Pleasure & Puglia
All 2026 Trips are Sold Out
Now booking for 2027: June 20-27
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.
Highlights & Details
Enjoy effortless travel, where all logistics, meals, and adventures are managed by us. All you have to do is show up.
Wander through the most beautiful city in Italy that you’ve never heard of before.
Taste fresh Burrata right where it originated
Have arguably the greatest 3-hour lunch of your life.
Shop magnificent farmers’ markets and then help cook an elaborate meal with what we purchase with your chef and guide.
Jump off a cliff into the deep blue Adriatic.
Meet and taste with the greatest winemaker in Southern Italy.
Eat a dinner you will never, ever forget. We promise.
Experience never seeing another tourist throughout the trip.
Taste Italy’s most delicious olive oil right where it’s made.
Fall in love with an ancient place and its vibrant people.
Slow down, watch glorious sunsets, and learn what aperitivo is really all about.
Dates & Availability
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2026: May 19-24, June 12-19, June 20-27
2027: June 20-27
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2026: SOLD OUT
2027: Limited to 12 Guests
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$7100 per person*
*Based on double occupancy. A $1500 surcharge applies for single occupancy.
25% deposit required to confirm booking
Final payment due 60 days prior to arrival
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Accommodations:
Boutique accommodations in Trani and Lecce
Exclusive access to our private Adriatic trulli gathering space and home base throughout the week
Transportation:
Private transportation throughout the itinerary
Airport transfers on designated arrival and departure days
Dining & Culinary Experiences:
Daily breakfasts
Curated regional lunches, dinners, aperitivi, and apericene throughout the journey
Fresh seafood dinner along the port of Trani
Market visits and collaborative cooking experiences with Chef Kevin Callaghan
Michelin-starred dining experience in Manduria
Street food and architecture tour in Lecce
Wine, Olive Oil & Local Producers:
Guided tastings with exceptional small producers across Puglia
Olive oil tasting experience in the heart of olive country
Exclusive winery visits and hosted tastings with winemakers shaping the future of Puglian wine
Cultural Immersion:
Boat excursion beneath the limestone cliffs of Polignano a Mare
Time to explore Alberobello, Lecce, Otrano, and Trani
Access to local artisans, food traditions, and hidden corners rarely experienced by outsiders
Hosts & Guides:
Daily hosting and leadership from Amy Hallett and Chef Kevin Callaghan
Trusted local guides and cultural experts throughout the journey
Personalized pre-trip planning support and travel guidance
Also Included:
Plenty of time to slow down, wander beautiful streets, sip wine by the sea, and experience the rhythm of life in southern Italy
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While the following are not included, they can be arranged free of charge by The Olive Road.
Airfare
Optional activities (spa treatments, extended excursions)
Personal expenses (souvenirs, laundry, extra drinks)
Travel insurance (strongly recommended)
