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Granted, there are many ways to visit Italy — but experiencing the real, authentic Italy can be rare. If boarding a bus at dawn each day, seeing tourist attractions and returning home exhausted is not what you are looking for, then this Italy travel itinerary is for you.
In other words, you may want to experience the “real” Puglia and live its lifestyle on a fully guided tour with me — an Italian-speaking citizen of Italy — and with Gianfranco, who grew up in Southern Italy and knows the people we’ll meet by name. All at a pace that’s naturally relaxing:
Plus, group size is small for this trip — 16 people — adding to this unique experience! Three home city bases – packing and unpacking every day.
| Ostuni - the White City | 3 nights | 4-star hotel in a historic palazzo overlooking the old town |
| Alberobello - the Town of Trulli | 4 nights | renovated 4-star hotel with a pool and its own restaurant - a short walk from the Trulli |
| Bari on the Adriatic Sea | 2 nights | brand-new 4-star hotel in the city center |
DAYS 1–4 · MAY 13–16
DAY 1 — THURSDAY, MAY 13
Departure from the U.S.A., flying overnight to Italy.
DAY 2 — FRIDAY, MAY 14 — ARRIVE IN PUGLIA
Arrive at Bari Airport mid-morning. You will be greeted by Carol and Gianfranco. After luggage delivery, your private coach takes you one hour south to Ostuni, a whitewashed town on a hill above a sea of olive trees. After a little time to “settle in,” we’ll enjoy a “meet and greet” dinner and group introductions. The rest of the evening is yours to rest or take a passeggiata (walk) through the white lanes.
DAY 3 — SATURDAY, MAY 15 — THE MASTER CHEESEMAKER
After a leisurely breakfast, a short drive into the countryside to a working masseria (farm) near Ceglie Messapica. You’ll watch the master cheesemaker pull mozzarella and burrata by hand right in front of us — and then we’ll taste it, still warm, with the farm’s own vegetables, cured meats and bread from the wood oven. Not to be missed! Afternoon free to relax in Ostuni.
DAY 4 — SUNDAY, MAY 16 — LECCE, THE FLORENCE OF THE SOUTH
We’ll depart for Lecce, the baroque jewel of Southern Italy, with an English-speaking guide: the Basilica of Santa Croce, Piazza Sant’Oronzo with its Roman amphitheater, and the charming old center. Lunch in Lecce, then return to Ostuni for the evening.
DAY 3 · SATURDAY, MAY 15
This is the morning you’ll talk about on the flight home! We’ll visit a working masseria near Ceglie Messapica — stables, gardens, cellars — where the master cheesemaker heats the curd, pulls it into long ropes and closes a burrata in his hands in about twenty seconds.
This is not a shop with a demonstration. It’s the farm’s real morning production, and we are standing in it — an experience you simply can’t book on your own.
Then we’ll sit down together: mozzarella still warm, burrata, the farm’s vegetables and cured meats, bread from the wood oven and a glass of local wine. A true Lunch of Longevity: fresh, simple food shared in good company — the Mediterranean diet as it’s really lived.
DAY 4 · SUNDAY, MAY 16
One hour south of Ostuni, Lecce is one of the most spectacular baroque cities in Italy — yet almost undiscovered by tourists outside Europe. Its soft golden limestone was carved into lace by generations of stonemasons; the façade of Santa Croce alone took nearly a century to complete.
We’ll enjoy a guided walking tour at a relaxed pace: the basilica, Piazza Sant’Oronzo with a Roman amphitheater right in the middle of it, the courtyards and cafés of the old center. You’ll have time for lunch and a pasticciotto, Lecce’s famous pastry, before we return to Ostuni for a free evening.
DAYS 5–7 · MAY 17–19
DAY 5 — MONDAY, MAY 17 — INTO THE VALLE D’ITRIA
After breakfast we’ll leave Ostuni for the scenic road through Martina Franca and Locorotondo, two charming villages of white stone, and arrive in Alberobello in the afternoon. After dinner, an evening guided walk through the trulli — the cone-roofed houses that make this UNESCO town unlike anywhere else in the world — lit up and quiet, once the day visitors have gone. You’ll see why we chose to sleep here!
DAY 6 — TUESDAY, MAY 18 — COOKING AND WINE
Immersion in local cuisine: an interactive cooking lesson at our hotel on homemade pasta and the typical dishes of Puglia, followed by lunch of what we prepared — putting into practice the principles of the Mediterranean diet, conviviality included! In the afternoon, a short walk to a wine tasting and a visit to the town’s wine museum.
DAY 7 — WEDNESDAY, MAY 19 — MATERA
A full day in Matera, the city of stone (see below for description).
DAY 8— THURSDAY, MAY 20 — FREE DAY
Enjoy the day in Alberobello to explore, shop or to relax by the pool! Enjoy some free time to prepare your luggage before we leave for the historic city of Bari the next morning.
DAY 7 · WEDNESDAY, MAY 19
About an hour and twenty minutes from Alberobello, just across the border into the region of Basilicata, Matera is one of the oldest continuously inhabited cities in the world — people have lived here for nine thousand years. The houses are caves carved into the side of a ravine, stacked one on top of the other, and the roof of a church is somebody else’s street.
With our English-speaking guide we’ll explore the Sassi: the two ancient quarters, a cave house furnished as it was when families still lived in it, the rock churches, and the breathtaking lookout over the gorge — a view you’ve seen in more films than you think. Lunch in Matera, free time to wander, and return to Alberobello for the evening.
DAYS 8–10 · MAY 20–22
DAY 9 — FRIDAY, MAY 21 — DEPART FOR BARI
A leisurely morning: breakfast, check-out, and an hour’s drive to Bari. We’ll arrive around noon and check in to our hotel in the afternoon. The rest of the day is yours to stroll, shop in the elegant Murat district, or relax on the lungomare (seafront promenade).
DAY 10 — SATURDAY, MAY 22 — BARI VECCHIA
After a leisurely breakfast, a guided walking tour of the old town: the Cathedral, the Basilica of San Nicola — a place of the heart for so many Italian-Americans — the maze of courtyards with their little shrines, and the street where the women still make orecchiette by hand at their doorsteps. Afternoon free. In the evening, our celebratory farewell dinner!
DAY 11 — SUNDAY, MAY 23 — RETURN TO THE U.S.A.
After breakfast at the hotel, we’ll say our goodbyes to new friends, new experiences and to Italy, and return home with new perspectives on living life well. Depart for Bari Airport (about 20 minutes from the hotel).
OUR HOTEL
A brand-new 4-star hotel in the city center, a short walk from the old town. Breakfast included
WANT TO LEARN MORE ABOUT AUTHENTIC ITALIAN TRAVEL ADVENTURES?
THE PRACTICAL PART
“Authentic Italy” excursions leave a rich and lasting mark on everyone who joins, offering fresh perspectives on life and living well. The vibrant culture, incredible regional cuisine, and beautiful accommodations are simply unforgettable.
International flights, travel insurance, lunches and dinners not listed, gratuities, optional activities, personal extras at the hotels.
Twelve rooms in each hotel: doubles, twins and single rooms. Traveling on your own? You are very welcome — there is no limit on single rooms.
For those interested in traveling together, a suggested flight itinerary from Chicago O’Hare to Bari will be provided.
Please note: Rates have been updated to reflect shifts in the USD/EUR exchange rate as well as rising hotel and transportation expenses in Italy.
Special Early Registration Savings: Lock in your spot before November 1, 2026 to receive a $500 discount per person! This offer ends on November 1, 2026.
Please note: There will be walking
The old towns are cobblestone, and Matera has stairs and slopes. You don’t need to be an athlete but able to be comfortable on your feet for a couple of hours at a time and able to walk at least a mile or two on uneven surfaces.
Italians walk and we will be living the Italian lifestyle. Streets and sidewalks are not smooth or paved, escalators do not exist and taxis are not available.
READY TO JOIN US?
I’d love to hear from you! If you have questions or would like to hold a room while you think it over, just send me an email. I answer personally, and I’m always happy to get on the phone.
Places are limited to twelve rooms, and we confirm them in the order we hear from you.
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