Villa Gamberaia in Tuscany, Italy
Italy is a top destination among five-star travelers and our best luxury Italy itineraries offer the finest experiences from Rome to Sicily and beyond, whether they be food tours or romantic vacations.
From an adventurous, private, island-hopping excursion to an exclusive, romantic culinary tour with a Michelin-starred chef, an insider's discovery of lesser-known towns to secluded countryside comforts, discover the luxuries of Italy on your tailored tour.
Extraordinary travel begins with a human touch and our destination specialists design every journey with care, insight, and personal attention. As you consider a visit to Italy, use the following itineraries as a guide before connecting with our travel experts to help you plan your trip.
Val d'Orcia in Tuscany, Italy
Why we recommend this sample itinerary:
Designed by Italy travel specialist Michela to celebrate history, heritage, and luxury, Best of Italy Vacation in 12 Days unveils a culture renowned for its glamour and zest for life through privileged access experiences. It features essential Italian highlights, including ancient sites and pristine beaches, with an exclusive private visit to the Vatican museums before opening hours when crowds are absent.
Enjoy intimate dinner experiences prepared by renowned chefs, while staying in carefully selected luxury accommodations that epitomize Italian elegance and sophistication.
Length: 12 days
Places Visited:
Learn more: 12-Day Italy Itineraries and Vacations
Maddalena archipelago near Costa Smeralda in Sardinia, Italy
Why we recommend this sample itinerary:
Travel expert Mario designed our Fully Immersive Tour of Italy: Highlights and Hidden Gems to immerse you in Italy's many cultural treasures through exclusive behind-the-scenes experiences. Enjoy the refined pleasures of gilded cities while discovering authentic charms in remote villages.
The perfectly curated pace balances adventure with leisurely indulgence, featuring activities ranging from private truffle-hunting expeditions with local experts to tracing the imperial grandeur of Amalfi through exclusive historical insights and privileged access to hidden gems.
Length: 21 days
Places Visited:
Learn more: Our 7 Best Italy Tours for Seniors
Church of San Biagio in Montepulciano surrounded by Tuscan countryside
Why we recommend this sample itinerary:
Designed by Samuele, an Italy travel specialist, Food-Lover's Tour of Tuscany and Umbria focuses on rich cultural and food traditions through intimate access to Italy's most celebrated artisan producers and family-owned establishments. Deepen your appreciation for Italian gastronomy through private heritage tastings, while discovering the endlessly enticing flavors of Umbria and Tuscany.
Taste exceptional olive oils, celebrated wines, and elusive local cheeses directly from master craftspeople, creating unforgettable connections between terroir, tradition, and those who preserve these ancient culinary arts.
Length: 9 days
Places Visited:
Learn more: Italy Food and Wine Tours • Tuscany Tours and Vacations
The coast of Sorrento, Italy
Why we recommend this sample itinerary:
Italy travel expert Veronica designed the Italian Adventure to Rome, Amalfi Coast, and Sicily tour to celebrate diversity, ancient history, and natural beauty through exclusive access and intimate cultural immersion. Discover Italy's layered past through private archaeological tours, from Greek temples to Capuchin necropolises, with expert historians sharing untold stories. Experience exclusive village-hopping along the Amalfi Coast via private yacht, while diving into Palermo's authentic flavors through curated food tours led by local insiders.
Sample indelible culture around every corner through privileged encounters that reveal the soul of each magnificent destination.
Length: 12 days
Places Visited:
Learn more: Rome to Amalfi Coast Tours • Sicily Tours and Vacations
Vineyards in Piedmont, Italy
Why we recommend this sample itinerary:
Travel specialist Giulio designed this exclusive oenological journey to capture the essential wine culture of Italy's most celebrated regions through intimate access to prestigious estates and renowned vintners. On his Luxury Italy Wine Tour of the Top Regions, you will visit enchanting medieval villages while enjoying private luxury wine tastings in historic cellars, guided by master sommeliers and passionate winemakers. Embrace extraordinary opportunities to sample bold, exceptional flavors while relaxing in exclusive luxury villas nestled among pristine vineyards.
Indulge deeply in one of Italy's most treasured artisan traditions through personalized encounters that reveal the profound connection between terroir, heritage, and winemaking excellence.
Length: 9 days
Places Visited:
Learn more: Best Italy Wine Tours and Vacation Packages
Market in Florence, Italy
Why we recommend this sample itinerary:
Cooking represents the heart and soul of Italian culture, and Robert, an Italy travel expert, highlights the diverse culinary legacy through exclusive access to master chefs and family-owned establishments on his Heart of Italian Cuisine: 10-Day Gastronomy and Culture Tour. Perfect for sophisticated food enthusiasts, this immersive journey focuses on heritage through intimate encounters in vibrant open-air markets with local vendors. Experience private cooking classes with renowned chefs in their personal kitchens, alongside exclusive gelato experiences with artisan masters.
Each carefully curated encounter reveals the passionate stories behind Italy's most treasured recipes and time-honored culinary traditions passed down through generations.
Length: 10 days
Places Visited:
Learn more: Italy Tour for Food Lovers • Best Rome Tours and Vacations
The Spanish Steps in Rome, Italy
Why we recommend this sample itinerary:
Travel specialist Daniela crafted Honeymoon Highlights, Rome, Florence, and Venice Tour with newlyweds in mind, revealing Italy's passion, color, and beauty through exclusive couple-focused experiences. Visit prestigious family-owned wineries in the Tuscan countryside for private tastings in romantic settings, while enjoying the simple yet sophisticated pleasures of Cinque Terre through personalized coastal excursions. Take in Rome's magnificent highlights and Florence's artistic treasures via exclusive after-hours access to iconic sites.
Bask in Italy's renowned romantic beauty through carefully orchestrated moments designed to create unforgettable memories in the world's most enchanting destinations for couples.
Length: 12 days
Places Visited:
Learn more: Best Italy Honeymoon Packages • Best Romantic Italy Tours for Couples
Miramare Castle in Trieste, Italy
Why we recommend this sample itinerary:
Travel expert Mario designed Unexplored Northern Italy Tour: A Different Side of Italy to immerse you in an entirely different perspective of Italy, far from conventional tourist paths. Focus on unfamiliar yet extraordinary highlights through privileged access to hidden cultural treasures and intimate encounters with local artisans. Discover the sophisticated splendor of multicultural Udine while experiencing the rejuvenating luxury of Grado's exclusive thermal spa treatments.
Celebrate the rich history and effortless charm of northern Italy's natural beauty through carefully curated experiences that showcase the region's welcoming authenticity and refined cultural sophistication.
Length: 8 days
Places Visited:
Learn more: Northern Italy Itineraries and Tours
Ponza, Italy
Why we recommend this sample itinerary:
This exclusive luxury sailing adventure around Italy's most gorgeous islands comes to life through a unique maritime experience crafted by Mario and Veronica to allow you to dive into vibrant Mediterranean colors and pristine coastal beauty. On their Pontine Islands, Ischia, and South of Naples Sailing Tour, follow in the footsteps of ancient emperors while relaxing on enchanting, uncrowded Tyrrhenian beaches accessible only by private yacht.
Sail between renowned islands and remote, untouched corners that few travelers ever experience, enjoying personalized service aboard luxury vessels while discovering hidden coves, secluded beaches, and authentic island culture through intimate, privileged encounters.
Length: 8 days
Places Visited:
Learn more: Southern Italy Itineraries and Tours
Trulli houses in Alberobello, Italy
Why we recommend this sample itinerary:
Puglia is a sophisticated corner of Italy often overlooked by travelers, yet it deserves attention from discerning visitors seeking authentic experiences. Travel specialist Rose showcases the region's extraordinary beauty through her Perfect 9-Day Puglia Exploration, giving you exclusive access to the southeastern peninsula's hidden treasures and intimate cultural encounters. Immerse yourself in ancient history while wandering through charming, centuries-old olive groves with local farmers sharing generational knowledge.
Visit pristine, uncrowded beaches while enjoying exceptional cuisine prepared by passionate local chefs, embracing Puglia's authentic joys and Italy's simple yet refined pleasures through carefully curated experiences.
Length: 9 days
Places Visited:
Learn more: Best Italy Coast Tours and Vacations
Siena, Italy
Embrace the luxuries of Italy on itineraries that include exclusive experiences, whether private romantic sunset cruises or insider tours of ancient landmarks. Find inspiration in the beautiful traditions, gorgeous landscapes, and delicious flavors with our Italy tours and trip packages.
To discover more ideas and advice from our Italy travel specialists, from the best places to visit to the top things to do, explore our Italy travel guide when planning your luxury Italy itinerary.
Trips curated by the world’s top destination experts
Concierge-level service leading up to and during your trip
Unique, exclusive experiences and insider access