Southern Italy Family Trip

Family Adventure Through Southern Italy’s Hidden Treasures

ROME |  NAPLES |  MATERA |  PUGLIA

Ideal Length
11 Nights

Price Guide (excl. flights)
€1,300-€1,800 per person per day (based on double occupancy)

Best Time to Go
Apr-Oct

Embark on a luxury family adventure through Southern Italy’s hidden treasures, designed exclusively for multigenerational travelers—together at every age and stage. This private journey blends timeless beauty with immersive discovery as you explore Rome’s imperial grandeur, Naples’ vibrant traditions, Puglia’s rustic charm, and Matera’s ancient cave dwellings—each destination thoughtfully chosen to captivate all ages.

Go beyond sightseeing with authentic, enriching experiences. Step inside the Colosseum with privileged skip-the-line access, savor Naples’ culinary gems with passionate local experts, explore Matera’s UNESCO-listed Sassi with an archaeologist, and uncover the secrets of Puglia’s Trulli alongside master artisans—bringing Italy’s heart to life for everyone, from grandparents to grandchildren.

Tailored with care and elevated in every detail, this bespoke journey features premium accommodations, engaging guides, and hands-on activities that foster connection. More than a vacation, it’s a transformative adventure celebrating family, culture, and the unforgettable spirit of Southern Italy.

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Your Bespoke Italian Masterpiece Expertly Crafted, Uniquely Yours

This suggested journey is just the beginning of a remarkable adventure, tailored to your desires. Choose your preferred hotels, enhance with extra experiences, or explore new destinations. Every Italy trip is a unique masterpiece awaiting your personal touch. Share your dreams, and our experts will craft the perfect itinerary for your heart’s desire.

Itinerary Highlights

ROME – 3 NIGHTS

NAPLES – 3 NIGHTS

MATERA – 2 NIGHTS

PUGLIA – 3 NIGHTS

Included with Every Private Journey

More Itinerary Details

Begin your Southern Italy multigenerational luxury family tour in the Eternal City, where the glory of Rome’s empire forever shaped Western civilization. Discover the city’s treasures via eco-friendly private golf cart adventures through ancient streets, covering significantly more ground than possible on foot—perfect for family members of all ages.

Experience privileged access to the Colosseum and Roman Forum with expert guides who bring gladiatorial tales to life, then enjoy skip-the-line access to the Vatican’s artistic and spiritual treasures. These carefully curated experiences ensure that grandparents, parents, and children alike connect meaningfully with Rome’s rich historical tapestry while avoiding crowds and maximizing precious family time.

Accommodation Options 

Continue your journey to vibrant Naples, where your local guide will lead you through bustling streets to taste sensational authentic street food—from crispy fried pizza to fresh seafood cuoppo and sweet babà pastries—offering an unfiltered glimpse into this city’s unapologetic “live for today” philosophy that captivates visitors of all ages.

Open a window onto antiquity with a private tour of Pompeii’s perfectly preserved ancient streets, then venture to the sun-drenched Amalfi Coast for a day of coastal charm, artisanal shopping, and refined Mediterranean dining overlooking the azure sea. These diverse experiences showcase Naples’ unique position as a gateway to both living cultural traditions and extraordinary historical treasures.

Accommodation Options

Your family adventure deepens in Matera, among the world’s oldest continuously inhabited settlements dating back 7,000 years. Discover the UNESCO-listed Sassi districts through privileged access tours, as your expert guide reveals rock-hewn churches, 17th-century monasteries, ancient caves, and deep cisterns that tell the story of human ingenuity across millennia.

Experience the extraordinary blend of ancient atmosphere and modern luxury in meticulously restored accommodations that connect your family with Matera’s remarkable history while ensuring contemporary comfort. This unique destination creates an unforgettable chapter in your multigenerational journey, where the past feels tangibly present and shared discovery strengthens family bonds.

Accommodation Options

The final chapter of your journey unfolds in Puglia’s enchanting Itria Valley, where you’ll explore Alberobello’s fairy-tale trulli houses—distinctive cone-shaped dwellings that have earned UNESCO World Heritage status. Continue to breathtaking Polignano a Mare, perched dramatically on limestone cliffs above the Adriatic, for a seafood aperitivo at a traditional restaurant with panoramic views that will captivate family members of all ages.

Complete your Puglian experience by discovering Locorotondo’s circular perfection and Ostuni’s dazzling white cityscape, with their winding streets and artisan workshops. Enhance your cultural immersion through exclusive tastings at prestigious local wineries, where adults savor regional vintages while younger family members enjoy the scenic countryside—creating a perfect finale to your Southern Italian adventure.

Accommodation Options 

  • Masseria Torre Coccaro
  • Masseria Torre Maizza

This exclusive 12-day custom travel experience reveals the best-kept secrets of Rome, Naples, Matera, and Puglia through luxury accommodations, private tours, and curated experiences that promise an unforgettable multigenerational adventure.

If Southern Italy’s charm has captured your hearts, our expert Travel Advisors can seamlessly extend your stay—perhaps exploring more of Puglia’s serene landscapes, delving deeper into Naples’ vibrant culture, or discovering additional layers of Rome’s rich history. Whatever your family desires, we’ll tailor an exclusive itinerary that makes your journey as extraordinary as Southern Italy itself.

Need More Inspiration for Your Italian Adventure?

Explore our curated sample trips for inspiration, then let us craft a personalized itinerary just for you.

A Classic Italian Family Adventure

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From Venice’s enchanting canals, to Florence’s artistic treasures, and Rome’s ancient wonders this adventure is tailored to create unforgettable memories for all.

Ideal Length
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Price Guide (excl. flights)
euro 900-1300 Per Person Per Day (based on 2 ppl sharing)

An Unforgettable Roman Family Adventure

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Unleash the magic of Rome with your family. Discover hidden gems, indulge in culinary delights, and create cherished memories on this captivating tour.

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A Luxury Family Exploration of Italy

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Forge lifelong family memories on this luxury vacation through Venice, Florence, Sorrento and Rome, all while indulging in private and bespoke experiences.

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euro 1300-1800 Per Person Per Day (based on 2 ppl sharing)

A Luxury Mother-Daughter Adventure in Italy

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Indulge in La Dolce Vita in Rome, savor the delights of Florence, and discover the magic of Venice. This trip will strengthen your bond in unforgettable ways.

Ideal Length
clessidra 10 nights

Price Guide (excl. flights)
euro 1300-1800 Per Person Per Day (based on 2 ppl sharing)

A Magical Christmas Family Vacation in Italy

christmas italy

Enchant your family this Christmas with a luxurious Italian adventure. Explore Venice, Florence, and Rome, where festive magic awaits.

Ideal Length
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Price Guide (excl. flights)
euro 1300-1800 Per Person Per Day (based on 2 ppl sharing)

Why Choose Nancy Aiello Tours?

Destination Experts

  • At Nancy Aiello Tours, we live, breathe, eat, and sleep Italy, the country we are proud to call home.
  • We use our insider knowledge, relationships, and expertise to create one-of-a-kind journeys and experiences that you will cherish for a lifetime.
  • Whether you’re planning a family vacation, honeymoon, or romantic escape, we’re here to create an authentic luxury travel experience that will stay with you forever.

Unique to You

  • You won’t find packaged trips here, or any set dates either. That’s because every one of our trips is specifically designed and scheduled around your interests and needs.
  • From honeymooners to baby boomers, millennials to multi-generational families, every itinerary we design is unique to each client's travel style.
  • We want to give you the most memorable and rewarding luxury vacation possible, and we’ll work closely with you to create an itinerary that exceeds your hopes and expectations.

Carefully Curated

  • With 16+ years of success, we’ve built a coveted collection of top-notch properties, immersive experiences, and local experts.
  • Our insider connections mean that these extraordinary luxury travel opportunities are always a part of our itineraries no matter where you decide to go.
  • Wherever you go, we can connect you with some incredible people, including artists, art historians, chefs, and many more so you have a truly personalized and enriching luxury travel experience.

Customize IT