Luxury Tailor Made Journeys depart on the dates that work for you and feature expert local guides throughout your journey. The itinerary below can be customized to your interests.
Arrive Bari, Puglia
Arrive in historic, lively Bari, where you are transferred to your luxurious hotel.
Puglia | Cone-Shaped Trulli Dwellings
Today, explore central Puglia, beginning in crown-shaped Locorotondo, among the most beautiful villages in Italy. Perched majestically atop a hill overlooking the countryside, the town is stippled with whitewashed, flower-adorned houses with stone staircases and balconies. Continue to Cisternino, where you intersect alleys, climb staircases and walk beneath arches marked with decorative figureheads that are believed to ward off evil spirits. Next, meet a local butcher, who has been providing superior cuts to locals since 1948, and savor a chef-prepared meal in these quaint environs. Proceed to the town of Alberobello, a UNESCO World Heritage Site dotted with distinct, cone-shaped trulli dwellings. Constructed as immigrant domiciles in the 15th century, they were built without binding materials so they could quickly be demolished to avoid property taxes. Before returning to your hotel, meet a maestro trullaro, one of few remaining locals still building trulli the old fashioned way (subject to availability). Seasonally, you can also visit the breathtaking medieval village of Polignano a Mare, enjoying a seafood aperitivo accompanied by local wine at a traditional restaurant overlooking the sea. Return to your hotel, spend the remainder of the evening at leisure.
Lecce | Liquid Gold
After breakfast, head south to Lecce, stopping en route to visit an olive oil producer at an ancient masseria (farming estate). Watch how olives are pressed and sample a variety of local olive oils. Learn how olives have been central to the region’s evolution since Roman times, including its hey-day, when its oil was considered “liquid gold,” a commodity once used to fuel all the streetlights in London. Next stop in the “White City” of Ostuni, a monumental olive-tree-swathed plateau of the lower Murgia. Take a guided walk along its sun-drenched streets and quaint, cobbled alleyways, taking in panoramas of the surrounding landscape and Adriatic Sea. See the Rione Terra district at the heart of the medieval walled village and the magnificent Gothic cathedral. Also behold the city’s iconic olive trees, with their massive gnarled trunks, some of which may date back 3,000 years. Continue to the oldest bakery in Ostuni, set in a 14th-century building, to discover how this family-run business has turned out renowned bread, focaccia and cookies from an olivewood-fired oven since the 1920s. Then, proceed to Lecce, where you check in to your hotel.
Lecce | Jewel of Salento
Spend today exploring Lecce, a Baroque “Florence of the South.” Take a scenic walking tour through town, seeing the Piazza del Duomo, the masterful Basilica of Santa Croce and the Roman amphitheater. Attend a pasticciotto pastry-making class, learning the secrets behind preparing this beloved, custard-filled confection. Next, master the intricate art of papier-mâché, which has played a significant role in Lecce’s culture and religious heritage since the 17th century. After creating your own masterpiece, return to your hotel for an afternoon at leisure.
Otranto | Bridge to the Mediterranean
Travel to Otranto, Italy’s easternmost city, a “bridge” linking the country to the Mediterranean. Upon arriving in the afternoon, take a scenic drive along the coast, seeing the Castro, Tricase Porto and Grotta della Poesia. Enclosed by Aragonese walls, Otranto’s Old Town overlooks the crystalline waters. Punctuated by white houses and alleys paved in stone, it was founded by the Greeks in the Byzantine period as a commercial, political and religious hub and a major port of trade with the Orient. The medieval town center — once a vast stronghold — reminds visitors of the threats posed by the Turks, the culmination of which involved a tragic invasion in 1480. Otranto’s cathedral houses a spectacular mosaic floor from the 12th century that blends pagan, Old Testament and New Testament imagery to capture the culture of the time. Return to your hotel in Lecce for an evening at leisure.
Matera | Singular Cave Dwellings
Transfer to Matera, among the most ancient cities on earth. Continually inhabited for 10,000 years, this magical open-air museum — a UNESCO World Heritage Site — is an inimitable tangle of cave-dwellings, magnificent Baroque palaces and beautiful stone churches. At dusk, the biblical landscape resembles an enormous crèche. Make your way through the sassi (districts of the city) to see the dark caves of the Murgia; the rock-hewn churches of religious communities; and the elegant streets of the Piano, replete with 17th-century monasteries and palaces. Descend into deep cisterns and canals once used for water collection to complete your exploration of this ancient city.
Amalfi Coast | Ruins of Pompeii
Depart for the beautiful Amalfi Coast, stopping en route in Pompeii, where you set out on a two-hour walking tour of the once-opulent town. The extensive and varied ruins of Pompeii offer rich insight into the history of the Roman Empire. Destroyed by the volcanic eruption of Mount Vesuvius in AD 79, this unearthed treasure reveals temples, forums, an amphitheater, brothels, and the casts of the people killed by the falling ash and pumice stone. Continue to your luxury hotel in Sorrento, featuring unrivaled views of the Gulf of Naples.
Capri | Breathtaking Blue Grotto
Leave mainland Italy behind as you board a ferry (weather permitting) to stunning Capri. Alternately, transfer to the island by private boat. Upon arrival, stroll Capri’s charming, boutique-lined streets. Then, board a public boat that whisks you to the spellbinding, iridescent Blue Grotto. Observe the magical light that illuminates the cave’s rocky walls. Continue sightseeing, or choose to explore beautiful Villa San Michele in Anacapri the Church of San Michele or the summit of Monte Solaro, reached by chairlift. Return to your hotel on the mainland for an evening at leisure. You can also choose to meet your Guardian Angel for a tasting of exquisite, neon-yellow limoncello, a locally produced liqueur and digestive made from lemon zest-infused alcohol.
Amalfi Coast | Gorgeous Coastal Villages
Skirt the fabled Amalfi coast by private vehicle, starting with a visit to the enchanting village of Ravello, with its stunning coastal views. Take in vistas from the lovely Villa Rufolo before continuing to Amalfi. See the Duomo, fronted by a beautifully hued, 13th-century façade. Pause for lunch in a delightful, sea-view restaurant. Continue north seeing a kaleidoscope of lagoons, sandy coves, vertiginous cliffs and sun-baked villages en route to vibrant Positano. Meander along the village’s narrow lanes, descending toward the glistening sea, where elegant restaurants serve the catch of the day. You may choose to take a sunset cruise along the beautiful Amalfi Coast, at an additional cost, jetting by private motor boat as you savor a twilight dinner cooked by your onboard chef. Follow the coast to elegant Sorrento, a Belle Époque treasure of graceful streets with stunning views across the Gulf of Naples. Alternately, spend the day privately exploring the Sorrentine Peninsula by Vespa, discovering neighborhoods and sights not reachable on foot. Along the way, pause to take photos, learn the wondrous history of the region and interact with locals. You can also stop for coffee and a delicious pastry. Conclude with an unforgettable ride along the Sorrento coast.
Transfer to the Naples airport and board your departure flight.
Enhance Your Journey
Elevate your experience with a host of options available for an additional cost.
TAKE A FOOD-THEMED WALKING TOUR IN BARI
Explore Bari, Puglia’s bustling capital city, where you traverse its winding streets and pedestrian squares on a food tour. Taste culinary treasures, including creamy burrata, handcrafted salami, handmade pasta and garden-grown vegetables sold from doorways, local beer and focaccia. Finish with a scoop of lush gelato or cartellate, traditional Christmas fritters.
Enjoy A Wine Tasting
Attend a wine tasting of celebrated Puglian vintages at 16th-century Castello Monaci. Tour its impressive wine museum, taking a moment to appreciate sweeping views over the stunning vineyard. Then, sit down to a candlelit Puglian dinner in a grand, private room within the historic castle.
SAVOR CRUDITÈ DI PESCE IN GALLIPOLI
Take an evening stroll through the historic town center of medieval, seaside Gallipoli. The waters off its coast offer up a veritable feast, which you can discover firsthand at the fisherman’s market. Enjoy a glass of white wine and a dish of fish crudités. Finished with a whirl of olive oil and turn of black pepper, it’s enjoyed directly in front of the stalls.
VISIT A LOCAL DAIRY FARM
Visit a local dairy farm along coastal Litoranea Salentina, a scenic area that inspired Virgil’s epic poem The Aeneid. The stunning landscape is dominated by scrubland and steep, myrtle-covered cliffs that plunge to the azure Cape of Otranto. As you appreciate the farm’s rambling, sheep-dotted pastures, sample specialties in this beautiful, tranquil paradise.