• A fully guided small-group experience with Heather accompanying the group from arrival in Brindisi through departure from Bari

• A women-only group limited to six travelers

• Single-occupancy accommodations throughout the tour, no roommates required

• Pre-departure guidance and support before you travel

• A detailed digital itinerary with daily plans, confirmations, and important travel information

• On-tour support throughout the journey

Our journey begins just south of Lecce, where we’ll settle into a traditional masseria surrounded by the quiet beauty of the Salento countryside. After arriving, the day is yours to slow down, unpack, and ease into the rhythms of southern Italy before we gather that evening for a welcome dinner at the farm. We will enjoy a feast of local, traditional foods as we get to know one another.

The following day, we’ll spend a full day exploring the historic city center of Lecce, a Baroque jewel known for its honey-colored stone, ornate churches, and lively local atmosphere. From its ancient Roman Amphitheater to the stunning Baroque facades, Lecce is filled with interesting spots. We’ll have time to wander, learn the city's stories, and enjoy dinner together in Lecce before returning to the peaceful comfort of our masseria.

• Private transfer from Brindisi Airport to the Masseria upon arrival

• Two nights at the four-star Masseria Lilei, located in the countryside south of Lecce. You have a double room of your own and breakfast each morning

• Welcome dinner at the Masseria as we begin our journey together

• Private transfers to and from Lecce

• Private departure transfer from the Masseria to our next destination

From Lecce, our private driver will take us north along the Adriatic coast, where we’ll spend the day discovering seaside towns, quiet villages, and scenic stretches of coastline before settling into Ostuni for the next three nights.

Known as the “White City,” Ostuni will be our home base in Puglia, where we’ll stay in a private villa in the heart of the historic city center. The residence will be ours to enjoy, with private rooms, inviting shared spaces, and breakfast served each morning; an intimate and comfortable way to experience life in one of Puglia’s most beautiful hill towns.

During our stay, we’ll have a private driver each day to take us into the surrounding countryside, villages, and coastal towns, and a private guide to lead us through the history of the area. From Grottaglie, celebrated for its beautiful ceramics, to Monopoli, a fortified seaside town with winding lanes and a lively harbor, we’ll spend our days exploring, tasting, and discovering the traditions that make this region so memorable.

We’ll also experience Puglia from the water with a private half-day boat tour along the Adriatic coast, traveling between Polignano a Mare and Monopoli. With time to swim in the clear blue sea and enjoy snacks and drinks on board, this will be a relaxed and scenic way to take in the coastline.

• Private transfer from the Masseria in Lecce to the Villa in Ostuni

• Private driver each day for our regional outings

• Three nights at a private villa in the historic city center in Ostuni with breakfast included each day. Each guest has their own private room and bathroom

• A private guide joining us in the towns and villages we visit

• Visits to coastal towns, villages, and countryside locations throughout the region

• Private half-day boat tour along the coast between Polignano a Mare and Monopoli, including time to swim during the boat tour, as well as snacks and drinks served on board

• A visit to a family-owned vineyard for a tasting of the local wines

Matera is one of the most extraordinary places in southern Italy, a city carved into stone and shaped by thousands of years of human history. Known for its ancient cave dwellings, or Sassi, Matera offers a glimpse into one of the world’s oldest continuously inhabited settlements, where homes, churches, cisterns, and passageways were built directly into the rock.

During our time here, we’ll explore the winding stone lanes, cave churches, sweeping overlooks, and layered history that make Matera feel unlike anywhere else in Italy. A private guide will bring the city’s remarkable story to life, helping us understand how early civilization, sacred spaces, and everyday life were etched into the landscape. A walk across the river gorge to the ancient caves will give us a glimpse of what life was like in this early human settlement.

We’ll also take part in a hands-on bread-making experience, connecting us to one of Matera’s most meaningful food traditions before we close our journey with a farewell dinner.

• Private transfer from our villa in Ostuni to our hotel in Matera

• Two nights at the four-star La Locanda di San Martino in a superior room with breakfast included

• Traditional bread-making experience

• Private guided tour

• River gorge walk to Matera caves

• Private departure transfer from our hotel to the Bari Airport