Italy Depart on your overnight flight to Bari, Italy.

Group flight options to/from PDX and prices will be offered once the trip reaches the minimum number of travelers and is officially confirmed, or approximately 10 months prior to the trip start (whichever comes later). Travelers are welcome to join the group flight arrangements or make independent air arrangements.

UArrive in Bari, where the Adriatic meets a lively port city shaped by history, trade, and everyday life close to the sea. A private driver will meet you at the airport and transfer you to your centrally located hotel.

The afternoon is left open to rest or take a first walk through the historic center, where narrow streets, small shops, and open doorways offer a glimpse into local life.

In the evening, we gather for a welcome drink and dinner—an easy, welcoming start to the trip and a chance to get to know one another. Overnight in Bari

Pre-nights are available for those wish to arrive early.

Bari is a city best experienced through its daily rhythms. In the old town, women still make fresh orecchiette pasta by hand, working just outside their homes as they have for generations.

This morning, we will explore the city in a fun and relaxed way with a rickshaw tour, moving through its historic streets and stopping along the way for small tastings that highlight the region’s food traditions. We’ll also visit the Basilica of San Nicola, an important and peaceful landmark in the heart of the city.

In the afternoon, we leave the city behind and head into the countryside, where olive groves stretch in every direction and the pace begins to slow.

After settling in, there is time for an optional, gentle Pilates session to stretch and reset after travel. Dinner this evening is at our countryside resort, known for its local cuisine and warm atmosphere. Overnight in Puglia countryside.

The day begins with a morning mat Pilates session set against the peaceful surroundings of the countryside—a relaxed and energizing way to start the day.

We then travel to Polignano a Mare, one of the most iconic towns along the Adriatic coast, where dramatic cliffs rise above bright blue water. From here, we experience the city from the sea with a private boat ride along the coast including a chance to swim from the boat if you wish.

Afterward, you’ll have free time in town to enjoy lunch by the sea, browse local shops, or simply take in the views.

We return to the countryside in the late afternoon. Tonight dinner is at our resort, once again highlighting fresh, local ingredients. Overnight in Puglia countryside

This morning offers another opportunity for movement in a mat Pilates session before we set out into the Valle d’Itria, one of the most beautiful regions in Puglia. Rolling hills are dotted with olive groves, vineyards, and the region’s iconic trulli—whitewashed stone houses with conical roofs. In Ostuni, known as the “White City,” the sunlight reflects off the limestone buildings, creating a bright and beautiful atmosphere.

We’ll visit a local olive oil producer to learn about (and taste) one of the region’s most important products, followed by a special lunch in the charming town of Cisternino.

Later, we arrive in Alberobello, where entire neighborhoods are made up of trulli houses—especially magical in the late afternoon light. We’ll enjoy a special aperitivo and snacks as we soak up the atmosphere. Overnight in Puglia countryside

After a final morning mat Pilates session at our resort, we depart for Lecce. Along the way, we’ll stop along the Adriatic coast to experience the region’s beautiful white sand beaches with a picnic lunch and possibly a dip in the sea. By afternoon, we arrive in Lecce, often called the “Florence of the South.” The city is known for its intricate Baroque architecture—ornate, expressive, and full of personality. After checking into our centrally located hotel, we’ll take a walk together through the city as it begins to come alive in the evening, followed by dinner. Overnight in Lecce

Today will be another highlight of the trip. We begin with a visit to a local market, where the ingredients of the region come into focus—fresh produce and everyday staples of Southern Italian cooking.

From there, we join a well-known local chef for a hands-on cooking experience, preparing a meal together that reflects the traditions of the area. The experience ends, of course, around the table, enjoying everything we’ve created. The afternoon is free to rest, shop, or continue exploring Lecce at your own pace. Overnight in Lecce

Today we explore both sides of the Salento peninsula—the “heel” of Italy—where two very different coastlines meet. We begin in Otranto, a charming harbor town known for its historic center and cathedral, home to an impressive mosaic floor. There is time to wander, take in the views, and enjoy a relaxed farewell lunch.

Later, we continue to Gallipoli, set along the Ionian Sea. Its old town, surrounded by water, has a distinctly different feel—lively, atmospheric, and deeply connected to the sea.

In the late afternoon, we return to Lecce. Being a Saturday evening, the city has a wonderful energy—families out for a passeggiata (stroll), friends gathering in piazzas, and a lively but relaxed atmosphere that makes for a perfect final night. Overnight in Lecce

This morning you will be transferred to the Brindisi airport for your flight back home. A group transfer to Bari airport is also possible for afternoon flights. For those looking to extend their time in Southern Italy, a post-trip extension to Matera and the Amalfi coast is available.