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BELLA SICILY AND PUGLIA
contact us
May 11 - 24, 2027
with Tour Director, Sandy Gregory

SICILY
​Catania, Neapolis Archaeological Park, Ortigia, Taormina, and 
Mt. Etna

PUGLIA
​Valle D'estria, 
Alberobello, ​Martina Franca, Castellana Caves, Locorotondo, ​Polignano a Mare, Ostuni, Salento, Lecce, Otranto, Gallipoli, Matera

May 11 - 24, 2027
$12,826/person double-occupancy
based on a minimum of 12 travelers. 


Please join us!

Please join Tour Director Sandy Gregory for this wonderful adventure through Italy, or contact us to help you create your own independent travel experience with our Concierge Travel Services.

Suggested time to travel: May and October



Picture
Sicily:
2 nights Catania
2 nights Ortigia
2 nights Taormina

Puglia:
3 nights at a masseria villa in Valle d'Esria 
3 nights Lecce
​2 nights Matera






Trip Highlights

• Catania’s lava-stone elegance, market life and Sicilian street energy 
• Ortigia’s sea-wrapped beauty, ancient layers and sunset promenades 
• Taormina’s iconic viewpoints and timeless atmosphere above the Ionian Sea
• Mount Etna’s volcanic landscapes on black-lava soil
• A luxury villa in the Valle d’Itria, wrapped in olive groves and stone walls
• Alberobello’s trulli fairytale, with artisan corners and photogenic white lanes 
• Underground wonders at Castellana Caves
• Polignano a Mare’s cliffside blues
• Ostuni, the White City
• Lecce by sunset, honey-colored Baroque lacework, cafés and boutiques
• Two seas in one day, from Gallipoli’s Ionian softness to Otranto’s Adriatic brilliance 
• Private Sunset Boat in Salento, the signature “movie scene” moment 
• Matera’s Sassi, a stone world of stairways, silence, and breathtaking viewpoints 

• Luxury 4+ and 5-star accommodations
• 13 included meals in 14 days
• Cooking lesson, winetasting lunches and market visits
• Included group flight from Sicily to Puglia
• ​City tours with expert guides and all admissions.

DAY 1: MAY 11. ARRIVE CATANIA

Southern Italy doesn’t feel like a single destination. It feels like a sequence of worlds, each defined by its own light, textures, and tempo. This journey begins in Sicily: volcanic stone, sea wind, Baroque façades, and streets that pulse with real life. In Catania, built from black lava rock, you immediately sense Mount Etna’s presence in the architecture, the energy, the contrast of shadow and sun. 

​Your driver will be waiting for you as you exit baggage claim and take you to your hotel. 

1 night in Catania.

Welcome Rooftop cocktails and Welcome Dinner

​About Che Bella Included Dinners: Hosting this celebra​tion is one of the joys of being a Che Bella Tour Director. On our tours, we take you to our favorite restaurants, guide you through the menu, inspire you to choose something you’ve never tried before, choose the perfect wine pairings and throw in some local delicacies to broaden your palate and surprise you a bit. You’ll go home with a new knowledge that will draw you under Italy’s spell and increase your hunger for more. Waiter gratuities are included in all included dinners. 

DAY 2: MAY 12. MORNING TOUR OF CATANIA AND ON TO ORTIGIA

Private walking tour through the historic center of Catania. This morning, Catania unfolds through contrasts: elegant Baroque façades built from volcanic rock, bright squares, and stories shaped by fire and sea. Our tour will take us to the heart of the city, Piazza del Duomo and the symbol of Catania, the black lava elephant, Catania’s Cathedral, City Hall, and a stroll down Via Crociferi. 

Our tour will end at Catania’s famed and ancient fish market, one of largest and most colorful markets in Sicily. Choose from every form of seafood life imaginable and learn the importance of seafood on the Sicilian table. 

After lunch (not included), we will travel to Siracusa, arriving in Ortigia as the light turns warmer.

The island of Ortigia is the historical heart of Siracusa with a 2700 year history. It is famous for its rich Greek and Roman history and is also the birthplace of the famous mathematician and engineer Archimedes. Ortigia is wrapped by water, and the beauty here is quiet but constant: pale stone lanes, hidden courtyards, small churches, and seafront promenades that glow as afternoon turns to gold. 

​Included dinner.

​2 nights in Ortigia with included breakfast.

DAY 3: MAY 13. ORTIGIA

Our day will start with the Neapolis Archaeological Park, the most characteristic part of Syracuse, where you will see the Greek theatre, Latomie del Paradiso, Ear of Dionysius and the Roman amphitheater. 
​
We are then back in Ortigia with the ruins of the earliest Greek constructions. We'll stroll through the charming streets and limestone palazzi. Along the way, we stop to see the 6th century Temple of Apollo, the stunning square, Piazza Duomo and the extraordinary Cathedral of Siracusa. We will also stop by the famous mythological Fountain of Aretusa, and see the church of Santa Lucia alla Badia containing Caravaggio’s masterpiece, Burial of Saint Lucy.

The rest of the day is yours to wander this lovely town. 

Overnight in Ortigia

DAY 4: MAY 14. TO TAORMINA

This morning we continue our journey through Eastern Sicily with a short drive to Taormina. We travel north along one of Sicily’s most atmospheric coastal roads, where lava rock meets the Ionian Sea and the landscape feels sculpted.

Enroute, we'll take time to stretch out legs and have lunch (not included) in the Riviera dei Ciclopi, a place of myth and dramatic seascapes. In the town of Aci Trezza, the iconic Faraglioni sea stacks rise from the water like dark volcanic sculptures, while fishing boats and sea breeze give the village its authentic coastal pulse. Nearby, Aci Castello adds a striking scene: a Norman castle built on black lava rock, perched above the sea with commanding views, perfect for a short stroll and unforgettable photos.

After lunch, we continue to Taormina. By late afternoon, terraces open over the coastline and the light turns soft, setting the tone for an elegant evening.

Founded by in the 5th century B.C.E., Taormina was conquered by the Greeks, Romans, Byzantines, Arabs, Normans and Bourbons. Taormina’s tumultuous history has left a legacy of fine architecture. Idyllically perched ‘Tra Cielo e Mare’ - between sky and sea. The turquoise views of the crystal clear waters of the Ionian Sea contrast with the looming presence of the volcano Etna in the background, ever the reminder of the great natural forces at play on this island. Taormina has everything you could wish for in an Italian getaway: food, wine, history, culture and gorgeous landscapes. Taormina’s atmosphere is refined and cinematic, terraces, viewpoints, and evenings that feel designed around soft light.

Included Dinner

​2 nights in Taormina with breakfast 

DAY 5: MAY 15. A DAY AT LEISURE IN TAORMINA

Taormina is one of those towns where you just want to wander; it is timeless and effortlessly elegant. Today is yours to relax. You may want to venture down the hill to one of Taormina’s delightful beaches or climb the hill above the town to enjoy a cappuccino and eye-popping views of the coastline. The town’s most iconic scene is the Greek Theatre (Teatro Greco), where history and landscape share the same stage: stone seating carved into the hillside, the Ionian shimmering below, and Etna rising in the distance like a guardian. ​You’ll find boutiques filled with sophisticated Italian fashions and super-cute local stores filled with handmade shoes and handbags. Look for typical local products like colorful ceramics, honey and marzipan fruits. 

DAY 6: MAY 16. MT. ETNA AND ON TO PUGLIA

This morning begins high above Sicily, where the landscape turns lunar and the air becomes crisp and clean. Your private driver collects you in Taormina for a private sightseeing transfer to Mount Etna, climbing through changing scenery, from coastal brightness to pine forests, then into the stark beauty of black lava fields.

On Etna, you reach the crater zone, where the ground is shaped by ancient eruptions and the views stretch wide across the island. You walk among volcanic craters and lava formations, feeling the scale of the volcano under your feet, a place that is both dramatic and strangely quiet. If conditions allow, you can extend the experience with a higher-altitude option (weather and local regulations permitting), but even at the main crater areas, Etna delivers a powerful, unforgettable Sicilian finale.

We are then on to the Catania Airport, for our included group flight to Bari, Puglia.

Upon arrival in Bari, we will be transferred to the Valle d’Itria, where olive trees shimmer like silver and dry-stone walls trace the countryside. Our luxury masseria (vila)is waiting, a limestone sanctuary designed for slow luxury. We will let the evening drift into a golden-hour aperitivo and a warm included Puglian dinner.

3 nights with included breakfast

DAY 7: MAY 17. ALBEROBELLO

Morning starts softly in the countryside as we head out until, Alberobello appears, as if someone placed a fairytale village in the middle of the landscape. Alberobello is famous for their trulli: whitewashed stone huts with conical roofs that have been around for centuries. Today, 1,500 of these tiny, fairytale-like huts house hotels, private residences, small artisan ateliers, restaurants and bars. 

You will have time to explore this town and have some lunch. 

Our journey continues to the Baroque town of Martina Franca. Balconies curve above narrow streets, façades glow in pale limestone, and quiet piazzas feel like private stages set for golden hour. As the day turns gentler, the city becomes almost cinematic, less about monuments and more about atmosphere, the kind of place that lingers in your mind long after you’ve left.
​ 
Tonight at our villa, we’ll toast to the sunset with a cocktail party and dinner watching the chef's make the area's regional pastas and tasting their specialties.

DAY 8. MAY 18. COOKING AND CAVES

This morning, we master the art of orecchiette! Orecchiette literally means “little ears” in Italian. It originated in Puglia centuries ago and is still strongly tied to the region’s cultural identity. Making orecchiette is a communal activity. Families gather to prepare large batches together, especially for Sundays and holidays. The technique, dragging dough with a knife and flipping it over the thumb, is passed down through generations. We will make a 3-course lunch at our villa and enjoy the fruits of our labor. 
After lunch, we are on to The Castellana Caves, ​one of the most spectacular natural highlights of Puglia. As we step down into the network of caves, the air cools, the sound changes, and suddenly the world above feels far away. Vast chambers open one after another like underground cathedrals, vaulted ceilings of stone, mineral curtains, formations that look impossibly delicate for something carved by water and patience.

We are then on to Locorotondo, perched on the top of a hill. It's a maze of little lanes lined with historic buildings, some humble and faded, others retaining their grand baroque archways and architectural details. You'll have some time to explore the town before we head to the coast, where Polignano a Mare appears suspended above the Adriatic like a balcony over infinity. White cliffs drop into cobalt water, the air is salted and alive, and every viewpoint feels made for lingering. 

A Special Included Dinner at the Cave of Polignano a Mare. 

DAY 9. MAY 19. OSTUNI'S WHITE MAZE AND LECCE

This morning we head to Ostuni, the White City. Streets brighten as you climb, stairways twist into arches, terraces open unexpectedly, and every turn reveals a new view over an endless sea of olive trees. With our local guide, we'll slip into the city’s most beautiful corners, the quiet lanes, and the hidden vantage points. 

After lunch, the journey continues south into Salento, where the landscape grows more Mediterranean, the colors deepen, the air feels warmer and more intense.

​By late afternoon, Lecce welcome us. Lecce feels less built than carved, as if the city were sculpted from honey-colored stone with the delicacy of lacework. By day it glows softly; by evening it turns to pure gold, lit from within. 

Included dinner. 

3 nights in Lecce with included breakfast

DAY 10. MAY 20. LECCE

Morning tour of Lecce, including Piazza Sant’Oronzo, the Roman amphitheatre, and Santa Croce, a Baroque masterpiece so intricate it almost looks weightless, like stone pretending to be embroidery.

The rest of the day is left deliberately open for the city’s quieter pleasures: boutique windows, slow cafés, hidden courtyards, and that unmistakable Salento rhythm where wandering is the point. Nothing to chase, nothing to hurry, just the warm light, the soft streets, and the feeling that you’re exactly where you’re supposed to be.

DAY 11. MAY 21. IONIAN & ADRIATIC WONDERS

This morning, we head out of Lecce to Otranto. We'll stroll through its historic heart and discover the cathedral’s extraordinary mosaic floor, then admire the Aragonese Castle (15th century) standing watch over the sea.

After a leisurely lunch in town (not included), we continue west toward Gallipoli, where the atmosphere turns warmer and more Mediterranean. With our local guide, we will walk the old island town, the port, and the historic lanes where sea air and sunlit stone set the rhythm.

We are then on to the harbor for our Private Sunset Boat Tour in Gallipoli. Step aboard as the Ionian Sea turns liquid silver and the coastline glows amber. Enjoy an aperitivo on board while the sun drops into the water. Hop in for a swim. 

​After the cruise, we will return to Lecce and the evening is yours to enjoy. 

DAY 12. MAY 22.
BASILICATA & MATERA

Today we leave Puglia behind, watching the landscape shift from coastal light to quieter inland horizons toward Basilicata.

By afternoon, Matera begins to reveal itself, carved into stone and layered with time. This extraordinary city, where until the 1950s many residents still lived in cave dwellings, feels almost unreal at first sight, a place of stairways, silence, and golden rock that glows as the light changes.

Our evening is left beautifully open: a gentle stroll, a panoramic viewpoint, or simply letting the atmosphere settle in.

2 nights in Matera with included breakfast.

DAY 13. MAY 23. THE SASSI, GOLDEN LIGHT AND A FAREWELL DINNER TO REMEMBER

This morning, our private tour will take us into the Sassi, a labyrinth of stone stairways, ancient passageways, and cave-dwellings. Doorways cut into tuff, hidden courtyards, tiny chapels tucked where you’d never expect them, and viewpoints that open suddenly onto a landscape of rooftops and ravines.

We'll hear the human stories that make Matera so powerful, the resilience of families who lived inside these caves until the mid-20th century, the transformation of an “invisible” place into one of Italy’s most cinematic destinations, and the way light moves across the stone, changing the city’s mood hour by hour.

The afternoon is yours enjoy the town. Sit on a panoramic terrace with an espresso, wander into artisan ateliers where ceramics and local crafts are still made by hand, or simply let yourself get lost on purpose, following staircases until you find a viewpoint that feels like it belongs only to you. Matera rewards the unplanned moments: a quiet church, a sunlit archway, a staircase that turns into a balcony over the canyon.

Included Farewell Dinner with wine pairings. 

DAY 14: MAY 24. FLIGHTS OUT 

Included transfers to the Bari Airport for flights our or on to your Post-tour option. Below are a few suggestions:
EXCURSION SUGGESTION TO rome
Day 1. “Tutte e strade portano a Roma” – “All Roads lead to Rome.” Rome is one of the most beautiful, exciting cities in the world. Today’s Rome is a combination of romance, relics and ruins amidst a modern, sprawling, living city. Medieval churches sit atop ancient basilicas above Roman palaces. Gleaming office buildings incorporate fragments of eroded Roman columns. Roads and piazzas follow the lines of ancient city walls. Rome’s history began over 2000 years ago, far before the time of Jesus Christ. It was the capital of the Roman Empire and is still the capital of Italy. We’ll arrive in Rome in the late afternoon and check in to our hotel, located right in the historic centre of Rome. It’s walking distance from all the major sites and serves breakfast right at the foot of the Pantheon. 

Tonight we’ll take a walking orientation enroute to included dinner.
​

Day 2. This morning your guide will pick you up at your hotel to enjoy a private tour of Ancient Rome, including the Capitoline, Forum and Colosseum. The rest of the day is yours to enjoy at your leisure. 

In that area after the tour, you might want to think about:

• Visiting the Wedding Cake (Tomb of Victor Emmanuel) and go up the elevator for a great view of Ancient Rome, then go next door to the Capitoline Museum which is really good. Then go over and see Michelangelo’s Moses at St. Peter’s in Chains. 

• San Clemente, a church where you can walk down various levels to view centuries of archaeological finds. 

​• Stroll up Via del Corso and do some shopping and finish at the Spanish Steps. The Spanish Steps are crowded, and are ... steps, but a good afternoon destination for gelato and people watching. This is also at the top of a major shopping district in Rome - Via Condotti.

• Walking along the Tiber and then visiting the synagogue at the ghetto, or Jewish Quarter. There is a whole lively street of great restaurant choices. Not to be missed: The Jewish Artichoke! This local treat dates back to Imperial times, when the Roman Jewish community numbered about 50,000. They look like golden sunflowers and their leaves have a delicious nutty crunchiness. You can also visit the synagogue after lunch. You don’t need advanced reservations, but can go get tickets before lunch for an afternoon tour.

Day 3. 
This morning we enjoy a private tour of the Vatican Museum, Sistine Chapel and St. Peter’s square.

This afternoon you can:
• Stay in the Vatican area for lunch and then stroll down to the Castle of the Angels. It’s a lovely museum with great views of Rome.
 
• Take a taxi to the orange grove to peek through the keyhole to see a cool view of St. Peter’s dome. Ask your guide for details.

• Dig a Little Deeper with our optional Rome excursions listed above

Tonight: Included Farewell Dinner

Dig a Little Deeper private optional tour excursions:

Before and After-Hours VIP Tours to the Vatican and St. Peter's.
 Che Bella is now offering off-hour tours, away from the heat of the day and the crowds of the general public. 

Opera at the Baths of Caracalla. Formerly public baths for Romans and later enhanced with libraries, the Baths of Caracalla date back around 212-217 AD. the Baths of Caracalla today serve as the perfect backdrop for enjoying an opera. Not only does this outdoor theater offer marvelous acoustics, but there are also stunning lightshows projected onto the Baths’ ruins that accompany and enhance all operatic performances. Every summer, the Baths of Caracalla host a selection of operas from the Teatro dell’Opera. Beginning promptly at 9:00pm, these evening performances are all set in the outdoor theater, Teatro alle Terme di Caracalla. With English and Italian subtitles provided, tickets range from €25 to €100. Please inquire about the performance schedule. 

Underground Rome Tour. Every time I'm in Rome, I see new diggings. Be it for the new metro line, a shopping mall or sewage pipes, a new piece of underground Rome is excavated, examined and cataloged. There is a whole world to discover beneath Rome's surface. This tour Peel back Rome's layers of history with visits to three of Rome's eeriest sights: the Capuchin Crypt, the Prscilla Catacombs and the Basilica of San Clemente.

Trastavere Foodie Tour. We came! We saw! We ate! Trastevere is a neighbourhood like no other. Its ivy-coated, cobblestone streets come alive at night, earning it comparisons to Greenwich Village and Paris’s Left Bank. It’s where Romans choose to eat with their families on a Sunday and where young Romans go for buzzing nightlife at evenings and weekends. You can’t leave Rome without walking these streets and tasting the best food in Rome. During this local walking tour, you'll enjoy learning about the history of the area, visit the local food spots, taste along the way, enjoy a magnificent sit down dinner and end with some of the best gelato in Rome.

Enroute to or from Rome, we'll make a 3-hr. stop in wonderful Orvieto, Umbria. It’s a great pedestrian town with artisan shops and a city wall that offers gorgeous views of the surrounding countryside. You can tour Orvieto’s famous cathedral or see some of the best artifacts in Tuscany in an underground system of tunnels and caverns carved by the Etruscans. ​
​​
EXCURSION SUGGESTION TO NAPLES AND THE AMALFI COAST
Post-Tour Day 1. Train to Naples for day tour and on to Sorrento

We’ll begin with a stop at the Naples Archaeological Museum, where you’ll have a private tour and time to see the best of the artifacts from both Pompeii and Herculaneum … and the secret erotica room! After your museum tour, we’re on to Pizza to fortify you for the afternoon. We’re then on our way to our private tour of Herculaneum, with its expansive houses, impressive mosaics and lavish marble in the remains. 

We’re then on to the Amalfi Coast, one of the most breathtaking drives in the world. 

Our Sorrento hotel located above the town. All rooms will have balconies that look over the Bay of Naples and Mt. Vesuvius, with included breakfast and a pool.

Tonight we’ll enjoy our passagiatta strolling through the winding streets of Sorrento enroute to Included Dinner.

 
Post-Tour Day 2. A Day in Positano 
Today is a day of leisure in the beautiful town of Positano. We’ll be back in the late afternoon so you can walk down in to Sorrento as well. Transfers from and back to Sorrento included. 

Dinner tonight is on your own in Sorrento. 

Post-Tour Day 3. A Day in Capri
This morning we’ll board the fast ferry for a day on the island of Capri. 
​
You’ll have the afternoon to explore more of Sorrento and tonight we’ll have an included Farewell dinner to say arrivederci to Italy.

Post-Tour Day 4. Arrivederci Italia! 
Transfers to the Naples Airport.
​​

READY TO TRAVEL?

303-596-4593

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