14-Day Luxury Fall Italy Itinerary

ItalyHotel Reviews
Written By Karissa Long

Planning a luxury trip to Italy in the fall? 🍂 Italy in September, October, and November offers cooler temperatures, fewer crowds, and a golden glow across vineyards, historic cities, and lakeside landscapes.

This 14-day luxury fall Italy itinerary takes you through the country’s most iconic destinations—combining culture, food, wine, and breathtaking scenery—with stays at some of Italy’s most luxurious hotels. Whether it’s your first time in Italy or you’re returning to explore in style, this itinerary is designed to showcase the very best of Rome, Tuscany, Florence, Venice, the Dolomites, and Lake Como.

Day 1–2: Rome – History, Culture & Timeless Elegance

Fly into Rome, the Eternal City, and start your journey with two nights at Hotel Eden, a jewel of the Dorchester Collection. Just steps from the Spanish Steps and Villa Borghese, this elegant 5-star hotel combines timeless glamour with a warm, intimate feel. Its Michelin-starred rooftop restaurant offers sweeping views across Rome—an unforgettable way to begin your Italian adventure.

Highlights in Rome:

  • Explore the Colosseum, Roman Forum, and Pantheon.

  • Visit Vatican City, including St. Peter’s Basilica and the Sistine Chapel.

  • Enjoy authentic Roman cuisine—don’t miss cacio e pepe or carbonara.

Day 3–4: Tuscany – Rolling Vineyards & Countryside Charm

Next, take a private transfer to Tuscany, where you’ll spend two nights at Il Falconiere Relais, a historic villa surrounded by vineyards and olive groves near Cortona. This Relais & Châteaux property blends rustic elegance with Michelin-starred dining and a world-class spa.

Highlights in Tuscany:

  • Wine tastings at family-run vineyards and prestigious wineries.

  • Explore Cortona, Montepulciano, and Siena.

  • Enjoy truffle hunting, cooking classes, or simply relaxing by the pool with vineyard views.

Day 5–6: Florence – Renaissance Splendor

From Tuscany, travel to Florence, the heart of the Renaissance, for two nights at the luxurious Four Seasons Florence. Set in a restored Renaissance palace surrounded by private gardens, it’s a destination in itself.

Highlights in Florence:

  • Climb to the top of the Duomo for panoramic views.

  • Visit the Uffizi Gallery and Accademia to see masterpieces like Botticelli’s Birth of Venus and Michelangelo’s David.

  • Indulge in Florentine steak paired with Chianti Classico wine.

Day 7–8: Venice – Canals, Palaces & Gondolas

Take the train to Venice for two nights at The Gritti Palace, a 15th-century palazzo on the Grand Canal. This legendary hotel exudes Venetian glamour and offers one of the most iconic views in the city.

Highlights in Venice:

  • Take a gondola ride through the canals.

  • Visit St. Mark’s Basilica, Doge’s Palace, and Rialto Bridge.

  • Explore Murano and Burano islands for glassmaking and colorful charm.

Day 9–10: The Dolomites – Alpine Escape

From Venice, a private transfer brings you to the Dolomites for three nights at the enchanting San Luis Lodges. Nestled in the alpine forest, this luxury retreat offers lakefront chalets and treehouses, perfect for cozy fall nights.

Highlights in the Dolomites:

  • Take scenic hikes through UNESCO-protected mountains.

  • Relax at the alpine spa with mountain views.

  • Experience gourmet dining featuring local South Tyrolean flavors.

Day 11–14: Lake Como – Lakeside Luxury

Your final stop is Lake Como, where you’ll spend three nights at the legendary Grand Hotel Tremezzo. With its floating pool on the lake, 5-star dining, and views of Bellagio, it’s the perfect finale to your Italian journey.

Highlights in Lake Como:

  • Take a private boat tour of the lake.

  • Visit Bellagio, Varenna, and Menaggio.

  • Stroll the gardens of Villa Carlotta or Villa Balbianello.

Departure from Milan

Conclude your trip with a private transfer to Milan for your international flight home. After two unforgettable weeks, you’ll leave with memories of world-class hotels, extraordinary food and wine, and Italy’s breathtaking fall scenery.

Why Visit Italy in the Fall?

Fall is one of the best seasons to visit Italy. The weather is cooler but still pleasant, crowds are smaller than in summer, and harvest season brings wine festivals, truffle markets, and seasonal delicacies. From the golden vineyards of Tuscany to the crisp mountain air of the Dolomites, autumn adds an extra layer of magic to every destination.

Ready to Book Your Own Luxury Fall Trip to Italy?

This 14-day luxury Italy fall itinerary combines the very best of the country—historic cities, charming countryside, alpine escapes, and lakeside glamour—paired with stays at some of Italy’s most iconic 5-star hotels.

Want me to design a trip like this for you? Contact me today to start planning your bespoke Italian journey.

From private transfers and exclusive tours to handpicked hotels, I’ll ensure every detail is perfectly tailored to your travel style.

Karissa Long
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