Italy: Puglia
Puglia & Matera | October 17–24, 2027
From the whitewashed hilltop town of Ostuni to the sun-drenched coast of Polignano a Mare, discover a thoughtfully curated journey featuring local food, meaningful experiences, beautiful boutique accommodations and daily yoga.
Booking will be live for this trip coming soon!
See our itinerary below and join the first access list below.
Sample Itinerary
Saturday, October 16 | Arrival Day
Arrive in Brindisi
Transfer to hotel and settle in
Dinner at the hotel
Stay at a 5-star boutique masseria in the countryside near Ostuni
Sunday, October 17 | Alberobello, Locorotondo & Cisternino
Visit the trulli houses of Alberobello
Lunch in the hilltop town of Locorotondo
Chestnut festival in Cisternino
Aperitivo and a vineyard visit
Dinner at the hotel
Monday, October 18 | Martina Franca, Vineyards & Ostuni
Drinks in Martina Franca
A second vineyard visit
Tuk-tuk tour of Ostuni, the White City
Lunch and wine tasting in Ostuni
Dinner in Ostuni
Tuesday, October 19 | Polignano a Mare
Private boat tour along the coast
Wander and lunch in Polignano a Mare
Street food tour and wine tasting
Dinner at a cliffside restaurant
Wednesday, October 20 | A Day at the Hotel
Cooking class
Wine tasting
Pizzica dance class
Optional massage
Dinner at the hotel
Thursday, October 21 | Travel to Matera
Check out and travel to Matera
Check in to a boutique cave hotel in the historic Sassi district
Curated dinner
Stay at a restored cave hotel in the Sassi di Matera
Friday, October 22 | Exploring Matera
Private walking tour of Matera's cave dwellings and churches
Optional hot air balloon ride at sunrise
Special dinner in a candlelit chapel
Saturday, October 23 | Departure Day
Transfer to the airport
Fly home, or continue on to the optional Rome extension
Optional 3-Day Rome Extension
Saturday, October 23 | Arrive in Rome
Fly or train from Brindisi to Rome
Transfer to hotel
Aperol spritzes on the rooftop
Dinner near the hotel
Sunday, October 24 | Trastevere & the Jewish Ghetto
Explore Trastevere and the Jewish Ghetto
Wine tasting
Dinner at a local trattoria
Monday, October 25 | Ancient Rome
Underground Colosseum tour
Lunch at a historic salumeria
Cocktails on a rooftop
Dinner on your own
Tuesday, October 26 | Final Day in Rome
A leisurely final day in the city
Dinner at a secret supper or local osteria
Wednesday, October 27 | Return Home