâché tradition, begun in the 17th and 18th century as a way to create sacred objects for the city’s churches using inexpensive materials. Learn how artisans craft all manner of figures and objects during a special papier-mâché demonstration. Then enjoy a free afternoon to explore before dinner together this evening. (B,D)

Day 10 — Otranto and Lecce

Venture to the beautiful walled town of Otranto, set on the shores of the Adriatic. On a walking tour, visit the Aragonese castle, an imposing fortress surrounded by a moat that was built in the 15th century shortly after the town was invaded by the Ottomans. In the town’s Norman cathedral, admire a wall-to-wall mosaic floor created in 1166. Then head to a local winery for a tasting and lunch, before returning to Lecce mid-afternoon. Dinner tonight is on your own. (B,L)

Day 11 — Polignano a Mare and Sorrento

Depart this morning for Polignano a Mare, a historic coastal town set on limestone cliffs above the Adriatic. After lunch at a trattoria, head west across Italy to the Bay of Naples, where your home for the next four nights is the waterside town of Sorrento. (B,L)

Day 12 — Pompeii and Sorrento

Step into history at the World Heritage site of Pompeii, a city frozen in time when the eruption of Mt. Vesuvius in A.D. 79 covered it in a thick layer of ash. On a special guided tour, stroll ancient streets, viewing the remains of homes and shops, and learn about the ongoing archaeological work that is shedding light on life during the Roman Empire. Late this afternoon, roll up your sleeves for a hands-on Neopolitan cooking lesson, then sit down to dinner to savor the fruits of your labor. (B,D)

Day 13 — Sorrento and Capri

A morning hydrofoil ride whisks you to the nearby island of Capri, a popular resort since Roman times. Meander through the charming Capri town and visit the terraced Gardens of Augustus, set high on a hillside and affording gorgeous views of the azure sea. After free time to discover the island at your own pace, return to Sorrento in the early afternoon and enjoy the remainder of the day at leisure. (B)

Day 14 — Sorrento and the Amalfi Coast

Embark on a breathtaking drive along the Amalfi Coast, one of Europe’s most scenic routes, which hugs the cliffside above the Tyrrhenian Sea. As you wend your way toward Amalfi, make stops to take photos or visit interesting sites. Your final afternoon is yours to spend as you wish. Tonight, bid “arrivederci” to Italy at a farewell dinner. (B,D)

Day 15 — Depart for the U.S.

This morning, transfer to the Naples airport and connect with your return flight to the U.S. (B)