2 Weeks in Italy - 4 Luxury Itinerary Ideas

Itinerary #1: Luxury Italian Highlights: Venice, Florence, Chianti, Rome & Amalfi Coast

Ideal for first-time visitors to Italy, this luxurious two-week vacation takes you through four iconic cities, blending history with indulgence. Throughout, private city tours and exclusive excursions ensure you not only see but also learn about the history and lesser-known stories of famous landmarks, including the Vatican Museums, the Colosseum, and the Galleria dell'Accademia. Along the way, indulge in opulent experiences such as a sunrise hot-air balloon ride, a helicopter flight over Pompeii, and first-class train journeys.

Welcome to Italy! Your luxurious highlights adventure begins with a two-day stay in Venice, which you'll spend uncovering the city's highlights alongside a guide and learning about the evolution of gondolas at a boatyard. Next, glide to Florence by first-class train, where more exclusive city tours await. An art historian will lead you to stunning cathedrals and galleries, and you'll also be treated to a private tour of the Galleria dell'Accademia and a sunset boat ride. Then, continue to Tavarnelle Val di Pesa and enjoy a leisurely first evening, as the following morning you'll rise early for a private hot-air balloon ride.

The second half of your adventure kicks off in Rome, and over four days, you'll have plenty of time to admire the city's iconic sights. Highlights include a private walking tour, an insider's Vatican Museums experience, and a visit to the Colosseum. Additionally, join a local-led cooking class and meander through the gardens at Villa Borghese before transferring to Praiano. Located on the Amalfi Coast, this cliff-tucked town is just the place to wrap up your trip in style, especially with a helicopter tour, a visit to a local lemon farm, and a private yacht cruise to Capri on the agenda. Learn more

Itinerary #2: Luxury Northwest Italy: Riviera, Piedmont, Valle d'Aosta & Lake Maggiore

From your arrival in Portofino to a farewell dinner at a waterfront restaurant in Stresa, every detail of this culinary-focused journey through northwestern Italy is designed to impress. Indulge in sweet wine in the Cinque Terre village of Manarola, dine at a Michelin-starred restaurant in the Langhe Wine Region, admire expansive views from the ancient monastery of Sacra di San Michele, and sample cheese straight from an Alpine farm in La Thuile. With a balance of private tours, vineyard visits, and gourmet dining, you'll depart with a deep appreciation for the elegance of the Italian Riviera and Lake District.

While your trip begins in Milan, the delightful Italian Riviera awaits your arrival, and straight after landing you'll transfer to its charming village of Portofino. A three-night stay here ensures you have time to explore the city independently, boat to the medieval Abbey of San Fruttuoso, and train between enchanting Cinque Terre towns. Next, transfer to the prestigious Langhe Wine Region, where you'll sip and savor your way through the area's finest. Dinner at a Michelin-starred restaurant promises to be a highlight, and you'll also join a truffle hunting excursion and explore the medieval town of Alba. 

Next up on your tour is Turin, where you'll enjoy a private tour of the Library of the Academy of Sciences and visit the historic Sacra di San Michele monastery. Continuing north, you'll soon find yourself in the delightful ski town of La Thuile, riding the scenic Skyway Monte Bianco cableway and exploring the trails of Grand Paradiso National Park. You'll also relax in natural hot springs and learn about the meticulous process of fontina cheese production before transferring farther north to Stresa. Here, spend your final full day boating around the Borromean Islands and tucking into exceptional local seafood. Learn more

Itinerary #3: Luxury Southern Italian Escape: Sicily, Amalfi Coast & Capri

Those dreaming of quaint countryside wineries, dreamy hilltop towns, and lazy afternoons on a yacht will find this leisurely southern Italian getaway the perfect fit. With a week in Sicily and three days each on the Amalfi Coast and the island of Capri, you can forget about lengthy drives and instead focus on relaxing with a wine in hand and exploring ancient Roman wonders and stunning coastlines. Highlights include a luxury yacht tour around Capri, a hands-on cooking lesson at a local farm, and a private tour of the historic Valley of the Temples.

Renowned for its abundance of historic landmarks, fabulous beaches, and volcanic wines, Sicily is the perfect place to indulge in both adventure and relaxation—which is exactly what you'll be doing over the first week of your trip. Starting in Palermo, meander medieval streets and sip excellent wine in the Marsala region. Then, using Agrigento as a base, explore the Valley of the Temples and boat under the cliffs of Scala dei Turchi. Next up is the hilltop town of Taormina, where a visit to the Mount Etna wine region and back-to-back tours in Catania wrap up your lavish week in Sicily.

A short plane ride and a transfer kick off the second leg of your trip, bringing you to the Amalfi Coast. Spend your first night here settling in, which ensures you're plenty rested for a thrilling Vespa tour and an exclusive cooking class at a lemon farm. Then, on the morning of Day 11, pack your bags, hop into a boat, and transfer to the glamorous island of Capri. With its dramatic cliffs, and hidden coves, Capri is best explored by boat—and with a private yacht booked in for two days, you'll have plenty of time to do exactly that before bidding farewell. Learn more

Itinerary #4: Luxury Italian & Swiss Lakes by Train

Blending picturesque lakeside towns, mountain vistas, and historic cityscapes, this upscale Alpine adventure introduces you to the refined luxury of some of northern Italy and Switzerland's most iconic destinations. Experience world-renowned train journeys as you glide between Gargnano and St. Moritz and from Tremezzina to Lucerne and take in panoramic mountain views from the summit of Monte Baldo, Muottas Muragl, and Mount Pilatus—reachable by cable car. In between excursions, winery visits, free days to explore, and nights at 5-star accommodations ensure you unwind in style.

From Milan's airport, head straight to the charming town of Gargnano in the Lake District, where, over a two-day stay, you'll explore the village of Sirmione and ride a cable car to the summit of Monte Baldo. Next, transfer to St. Moritz via the Bernina Express train line and spend the evening and following day hopping between charming boutiques and local restaurants. You'll also zip up to the summit of Muottas Muragl in a gondola before setting your sights on Lake Como. Your base here is the chic town of Tremezzina, perfectly located for visiting Bellagio, Varenna, and glamorous 18th-century villas.

Continuing north through Switzerland by train and boat, you'll arrive in the historic and very colorful town of Lucerne. Here, the choice is yours to take in spectacular views from the summit of Mount Pilatus, reachable by gondola and cableway, or enjoy a leisurely day strolling through Old Town. Then, you're off to Interlaken, which will serve as your base to visit the charming city of Thun and admire the UNESCO-listed Trümmelbach Falls. Your final destination is Zürich, but before catching your onward flight, check out the city's exclusive shopping areas and pretty squares. Learn more

More Great 2-Week Italy Itineraries

Looking for more inspiration for your trip to Italy? Check out these other two-week Italy itineraries, with outdoor adventures, cultural trips, and best-of tours to hit the highlights.