14 days tailor made from $6,480 pp
From $6,480 pp
At a glance
?
Don't forget that all of our itineraries are totally customized and so this is just an idea of what we can build for you.
There are few places in Europe quite like Matera. Carved into a limestone ravine, its ancient Sassi are a maze of cave dwellings, rock-cut churches, hidden courtyards and steep lanes that seem to fold into one another.
Stay in the historic heart of the city and you can wake to views across the Sassi from your balcony, then step straight into a labyrinth of stone streets where frescoed churches and centuries of history sit behind almost every corner.
Matera feels dramatic and elemental, especially in the early morning and at dusk when the stone changes color and the city becomes quieter.
It is the kind of place where getting slightly lost is part of the experience, with stairways, passages and viewpoints appearing where you least expect them.
Then Puglia changes the mood completely. The landscape opens into olive groves, vineyards and whitewashed towns, with elegant places such as Ostuni, Locorotondo and Lecce to explore at an easy pace.
Days become less about sightseeing and more about long lunches, private tastings, beach clubs and returning to a beautiful masseria for the pool and a quiet evening in the countryside.
By the time you reach Salento, the trip has shifted again towards the coast, with clear water, private boat days and the option to dip into Gallipoli’s summer gay scene. The contrast is what makes the itinerary work so well: ancient Matera first, and then the understated luxury of Puglia.
In detail
?
Don't forget that most of our itineraries can be totally customized. Our expert team will be able to talk you through all the options.
Days 1–2: Matera
On arrival at Bari Airport, your private driver will meet you for the journey to Matera.
Stay in the Sassi, Matera’s historic quarter and the most atmospheric place to experience the city. Many of its old cave dwellings have been transformed into beautiful luxury hotels, combining original stone interiors with contemporary design and views across the ravine.
The first evening is deliberately unhurried, with time to settle in and explore the Sassi once the daytime visitors have started to leave.
The following day, meet a private guide to discover Matera properly. Walk through its steep stone lanes, visit the rock-cut churches and learn how people lived in the caves for centuries. The city is particularly striking towards sunset, when the limestone buildings begin to glow and the Sassi take on a completely different character.
Days 3–5: Ostuni & the Valle d’Itria
Leave Matera by private transfer and cross into Puglia, where the landscape opens into olive groves, vineyards and whitewashed hill towns.
Your base for the next three nights is a luxury masseria around Ostuni or the Valle d’Itria. These former agricultural estates are one of the defining experiences of Puglia, with restored limestone buildings, gardens, pools and restaurants centered around local produce.
Explore Ostuni and the smaller towns of the Valle d’Itria with a private driver, stopping in places such as Locorotondo and Cisternino rather than trying to rush between them.
There is also time for the experiences that make this part of Puglia special: a private olive oil tasting, a winery visit, a cooking class or simply a long lunch followed by an afternoon at the pool.
Alberobello can be included too, ideally early in the day before it becomes busy, for a look at the region’s famous trulli.
Days 6–8: Lecce & Salento
Continue south to Lecce, where the character of the trip changes again.
Spend time exploring Lecce’s richly decorated Baroque center with a private guide, then enjoy the city at a slower pace in the evening, when its piazzas and restaurants come into their own.
The rest of the stay is about the coast. Charter a private boat, spend a day at a beach club or head towards Otranto and the southern tip of Salento for swimming, small coastal towns and some of Puglia’s clearest water.
If you want to experience Puglia’s LGBTQ+ scene, Gallipoli is the place to add it. During the summer, its beaches and nightlife attract a large gay crowd, giving you the option of something more social without making the entire trip about the scene.
It is a particularly good final stop because you can choose exactly how much you want to do. One day might mean a boat and a long seafood lunch, another a beach club and an evening in Gallipoli, and another almost nothing beyond the hotel and the sea.
Day 9: Departure
After breakfast, your private driver will collect you for the transfer to Brindisi or Bari Airport for your flight home.
Other Suggested Trips
?
Our itineraries are here to inspire you. Everything we do is tailor-made so our team of luxury travel experts will customize an itinerary for you.
Classic Italy by Train
Tailor-made Vacation
Two weeks, four cities, and not a single flight between them. Italy’s high-speed rail network turns city-hopping into the easiest part of the trip, Venice to Florence in a little over two hours, Florence to Rome in ninety minutes, each...
Gay Honeymoon in Italy and Greece: Rome, Amalfi, Santorini, Mykonos
Tailor-made Vacation
Italy and Greece are Europe’s most sought-after honeymoon destinations. Couples flock to see Rome’s ruins and rooftop restaurants, the Amalfi Coast’s cliffside towns, Santorini’s caldera views, Mykonos’s beach clubs and whitewashed lanes. This 12-night honeymoon is built for couples of...
Luxury Italy Tour: Lake Como, Tuscany, & Amalfi
Tailor-made Vacation
This fully customizable itinerary moves through four of Italy’s most distinctive regions, Lake Como’s lakeside villas, Tuscany’s vineyard hills, Rome’s history, and the Amalfi Coast’s cliffside towns, each with its own character. Expect regional wine, Michelin-starred dining, and produce sourced...
Why book with us?
Personal Service
We want to ensure you have the best experience with us so we’ll keep working on your itinerary until perfect. You will have your own personal dedicated member of our team who will help build a trip that is bespoke to you.
Call our travel experts on +44 (0)20 7157 1570
Our 5* Reviews
We pride ourselves in the number of clients that are referred to us by our existing customers. Our 5* Trustpilot rating is important to us, so we encourage you to browse our reviews. They speak for themselves and that's why you are in safe hands.