Meals included: Breakfast, Lunch

Overnight:  Bari, Grand Hotel Delle Nazioni (or similar)

Late Morning/Lunch:  Winery and Olive Estate

This morning we head to an historic estate in the middle of almost 40,000 olive trees in the heart of the DOCG wine appellation Castel del Monte.  We will enjoy a guided tour of the estate which includes impressive underground cellars deep in the tufa rock.  We will have lunch paired with their delicious wine and olive oils.

Late Afternoon:  Castel del Monte Fortress

We will drive through the scenic Murgia region, home to one of the last wild steppe ecosystems in Italy with abundant olive groves and typical white stone walls. Our destination is the otherworldly octagonal castle Castel del Monte built by Emperor Frederik II in A.D. 1240.  We will visit the interior with a local guide to learn about this eclectic emperor and this architectural wonder. 

Evening: OYO in Bari

Tonight you have the rest of the evening and dinner on your own. Talk a walk along the promenade, shop, and enjoy our last night in this historic seaside gem.

Meals included: Breakfast, Dinner

Overnight:  Casalabate, Masseria Caretti Grande (or similar)

Late Morning:  Check-out and Drive to Monopoli

We are driving south along the sea today to our next hotel location. En route we will make a stop at scenic Monopoli.

Lunch:  OYO in Monopoli

Spend a relaxing few hours of free time to wander this quaint little town and savor lunch on your own. 

Late Afternoon:  Caves of Castellana

Our next stop is at a unique destination unlike anywhere I have ever visited in Italy!  The limestone cave complex at Castellana is a unique natural system of tunnels and grottos. We will walk the accessible portions of the cave with a local expert to discover unique features such as The White Cave, The Owl, and more. 

Evening:  Masseria Check-in

We have a traditional homemade dinner at this fortified farmhouse, our home for the next three nights. With gardens, large grounds, a pool, and indoor lounging areas this masseria is a wonderfully relaxing place. 

Meals included: Breakfast, Lunch

Overnight:  Casalabate, Masseria Caretti Grande (or similar)

Late Morning:  Gallipoli

This morning we will take a walk through the beautiful city of Gallipoli. The old town center sits on a tiny island connected to the mainland by a 17th-century bridge, and is almost completely surrounded by defensive walls built mainly in the 14th century.

Lunch:  Winery

We will visit a winery that marries the old and new with a modern facility for wine-making and a museum focused on the family's extensive history with the property. We will have lunch in the garden, surrounded by grapevines, olive trees, flowers, and cacti.

Late Afternoon:  Lecce

This stunning city is known as the Florence of the South, but Lecce also has its own Baroque style.  We will get to know this city with a local guide, and the late afternoon is the perfect time to see the soft pink light reflecting on the white local stone.

Dinner:  Lecce OYO

Dinner is on your own this evening. Your local guide and tour leader can offer recommendations.

Meals included: Breakfast, Lunch, Dinner

Overnight:  Casalabate, Masseria Caretti Grande (or similar)

Late Morning:  Garden Foraging  & Cooking Class

The owner of the masseria will take us on a stroll around the property's gardens, gathering vegetables and herbs for our cooking class in the kitchen.

Lunch: Masseria 

We will enjoy a relaxed lunch with our cooking class bounty, with perhaps a little time for nap or stroll around the property or a quick dip in the pool. 

Late Afternoon:  Abby of Santa Maria di Cerrate & Ostuni

En route to our dinner destination this evening, we will stop at this Abby, a hidden gem of medieval art and architecture, before reaching Ostuni with its traditional homes. 

Dinner:  Local restaurant

Dinner tonight is served in a well-known restaurant favored by locals.

Meals included: Breakfast, Dinner

Overnight:  Matera, Luxury Boutique Hotel Lo Stemma (or similar)

Morning:  Hotel check-out and Drive to Alberobello

We say good-bye to our rustic masseria and head to some of the most beautiful towns of the region. Alberobello is know for the iconic trulli, or beehive shaped houses and workshops. We will explore the structures and have a walk about town.

Lunch:  Alberobello OYO

Lunch and some time to explore are on your own.

Late Afternoon:  Altamura

This town is one of the last towns in Puglia, right at the border of Basilicata.  We will explore this town on foot and incorporate a little afternoon snack.  This city is renowned for the production of sourdough bread, and we will visit a historic bakery with their wood-fired oven to taste some of their delicious breads. Before continuing on our way, we will stop at a small local pastry place for espresso and to taste the traditional dessert of the area. 

Early Evening/Dinner:  Matera

We head finally to Matera to check in for the next two nights at our luxury boutique Hotel Lo Stemma.  Dinner this evening will be a simple meal in a local trattoria.

Meals included: Breakfast, Dinner

Overnight:  Matera, Luxury Boutique Hotel Lo Stemma (or similar)

Late Morning/Afternoon:  Tour of Matera

We will have a local guide meet us for a 2 hour walk in this lovely city. 

Lunch/Late Afternoon 

You'll have the balance of the day until dinner to enjoy Matera, pick up any last-minute souvenirs and have lunch at your leisure. 

Dinner:  Michelin-star restaurant

We will celebrate our time together in one of the caves in Matera with a full tasting menu at this lovely and unique restaurant.