Tailor-made Vacation · Italy
Luxury Gay Matera & Puglia Tour: Caves, Masserie & Coast
Tailor-made, always
Every trip built from scratch around your dates, pace and preferences.
Your own specialist
One named person and a 24-hour number while you travel.
Hundreds of five-star reviews
Rated Excellent on Trustpilot across ten years of LGBTQ+ luxury travel.
At a glance
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.
Read more
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.
Day by day
This is a sample plan, not a fixed departure. Days can be added, removed or reordered, and almost every client changes something. Prices are an entry-level guide; your quote will be exact.
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.
Our Experts
Italy is one of the best places in Europe to experience culture, food and beautiful scenery. With so much character and colour, the Amalfi Coast is a personal favourite of mine.
I never get tired of planning luxury vacations in Italy. There are so many magical cities and experiences to be enjoyed. Beaches, mountains and rolling countryside, there really is something for everyone.
Stellar service. Stellar products. Stellar people and it gets so much better when you pick up the phone and call.
Anthony S.
Super client centred service. From first contact I have had warm, efficient, friendly and flexible service.
John
I’m confident in giving Out Of Office a 5-star review! They are one of the leaders in this space without a doubt.
Tiberiu
Similar tours
Gay Group Trip: Sicily & Malta Explorer
Catania · Siracusa · Malta Group TripTwo islands and three thousand years of Mediterranean history, brought together in ten days. This LGBTQ+ group trip moves from the volcanic baroque of Catania and the slopes of Mount Etna, through the old island city of Ortigia in Siracusa, and across the sea from Sicily to Malta, one of the most progressive countries in Europe for LGBTQ+ travelers.
10 days group departure from $4,790 per person View trip
Luxury Gay Honeymoon in Italy: Rome & Amalfi Coast
Tailor-made VacationItaly is one of the best destinations on the planet for a honeymoon. Rome comes first: four nights in a city where ancient history and exceptional restaurants occupy the same street. Then the Amalfi Coast for five nights, where the agenda shifts to boat trips, cliff-top dinners, and endless views over the Mediterranean. The itinerary runs nine nights across two bases, with private transfers connecting every stage.
8 days tailor-made from $9,240 per person View trip
Rome’s Gay Legacy: A Luxury LGBTQ+ Tour Through the Roman Empire
Tailor-made VacationThe Roman Empire's relationship with sexuality was fundamentally different from the morality imposed by later Christianity. Same-sex relationships existed openly among the elite, were documented in historical records, and shaped the empire's political and cultural landscape. What's often sanitized in standard history books becomes viscerally real when you stand in the actual spaces where these emperors lived, ruled, and loved. This isn't revisionist history.
10 days tailor-made from $7,580 per person View tripFeatured Itineraries
Movie Inspired
Call Me By Your Name: Italy Filming Locations You Can Visit
Tailor-made VacationCall Me By Your Name made the landscapes of northern Italy almost as memorable as Elio and Oliver themselves. This tailor-made journey takes you through the real towns, piazzas and countryside that framed their story, while giving you plenty of reasons to fall for Italy beyond the film. Begin in Milan, with its art, architecture and fashion, plus time in Porta Venezia, the heart of the city’s gay scene.
9 days tailor-made from $4,640 per person View trip
Classic Italy by Train
Tailor-made VacationTwo 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 transfer short enough that you spend your time seeing the country rather than getting to it.
14 days tailor-made from $6,435 per person View trip
Milan, Venice, Florence and Rome
Tailor-made VacationExperience the quintessence of Italian elegance and history with this luxury tour. This journey invites you to immerse yourself in the diverse cultural tapestry of Italy, exploring its most iconic cities. Your Italian sojourn begins in Milan, the world-renowned fashion capital. Here, amidst the glamour of Via Montenapoleone and the historical grandeur of the Milan Cathedral, you will discover the city's unique blend of modern chic and classical beauty.
10 days tailor-made from $4,505 per person View tripFeatured Hotels
Palazzo Gattini
Matera Luxury HotelPalatial rooms carved from ancient stone, a spa buried in centuries-old cisterns, and a front-row seat to one of Italy's most extraordinary UNESCO-listed landscapes: Palazzo Gattini is Matera at its most luxurious. Once the aristocratic seat of the Gattini Counts, this landmark palazzo on Piazza Duomo has been transformed into one of southern Italy's most exceptional retreats.
View hotel
Bulgari Hotel, Rome
Rome Luxury HotelBvlgari Hotel Roma brings the jewelry house's Italian legacy to its most powerful address: Piazza Augusto Imperatore, in the historic heart of Campo Marzio. The 106-room hotel draws its design from the imperial grandeur surrounding it, working travertine and marble into large-format contemporary interiors that look out directly over the Mausoleum of Augustus. Rooms and suites follow a palette calibrated to ancient Rome, blending historical weight with precision craftsmanship.
View hotel
COMO Castello del Nero
Luxury HotelA 12th-century castle in the bull's-eye of Chianti, reimagined by COMO Hotels as a design-led retreat with one of Tuscany's most considered wellness programs. The estate covers 740 acres of vineyards, olive groves and woodland in Tavarnelle, 30 minutes from Florence and 40 minutes from Siena.
View hotel
Borgo Santo Pietro, Tuscany
Tuscany Luxury HotelA 13th-century estate on 300 acres of organic Tuscan farmland near Chiusdino, combining a 22-room boutique hotel with a working farm, Michelin-starred dining and an on-site skincare laboratory. The property was a healing stopover for medieval pilgrims on the Via Francigena, and that sense of restorative purpose still runs through it.
View hotelWe know where you will be welcome, and where to take more care.
Frequently asked questions
What does Out Of Office do?
Out Of Office is a luxury LGBTQ+ travel company specializing in tailor-made vacations and extraordinary journeys around the world. We create bespoke luxury vacations, LGBTQ+ honeymoons, safaris, cruises, beach escapes, private tours and group trips, with every itinerary designed around you. Our travel specialists combine global expertise, first-hand destination knowledge and trusted local partners to create seamless, highly personalized experiences.
Is Out Of Office a gay travel agency?
Out Of Office is an LGBTQ+ owned and run luxury travel specialist, with particular expertise in gay and LGBTQ+ travel. We understand the additional considerations that can come with traveling as an LGBTQ+ person or couple, from local laws and customs to finding genuinely welcoming hotels and experiences.
We welcome every traveler, including friends, families and allies. Many of our clients are not members of the LGBTQ+ community, but choose Out Of Office for our luxury travel expertise, personalized service and discretion.
Do you create tailor-made LGBTQ+ vacations?
Yes. Every tailor-made trip with Out Of Office is designed from scratch around your interests, travel style, budget and the way you want to experience a destination. We can arrange luxury hotels, private transfers, flights, guides, excursions, cruises and special experiences as part of one personalized itinerary. The journeys shown on our website are there to inspire you rather than restrict you; only clearly identified group departures operate as fixed itineraries.
How do you choose LGBTQ+ friendly hotels and destinations?
We combine first-hand destination knowledge with trusted local expertise to recommend luxury hotels, resorts and experiences where LGBTQ+ travelers can feel informed and welcome. We also consider the laws, customs and attitudes of each destination, because LGBTQ+ rights and experiences differ around the world. Our team regularly visit many of the properties we work with and where a destination requires greater awareness, we give you clear and considered advice so that you can make an informed decision about where and how you travel.
We plant trees for every booking
For every booking made with Out Of Office we commit to planting trees in your name to help reduce the impact of travel on future generations. You'll even get a link to see where your trees are planted in the world via our partner Ecologi.
We donate to Rainbow Railroad with every booking
Rainbow Railroad helps LGBTQ+ people escape state-sponsored violence and persecution. A donation goes with every trip we sell, funded by us and never added to your price.
Start Planning Your Trip
Tell us where you would love to go, when you are thinking of traveling and what kind of trip you have in mind. One of our LGBTQ+ travel specialists will create a tailor-made itinerary designed around your destination, style and preferences.
One named specialist, first inquiry to homecoming. No call center, and nothing is charged until you decide to book.