Top sights of Italy trip

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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.

Share your dates and priorities to start planning. We'll design exclusive experiences, handle the logistics, and connect you with trusted local hosts. Travel with intention, reserve your personalized trip to Italy today.

Top sights of Italy trip highlights

  • Ancient Rome and Vatican private tours: Skip the lines with private guides through the Colosseum and Vatican.
  • Amalfi Coast by boat and local flavors: Cruise secluded coves, swim in turquoise waters, and dine in family-run trattorias.
  • Cinque Terre hiking and village stays: Walk terraced trails between pastel villages, stay with locals, and savor regional pesto and seafood.
  • Tuscan countryside and wine experiences Personalized winery visits, olive oil tastings, and cooking classes in a historic villa.
  • Tailor-made luxury with local experts: Custom itineraries, private transfers, and insider connections ensure a seamless, genuine Italian journey.
DayMorningAfternoonEvening
Day 1Arrival in Rome; private transfer to hotelExplore ancient highlights or enjoy a curated introductionOptional food tasting or evening passeggiata
Day 2Small-group Colosseum and Forum tourWalk the Via Sacra and see ancient ruinsEvening at leisure in Rome
Day 3Small-group Vatican tour; Sistine Chapel and MuseumsExplore over 1,400 rooms and 65,000 artworksFree evening or guided dining experience
Day 4High-speed train to Naples; private transfersExplore historic streets and seaside viewsSample authentic pizza in Naples
Day 5Guided walking tour of Naples: markets, monuments, local storiesPanoramic drive with private driverViews from Lungomare Caracciolo
Day 6Explore Pompeii with local guideMount Vesuvius hike and wine tasting or pizza lunchReturn to Naples for a relaxed evening
Day 7Transfer to Sorrento with scenic stops and Limoncello tastingVisit Positano and AmalfiGelato and cathedral visit in Amalfi
Day 8High-speed train to Florence; private transfersExplore with local tips or guided walking tourArtisan shopping or aperitivo in Florence
Day 9E-bike tour through historic Florence and Piazzale MichelangeloMedici-themed walking tour with expert guideLeisure time or riverside dining
Day 10Travel to Siena with guided tourPisa & San Gimignano visits with local food tastingsReturn to Florence
Day 11Regional train to La Spezia, private transfer to LericiFree time to explore coastline or villagesSeafood dinner or sunset walk
Day 12Private full-day Cinque Terre tour with guideVisit Manarola, Riomaggiore, Vernazza, MonterossoReturn to hotel after boat ride
Day 13Free day in La Spezia with custom optionsOptional boat tour, hike, or cooking classTailored experiences or relaxed evening
Day 14Train to Milan with private station transfersExplore Duomo terraces, Brera, or GalleriaBespoke culinary or fashion tour
Day 15Small-group walking tour of Milan with local guideVisit Duomo, La Scala, and landmark squaresFinal night in Milan at your pace
Day 16Final espresso or stroll through MilanPrivate transfer to airport or train stationDeparture from Italy

Places you'll visit

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Milan
MilanLombardy and the Lakes
Naples
NaplesCampania
Day01

Day 1: Welcome to Rome

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.

Colosseum with clear blue sky, Rome, Italy. Rome landmark and antique architecture. Rome Colosseum is one of the best known monuments of Rome and Italy
Day02

Day 2: Colosseum half-day tour

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.

Inside the old Colosseum (Coliseum), Rome, Italy © Viacheslav Lopatin/Shutterstock
Day03

Day 3: Vatican half-day tour

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.

Piazza San Pietro in Vatican City
Day04

Day 4: From Rome to Naples

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.

Naples Italy
Day05

Day 5: Naples walking tour and panoramic drive

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.

Margherita Pizza Naples
Mount Vesuvius overlooking Naples
Day06

Day 6: Pompeii and Mount Vesuvius

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.

Pompeii
Day07

Day 7: Sorrento, Positano and Amalfi

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.

Scenic picture-postcard view of the beautiful town of Amalfi at famous Amalfi Coast with Gulf of Salerno, Campania, Italy
Day08

Day 8: Naples to Florence

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.

Florence cityscape © Bob Hilscher/Shutterstock
Day09

Day 9: E-bike and walking tours of Florence

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.

Uffizi art gallery in Florence, Tuscany, Italy
Duomo Santa Maria Del Fiore in Florence Italy © Songquan Deng/Shutterstock
Day10

Day 10: Tuscany tour

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.

Leaning Tower Pisa
Day11

Day 11: Florence to Lerici and La Spezia

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.

Lerici Italy
Day12

Day 12: Cinque Terre full-day private tour

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.

Riomaggiore is the first city of the Cique Terre sequence of hill cities, Liguria, Italy.
Day13

Day 13: Free day in La Spezia

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.

Golfo dei Poeti, La Spezia, Italy
Annalisa

Tips from Annalisa

Italy Travel Expert

quotes

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.

Day14

Day 14: La Spezia to Milan

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.

Milan duomo cathedral roof, Italy
Day15

Day 15: Best of Milan walking tour

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.

Milan Italy
Day16

Day 16: Departure from Milan

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.

Flag of Italy hanging on the balcony in Milan, Italy © DELBO ANDREA/Shutterstock