Pleasure & Puglia, Italy

May 19th - 26th 2024

May 26th - June 2nd, 2024

Italy and Puglia. An ancient place crafted by nature and by time and by three millennia of human endeavor. But old as it is, Puglia is abundantly alive. It’s a place where food and wine take center stage in their way of life. This is a land of olive trees and white washed hill towns, epic ocean cliffs and brilliant blue skies. But it’s also a place with people crafting great wine from the land, using ancient techniques and modern technology. 


Exploring this ancient land together, we’ll pay close attention to how effortlessly the food and wine of Puglia match up with each other. That’ll be abundantly clear in our trips to great regional restaurants, markets, food stalls and, of course, a collective foray into sourcing local ingredients at the market and cooking a delicious meal together. 

The brilliant blue water of the Adriatic has carved the Italian coast for millenia. Trani feels like a city born from that ocean, the arced port embracing the myriad boats that are moored there, gently rising and falling with the tide. The city’s cathedral almost feels like a lighthouse at the edge of the water, calling fisherman home. But for us, the city itself is a beacon, beckoning us to wander the narrow streets and taste the glorious seafood those same fishermen sell at the waterside day after day. It’s a way of life that has been the heartbeat of Trani for well over a thousand years. The romantic waterfront glitters to life at night with people chatting and laughing at outdoor bars all along the stone promenade, just steps from the ocean.

It’s a day for the food lover in you. The gnarled olive trees that carpet Puglia aren’t just beautiful to look at, they make some of the world’s greatest olive oils. We’ll go to arguably the single best producer in the entire region to taste their array of olive oils and learn how they make their famed oils. Luckily the city of Andria is also the birthplace of burrata and when you put those two delicacies together - oh my. Then there is lunch; I wish there was a better name for it. It’s really somewhere between a feast and a culinary magic act. In a small town restaurant, we’ll get a rare glimpse into the soul of Puglia, almost never seen by outsiders. The night will be yours to enjoy Trani on your own.

As we journey south, we’ll settle for a few nights in another pearl of the Adriatic, Monopoli. Again, the marriage of land and sea takes center stage. It’s easy to get lost wandering the narrow streets that weave through the whitewashed old town to the waterfront. There are perfect beaches that stretch away from the town, if that’s more your thing. Our first stop that morning is the farmers’ market to purchase all the seasonal fruits and vegetables (think wild fennel and sour cherries) and other local ingredients for the grand feasts that we will prepare together over the next two nights. After the market, we will settle into the city and our new lodgings. For the evening, we will split into two groups with each group allotted one of the nights to help prepare the dinner with Kevin. For the non-feasting group each night, the night is yours to explore the beautiful city and prepare for a sublime nighttime fritto misto extravaganza, an absolute celebration of Monopoli’s seafaring legacy.

Today we will head to Polignano a Mare, the famed town built on cliffs that jut out over the Adriatic. There are dramatic beaches tucked into coves, Roman roads and bridges, but our main destination is a boat tour of the many spectacular caves slowly carved from the limestone cliffs by the Adriatic. For your inner-adventurer, there will be a chance to jump off of these same cliffs and into the chilly sea. With your appetite worked up, we’ll walk into town and settle down for some of the best sandwiches anywhere. Then it’s back to Monopoli for feast preparation or a night of fritto misto and the magic of the city at night.

We’ll venture inland today to explore the burgeoning artisan wine scene. Small production. Family run. 100% Puglia. We’ll meet fascinating people deeply invested in the land and the true spirit of the wine forged from that land. We’ll taste award winning wines from the DOC Gioia del Colle over an exclusive three hour lunch that you won’t soon forget - in a restaurant you’d never find. Like so much of Puglia, it feels like a secret - a wonderful, well-kept secret. The seasonal menu made exclusively for us will highlight the very personal wines and the intimate connection between wine and food that is central to Puglian tradition. 

On our way back to Monopoli, we will stop in one of the most iconic cities in the South. Like so much of Puglia, the trulli of Alberobello have this rare combination of authenticity and whimsy. The stone buildings seem to grow right out of the ground. We’ll explore the legendary town and hunt down the best gelato before heading back for our last night on the water. 

Fun fact: the best wine made in Puglia is made by an Australian woman. Better fact: she’s a friend of the Olive Road and will give us an exclusive tasting of those wines at her beautiful winery in Manduria as we continue to wind our way south and to Lecce, our final destination. After visiting Morella and whetting our appetites, we will have an exclusive lunch at Michelin starred Casamatta, just outside of Manduria. The lunch - curated by The Olive Road - is a 6-course tasting menu paired with regional wines. The restaurant is situated in a castle with a fabulous art collection. A good bit of the vegetables used for our lunch are grown on the property.  After lunch, we will find our way to Lecce. The “Florence of the South” is an ancient walled city with a Roman amphitheater at its center and a thriving university at its heart. And tonight, we will get our aperitivo on. We’ll make our curated way, bar to bar, with the rest of the city and sample the necessary evening beverages and the delightful snacks that are the aforementioned aperitivo hallmark. 

On our last full day, Lecce takes center stage. You will go on a fascinating tour of the stunning architecture of the city and get a first class sampling of the local street food scene - all at the same time. The afternoon can be spent as you like - wandering the city and its many family-run stores and art galleries. There are many wonderful piazzas to sit and watch the city swirl around you. But the night belongs to pizza. What better way to end an excursion into the real Italy than arguably the best pizza place in the country? We heartily recommend that you come hungry.

Following breakfast, we will make our way to the airport via private transport for the journey home.

Or wherever the winds may take you.