Puglia By
Hermes Holidays

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Join Hermes Holidays for a luxury LGBTQ+ small group holiday through Puglia, with a spectacular taste of neighbouring Basilicata, where ancient cities, whitewashed villages, glamorous masserias, turquoise seas and extraordinary food come together in one unforgettable journey.

From Matera and Polignano al Mare to Lecce, Otranto and Santa Maria di Leuca, this is Southern Italy at its best, personally hosted by Kyle and Wayne, with beautiful hotels, private experiences, long lunches, sunset drinks and plenty of Hermes magic along the way.

Picture This

You, sitting under the warm golden light of a Puglian late afternoon, a chilled glass of local rosato in hand, listening to the soft rustle of ancient olive trees that have stood here for centuries. There’s no rush, no schedule to chase—just the effortless, sun-drenched magic of Southern Italy unfolding around you.

Imagine waking up inside a centuries-old cave room built into the limestone cliffs of Matera, where thousands of years of history blend seamlessly with five-star luxury. Picture yourself floating along the Adriatic on a private boat, prosecco in hand, gazing up at dramatic sea caves and limestone cliffs before dipping into water so ridiculously blue it barely looks real.

Just a Small Taste

One day you’re learning the secrets to fresh burrata and hand-rolled orecchiette from an Italian nonna in a sun-lit garden under lemon trees. The next, you’re indulging in a long, lazy afternoon on a reserved sunbed at a private beach club on the turquoise shores of Pescoluse—Italy’s very own Maldives—with champagne served right to your lounger.

From rooftop aperitivos overlooking Baroque palazzos in Lecce to passeggiata evening strolls along Otranto’s buzzing waterfront, this isn’t just a holiday. It’s 12 days of unadulterated luxury, authentic local soul, and unforgettable memories made in absolute style.

Map of southern Italy highlighting Apulia and nearby regions in green with inset map at lower left.

Puglia, Italy.

Located right at the heel of Italy’s boot, Puglia is Southern Italy at its most authentic, intoxicating, and effortlessly stylish. This is a land shaped by ancient history, dramatic coastal beauty, and simple, refined pleasures: endless groves of gnarled, centuries-old olive trees stretching toward a sapphire horizon, dramatic limestone sea cliffs dropping into crystal-clear waters, and fairy-tale hilltop towns dusted in pristine white lime.

Life here moves to a richer, gentler rhythm. Across its landscape, centuries-old masserias and conical trulli sit near medieval alleys where nonnas hand-roll fresh orecchiette. Along 800 kilometres of coastline, dramatic sea caves and limestone coves drop into vivid blue waters.

The Hotels

We’ve handpicked an extraordinary collection of accommodations that are much more than just a place to sleep—they are iconic destinations in their own right. From a 5-star Relais & Châteaux boutique hotel carved directly into the ancient cave cliffs of Matera to a restored 18th-century Baroque palazzo in Lecce, a historic 16th-century masseria featuring an underground party cave, and an ultra-chic coastal sanctuary near Otranto.

Every single stay strikes the perfect balance between authentic regional heritage, bespoke design, and pure five-star indulgence.

Details

Welcome to Bari, the gateway to Puglia and the start of our Southern Italian adventure.

After landing, make your way to our centrally located hotel, the Mövenpick Bari. Our gang will be arriving from all over the world today, so take some time to settle in, unwind and ease into holiday mode.

Later this afternoon, we’ll all come together for the first time and head out on a walking food tour through Bari. It’s a relaxed introduction to the city, with historic streets, local flavours, plenty of delicious bites, and a chance to see the famous nonnas making orecchiette by hand outside their homes.

We’ll finish in a neighbourhood piazza as Bari hits its Saturday night stride, the streets filling, locals loving life, glasses in hand, and us easing straight into the rhythm of it all. Welcome to Puglia. This is where the fun begins.

Accommodation: Mövenpick Bari

Meals: Dinner and Drinks

Narrow cobblestone alley under a stone arch, lined with flowers and colorful buildings after rain.


DAY 2: Sunday, 12th September.

Bari to Matera

This morning, we’ll make our way from Bari to the remarkable city of Matera, one of the oldest continuously inhabited places in the world, with a history dating back more than 9,000 years.

Carved into the rocky landscape of Basilicata, Matera is famous for its ancient cave dwellings, honey coloured stone, winding lanes and sweeping views. It is dramatic, atmospheric and unlike anywhere else in Italy. Our home for the night is Vetera Matera, a beautiful Relais & Châteaux property set right in the heart of the Sassi.

This is no ordinary hotel stay. Many of the rooms are built into the ancient caves themselves, where raw stone and understated luxury come together beautifully
.

This afternoon, we’ll explore Matera with our local guide Nico, who was born and raised here. He has a wonderful way of bringing the city’s story to life, from its ancient beginnings to its extraordinary reinvention as one of Southern Italy’s most fascinating destinations.


Accommodation: Vetera Matera Hotel

Meals: Breakfast, Drinks and Canapes

Hilltop village at dusk with stone buildings, glowing streetlights, and a tall cathedral tower under a pink sky


DAY 3: Monday, 13th September.
Matera to Masseria Montenapoleone

Our first stop is Alberobello, famous for its extraordinary trulli, the whitewashed stone houses with their conical roofs that look like something from another world.

You’ll have time to wander the streets, browse the little shops and find somewhere local for a bite to eat before we continue south. This afternoon, we arrive at our home for the next three nights, Masseria Montenapoleone.

A masseria is a traditional Puglian farmhouse, but trust us, this is no ordinary farmhouse. Dating back to the 16th century, Masseria Montenapoleone is rustic, chic and full of character. It’s easily one of the most Instagrammable places to stay in Puglia.

Set among olive groves, vineyards and open countryside, the property is all about true farm-to-table living. Much of what you’ll eat and drink here is grown, made or produced on the estate itself, from seasonal vegetables to their own olive oil and wine.

Tonight is one of our highlight dinners, as we gather in the vineyards for a long, beautiful evening of local food, estate wine and that unmistakable southern Italian magic as the sun sets over the countryside.

This is Puglia doing what Puglia does best.

Accommodation: Masseria Montenapoleone
Meals
: Breakfast, Dinner and Drinks

Person posing on a sunlit stone path by white walls and pink flowers in a rustic courtyard, smiling in sunglasses.


DAY 4: Tuesday, 14th September.
Masseria Montenapoleone & Polignano al Mare

Today, the masseria is the destination and relaxation is on the menu. Spend the day by the lagoon pool, top up the tan, order a cocktail and simply relax. If you feel like something more indulgent, head to The Herbarium for a spa treatment inspired by the plants, flowers and botanical wonders of the region, or find a quiet corner of the grounds and disappear for a while.

When hunger calls, keep it relaxed by the pool, enjoy a long lazy bite at the masseria ristorante, or even have them arrange a romantic picnic somewhere beautiful in the grounds.

This afternoon, we’ll come together for a tasting of the wines produced on the estate. We’ll wander through the farm and vineyards with the masseria’s farmer, before tasting a selection of their organic wines, including their own Susumaniello red.

Just before sunset, we’ll head to spectacular Polignano al Mare, one of Puglia’s most famous seaside towns. The evening is yours to wander the old streets, find a terrace for aperitivo, or book dinner somewhere special, perhaps even the world-renowned Grotta Palazzese, set inside a cave above the sea.

Accommodation: Masseria Montenapoleone

Meals: Breakfast, wine tasting

Sunny resort pool with turquoise water, white lounge chairs, and trees under a clear blue sky


DAY 5: Wednesday, 15th September.
Polignano al Mare & Monopoli

This morning, we’ll head out on a flotilla of small boats to explore one of the most photographed stretches of coastline in Puglia. Dramatic limestone cliffs, hidden coves, sea caves, swim stops and that ridiculous blue Adriatic water. It's absolute paradise. And because it’s important to stay hydrated, there’ll be prosecco and a few local Puglian bites on board. Sun, sea, bubbles, you get the idea.

Afterwards, we’ll make our way to nearby Monopoli, another gorgeous coastal town with a beautiful old harbour, whitewashed streets and plenty of places to sit, sip and watch the world go by. There’ll be time here to explore at your own pace, browse the little boutiques, find a spot for a drink, or simply lose yourself in the old town for a while.

Later, we return to the masseria before tonight’s very special change of pace.

Dinner, drinks and dancing await in the Babylon Cave — an underground club set right within the grounds of Masseria Montenapoleone. Yes, really.

Accommodation: Masseria Montenapoleone

Meals: Breakfast, Dinner and Drinks

Group of friends smiling on a boat in a turquoise sea near rocky cliffs


DAY 6: Thursday, 16th September.
Ostuni, Cooking Class & Lecce

This morning, we say arrivederci to Masseria Montenapoleone and make our way south towards Lecce, the capital of the Salento region. But first, we stop in Ostuni, known as La Città Bianca, the White City. Sitting high above a sea of ancient olive groves, Ostuni is all whitewashed walls, winding medieval alleys, hidden courtyards and views stretching out towards the Adriatic.

You’ll have time to explore at your own pace, slip into a few boutiques, grab a coffee or simply soak up one of Puglia’s most beautiful hilltop towns.

From here, it’s just a short drive to a local family home, where we’ll be welcomed with that warm Southern Italian hospitality Puglia does so well.

Our cooking class takes place under the lemon and olive trees in the garden, with recipes, stories and little kitchen secrets passed down through generations.

Nonna is going to show us how to make Puglian classics like focaccia, fresh burrata and orecchiette. While lunch cooks, we’ll settle into proper Southern Italian mode, with music, singing, a little Taranta, and yes, probably more glasses of wine, before sitting down together for a long family lunch around the table. This is the kind of experience you don’t get in a restaurant.

It’s generous, personal and designed to make you feel at home. Later, we’ll make our way to Lecce and check into the stunning five star Patria Palace, a former Baroque Palazzo and member of The Leading Hotels of the World. Perfectly located in the heart of the city, you’ll have restaurants, bars, cafés and gelaterias all within easy walking distance.


Accommodation: Patria Palace

Meals: Breakfast, Lunch with Drinks

People gathered around a long outdoor table under a leafy canopy, chatting and eating at a garden meal.


DAY 7: Friday, 17th September.
Lecce

After a relaxed morning, we’ll meet our local specialist Francesca and head out on a walking food tour through Lecce’s historic centre, the beautiful Baroque capital of Salento. Lecce is often called the Florence of the South, which sounds like a big claim, until you arrive and realise it absolutely lives up to it. This is the perfect way to get under the skin of the city.

As we explore the old town with Francesca, she’ll bring the history, stories and architecture to life, from the extraordinary Basilica di Santa Croce to Piazza Sant’Oronzo, the Roman amphitheatre and the elegant lanes that make this city so easy to fall for.

Of course, this is Hermes Holidays, so we’ll also be eating and drinking along the way.

Today is all about the flavours of Lecce and Salento, from Caffè Leccese and pasticciotto to local taralli, olive oil, rustico leccese, local wines and spumone.

It’s a beautiful mix of food, history, culture and local life, giving you a real taste of the city and the region around it.

The tour finishes early afternoon, leaving the rest of the day and evening yours to enjoy Lecce at your own pace. Browse the boutiques, discover why Lecce has such a reputation for great fashion, find a sunny table for an aperitivo, or head back out later for a gorgeous dinner in one of the city’s local restaurants.

Accommodation: Patria Palace

Meals: Breakfast, Lunch with Drinks

Outdoor table with salads, fried snacks, bread, and two glasses of red wine in a sunny courtyard

DAY 8: Saturday, 18th September.
Lecce to Otranto

After another incredible breakfast at Patria Palace, and yes, breakfast here is very much an experience, we’ll enjoy a relaxed morning before making our way further south to Otranto. Our home for the next three nights is the spectacular Baglioni Masseria Muzza Resort and Spa, our most luxurious stay yet. Whitewashed walls, olive trees, infinity pools, gorgeous terraces, sea air and fine dining.

This is Puglia at its most glamorous, and you’ll feel like a celebrity the moment you arrive. Once we reach the resort it’s straight to the pool while the team prepares our rooms. Claim a sun lounger, order something cold, grab a bite at the poolside restaurant and let the afternoon drift beautifully by.

After time to settle in, we’ll head into Otranto just before sunset, when the town is at its most beautiful. The waterfront is lined with bars and restaurants, but tucked behind it is a maze of little streets that really come alive at night. Evening shopping is a major part of the passeggiata, the Italian evening stroll, and as it’s Saturday, the whole town will be absolutely buzzing.


Accommodation: Baglioni Masseria Muzza Resort and Spa

Meals: Breakfast

Friends dining at a lively lantern-lit street restaurant, smiling and raising drinks at a shared table


DAY 9: Sunday, 19th September.
Otranto

Today is completely yours. After a big few days of exploring, eating, drinking, cooking, dancing and generally living your best Southern Italian life, this is your day to slow down and do exactly as you please.

Our hope is that you return home feeling rested, recharged and properly relaxed.

You may want to spend the day by the pool, tucked into a cabana with a book, a cold drink and absolutely no plans. You may want to disappear into the spa, where hydromassage pools, steam, sauna, sensory showers and beautiful Italian treatments are all waiting to work their magic.

The hotel also runs a complimentary shuttle throughout the day and evening, so you can head back into Otranto whenever the mood strikes. Wander the old town, browse the shops, settle in somewhere for lunch or simply find a table by the water and stay there longer than intended.

For those craving a proper beach day, jump on the hotel shuttle to nearby Coco Bay Beach Club, with sunbeds, sea views and the kind of long, lazy lunch that feels exactly right in this part of the world.

Accommodation: Baglioni Masseria Muzza Resort and Spa

Meals: Breakfast

People relaxing in a turquoise pool; one reads on a lounge chair while others stand and chat nearby.

DAY 10: Monday, 20th September.
Santa Maria di Leuca

This morning, we head right down to the very tip of the heel of Italy’s boot, to Santa Maria di Leuca, where the Adriatic and Ionian seas meet. From here, we’ll board our private boats for a three hour cruise exploring both coastlines, including the meeting point of the two seas.

We’ll spend plenty of time on the Ionian side, where the coast is all sea caves, hidden coves and water so turquoise it barely looks real, with swim stops in all the right places. And because it would be rude not to, there’ll be a light lunch on board with local Salento specialities, including puccia, frise with tomato and olive oil, seasonal fruit, prosecco, and a few more delicious local bites.

After our cruise, we’ll make the short drive to Pescoluse, often called the Maldives of Italy, for an afternoon at Le Cinque Vele, one of the most luxurious beach clubs on the Salento coast. Sun loungers, umbrellas and champagne are included, so all you need to do is settle in, swim, sip and enjoy one very glamorous afternoon by the sea.

Accommodation
: Baglioni Masseria Muzza Resort and Spa

Meals: Breakfast, Lunch with Drinks

Two people relaxing on beach chairs facing the ocean, with a picnic basket and fruit in the foreground.

DAY 11: Tuesday, 21st September.
Bari

After a relaxed morning at the resort, we begin our journey north, returning to Bari for our final night together. There is something lovely about finishing where we began. By now, the strangers from Day 1 are friends, the stories are already legendary, and Puglia has well and truly worked its magic.

We’ll stop for lunch along the way before checking back into the Mövenpick Bari. The rest of the afternoon is yours to enjoy the city at your own pace. Head back into Bari Vecchia for a wander, a gelato from the famous Gelateria Gentile, a little shopping, or a prosecco in the sun.

This evening, we’ll come together and walk into Bari Vecchia for our farewell dinner at one of the best restaurants in town. It’s our chance to celebrate the places we’ve discovered, the experiences we’ve shared, the ridiculous amount of food we’ve eaten, the drinks we’ve drunk, and most importantly, the wonderful friends we’ve shared it all with.

Accommodation: Mövenpick Bari

Meals: Dinner with Drinks

Street café scene with flower-lined stairs, pastries on tables, and people chatting in a narrow alley

DAY 12: Wednesday, 22nd September.
Onward Journeys

And just like that, our Puglian adventure comes to an end. The tour concludes after breakfast this morning, as we say our goodbyes and begin our onward journeys.

Thank you for joining us, for being part of the magic, and for bringing your wonderful energy to this very special Hermes Holidays adventure.

We wish you safe travels, buon viaggio, and hope it won’t be too long before we see your beautiful faces again. Until the next one.

Meals: Breakfast

View from airplane window of wing over a coastal city and blue sea under a clear sky

DAY 1: Saturday, 11th September.
Arrival in Bari

Welcome to Bari, the gateway to Puglia and the start of our Southern Italian adventure.

After landing, make your way to our centrally located hotel, the Mövenpick Bari. Our gang will be arriving from all over the world today, so take some time to settle in, unwind and ease into holiday mode.

Later this afternoon, we’ll all come together for the first time and head out on a walking food tour through Bari. It’s a relaxed introduction to the city, with historic streets, local flavours, plenty of delicious bites, and a chance to see the famous nonnas making orecchiette by hand outside their homes.

We’ll finish in a neighbourhood piazza as Bari hits its Saturday night stride, the streets filling, locals loving life, glasses in hand, and us easing straight into the rhythm of it all. Welcome to Puglia. This is where the fun begins.

Accommodation: Mövenpick Bari

Meals: Dinner and Drinks

Narrow cobblestone alley under a stone arch, lined with flowers and colorful buildings after rain.


DAY 2: Sunday, 12th September.

Bari to Matera

This morning, we’ll make our way from Bari to the remarkable city of Matera, one of the oldest continuously inhabited places in the world, with a history dating back more than 9,000 years.

Carved into the rocky landscape of Basilicata, Matera is famous for its ancient cave dwellings, honey coloured stone, winding lanes and sweeping views. It is dramatic, atmospheric and unlike anywhere else in Italy. Our home for the night is Vetera Matera, a beautiful Relais & Châteaux property set right in the heart of the Sassi.

This is no ordinary hotel stay. Many of the rooms are built into the ancient caves themselves, where raw stone and understated luxury come together beautifully
.

This afternoon, we’ll explore Matera with our local guide Nico, who was born and raised here. He has a wonderful way of bringing the city’s story to life, from its ancient beginnings to its extraordinary reinvention as one of Southern Italy’s most fascinating destinations.


Accommodation: Vetera Matera Hotel

Meals: Breakfast, Drinks and Canapes

Hilltop village at dusk with stone buildings, glowing streetlights, and a tall cathedral tower under a pink sky


DAY 3: Monday, 13th September.
Matera to Masseria Montenapoleone

Our first stop is Alberobello, famous for its extraordinary trulli, the whitewashed stone houses with their conical roofs that look like something from another world.

You’ll have time to wander the streets, browse the little shops and find somewhere local for a bite to eat before we continue south. This afternoon, we arrive at our home for the next three nights, Masseria Montenapoleone.

A masseria is a traditional Puglian farmhouse, but trust us, this is no ordinary farmhouse. Dating back to the 16th century, Masseria Montenapoleone is rustic, chic and full of character. It’s easily one of the most Instagrammable places to stay in Puglia.

Set among olive groves, vineyards and open countryside, the property is all about true farm-to-table living. Much of what you’ll eat and drink here is grown, made or produced on the estate itself, from seasonal vegetables to their own olive oil and wine.

Tonight is one of our highlight dinners, as we gather in the vineyards for a long, beautiful evening of local food, estate wine and that unmistakable southern Italian magic as the sun sets over the countryside.

This is Puglia doing what Puglia does best.

Accommodation: Masseria Montenapoleone
Meals
: Breakfast, Dinner and Drinks

Person posing on a sunlit stone path by white walls and pink flowers in a rustic courtyard, smiling in sunglasses.


DAY 4: Tuesday, 14th September.
Masseria Montenapoleone & Polignano al Mare

Today, the masseria is the destination and relaxation is on the menu. Spend the day by the lagoon pool, top up the tan, order a cocktail and simply relax. If you feel like something more indulgent, head to The Herbarium for a spa treatment inspired by the plants, flowers and botanical wonders of the region, or find a quiet corner of the grounds and disappear for a while.

When hunger calls, keep it relaxed by the pool, enjoy a long lazy bite at the masseria ristorante, or even have them arrange a romantic picnic somewhere beautiful in the grounds.

This afternoon, we’ll come together for a tasting of the wines produced on the estate. We’ll wander through the farm and vineyards with the masseria’s farmer, before tasting a selection of their organic wines, including their own Susumaniello red.

Just before sunset, we’ll head to spectacular Polignano al Mare, one of Puglia’s most famous seaside towns. The evening is yours to wander the old streets, find a terrace for aperitivo, or book dinner somewhere special, perhaps even the world-renowned Grotta Palazzese, set inside a cave above the sea.

Accommodation: Masseria Montenapoleone

Meals: Breakfast, wine tasting

Sunny resort pool with turquoise water, white lounge chairs, and trees under a clear blue sky


DAY 5: Wednesday, 15th September.
Polignano al Mare & Monopoli

This morning, we’ll head out on a flotilla of small boats to explore one of the most photographed stretches of coastline in Puglia. Dramatic limestone cliffs, hidden coves, sea caves, swim stops and that ridiculous blue Adriatic water. It's absolute paradise. And because it’s important to stay hydrated, there’ll be prosecco and a few local Puglian bites on board. Sun, sea, bubbles, you get the idea.

Afterwards, we’ll make our way to nearby Monopoli, another gorgeous coastal town with a beautiful old harbour, whitewashed streets and plenty of places to sit, sip and watch the world go by. There’ll be time here to explore at your own pace, browse the little boutiques, find a spot for a drink, or simply lose yourself in the old town for a while.

Later, we return to the masseria before tonight’s very special change of pace.

Dinner, drinks and dancing await in the Babylon Cave — an underground club set right within the grounds of Masseria Montenapoleone. Yes, really.

Accommodation: Masseria Montenapoleone

Meals: Breakfast, Dinner and Drinks

Group of friends smiling on a boat in a turquoise sea near rocky cliffs


DAY 6: Thursday, 16th September.
Ostuni, Cooking Class & Lecce

This morning, we say arrivederci to Masseria Montenapoleone and make our way south towards Lecce, the capital of the Salento region. But first, we stop in Ostuni, known as La Città Bianca, the White City. Sitting high above a sea of ancient olive groves, Ostuni is all whitewashed walls, winding medieval alleys, hidden courtyards and views stretching out towards the Adriatic.

You’ll have time to explore at your own pace, slip into a few boutiques, grab a coffee or simply soak up one of Puglia’s most beautiful hilltop towns.

From here, it’s just a short drive to a local family home, where we’ll be welcomed with that warm Southern Italian hospitality Puglia does so well.

Our cooking class takes place under the lemon and olive trees in the garden, with recipes, stories and little kitchen secrets passed down through generations.

Nonna is going to show us how to make Puglian classics like focaccia, fresh burrata and orecchiette. While lunch cooks, we’ll settle into proper Southern Italian mode, with music, singing, a little Taranta, and yes, probably more glasses of wine, before sitting down together for a long family lunch around the table. This is the kind of experience you don’t get in a restaurant.

It’s generous, personal and designed to make you feel at home. Later, we’ll make our way to Lecce and check into the stunning five star Patria Palace, a former Baroque Palazzo and member of The Leading Hotels of the World. Perfectly located in the heart of the city, you’ll have restaurants, bars, cafés and gelaterias all within easy walking distance.


Accommodation: Patria Palace

Meals: Breakfast, Lunch with Drinks

People gathered around a long outdoor table under a leafy canopy, chatting and eating at a garden meal.


DAY 7: Friday, 17th September.
Lecce

After a relaxed morning, we’ll meet our local specialist Francesca and head out on a walking food tour through Lecce’s historic centre, the beautiful Baroque capital of Salento. Lecce is often called the Florence of the South, which sounds like a big claim, until you arrive and realise it absolutely lives up to it. This is the perfect way to get under the skin of the city.

As we explore the old town with Francesca, she’ll bring the history, stories and architecture to life, from the extraordinary Basilica di Santa Croce to Piazza Sant’Oronzo, the Roman amphitheatre and the elegant lanes that make this city so easy to fall for.

Of course, this is Hermes Holidays, so we’ll also be eating and drinking along the way.

Today is all about the flavours of Lecce and Salento, from Caffè Leccese and pasticciotto to local taralli, olive oil, rustico leccese, local wines and spumone.

It’s a beautiful mix of food, history, culture and local life, giving you a real taste of the city and the region around it.

The tour finishes early afternoon, leaving the rest of the day and evening yours to enjoy Lecce at your own pace. Browse the boutiques, discover why Lecce has such a reputation for great fashion, find a sunny table for an aperitivo, or head back out later for a gorgeous dinner in one of the city’s local restaurants.

Accommodation: Patria Palace

Meals: Breakfast, Lunch with Drinks

Outdoor table with salads, fried snacks, bread, and two glasses of red wine in a sunny courtyard

DAY 8: Saturday, 18th September.
Lecce to Otranto

After another incredible breakfast at Patria Palace, and yes, breakfast here is very much an experience, we’ll enjoy a relaxed morning before making our way further south to Otranto. Our home for the next three nights is the spectacular Baglioni Masseria Muzza Resort and Spa, our most luxurious stay yet. Whitewashed walls, olive trees, infinity pools, gorgeous terraces, sea air and fine dining.

This is Puglia at its most glamorous, and you’ll feel like a celebrity the moment you arrive. Once we reach the resort it’s straight to the pool while the team prepares our rooms. Claim a sun lounger, order something cold, grab a bite at the poolside restaurant and let the afternoon drift beautifully by.

After time to settle in, we’ll head into Otranto just before sunset, when the town is at its most beautiful. The waterfront is lined with bars and restaurants, but tucked behind it is a maze of little streets that really come alive at night. Evening shopping is a major part of the passeggiata, the Italian evening stroll, and as it’s Saturday, the whole town will be absolutely buzzing.


Accommodation: Baglioni Masseria Muzza Resort and Spa

Meals: Breakfast

Friends dining at a lively lantern-lit street restaurant, smiling and raising drinks at a shared table


DAY 9: Sunday, 19th September.
Otranto

Today is completely yours. After a big few days of exploring, eating, drinking, cooking, dancing and generally living your best Southern Italian life, this is your day to slow down and do exactly as you please.

Our hope is that you return home feeling rested, recharged and properly relaxed.

You may want to spend the day by the pool, tucked into a cabana with a book, a cold drink and absolutely no plans. You may want to disappear into the spa, where hydromassage pools, steam, sauna, sensory showers and beautiful Italian treatments are all waiting to work their magic.

The hotel also runs a complimentary shuttle throughout the day and evening, so you can head back into Otranto whenever the mood strikes. Wander the old town, browse the shops, settle in somewhere for lunch or simply find a table by the water and stay there longer than intended.

For those craving a proper beach day, jump on the hotel shuttle to nearby Coco Bay Beach Club, with sunbeds, sea views and the kind of long, lazy lunch that feels exactly right in this part of the world.

Accommodation: Baglioni Masseria Muzza Resort and Spa

Meals: Breakfast

People relaxing in a turquoise pool; one reads on a lounge chair while others stand and chat nearby.

DAY 10: Monday, 20th September.
Santa Maria di Leuca

This morning, we head right down to the very tip of the heel of Italy’s boot, to Santa Maria di Leuca, where the Adriatic and Ionian seas meet. From here, we’ll board our private boats for a three hour cruise exploring both coastlines, including the meeting point of the two seas.

We’ll spend plenty of time on the Ionian side, where the coast is all sea caves, hidden coves and water so turquoise it barely looks real, with swim stops in all the right places. And because it would be rude not to, there’ll be a light lunch on board with local Salento specialities, including puccia, frise with tomato and olive oil, seasonal fruit, prosecco, and a few more delicious local bites.

After our cruise, we’ll make the short drive to Pescoluse, often called the Maldives of Italy, for an afternoon at Le Cinque Vele, one of the most luxurious beach clubs on the Salento coast. Sun loungers, umbrellas and champagne are included, so all you need to do is settle in, swim, sip and enjoy one very glamorous afternoon by the sea.

Accommodation
: Baglioni Masseria Muzza Resort and Spa

Meals: Breakfast, Lunch with Drinks

Two people relaxing on beach chairs facing the ocean, with a picnic basket and fruit in the foreground.

DAY 11: Tuesday, 21st September.
Bari

After a relaxed morning at the resort, we begin our journey north, returning to Bari for our final night together. There is something lovely about finishing where we began. By now, the strangers from Day 1 are friends, the stories are already legendary, and Puglia has well and truly worked its magic.

We’ll stop for lunch along the way before checking back into the Mövenpick Bari. The rest of the afternoon is yours to enjoy the city at your own pace. Head back into Bari Vecchia for a wander, a gelato from the famous Gelateria Gentile, a little shopping, or a prosecco in the sun.

This evening, we’ll come together and walk into Bari Vecchia for our farewell dinner at one of the best restaurants in town. It’s our chance to celebrate the places we’ve discovered, the experiences we’ve shared, the ridiculous amount of food we’ve eaten, the drinks we’ve drunk, and most importantly, the wonderful friends we’ve shared it all with.

Accommodation: Mövenpick Bari

Meals: Dinner with Drinks

Street café scene with flower-lined stairs, pastries on tables, and people chatting in a narrow alley

DAY 12: Wednesday, 22nd September.
Onward Journeys

And just like that, our Puglian adventure comes to an end. The tour concludes after breakfast this morning, as we say our goodbyes and begin our onward journeys.

Thank you for joining us, for being part of the magic, and for bringing your wonderful energy to this very special Hermes Holidays adventure.

We wish you safe travels, buon viaggio, and hope it won’t be too long before we see your beautiful faces again. Until the next one.

Meals: Breakfast

View from airplane window of wing over a coastal city and blue sea under a clear sky

DAY 1: Saturday, 11th September.
Arrival in Bari

Our Moments

Infinity pool with a central walkway, reflecting sunset sky and surrounding trees
Dusk view of a hilltop village with stone buildings, glowing streetlights, and a tall bell tower under a pink sky

Words From Our Friends

"
My wife and I were newbies to Hermes’ Holidays; we were welcomed with open arms by Kyle, Wayne and all our fellow travellers. What an experience! So much thought and detail went into 12 days of luxury travel. All we needed to do was relax and enjoy the experience. The moment the tour started we were well looked after by Kyle and team!
We can’t wait for the next one.
"
This is my third fabulous tour with Hermes Holidays. I say each time "this holiday can't be topped". However the accommodation, unique and wonderful inclusions, all the tours, the food and wine all sublime. However, what makes a holiday with Hermes truly a cut above is the people. Kyle and Wayne are simply the best hosts you could ask for. The tour guides, all sassy and fabulous and the other guests you can honestly call new friends for life when you leave. Am looking forward to the next!
"
We are very happy to have travelled with Hermes Holidays many times previously - from the Queen of the Rhine river boat down classic river sites, the Dalmatian Dream on a super yacht in Croatia, the recent Taste of Tuscany based in a magnificent medieval Italian castle and now the Rose Royale. All have been superbly planned and executed with absolute excellence, but there was something even more special about the Rose Royale. From the incredible weekend in Paris to our Provencal Chateau then the stunning French Riviera in France, every adventure was next level. Kyles organization and knowledge ensured a smooth and fascinating time the whole time and his use of great local specialists added extra interest and excitement. However the most important feature of all Hermes adventures are the wonderful people that Kyle brings together. Many have travelled before but there are always great new folks to meet and become firm friends over the course of the trip. We arrived home having had easily the best yet of our many travel adventures - some alone, many with other companies and so we do not hesitate to recommend Hermes Holidays for any boutique travel in the future. Thanks Kyle and Wayne for the BEST time together!
"
Once again Hermes pulled together a truly memorable experience for a group of dear friends to enjoy. Well done Hermes.
"
We’ve been lucky to have enjoyed Hermes Holidays trips with Kyle and Wayne since 2015 and know we are always going to be totally looked after with unforgettable food, accommodation and experiences with the best group of friendly people. If you are looking for a five-star holiday where every detail is carefully planned so you can relax and fully enjoy it, then look no further than Hermes Holidays! We can’t wait for our next Hermes Holidays travel adventure!

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