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Our 10 Best Luxury Italy Itineraries for 2021 & 2022

Ratings of Zicasso's Service
Saint Peter's Basilica in Rome, Italy

Saint Peter's Basilica in Rome, Italy

From Rome to Palermo, Florence to Milan, Tuscany to the Amalfi, Alberobello to Lake Como, Italy is an ideal vacation destination for 2021. Find inspiration in the following sample tours that immerse you in essential exploration of a country that overflows with options. From an adventurous sailing excursion to a romantic culinary tour, a discovery of lesser-known towns to secluded countryside comforts, see why Italy is the perfect destination for every type of traveler.

1. Best of Italy for 2021

Val d'Orcia in Tuscany, Italy

Length of trip: 12 days

Places Visited: Venice | Lake Garda | Florence | Rome | Amalfi Coast | Capri | Ravello | Amalfi | Val d’Orcia | Atrani

Why we recommend this sample itinerary:

Best of Italy for 2021 is a perfect example of a culture known for glamour and a zest for life. Michela, an Italy travel specialist, designed the tour to celebrate history, heritage, and luxury. You can find essential Italian highlights and personalized experiences away, including an exclusive visit to the Vatican Museums before opening hours and dinner cooked by a famous chef.

2. Fully Immersive Tour of Italy: Highlights and Hidden Gems

Riomaggiore in the Cinque Terre, Italy

Riomaggiore in the Cinque Terre, Italy

Length: 21 days

Places Visited: Venice | Bologna | Cinque Terre | Siena | Sorrento | Costa Smeralda | Rome

Why we recommend this sample itinerary:

Travel expert Mario designed the Fully Immersive Tour of Italy: Highlights and Hidden Gems to engage you in Italy's many cultural treasures. Not only can you experience the pleasures of gilded cities, but you can also discover the authentic charms of Italy at a perfect pace. This sample itinerary brings a balance of adventure and leisure from a truffle hunt to tracing the imperial grandeur of Amalfi.

3. Food-Lovers Tour of Umbria and Tuscany

Church of San Biagio in Montepulciano surrounded by Tuscan countryside

Church of San Biagio in Montepulciano surrounded by Tuscan countryside

Length: 9 days

Places Visited: Perugia | Montepulciano | San Gimignano | Montefalco | Assisi | Bevagna | Bagno Vignoni | Siena | Lucca | Pisa

Why we recommend this itinerary:

Food-Lover's Tour of Umbria and Tuscany concentrates on Italy’s culinary greatness. Samuele, an Italy travel specialist, designed this sample tour to focus on Italy's rich culture and food traditions. Your love affair with Italian food will further as you taste the heritage and enjoy the endlessly enticing flavors in Umbria and Tuscany. Taste fine olive oils, celebrated wines, and elusive local cheeses on this remarkable tour.

4. Italian Adventure Rome, Amalfi Coast and Sicily

The coast of Sorrento, Italy

The coast of Sorrento, Italy

Length: 12 days

Places Visited: Rome | Sorrento | Capri | Amalfi | Positano | Ravello | Palermo (City) | Erice Segesta

Why we recommend this itinerary:

Italy travel expert Veronica has designed Italian Adventure Rome, Amalfi Coast and Sicily tour to celebrate diversity, ancient history, and natural beauty. This elegant adventure is a discovery of Italy’s layered past from Greek temples to Capuchin necropolises. Whether village-hopping along the Amalfi Coast or diving into the flavors of Palermo with a private food tour, you will sample the indelible culture around every corner.

5. Extravagant Italy Wine Tour of the Top Regions

Vineyards surrounding Castiglione Falletto in the Piedmont region of Italy

Vineyards surrounding Castiglione Falletto in the Piedmont region of Italy

Length: 9 days

Places Visited: Piedmont | Lombardy | Chianti

Why we recommend this itinerary:

Travel specialist Giulio designed the Extravagant Italy Wine Tour of the Top Regions to capture the essential wine culture of the most celebrated regions in the country. With a mixture of medieval villages and luxurious wine tastings, this sample itinerary brings exclusive opportunities to sample bold flavors, relax in luxury villas, and truly indulge in one of Italy’s most famous artisan traditions.

6. Heart of Italian Cuisine: 10-Day Gastronomy and Culture Tour

Florence, Italy

Florence, Italy

Length: 10 days

Places Visited: Palermo (City) | Rome | Florence

Why we recommend this itinerary:

Cooking is the heart and soul of Italian culture. Robert, an Italy travel expert, has shared the Heart of Italian Cuisine: 10-Day Gastronomy and Culture Tour to highlight the diverse legacy that feeds Italian gastronomy. Whether you are a foodie or simply enjoy a good meal, your customized tour will focus on heritage through food, immersing you in vibrant open-air markets, private cooking classes, and gelato’s effortless charisma.

7. Honeymoon Highlights: Rome, Florence, Venice Tour

The Spanish Steps in Rome, Italy

The Spanish Steps in Rome, Italy

Length: 12 days

Places Visited: Rome | Florence | Venice | Chianti | Pompeii | Castellina | Tuscany

Why we recommend this itinerary:

Travel specialist Daniela has crafted the Honeymoon Highlights, Rome, Florence, and Venice Tour to reveal the passion, color, and beauty of Italy with newlyweds in mind. From wineries in the Tuscan countryside to the simple pleasures of Cinque Terre, the highlights of Rome to the beauty of Florence, you can bask in Italy’s renowned beauty.

8. Unexplored Northern Italy Tour: A Different Side of Italy

Miramare Castle in Trieste, Italy

Miramare Castle in Trieste, Italy

Length: 8 days

Places Visited: Udine | Spilimbergo | San Daniele del Friuli | Grado | Trieste

Why we recommend this itinerary:

Travel expert Mario has designed Unexplored Northern Italy Tour: A Different Side of Italy to immerse you in a different perspective of the country. Instead of the familiar highlights, you discover the splendor of multicultural Udine and the relaxing thermal spa town of Grado. This tour celebrates the history and effortless charm of Northern Italy’s natural, cultural, and welcoming beauty.

9. Pontine Islands, Ischia and South of Naples Sailing Tour

Aragon Castle on Ischia Island near Sicily

Aragon Castle on Ischia Island near Sicily

Length: 8 days

Places Visited: Ponza | Palmarola | Ventotene | Ischia | Procida | Capri | Castellammare

Why we recommend this itinerary:

A luxury vacation around gorgeous Italian islands comes to life in this sample itinerary,  Pontine Islands, Ischia, and South of Naples Sailing Tour Crafted by Mario and Veronica, this vacation will immerse you in the vibrant colors of the Mediterranean. You can follow in the footsteps of emperors and relax on enchanting Tyrrhenian beaches as you sail between renowned islands and remote corners on this unique experience.

10. Perfect 9-Day Puglia Exploration

Trulli houses in Alberobello, Italy

Trulli houses in Alberobello, Italy

Length: 9 days

Places Visited: Savelletri | Lecce | Matera | Alberobello | Ostuni

Why we recommend this itinerary:

Puglia is a corner of Italy often overlooked by travelers but deserves much more attention. Travel specialist Rose had crafted Perfect 9-Day Puglia Exploration to showcase the exceptional beauty of the southeastern peninsula. With ancient history and charming olive groves, picturesque beaches, and mouthwatering cuisine, this tour embraces the authentic joys of Puglia and the simple pleasures of Italy.

More Travel Information & Tips

Siena, Italy

Siena, Italy

Italy is the ultimate destination for historians and romantics, families and explorers. You can find more inspiration in the brimming tradition, gorgeous landscapes, and delicious flavors on our Italy Page or check Zicasso’s Italy Travel Guide for more information on how to have the best experience tailored to the trip you want. The Travel Blog is a great place to find new insights and information on exciting international destinations you can visit. Planning a trip? You can speak with an Italy travel expert for free by filling out a Trip Request Form or by calling our team at 1-888-265-9707.

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