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Hidden Italy – Puglia & Sicily • September 3-11 and 13-21, 2026

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Explore untrampled Italy…

Discover the quiet charms of Southern Italy on a journey through Puglia and Sicily. Explore whitewashed villages, ancient ruins, olive groves, and seaside towns. Savor regional cuisine, local wines, and warm hospitality. This off-the-beaten-path adventure is perfect for curious, active travelers seeking culture, beauty, and authenticity—without the crowds. Italy’s soulful south awaits.

Overview

Puglia Main Trip

September 3-11, 2026

September 13-21, 2026

Double occupancy ~ $9,475.00 per person

Single occupancy ~ $10,615.00

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Sicily Extension

September 21-26, 2026

Double occupancy ~ $5,995.00 per person

Single occupancy ~ $7,915.00

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One-way airfare between Puglia and Sicily is an additional $195.00 per person

Activity Level

Our tours are designed for travelers who are comfortable with daily mobility. Each day offers the opportunity to explore a new town or village, which may involve walking for up to an hour or more. This walking can occur on uneven terrain, including navigating stairs, and often requires getting in and out of vehicles. While the pace is manageable, it is essential that you can walk independently with the group and do not require assistance.

Highlights & Inclusions:

  • Round-trip airport transfers in and out of Brindisi or Bari Airport
  • Eight (8) nights total accommodations in unique deluxe hotels (Puglia Main Trip)
  • Five (5) nights total accommodations in unique deluxe hotels (Sicily Optional Post-Trip)
  • Most meals, as referenced in the itinerary, including wine, beer, soft drinks, water & coffee/tea
  • All transportation within Puglia and Sicily (optional post-trip) in deluxe, climate-controlled vehicles 
  • Excursions and tours as outlined in the itinerary (subject to change)
  • Expert guides with passion and personality
  • Gratuities included for guides, drivers, restaurant staff, and hotel porters
  • Pre-trip documents with essential travel information, including “Know Before You Go,” luggage tags, and signature WOW! surprises
  • Assistance with air booking (complimentary for repeat “WOWees”; service fee of $75 for first-time “WOW!” travelers)
  • Basic emergency medical insurance
  • “WOW!” surprises along the way!
  • The experience and expertise of a member of the WOW! Travel Club team for pre-trip planning and on-site escorting

Exclusions:

  • International airfare (fare will be quoted upon request)
  • One-way airfare between Puglia and Sicily (it is an additional $195 pp)
  • Baggage fees and/or seat assignments not listed as an inclusion
  • Extra hotel nights, if requested
  • Meals not noted in itinerary
  • Incidental charges (shopping, spa, food and beverage not included in the itinerary, etc.)
  • Supplemental travel insurance (for trip cancellation, pre-existing conditions, lost luggage, trip delay reimbursement, etc.)

   **Itinerary Subject to Change**

Puglia Main Trip • September 3-11, 2026 and September 13-21, 2026

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DAY ONE – Brindisi Airport – Arrival

Departure One: Thursday, September 3rd
Departure Two: Sunday, September 13th

Arrive at Brindisi International Airport. Upon exiting the Arrivals Hall, A representative will greet you and assist with your transfer to your elegant home for the next four nights —Risorgimento Hotel, nestled in the heart of Lecce’s historic center. Dinner this evening will be on your own—an ideal opportunity to wander Lecce’s charming streets and enjoy a leisurely meal at one of its many inviting trattorias.

** Arrivals ~ Bari International Airport is another option; however, it’s further than Brindisi. Transfers are included only from Brindisi.

WOW! Travel Club  No Meals Included
WOW! Travel Club  Risorgimento Hotel

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DAY TWO – Lecce

Departure One: Friday, September 4th
Departure Two: Monday, September 14th

Begin your day with a guided walking tour of Lecce, often called the “Florence of the South” for its stunning Baroque architecture. We’ll explore the charming old town, where golden-hued pietra leccese stone gleams in the morning sunlight. Discover hidden art studios, historic palazzi, and stylish alleyways that embody the charm of Southern Italy.

After the tour, our driver will take us through the scenic Salento countryside, stopping for photos in a traditional village square and at a beautiful vineyard landscape.

Continue to a local Salento winery for a guided tasting featuring the region’s renowned grapes—Negroamaro and Primitivo—followed by lunch at a nearby restaurant.

Return to Lecce in the afternoon to participate in a local artisan activity.

This evening, enjoy a welcome dinner at a local restaurant.

WOW! Travel Club  Breakfast, Lunch & Dinner
WOW! Travel Club  Risorgimento Hotel

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DAY THREE – Otranto and Gallipoli

Departure One: Saturday, September 5th
Departure Two: Tuesday, September 15th

After breakfast, we’ll embark on a full-day exploration of Southern Salento, a region cherished by Italians for its sun-soaked coastal towns and laid-back Mediterranean spirit. Today, you’ll visit two iconic seaside destinations—Otranto and Gallipoli—each offering its unique charm and history.

Begin with a guided stroll through Otranto, perched on the Adriatic Sea. Its whitewashed old town and narrow alleyways give it a distinctly Greek feel, with breathtaking views of the turquoise sea steps away. Then continue to Gallipoli on the Ionian coast, known for its pastel-hued buildings, fishing boats, and lively energy. Both towns invite you to slow down, savor the sea breeze, and take in the beauty of Salento’s shoreline—don’t miss the chance to dip your toes in the soft sand.

Along the way, you’ll enjoy a lunch inspired by the culinary traditions of southern Salento—a special menu that highlights local flavors and seasonal ingredients. From seafood to fresh vegetables and regional specialties, it’s a feast that reflects the heart of the south.

Return to Lecce by late afternoon. The rest of the day and evening are yours to explore at leisure. Take a stroll through Lecce’s glowing streets, discover a tucked-away trattoria for dinner, or enjoy an aperitivo al tramonto—sunset aperitif—at one of the city’s many charming piazzas.

WOW! Travel Club   Breakfast & Lunch
WOW! Travel Club  Risorgimento Hotel

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DAY FOUR – Lecce

Departure One: Sunday, September 6th
Departure Two: Wednesday, September 16th

After breakfast, we’ll begin the day with a stroll through Lecce’s vibrant local market, where stalls brim with seasonal produce, fragrant herbs, cheeses, and freshly baked breads. As we wander with our hosts, you’ll gain insight into the ingredients that define Puglian cuisine and experience the lively rhythm of everyday life in the old town.

From the market, we’ll head to a hands-on cooking class with local chefs. Here, you’ll learn to craft orecchiette—the beloved “little ears” pasta of Puglia—entirely from scratch. As you roll and shape the dough, you’ll also be introduced to the region’s wine culture, sampling indigenous varietals that beautifully complement the local flavors.

Following the class, sit down to enjoy the fruits of your labor over a relaxed lunch featuring your handmade pasta and regional wines—a true taste of Puglia’s culinary soul.

The remainder of the afternoon and evening, including dinner, will be on your own to explore Lecce at your leisure—perhaps discovering a tucked-away trattoria, lingering over an aperitivo in a sunlit piazza, or simply soaking in the golden glow of this enchanting city.

WOW! Travel Club  Breakfast & Lunch
WOW! Travel Club  Risorgimento Hotel

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DAY FIVE – Lecce, Ostuni, Masseria

Departure One: Monday, September 7th
Departure Two: Thursday, September 17th

After breakfast, set out for a truly memorable day exploring the scenic beauty of Ostuni and its surrounding countryside. Known as “La Città Bianca,” Ostuni gleams with whitewashed buildings perched high on a hilltop, offering breathtaking views of the olive-dotted plains below.

For lunch, enjoy a relaxed meal set among the olive trees in a beautiful grove, where you’ll savor local olive oil and a curated selection of Puglian specialties. Surrounded by the countryside and the scent of sun-warmed olives, the rustic flavors and peaceful setting offer a true taste of the region’s culinary heritage.

Following lunch, we’ll check into our home-away-from-home for the next four nights, the Masseria Montenapoleone, a refined countryside retreat blending rustic elegance with modern comfort amid ancient olive groves.

Enjoy the remainder of the afternoon at your leisure—relax, explore, or simply soak in the peaceful surroundings. Later this evening, we’ll gather once again for dinner together at the Masseria.

WOW! Travel Club  Breakfast, Lunch & Dinner
WOW! Travel Club  Masseria Montenapoleone

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DAY SIX Itria Valley, Alberobello

Departure One: Tuesday, September 8th
Departure Two: Friday, September 18th

After breakfast, we’ll continue our journey through the heart of Puglia into the Itria Valley, a region famous for its rolling countryside, olive groves, and distinctive trulli—the iconic whitewashed homes with conical stone roofs that seem straight out of a fairy tale.

You’ll visit two of the valley’s most charming Trulli White Towns: Alberobello, a UNESCO World Heritage Site where clusters of trulli line the narrow streets and Martina Franca, known for its elegant Baroque architecture and lively atmosphere.

For lunch, savor a meal of local specialties highlighting the rustic flavors of the Itria Valley.

Enjoy the remainder of the afternoon at your leisure—relax, explore, or simply soak in the peaceful surroundings. Later this evening, we’ll gather once again for dinner together at the Masseria.

WOW! Travel Club  Breakfast, Lunch & Dinner
WOW! Travel Club  Masseria Montenapoleone

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DAY SEVEN – Altamura, Matera

Departure One: Wednesday, September 9th
Departure Two: Saturday, September 19th

After breakfast, we’ll set out on a scenic drive to Matera, one of Italy’s most extraordinary and historic cities, located on the border between Puglia and Basilicata. Along the way, we’ll stop in the town of Altamura, renowned for its traditional bread.

At a local panificio (bakery), we’ll get a firsthand look at how pane di Altamura and focaccia are made—bread that has been crafted here for centuries using time-honored techniques, local semolina flour, and wood-fired ovens. With their distinctive shape, dense crust, and impressive shelf life, these loaves are a true taste of Southern Italian tradition.

Upon arrival, we’ll explore Matera’s iconic Sassi District, a UNESCO World Heritage site made up of ancient cave dwellings and rock-hewn churches. As we wander through this timeless landscape of stone pathways and centuries-old homes carved into the hillside, it truly feels as though we are stepping into another era.

We’ll pause for lunch at a unique restaurant set inside one of Matera’s atmospheric caves, where the dramatic surroundings create an unforgettable dining experience. Here we’ll sample specialties of the cucina materana, known for its rustic flavors and hearty, locally sourced ingredients.

The afternoon is yours to relax, shop, or soak in the atmosphere of this remarkable city at your own pace.

WOW! Travel Club  Breakfast & Lunch
WOW! Travel Club  Masseria Montenapoleone

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DAY EIGHT – Polignano a Mar & Monopoli

Departure One: Thursday, September 10th
Departure Two: Sunday, September 20th

After breakfast, we’ll head out for a day of exploring the postcard-perfect coastal towns of coastal Puglia. Our local guide will lead us through the enchanting streets of Polignano a Mare, a city perched dramatically on cliffs overlooking the Adriatic Sea. Known for its sea-view terraces, winding alleys, and whitewashed buildings, Polignano is pure romance by the sea.

We’ll then continue to Monopoli, a historic port town with Greek influences woven into its architecture and city layout. Here, the narrow lanes and bright facades offer a glimpse into everyday life as locals go about their routines in this charming seaside setting. It’s an immersive way to experience the soul of the southern coast.

This afternoon, we’ll pause for a casual lunch featuring panzerotto, a beloved Puglian street food—crispy on the outside and warm, melty inside—followed by a taste of caffè speciale, the iconic coffee drink of Polignano that blends espresso with cream, citrus, and amaretto.

After lunch, we’ll take to the water for a relaxing three-hour catamaran experience along the Adriatic coast. From the sea, you’ll admire Polignano’s dramatic cliffs, hidden coves, and sparkling turquoise waters while enjoying the gentle rhythm of the Mediterranean—a perfect way to experience this breathtaking coastline from a new perspective.

Later, we’ll gather once more for a special farewell dinner. As we toast to the journey we’ve shared, we’ll reflect on the flavors, friendships, and unforgettable moments from our time in Southern Italy. Some of us will be heading home tomorrow, while others will continue the adventure with an optional post-trip extension to Sicily.

WOW! Travel Club  Breakfast, Lunch & Dinner
WOW! Travel Club  Masseria Montenapoleone

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DAY NINE – Depart to the United States or continue to Sicily

Departure One: Friday, September 11th
Departure Two: Monday, September 21st

After breakfast, we’ll begin to part ways, carrying with us the rich memories of our journey through Southern Italy—the golden light of Lecce, the flavors of Puglia, the charm of seaside towns, and the ancient wonder of Matera. For some, it’s time to return home, and transportation to the airport will be provided for onward flights.

For others, the adventure continues with our optional Sicily extension. They’ll head to the airport for a short flight, ready to explore a new chapter filled with island beauty, bold flavors, and more unforgettable moments. See Sicily Extension information below.

WOW! Travel Club  Breakfast

Optional Sicily Extension - September 21-26, 2026

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Monday, September 21st – Arrive in Sicily – B & D

After breakfast, our group will continue to the next chapter of our journey—Sicily. Some will say goodbye to Puglia and head to the airport for a quick flight to Catania on Sicily’s southeastern coast, while others might be joining us in Sicily before heading to Puglia later in the month. Upon arrival, all guests will be transferred to the elegant Minareto, a beautiful seaside retreat just outside Syracuse. Nestled on a cliff with sweeping views of the Ionian Sea, this luxurious resort will be our home base as we begin exploring Sicily’s rich culture, flavors, and history.

We’ll gather for dinner at a local restaurant.

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Tuesday, September 22nd – Syracuse, Ortigia -B & L

Today’s journey offers a rich mix of ancient history, coastal scenery, and local customs—an immersive day in the heart of southeastern Sicily.

We’ll begin with a guided tour of the Archaeological Park of Neapolis, one of Sicily’s most significant archaeological sites. Here, you’ll walk in the footsteps of ancient civilizations while exploring the Greek Theatre, Roman Amphitheater, and the Ear of Dionysius—a large limestone cave famous for its amazing acoustics and legends.

Enjoy a relaxed lunch and wine tasting at Pupillo Winery, one of the most historic and picturesque estates in the Syracuse area. Surrounded by old vines and fragrant citrus groves, this experience provides a perfect pairing of Sicilian flavors and excellent local wines in a peaceful setting.

From there, it’s off to Ortigia, the historic center of Syracuse, where a private boat tour along the coast offers breathtaking views of its Baroque architecture, sea caves, and turquoise waters.

Back on land, we’ll continue with a visit to Ortigia’s magnificent Duomo (Cathedral), built over the ruins of a 5th-century BC Greek temple. Its layered history, blending pagan columns with Christian elegance, makes it one of the most striking and symbolic religious sites in Sicily. Nearby, we’ll stop at the Papyrus Paper Workshop, where local artisans keep the ancient Egyptian technique of papyrus making alive—a nod to Syracuse’s historical connection to the craft.

After a day full of discovery and joy, you’ll head back to your hotel with a greater appreciation for the many layers—natural, cultural, and culinary—that make Sicily so unforgettable.

Dinner this evening is on your own.

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Wednesday, September 23rd – Syracuse – B & L

Today offers a vibrant and flavorful journey into some of Sicily’s most treasured artistic and culinary traditions. We’ll start with a visit to a traditional Sicilian cart workshop, where you’ll see the intricate craftsmanship behind these brightly colored, handcrafted carts—true symbols of Sicilian culture. You’ll meet the artisans who keep this centuries-old folk art alive and learn how each brushstroke and carved detail tells a story of Sicily’s rich history.

Then, enjoy a traditional Ragusan brunch, featuring a flavorful array of regional specialties: highlights include wood-fired bread served with local olive oil and oregano, creamy fresh ricotta, Ragusana provola and aged caciocavallo cheeses paired with fruit preserves, and local cured meats like fennel-scented sausage and pistachio-studded salami.

Next, we’ll indulge our sweet tooth with a visit to a local chocolate factory, where you’ll discover the unique process behind Modica-style chocolate. This ancient method, introduced during Spanish rule, involves cold-processing cacao to preserve its bold flavor and gritty texture. You’ll learn about its history and manufacturing, followed by a decadent tasting of different chocolate flavors—ranging from classic dark to those infused with citrus, cinnamon, or sea salt.

After indulging in Modica’s famously rich chocolate, we’ll balance things out with a guided walking tour through the town’s charming historic center.

Return to your hotel with the evening at leisure.

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Thursday, September 24th – Syracuse, Savoca, Taormina- B & L

Film history, ancient ruins, and breathtaking coastal scenery are on today’s itinerary. We begin with a visit to the famous “Godfather Villa,” nestled in the hillside town of Savoca. This charming village played a key role in the filming of Francis Ford Coppola’s classic. You’ll have the opportunity to explore the villa’s atmospheric interiors and stroll through the peaceful streets that served as Michael Corleone’s Sicilian retreat. It’s a must-see for film enthusiasts and anyone interested in Sicily’s cinematic heritage.

For lunch, we’ll dine at a seaside restaurant nestled along the cliffs overlooking Taormina Bay, where you can enjoy fresh seafood and Sicilian specialties while taking in breathtaking views of the nearby gorges and blue coastline.

After a relaxing lunch, head to the nearby cable car for a scenic ride up to the center of Taormina’s historic town. Perched high above the Ionian Sea, Taormina offers breathtaking views and a timeless charm that has captivated visitors for centuries.

Upon arrival, meet our local guide and start a walking tour through the charming streets of this hilltop jewel. The highlight of our visit will be the Ancient Greek Theatre—an impressively preserved amphitheater dating back to the 3rd century BC. With Mount Etna looming in the distance and the sea shining below, the scenery is as stunning as the history.

Enjoy dinner on your own this evening.

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Friday, September 25th – Syracuse, Mt. Etna – B, L & D

Today, we head to one of Sicily’s most iconic natural wonders—Mount Etna, Europe’s tallest and most active volcano. Dominating the island’s eastern landscape, Etna provides a stunning display of raw power and majestic beauty. Our day begins with a scenic drive up the mountain’s slopes, followed by a cable car ride. From this height, you’ll see dramatic lava fields, lunar-like craters, and—weather permitting—breathtaking views that reach all the way to the sea.

After exploring this otherworldly terrain, we’ll descend the mountain and head to one of the oldest wineries in the Etna region. Enjoy a relaxed, flavorful lunch, paired with a guided tasting of their renowned varietals. As you sip wine and taste dishes rooted in the local terroir, you’ll understand how deeply Mount Etna influences both the landscape and the flavors of this region.

In the evening, we’ll gather for a farewell dinner to toast the memories created during our time in Sicily.

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Saturday, September 26th – Depart for the United States – B

After breakfast, you’ll be transferred to the airport for your flight home, with memories to last a lifetime.

Accomodation - Sicily Extension

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Minareto – Syracuse, Sicily

Minareto is a luxurious seaside resort perched above the sparkling Ionian Sea, just across the bay from the historic center of Syracuse. Surrounded by lush gardens and dramatic coastal cliffs, this five-star retreat offers elegant rooms and suites, many with sea views or private pools. With direct beach access, a stunning infinity pool, and refined Sicilian cuisine, Minareto blends natural beauty, sophisticated comfort, and serene privacy—making it an ideal escape on the island’s southeastern coast.

Room Category: Superior

Accommodations - Puglia

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Risorgimento Hotel – Lecce

The Risorgimento Hotel in Lecce is an iconic palazzo hotel located in the heart of the city’s historic center, just steps from Lecce’s beautiful Baroque landmarks and lively piazzas. Recently transformed through a multi-million-dollar renovation, the hotel now blends historic elegance with refined modern design. Its beautifully updated rooms, stylish common spaces, and rooftop terrace create a sophisticated retreat that perfectly reflects the timeless charm and vibrant spirit of Lecce.

Room Category: Superior Room

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Masseria Montenapoleone – Fasano

Masseria Montenapoleone is a beautifully restored 16th-century farmhouse tucked into the olive groves of Puglia’s countryside near Fasano. Blending rustic charm with understated luxury, this family-run masseria offers whitewashed stone walls, arched ceilings, and serene outdoor spaces that capture the essence of southern Italy. Guests wake to homemade Apulian breakfasts, relax by the pool beneath ancient olive trees, and enjoy easy access to the Adriatic coast and nearby hilltop towns—making it an authentic and tranquil base for exploring the region.

Room Category: Deluxe Room

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