Itinerary Overview
Travel Styles: Gourmand Getaway, Honeymoon, Cultural, Seaside Luxury
This 11-day, 10-night journey takes you through Italy’s most stunning regions, blending breathtaking landscapes, rich history, exquisite cuisine, and world-class wine. With built-in moments to relax or explore at your own pace, it offers the perfect balance of adventure and leisure. As with all our itineraries, this one can be fully customized to align with your preferences and travel dreams.
Day 1
A Scenic Journey to the Amalfi Coast from Napoli
Welcome to Positano
Your private chauffeur will greet you upon arrival at Naples International Airport. From there, your private chauffeur will escort you for a scenic transfer along the Amalfi Coast to Positano. Relax and take in the breathtaking views of dramatic cliffs, sparkling seas, and vibrant villages during this famous journey.
Upon arrival in Positano, check into your luxurious sea-view room at your chosen hotel, where every detail has been curated for your comfort. Spend the afternoon unwinding at your leisure—perhaps exploring the cascading streets lined with artisan shops and fragrant florals or simply enjoying the serenity of your accommodations. End your day dining under the stars as the sound of the sea sets the rhythm for your Italian escape.
Day 2
Live La Dolce Vita in Positano
Free morning and afternoon.
Mediterranean cooking class & wine Tasting
Your cooking class takes place in one of Positano’s historic family-owned homes, a gorgeous property steeped in charm and tradition. Begin with a delightful selection of antipasti paired with local wines, setting the stage for an unforgettable culinary experience. Shortly after, you’ll step onto the property’s stunning terrace—a space that boasts panoramic views of the Amalfi Coast. While the vibrant garden and endless sea views may vie for your attention, the real magic lies in the kitchen.
Craft authentic recipes that have been passed down through generations, using only the freshest, locally sourced ingredients. As the three-hour hands-on session comes to a close, celebrate your newfound skills with a glass of wine and savor the fruits of your labor in this breathtaking coastal setting.
Day 3
Discover Capri and the Famous Blue Grotto
Private Full-day boat tour to capri
Board your private boat and set sail for the enchanting island of Capri, where time is yours to explore at your own pace. Cruise along the rugged coastline, stop for a refreshing swim in the crystal-clear waters, or simply bask in the Mediterranean sun. Known for its breathtaking landscapes, Capri has captivated travelers for centuries with its natural beauty, rich history, and panoramic vistas.
Explore the island’s iconic grottoes and dramatic cliffs plunging into turquoise seas, or wander its charming streets lined with designer boutiques and artisan shops. From fine dining to Roman ruins, manicured gardens to historic churches, Capri offers something for everyone—all with a backdrop of unparalleled beauty. Be prepared to indulge, as Capri is also known for its exclusivity and some of the finest experiences Italy has to offer.
Day 4
Dive Into the Sights and Flavors of the Amalfi Coast
Full-day food, wine & sightseeing tour
Your full-day culinary journey begins in the charming hilltop town of Ravello, where you’ll dive into the art of mozzarella making. Under the guidance of a local expert, craft fresh, creamy cheese and enjoy a tasting session that highlights its delicate flavors. Afterward, take a leisurely walking tour through Ravello’s quiet streets, discovering its serene ambiance and iconic gardens. Perched high above the sea, this picturesque town offers breathtaking views of the coastline and the shimmering Bay of Salerno.
For lunch, settle in at a cozy local trattoria, where a menu of fresh, seasonal dishes is perfectly paired with organic wines sourced from nearby vineyards. The meal captures the essence of the region’s culinary heritage, served in a setting that invites relaxation and connection.
On the return journey, you’ll visit the hidden gem of Minori, a quaint coastal town often overlooked by travelers. Here, enjoy a tasting of zesty, locally made limoncello, then stroll through the town’s charming center, soaking in its authentic, unhurried atmosphere. This day is a feast for the senses, blending culinary exploration with the stunning beauty of Italy’s Amalfi Coast.
Day 5
A Journey Through Time: Positano to Matera’s Prehistoric Marvels
After breakfast, check-out of the hotel. Private transfer to Matera hotel for check-in.
Private transfer to Matera & day at Leisure
Bid farewell to the Amalfi Coast and journey inland to Matera, a UNESCO World Heritage city unlike any other. Arrive in Matera, a city where time seems to stand still, and check into your boutique hotel—a masterpiece of design carved directly into the ancient stone of the Sassi, Matera’s iconic cave dwellings.
Take the afternoon to unwind and immerse yourself in the extraordinary surroundings. Explore the labyrinthine streets at your leisure, where centuries-old architecture tells stories of resilience and ingenuity. As twilight falls, wander Matera’s labyrinth of narrow alleys and illuminated caves, feeling the whispers of centuries past in every step. Cap off the evening with dinner at a local restaurant, savoring the flavors of Basilicata’s rustic cuisine paired with regional wines—a perfect end to your first night in Matera.
Day 6
Discover the Soul of Europe’s Oldest City
a full day tour of Matera – the 2019 Capital of Culture
Your full-day adventure begins with a guided walking tour of either Miglionico or Montescaglioso, two charming hilltop towns rich in history and culture. Wander through their narrow streets and ancient squares, immersing yourself in the timeless atmosphere of southern Italy.
From there, journey to the outskirts of Matera to visit the Crypt of the Original Sin, a remarkable gem of Rupestrian art. Dating back to the 9th century, the crypt’s vibrant frescoes depict biblical scenes in stunning detail, offering a window into early medieval life and artistry. Pause midday to enjoy a lunch of regional specialties at a local eatery, savoring the bold, earthy flavors that define Basilicata’s cuisine.
The afternoon is dedicated to exploring the iconic Sassi of Matera, a labyrinth of stone-carved dwellings, alleys, and stairways that tell the story of this ancient city’s evolution. Along the way, you’ll visit rock-hewn churches adorned with frescoes, traditional cave houses, and ingenious water collection systems that sustained the city for centuries. With every step, you’ll uncover the layers of history that make Matera one of Italy’s most fascinating destinations.
Day 7
Experience Puglia’s Dreamy Beaches
After breakfast, check out of your hotel in Matera and transfer to your hotel in Torre Canne di Fasano for check-in.
Private transfer to Puglia & day at Leisure
Travel to the shores of Puglia, where the Adriatic Sea meets golden beaches. Settle into a serene coastal retreat in Torre Canne di Fasano. Spend the afternoon unwinding by the sea or indulging in spa treatments, with the salty breeze and gentle waves providing the soundtrack to your relaxation.
Day 8
Bari’s Cultural & Culinary Secrets
Full-day walking tour with lunch
Bari, a hidden treasure along the Adriatic Sea, is a city that embodies the heart and soul of Puglia. Begin your day with a guided walking tour through Bari’s vibrant streets, where history and modern life intertwine seamlessly. Make a stop in the nearby town of Bitonto, known for its rich cultural heritage and picturesque charm.
Immerse yourself in the lively atmosphere of Bari’s famous fish market, where the morning’s catch glistens on ice and the air is filled with the hum of local vendors. As you explore, savor tastings of regional specialties, including perfectly baked focaccia, crunchy taralli, and the sweet, flaky delight of bocconotto pastries.
For lunch, indulge in a seafood feast crafted from the freshest ingredients and paired with Puglia’s renowned wines, a true celebration of the Adriatic’s bounty. Your culinary adventure concludes in Bari’s historic old town, where you’ll witness a timeless tradition: local women skillfully shaping orecchiette pasta by hand on the streets. This experience is a delicious and authentic window into Puglia’s rich culture and traditions.
Day 9
A Cultural Journey Through Puglia to Ostuni and Martina Franca
Itria Valley, Burrata, Organic Wines and Ostuni
Your full-day experience begins with a fascinating visit to a local dairy, where you’ll discover the artistry behind Puglia’s iconic cheeses—burrata, mozzarella, and scamorza. Watch skilled artisans at work and savor the rich, creamy flavors of these freshly made delicacies.
From there, continue to Martina Franca, often called the Baroque jewel of Puglia. Stroll through its charming town center, where ornate architecture and quaint piazzas tell the story of its elegant past. After exploring, head to the Manduria region for a delightful lunch at a traditional restaurant, perfectly paired with a wine tasting that highlights the region’s renowned Primitivo wines.
In the afternoon, visit the dazzling whitewashed town of Ostuni. Wander through its winding streets, where the bright facades reflect the Mediterranean sun and offer stunning views of the surrounding olive groves. If time allows, make a stop in Grottaglie, a town famed for its exquisite ceramics. Here, browse artisan workshops and perhaps pick up a hand-painted piece as a keepsake of your journey through Puglia. This day blends culinary delights, cultural discoveries, and Puglia’s breathtaking beauty into an unforgettable experience.
Day 10
Discover The Fairytale Towns of Alberobello and Polignano a Mare
Alberobello & Polignano, EVOO & Gelato
Begin your day with an exclusive olive oil tour and tasting, perfectly timed for the olive harvest season. Witness the craftsmanship behind Puglia’s liquid gold and savor its rich, peppery flavors as you learn about the region’s ancient olive-growing traditions.
Next, visit the serene hilltop village of Locorotondo, celebrated as one of Italy’s most beautiful towns. Stroll through its tranquil streets, where whitewashed facades and vibrant flower boxes create postcard-perfect views. Locorotondo is also renowned for its crisp, floral DOC white wines, which you’ll have the opportunity to sample during your visit.
Continue to Alberobello, the crown jewel of the Itria Valley and a UNESCO World Heritage Site. Wander the iconic streets lined with trulli, the region’s distinctive cone-roofed houses made of whitewashed stone. These whimsical homes create a setting that feels almost otherworldly. Take your time exploring the charming alleys and unique shops that bring this village to life. Pause for an independent lunch at a local trattoria, where you can savor traditional Puglian flavors surrounded by this magical setting.
In the afternoon, head to Polignano a Mare, a coastal gem perched above the Adriatic’s crystal-clear waters. This romantic town is filled with dramatic cliffs, hidden coves, and a charm that’s uniquely its own. As you explore, don’t miss the bronze statue of Domenico Modugno, the beloved singer of “Volare,” standing proudly as a tribute to his legacy. End your visit with a tasting of freshly made gelato or a cup of rich Italian coffee, a perfect way to soak in the town’s warm ambiance before returning to your hotel.
Day 11
Arrivederci, Puglia
Your Seamless Departure Day
As your unforgettable journey through the beauty and culture of Southern Italy comes to an end, your private chauffeur will ensure a smooth and comfortable transfer to Bari Airport. Relax during the scenic drive, reflecting on the breathtaking landscapes, incredible flavors, and cherished moments that have amde this trip truly extraordinary. Depart with a heart full of memories and the promise that Italy’s charm will always welcome you back.
Ready to Customize This Itinerary?
Start Personalizing Your Experience with Windows on Travel
The journeys featured on our website can be booked as they are or can be tailored to reflect your personal travel preferences. Each experience is designed with care and expertise offering you the opportunity to discover Italy through fascinating local perspectives.
Our itineraries blend unparalleled access and deep immersion in each destination, delivered with the assurance of quality built on extensive expertise and trusted connections. To start the booking process, please request a quote below.
