This top sights of Italy trip is your gateway to a tailor-made journey rooted in authentic discovery. Designed for discerning travelers, it features private guides, boutique stays, and home-cooked experiences that connect you with local life, at your pace, on your terms.
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| Day | Morning | Afternoon | Evening |
|---|---|---|---|
| Day 1 | Arrival in Rome; private transfer to hotel | Explore ancient highlights or enjoy a curated introduction | Optional food tasting or evening passeggiata |
| Day 2 | Small-group Colosseum and Forum tour | Walk the Via Sacra and see ancient ruins | Evening at leisure in Rome |
| Day 3 | Small-group Vatican tour; Sistine Chapel and Museums | Explore over 1,400 rooms and 65,000 artworks | Free evening or guided dining experience |
| Day 4 | High-speed train to Naples; private transfers | Explore historic streets and seaside views | Sample authentic pizza in Naples |
| Day 5 | Guided walking tour of Naples: markets, monuments, local stories | Panoramic drive with private driver | Views from Lungomare Caracciolo |
| Day 6 | Explore Pompeii with local guide | Mount Vesuvius hike and wine tasting or pizza lunch | Return to Naples for a relaxed evening |
| Day 7 | Transfer to Sorrento with scenic stops and Limoncello tasting | Visit Positano and Amalfi | Gelato and cathedral visit in Amalfi |
| Day 8 | High-speed train to Florence; private transfers | Explore with local tips or guided walking tour | Artisan shopping or aperitivo in Florence |
| Day 9 | E-bike tour through historic Florence and Piazzale Michelangelo | Medici-themed walking tour with expert guide | Leisure time or riverside dining |
| Day 10 | Travel to Siena with guided tour | Pisa & San Gimignano visits with local food tastings | Return to Florence |
| Day 11 | Regional train to La Spezia, private transfer to Lerici | Free time to explore coastline or villages | Seafood dinner or sunset walk |
| Day 12 | Private full-day Cinque Terre tour with guide | Visit Manarola, Riomaggiore, Vernazza, Monterosso | Return to hotel after boat ride |
| Day 13 | Free day in La Spezia with custom options | Optional boat tour, hike, or cooking class | Tailored experiences or relaxed evening |
| Day 14 | Train to Milan with private station transfers | Explore Duomo terraces, Brera, or Galleria | Bespoke culinary or fashion tour |
| Day 15 | Small-group walking tour of Milan with local guide | Visit Duomo, La Scala, and landmark squares | Final night in Milan at your pace |
| Day 16 | Final espresso or stroll through Milan | Private transfer to airport or train station | Departure from Italy |
Arrive in Rome and enjoy a personalized transfer to your hotel. Settle in with free time to begin your tailor-made Italy travel, with curated options available, such as private walking tours, food tastings, or an evening passeggiata.
Explore the city’s ancient wonders: the Colosseum, Roman Forum, and Circus Maximus. Wander the Baths of Caracalla, descend into a historic catacomb, admire the Pantheon, and take in the grandeur of Vatican City, St. Peter’s Basilica, and the Spanish Steps.

Skip the lines and explore the Colosseum and Roman Forum in a small group, guided by an English-speaking expert who brings ancient Rome to life with stories tailored to your Italy trip.
Walk the cobbled Via Sacra, passing the House of the Vestal Virgins, Trajan’s Column, and other iconic ruins that shaped the heart of the Roman Empire.

Discover the Vatican on a small-group half-day tour. Marvel at Michelangelo’s ceiling in the Sistine Chapel and explore the vast Vatican Museums, with over 1,400 rooms and 65,000 works of art.

Take a high-speed train from Rome to Naples and enjoy the 60-90 minute ride into the vibrant city known as the birthplace of pizza.
Explore historic streets, seaside views, and authentic pizzerias on a personalized itinerary that brings Italian food and culture to life. Private transfers to and from the train stations in both cities ensure a seamless, tailor-made experience.

Enjoy a tailor-made Naples experience with a passionate local guide who brings the city’s living traditions to life.
Wander through Piazza Plebiscito and the Royal Palace, take in views of the bay and Mt. Vesuvius, browse the bustling Pignasecca market, and sample classic street food. Stroll Spaccanapoli, visit a workshop showcasing handmade presepe figures, and step inside the Duomo while hearing the story of Saint Gennaro and the ancient origins of Parthenope.
In the afternoon, take a panoramic half-day tour with a private driver. Visit Castel Nuovo, the San Carlo Opera House, and Piazza del Gesù Nuovo, finishing with sweeping views from Lungomare Caracciolo.


Explore the extraordinary ruins of Pompeii with a local guide. Walk through ancient thermal baths, view the Lupanare frescoes, and visit the Macellum and Basilica, along with hidden gems, which may be swapped in depending on restoration work.
Afterward, drive up Mount Vesuvius for a pizza lunch or a wine tasting featuring local produce at a panoramic restaurant. Then ascend to 1,000 meters and hike to the crater rim with a National Park guide, taking in views of Mount Somma and the volcano’s dramatic cone.

Begin your day with a scenic 90-minute transfer to Sorrento, including coastal photo stops and a Limoncello tasting at a local artisan producer. Enjoy an hour of free time to explore the town’s narrow streets and boutique shops.
Continue along the Amalfi Coast to Positano, where steep stairs lead down to the vibrant beach. Enjoy lunch on a terrace with sea views before heading to Amalfi. There, spend an hour visiting St. Andrew’s Cathedral or relaxing with a handmade gelato.

Leave vibrant Naples behind and travel by high-speed train to Florence, a scenic three-hour ride that takes you from coastal energy to Renaissance elegance.
Later, enjoy tailor-made experiences such as a private walking tour around the Duomo area and time to browse artisan workshops and galleries. Private transfers to and from the train stations in both cities are included, ensuring a smooth and personalized journey.

Explore Florence by e-bike in a small group with an English-speaking guide. Ride through the centro storico and up to Piazzale Michelangelo on pedal-assist or fat-tire bikes.
Later, dive into the Mysteries of the Medici with a licensed guide. Visit the San Lorenzo Medici Chapel, Medici Palaces, the Uffizi Gallery, Ponte Vecchio, and Pitti Palace as you uncover the legacy of Florence’s most powerful family.


Explore three Tuscan highlights on this tailor-made day trip. In Siena, enjoy a one-hour guided walking tour, including a visit to the Cathedral. In Pisa, take a self-guided stroll through the iconic Piazza dei Miracoli. End the day in medieval San Gimignano, with free time to wander its tower-lined streets and sample local specialties.
Travel in comfort by air-conditioned coach or minivan, accompanied by a multilingual tour leader who offers local insight and flexible pacing for an authentic, personalized experience.

Catch a regional train from Florence to La Spezia, about two hours, then continue to Lerici. This stretch of Liguria is the gateway to Cinque Terre and offers dramatic coastal views.
Enjoy free time to explore fishing villages, coastal walks, boat tours, and fresh Ligurian cuisine. Private transfers to and from the train stations are included for a seamless, custom Italy trip experience.

Enjoy a private full-day tour with a professional guide, hotel transfers, and the Cinque Terre Card included. Tailor-made experiences, scenic walks, and boat rides create lasting memories of your Italy trip.
Start with a transfer to Manarola to explore this charming seaside village, then take the train to Riomaggiore. Continue by boat to Vernazza to visit its fortified historic center and picturesque harbor. After some free time for lunch, cruise to Monterosso before returning to your hotel.

After breakfast, enjoy a relaxed day in La Spezia and shape your own discoveries. Choose from tailored experiences such as a private boat to the Cinque Terre villages, guided coastal walks, seaside dining in hidden harbors, or a regional cooking class with local hosts.
Local experts are on hand to arrange transfers, scenic hikes, and exclusive tastings, crafting a personal and memorable Italy trip just for you.


Tips from Annalisa
Italy Travel Expert

Skip the waterfront restaurants near the port and head into the old town for an aperitivo at Enoteca dei Bardi, locals love it for its regional wines and small plates. It’s tucked away, low-key, and a great way to experience La Spezia without the cruise ship crowds.
The train from La Spezia to Milan takes about three hours, with private transfers to and from the stations included for a smooth, tailor-made Italy trip experience.
Spend the afternoon at your leisure: explore the Duomo terraces, stroll through the Galleria Vittorio Emanuele II, or enjoy an aperitivo in the stylish Brera district. For something more curated, opt for a bespoke fashion or culinary tour designed around your interests.

Join a local guide for a small-group walking tour of Milan, tailored for curious travelers. Explore lively streets, uncover hidden gems, and hear insider stories that bring the city to life.
See Milan’s crown jewel, the Duomo, up close, pause outside the iconic La Scala opera house, and admire historic façades and landmark squares along the way.

Savor a final espresso or take one last stroll through Milan’s elegant streets, soaking in the city’s signature style and flavor.
Your private driver will collect you at the hotel and provide seamless transfer to the airport or train station, with luggage assistance and timing tailored to your schedule, ensuring a smooth, personalized end to your Italy trip.
