With two weeks in Italy, you can experience Venice, Florence, Rome, and the Amalfi Coast on a luxurious highlights tour, or take a more leisurely approach by sticking to one or two regions. The Italian Riviera is an excellent choice for travelers with a passion for exceptional wine and cuisine, while southern Italy beckons to those who dream of yacht cruises and exploring ancient ruins. For nature enthusiasts, hop between the northern Italian lakes and neighboring Switzerland via scenic Alpine train journeys.

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.

This two-week grand tour of Italy includes exclusive guided experiences in Rome
This two-week grand tour of Italy includes exclusive guided experiences in Rome
Day Highlights Overnight
Day 1 Arrive in Venice, Guided City Tour Venice
Day 2 Explore Venice's Art & Culture, Venetian Boatyard Tour  Venice
Day 3 Train to Florence, Guided City Tour Florence
Day 4 Accademia Gallery Visit, Sunset River Boat Tour Florence
Day 5 Transfer to Tavarnelle Val di Pesa via San Gimignano & Chianti Winery Visit Tavarnelle 
Day 6 Luxury Hot-Air Balloon Ride Over Tuscany, Guided Day Trip to Siena Tavarnelle 
Day 7 Train to Rome, Guided City Tour Rome
Day 8 VIP Tour of the Vatican Rome
Day 9 Exclusive Colosseum & Forum Tour, Afternoon Cooking Class Rome
Day 10 Galleria Borghese Tour, Free Afternoon in Rome Rome
Day 11 Train to Naples, Transfer to Praiano via Pompeii, Vesuvius Helicopter Flight Praiano
Day 12 Guided Tour of Amalfi, Citrus Farm Visit & Limoncello Tasting Praiano
Day 13 Private Luxury Yacht Cruise to Capri Praiano
Day 14 Depart Praiano  


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.

Kick things off in true luxury style in the Riviera village of Portofino
Kick things off in true luxury style in the Riviera village of Portofino
Day Highlights Overnight
Day 1 Arrive in Milan, Transfer to Portofino Portofino
Day 2 Free Morning in Portofino, Boat Tour to San Fruttuoso Abbey Portofino
Day 3 Day Trip to Cinque Terre, Winery Visit & Ligurian Cooking Lesson Portofino
Day 4 Morning Trip to Genoa, Transfer to the Langhe Region Santo Stefano Belbo
Day 5 Truffle Hunting & Wine Tasting, Michelin-Starred Dinner  Santo Stefano Belbo
Day 6 Tour Alba, Slow Food Experience in Bra Santo Stefano Belbo
Day 7 Transfer to Turin, City Tour & Exclusive Library Visit Turin
Day 8 Morning Tour of Sacra di San Michele, Home-Hosted Dinner Turin
Day 9 Afternoon Tour of Aosta, Transfer to La Thuile La Thuile
Day 10 Cableway to Monte Bianco, Alpine Life Tour La Thuile
Day 11 Hot Springs, Hiking in Gran Paradiso, Alpine Cheese Farm Visit & Tasting La Thuile
Day 12 Transfer to Lake Maggiore, Visit the Rocco di Angera Medieval Fortress Stresa
Day 13 Motorboat Tour of the Borromean Islands Stresa
Day 14 Transfer to Milan, Depart  


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

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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.

End your two weeks of Italian luxury in Capri, with private yacht tours to hidden coves and islets
End your two weeks of Italian luxury in Capri, with private yacht tours to hidden coves and islets
Day Highlights Overnight
Day 1 Arrive in Palermo, Explore the Sicilian Capital Palermo
Day 2 Day Trip to Erice & Trapani: Salt Pans & Marsala Wine Tasting Palermo
Day 3 Drive to Agrigento via Monreale Agrigento
Day 4 Guided Tour of Agrigento's Valley of the Temples Agrigento
Day 5 Drive to Taormina via Villa Romana del Casale  Taormina
Day 6 Free Morning in Taormina, Mount Etna Wine Tasting Taormina
Day 7 Day Trip to Catania: Food & Folklore Experience & Sightseeing Tour Taormina
Day 8 Fly to Naples, Transfer to the Amalfi Coast via Pompeii  Amalfi Coast
Day 9 Explore the Amalfi Coast by Vespa Amalfi Coast
Day 10 Amalfi Lemon Groves Tour & Cooking Class Amalfi Coast
Day 11 Boat Transfer to Capri, Explore the "Isle of Sirens" Capri
Day 12 Cruise Capri's Coastline by Private Yacht  Capri
Day 13 Day Trip to Ischia & Procida by Private Yacht Capri
Day 14 Boat Transfer to Naples, Depart  


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.

You'll find plenty of compelling spots to soak up the views in Lake Garda
You'll find plenty of compelling spots to soak up the views in Lake Garda
Day Highlights Overnight
Day 1 Arrive in Milan (Italy), Transfer to Lake Garda Gargnano
Day 2 Tour of Malcesine, Cable Car to Monte Baldo Gargnano
Day 3 Bernina Express Train Journey Across the Alps to St. Moritz (Switzerland) St. Moritz
Day 4 Free Day in St. Moritz: Chocolates & Museums St. Moritz
Day 5 Funicular to Muottas Muragl, Mountaintop Hike St. Moritz
Day 6 Transfer to Lake Como (Italy), Winery Visit & Lunch Tremezzina
Day 7 Day Trip to Bellagio & Varenna Tremezzina
Day 8 Explore Villa Balbianello & Lenno  Tremezzina
Day 9 Gotthard Panoramic Train Journey & Boat Trip to Lucerne (Switzerland) Lucerne
Day 10 Free Day in Lucerne: Mountain Gondolas & Hiking Lucerne
Day 11 Transfer to Interlaken, Day Trip to Thun Interlaken
Day 12 Day Trip to Jungfrau Region & Trümmelbach Falls  Interlaken
Day 13 Transfer to Zürich, Afternoon City Tour Zürich
Day 14 Depart Zürich  


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.