PUGLIA ~ The Heel of the Boot of Italy

It’s a region and culture that’s like nothing you’ve encountered before. Think white-washed trulli, Baroque architecture, gnarled olive trees, grazing sheep and cows, hand-made pasta from local wheat, and fish caught fresh from the stunning azure sea. Plus it’s a laid-back, sun-kissed region, that makes you want to kick off your shoes and stay for a while – perhaps under the shade of an ancient olive tree.

RICH WITH Experiences

We’ve created an itinerary that reflects the unique culture of stunning, sun-kissed Puglia. We’ll visit the golden beaches and white-washed alleyways of Otranto, take in the stunning Baroque architecture of Lecce, meander the trulli-lined avenues of Alberobello and marvel at the ancient cave dwellings of Matera. Get ready to explore this spectacular region’s history, art and natural beauty while enjoying delectable meals that reflect the region’s rich mix of cultures. Each day we’ll experience a different aspect of Puglia, while leaving just enough time on your own to explore, shop, or simply relax take it all in.

ITINERARY

DAY 1: Arrival Otranto

• Highlights: Arrival and welcome
• Dinner

Benvenuti in Puglia! We’ll meet up on the afternoon of day 1 in the lobby of our stunning masseria (farm estate) to officially kick off our tour with an overview of the exciting itinerary. For easiest arrival, we recommend flying into Brindisi Airport (details will be supplied). After some time to relax, unpack and get settled, we’ll enjoy a special welcome dinner prepared by our excellent Pugliese chef.

DAY 2: Otranto

• Highlights: Excursion to Otranto
• Breakfast, dinner

This morning, after a delicious breakfast at the masseria, our drivers will shuttle us to the ancient town of Otranto, that enchants from the very first moment. Situated on a rocky bluff overlooking the Adriatic sea, its white buildings contrast with the dazzling azure waters below. Its roots are the ancient Greek city Hydrus, and its coastal position, overlooking the Balkan countries and Greece is an integral part of its deep history – including that of a bustling Roman port town. UNESCO awarded Otranto the cultural heritage title of “messenger site of peace”. Here, our guide will lead us through the town’s rich history, with visits to its most important sites. Afterwards, you’ll have free time to explore the historic center and enjoy lunch on your own – perhaps at a seaside cafe.

In the afternoon we’ll return to the masseria where you might enjoy a dip in the pool, a cool drink under the shade of an olive tree or even arrange a shuttle to a local beach. This evening we’ll return to Otranto for an authentic, Puglia-style dinner in a local trattoria.

DAY 3: Lecce

• Highlights: Excursion to Lecce, guided tour of historic center
• Breakfast, lunch

This morning, after breakfast, we’ll take an exciting excursion to Lecce, often referred to as the Florence of the South. Built in the Baroque style, with the local, cream-colored limestone, its architectural surprises are around every corner. The city is a an artistic masterpiece, with a blend of historical richness that includes ornate churches, grand piazzas, and ancient Roman ruins. Here you’ll find also find plenty of shops selling local olive oil, wine and ceramics. To thoroughly enjoy the local cuisine we’ve arrange lunch at an exceptional restaurant.

As the afternoon sun strengthens, we’ll head back to the masseria for time to relax and cool our toes in the pool. This evening you’re on your own for dinner, that you might enjoy right here at the masseria or our drivers can shuttle you to nearby Otranto.

DAY 4: Putignano

• Highlights: Transfer from Otranto to Putignano with stop at Ostuni
• Breakfast, lunch, dinner

This morning we say goodbye to our coastal accommodations are our private drivers transport us to the land of the ancient trulli and the village of Putignano, near Alberobello. Along the way we’ll make a stop at the village of Ostuni, where you can wander the winding avenues and shop and explore on your own. Then we’ll meet up to make our way to a nearby olive grove for a tour of a family grove (the size and age of the trees is truly astounding!) followed by an olive oil tasting and light lunch.

This afternoon we’ll arrive in Putignano, and our unique, historic accommodations – each room situated in different building along the ancient, white-washed avenues of the charming village. After an evening walking tour, we’ll gather for a regionally inspired dinner.

DAY 5: Alberobello

• Highlights: Excursion to Alberobello, food experience
• Breakfast, dinner

This morning, after we gather together for breakfast, our drivers will take us to the nearby town of Alberobello, known for its fascinating trulli building. These typical limestone dwellings are remarkable examples of dry-stone construction using a prehistoric building technique that is still in use in this region. Dating back centuries, trulli have characteristic conical roofs built up of limestone slabs, and their highest concentration, and best preserved examples, are in the town of Alberobello itself. Here we’ll take a short walking tour, followed by free time for lunch on your own.

In the afternoon we’ll return to Putignano for some time to relax and refresh. This evening it’s back to Alberobello for a delightful food experience. Details to come.

DAY 6: Matera

• Highlights: Excursion to Matera
• Breakfast, lunch, dinner

Today, after breakfast, our drivers will transport us to Matera, a UNESCO World Heritage site, and a city of stones, cave dwellings and rock churches. It is one of the oldest, still inhabited cities in the world, and still shows evidence of human settlements dating back to the Palaeolithic period in its natural caves. Here we’ll explore this magical town at its historic core, before enjoying lunch in one of our favorite restaurants, nestled in a cave.

This afternoon we’re back to Putignano where you’ll enjoy free time for some last-minute shopping, or perhaps shuttle to Alberobello. Our farewell dinner this evening will be served up at a local trattoria, as we celebrate a spectacular week spent together.

DAY 7: Departure 

This morning our drivers will provide a group transport to Brindisi Airport.

The Unexpected is Part of the Journey: Note that this itinerary is subject to slight changes. Should that happen, just know that we will include something that is equally as wonderful and interesting. The quality of your experience is never at risk. ☺️

WHAT’S INCLUDED

• 7 days/6 nights at 4-star accommodations (3 nights Otranto, 3 nights Putignano)
• Ground transportation (excluding arrival to Otranto)
• Private group transport on departure morning (Putignano to Brindisi Airport)
• All breakfasts
• 3 lunches with local wine
• 4 regionally inspired dinners with local wine
• Food experiences
• Olive oil tour/tasting
• Guided walking tours
• Daily accompaniment by Pamela Haack
• Daily excursions to some of Puglia’s most exciting and fascinating locations and sites
• Entrances fo all museums/sites included in the trip itinerary
• Free time to explore and shop on your own

Not included: Airfare, transportation and meals outside of that which is specifically listed in the trip package, gratuities for hotel staff and drivers.

ACCOMMODATIONS

Masseria dei Monaci 

The word masseria comes from the Latin word messa, which means farm estate. Masseria dei Monaci is a restored estate that has been tastefully converted to a modern, 4-star accommodation, while carefully preserving its past. Situated near the sea, you’ll enjoy sea breezes, inviting courtyards and beautifully appointed, spacious rooms.

Petrantiche Albero Diffuso

A fabulously unique accommodation, 4 star Petrantiche boasts chic, individual apartment-style rooms, situated in various avenues in the town’s adorable historic center. All within 200 meters of reception and breakfast room, and each with unmistakeable Pugliese character (think limestone arches and white-washed exteriors), here, one truly feels like a local.

DATES & DETAILS

• Dates:
  • June 14-20, 2026
• Trip Price: $3,995 – $4,495 USD (choose room type upon booking)
• Room Descriptions:
  • Masseria dei Monaci, Otranto: All rooms offer equal amenities and include a private bathroom with shower, bidet, hairdryer, air-conditioning, private entrance and mini-bar. Rooms are situated on two levels, with a bedroom loft.
  • Petrantiche Albergo Diffuso, Putignano: All rooms offer equal amenities, but differ in layout and unique features, and are situated throughout the historic center of Putignano – no more than 200 meters from the reception/breakfast room. All include a private bathroom with shower, bidet, hairdryer, air-conditioning and private entrance.
    • Single Occupancy Superior
    • Double Occupancy Deluxe
    • Double/Twin Occupancy Superior Deluxe 
• $700 deposit is required to book your space on this tour
• Terms and Conditions

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