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17 days, 16 nights · Best for First-time travelers seeking a comprehensive guided journey

Italian Peninsula and Sicily 17 Day Escorted Tour | Vacation Packages for 2025, 2026

Explore Rome, Florence, Venice and Sicily as art, history and breathtaking landscapes create the ultimate Italian journey.

Your Adventure Starts Here

This is a starting point. Change the nights, choose the style of hotel, add the experiences you want. Your planner takes it from there.

FlorenceStop 1

Florence, Tuscany

Florence

Renaissance heart and Umbrian pilgrimage en route

2nights

We meet you in Rome and cross Umbria to Assisi, where stone walls still hold the medieval quiet. The Basilica of St. Francis shelters frescoes by Giotto and Cimabue, artists who gave sacred figures new emotion and changed Western painting. After lunch in Assisi, we continue to Florence.

In the morning your guide walks you through the Duomo, Brunelleschi's dome, Giotto's campanile, and the Baptistery's gilded doors. Piazza della Signoria and Santa Croce follow. The afternoon is yours to shop leather workshops or add a visit to the Accademia for Michelangelo's David or the Uffizi for Botticelli and Leonardo.

Arranged for you: We arrange the journey from Rome through Assisi to Florence, guided entry to the Basilica of St. Francis, walking tour of Florence's cathedral quarter and historic squares, group dinners, and overnight stays.

Your hotel premium four-star near Piazza della Repubblica

Styles, not names. We name the property once we know your dates and your party.

Interests in Florence 15 available

  • Priority entry to the Uffizi with art historian Day Trips · Half day
  • Tuscan cooking lesson in a countryside villa Day Trips · Half day
  • Pisa with leaning tower climb and baptistery visit Day Trips · Half day
  • Accademia Gallery Guided Tour, Skip the Line with Advanced Reservation & Tickets Guided Tours and Sightseeing · Tour in a Day
  • Discovering Florence Walking Tour Guided Tours and Sightseeing · Tour in a Day
  • Florence and Fiesole Hills Small Group Guided Sightseeing Tour Guided Tours and Sightseeing · Tour in a Day
  • Florence Historical Center Walking Tour Guided Tours and Sightseeing · Tour in a Day
  • Florence Morning Guided Walking Tour Guided Tours and Sightseeing · Tour in a Day
  • Florence Tour Guided Tours and Sightseeing · Tour in a Day
  • Florence, Tuscany, Cooking Class package with Typical Dinner Food and Wine · Tour in a Day
  • Florence: Handmade Pasta Cooking Course with Lunch Food and Wine · Tour in a Day
  • Florence’s Art & Gourmet Private Walking Tour Guided Tours and Sightseeing · Tour in a Day
  • Guided Visit of Accademia & Uffizi Gallery Skip the Line with Advanced reservation & tickets included Guided Tours and Sightseeing · Tour in a Day
  • Guided Visit of Uffizi Gallery, Skip the Line with Advanced Reservation & Tickets Guided Tours and Sightseeing · Tour in a Day
  • Horse Riding through the Tuscany Countryside guided Tour Guided Tours and Sightseeing · Tour in a Day

Day by day in Florence 2 days, tap a day for the details

Day 1Rome, Assisi, Siena, FlorenceSee this day
Day 2FlorenceSee this day
VeniceStop 2

Venice, Veneto

Venice

Bologna's porticoes and Padua's basilica northbound

2nights

After breakfast we travel north through Bologna, where porticoed streets frame Podestà Palace and the Basilica of San Petronio. Lunch is your own among tortellini makers and mortadella counters. We continue to Padua for the Basilica of St. Anthony, a pilgrimage site since the thirteenth century, then arrive in Venice as the lagoon light softens.

Your guide leads you through St. Mark's Basilica, past the Doge's Palace and across the Bridge of Sighs. The afternoon is yours to shop mask ateliers, ride a gondola through the side canals, or add a boat to Murano to watch glass rods pulled and shaped in furnace heat. Group dinners both nights, the second after a day on your own schedule.

Arranged for you: We arrange the journey from Florence through Bologna and Padua to Venice, guided basilica visit in Padua, walking tour of St. Mark's and the Doge's quarter, group dinners, and overnight stays.

Your hotel four-star hotel near Rialto Bridge

Styles, not names. We name the property once we know your dates and your party.

Interests in Venice 14 available

  • Private evening gondola with serenade Day Trips · Half day
  • Doge's Palace and secret itineraries route Day Trips · Half day
  • Burano lace workshop and Torcello basilica Day Trips · Half day
  • Cicchetti tasting tour with local guide Day Trips · Half day
  • Ca’ Rezonico, the Doge’s Palace and St. Mark’s Basilica Shore Excursions · Tour in a Day
  • Doge’s Palace and Gondola Ride Shore Excursions · Tour in a Day
  • Murano and Burano Shore Excursions · Tour in a Day
  • San Giorgio, Murano Glass Factory and Gondola Ride Shore Excursions · Tour in a Day
  • Tour Venice by Gondola Shore Excursions · Tour in a Day
  • Venetian Costumes Tour Shore Excursions · Tour in a Day
  • Venetian Lagoon Cruise Shore Excursions · Tour in a Day
  • Venice and Jewish Ghetto Shore Excursions · Tour in a Day
  • Venice with Doge’s Palace and St. Mark’s Cathedral Shore Excursions · Tour in a Day
  • Walking Tour of Venice Shore Excursions · Tour in a Day

Day by day in Venice 2 days, tap a day for the details

Day 3Florence, Bologna, Padua, VeniceSee this day
Day 4VeniceSee this day
RomeStop 3

Rome, Lazio

Rome

Montepulciano wine country and three Roman days

3nights

We leave Venice and cross into Tuscany, stopping in Montepulciano for lunch among the medieval towers. Wine cellars tunnel beneath the town, aging Vino Nobile in oak. We continue to Rome and deliver you to your hotel with the evening free for dinner at a neighborhood trattoria.

In the morning we walk you past the Vatican ticket lines into the museums, the Sistine Chapel's vaulted ceiling overhead, then St. Peter's Basilica for Michelangelo's Pietà. The afternoon is yours to add the Colosseum and Forum or wander the centro storico. Day seven is unguided: Campo de' Fiori market, a cooking class, the Catacombs, or simply gelato and people-watching. Group dinner the first night, your choice the next two.

Arranged for you: We arrange the journey from Venice through Montepulciano to Rome, skip-the-line guided tour of the Vatican Museums, Sistine Chapel and St. Peter's Basilica, one group dinner, and overnight stays.

Your hotel four-star hotel near Piazza Navona

Styles, not names. We name the property once we know your dates and your party.

Interests in Rome 16 available

  • Colosseum underground and arena floor with archaeologist Day Trips · Half day
  • Borghese Gallery with art historian Day Trips · Half day
  • Roman cooking class in a chef's kitchen Day Trips · Half day
  • Catacombs and Appian Way with guide Day Trips · Half day
  • Ancient and Old Rome Walking Tour, Skipping the line at Colosseum Guided Tours and Sightseeing · Tour in a Day
  • Full Day Rome Tour Guided Tours and Sightseeing · Tour in a Day
  • Papal Audience in Saint Peter’s, Vatican City Guided Tours and Sightseeing · Tour in a Day
  • Rome by Bicycles Tour with English Speaking Guide Guided Tours and Sightseeing · Tour in a Day
  • Rome by Night Guided Tour Guided Tours and Sightseeing · Tour in a Day
  • Rome by Night guided Tour with Dinner & Show Guided Tours and Sightseeing · Tour in a Day
  • Rome: The Eternal & Ancient Rome Tour Combo Guided Tours and Sightseeing · Tour in a Day
  • Rome: The Eternal City Tour Guided Tours and Sightseeing · Tour in a Day
  • Skip the Line: Vatican Museums and Sistine Chapel Guided tours Guided Tours and Sightseeing · Tour in a Day
  • The Ancient Rome Tour Guided Tours and Sightseeing · Tour in a Day
  • The Ancient Rome Walking Tour, Skipping the line at Colosseum Guided Tours and Sightseeing · Tour in a Day
  • The Christian Rome & Catacombs Tour with Hotel Pick Up Guided Tours and Sightseeing · Tour in a Day

Day by day in Rome 3 days, tap a day for the details

Day 5Venice, Tuscany, Montepulciano, RomeSee this day
Day 6RomeSee this day
Day 7RomeSee this day
SorrentoStop 4

Sorrento, Campania

Sorrento

Pompeii's frozen streets and Capri's blue cave

2nights

After breakfast we travel south through Naples for a panoramic drive past Castel dell'Ovo, Plebiscito Square, and the Royal Palace. At Pompeii your guide walks you through streets, houses, and frescoes preserved by Vesuvius ash in 79 AD, daily life held in volcanic stone. The Sorrentine coast follows, cliffs and lemon groves to your hotel.

In the morning we take the ferry to Capri. When the sea is calm, rowboats enter the Blue Grotto, sunlight filtered through water to electric blue. The afternoon is yours to ride the chair lift between Capri town and Anacapri, shop the piazzetta, or walk the coastal paths. Lunch with the group at a local restaurant, then the return ferry. Both dinners included.

Arranged for you: We arrange the journey from Rome through Naples and Pompeii to Sorrento, guided tour of Pompeii, ferry to Capri with Blue Grotto entry when conditions allow, group lunch on Capri, group dinners, and overnight stays.

Your hotel four-star hotel in Sorrento's historic center

Styles, not names. We name the property once we know your dates and your party.

Interests in Sorrento 3 available

  • Positano and Ravello along the Amalfi Drive Day Trips · Half day
  • Limoncello tasting and lemon grove tour Day Trips · Half day
  • Herculaneum with archaeologist guide Day Trips · Half day

Day by day in Sorrento 2 days, tap a day for the details

Day 8Rome, Naples, Pompeii, SorrentoSee this day
Day 9Sorrento, Capri, SorrentoSee this day
PalermoStop 5

Palermo, Sicily

Palermo

Overnight ferry south and Monreale's golden mosaics

3nights

Your morning in Sorrento is unguided: shop ceramics, write postcards, or walk to the marina. In the afternoon we transfer you to Naples and board the overnight ferry to Palermo. Settle into your cabin as the ship crosses the Tyrrhenian. We dock in the morning, transfer you to your hotel, and leave the day free to explore the capital's markets, street food counters, and baroque palazzi. Group dinner that evening.

After breakfast we travel to Monreale, a hilltop town above Palermo, for the Norman cathedral built in the twelfth century. Inside, six thousand square meters of gold mosaic cover the walls and dome, Byzantine craft in a Sicilian church. We return to Palermo for a guided walk through the Palatine Chapel, the cathedral, the opera house, and Praetorian Square. The afternoon is yours, then group dinner and overnight.

Arranged for you: We arrange the afternoon transfer to Naples, overnight ferry to Palermo in private cabin, morning transfer to your Palermo hotel, excursion to Monreale Cathedral, guided city tour of Palermo's historic sites, group dinners, and overnight stays.

Your hotel four-star hotel in the historic center near Quattro Canti

Styles, not names. We name the property once we know your dates and your party.

Interests in Palermo 7 available

  • Street food tour with local guide Day Trips · Half day
  • Cappella Palatina mosaics with art historian Day Trips · Half day
  • Mondello beach and seaside lunch Day Trips · Half day
  • Teatro Massimo opera house tour Day Trips · Half day
  • City Tours with Coffee and Tasting Shore Excursions · Tour in a Day
  • Puppet Theatre Shore Excursions · Tour in a Day
  • Walking Tour of Palermo Shore Excursions · Tour in a Day

Day by day in Palermo 3 days, tap a day for the details

Day 10SORRENTO, PALERMO with overnight Ferry transferSee this day
Day 11PalermoSee this day
Day 12Palermo, MonrealeSee this day
AgrigentoStop 6

Agrigento, Sicily

Agrigento

Erice's hilltop ruins and Marsala's fortified wine

1nights

After breakfast we climb to Erice, a medieval town perched above the western coast. Stone streets, Norman castle ruins, and views across the sea to Africa on clear days. We continue to Marsala for a tasting of the amber fortified wine that carries the town's name, then pass the fishing port of Mazara del Vallo. Late afternoon brings you to Agrigento and the Valley of the Temples, a UNESCO ridge of Greek ruins. Your guide walks you past the Temple of Concordia, intact Doric columns against the sky, and the temples of Juno and Heracles. Group dinner and overnight stay.

Arranged for you: We arrange the journey from Palermo through Erice, Marsala, and Mazara del Vallo to Agrigento, wine tasting in Marsala, guided tour of the Valley of the Temples, group dinner, and overnight stay.

Your hotel four-star hotel near the Valley of the Temples

Styles, not names. We name the property once we know your dates and your party.

Interests in Agrigento 3 available

  • Sunset tour of the Valley of the Temples Day Trips · Half day
  • Scala dei Turchi beach and coastal drive Day Trips · Half day
  • Marsala wine cellar and historic center Day Trips · Half day

Day by day in Agrigento 1 day, tap a day for the details

Day 13Palermo, Erice, Marsala, AgrigentoSee this day
TaorminaStop 7

Taormina, Sicily

Taormina

Noto's baroque stone and Siracusa's Greek theater

2nights

After breakfast we travel to Noto, a UNESCO town rebuilt in baroque style after the 1693 earthquake. Honey-colored limestone facades line Corso Vittorio Emanuele. We continue to Siracusa for the Greek amphitheater carved into the hillside, the Ear of Dionysus cave, and the Roman theater. Your guide walks you through Ortigia Island, the medieval core of the city, before we drive north to the Taormina coast. Dinner and overnight with views of the Ionian Sea.

In the morning we take you up the slopes of Mount Etna, Europe's largest active volcano. When conditions allow, we ascend for panoramic views across the lava fields and the Sicilian interior. The afternoon is yours in Taormina town: the Greek theater, boutique shops, or the beach at Isola Bella. Group dinner both nights.

Arranged for you: We arrange the journey from Agrigento through Noto and Siracusa to the Taormina area, guided tours of Noto, Siracusa, and Ortigia Island, excursion to Mount Etna's slopes, group dinners, and overnight stays.

Your hotel four-star hotel in Giardini Naxos with sea views

Styles, not names. We name the property once we know your dates and your party.

Interests in Taormina 4 available

  • Etna crater ascent with volcanologist guide Day Trips · Half day
  • Godfather villages: Savoca and Forza d'Agrò Day Trips · Half day
  • Siracusa cooking class with market visit Day Trips · Half day
  • Alcantara Gorge hike and swim Day Trips · Half day

Day by day in Taormina 2 days, tap a day for the details

Day 14AGRIGENTO, NOTO, SIRACUSA, TAORMINA (GIARDINI NAXOS or surroundings)See this day
Day 15TAORMINA (GIARDINI NAXOS or surroundings)See this day
Catania Stop 8

Catania, Sicily

Catania

Godfather villages and a UNESCO port city

1nights

After breakfast we take you to Savoca and Forza d'Agrò, the hilltop villages where Francis Ford Coppola filmed The Godfather. Bar Vitelli in Savoca still serves lemon granita as it did in Michael Corleone's wedding scene. Walk the stone streets, meet villagers, and feel the slow tempo of interior Sicily. We arrive in Catania in the afternoon, a UNESCO port city rebuilt in baroque style after the 1669 lava flow. Check into your hotel, then gather for a farewell dinner with your travel companions in this vibrant university city built from black volcanic stone.

Arranged for you: We arrange the journey from the Taormina area through Savoca and Forza d'Agrò to Catania, guided village visits with lemon granita tasting, hotel check-in, and farewell group dinner.

Your hotel four-star hotel in Catania's historic center near Piazza Duomo

Styles, not names. We name the property once we know your dates and your party.

Interests in Catania 3 available

  • Catania fish market and street food tour Day Trips · Half day
  • Baroque Catania walking tour with art historian Day Trips · Half day
  • Private farewell dinner at countryside masseria Day Trips · Half day

Day by day in Catania 1 day, tap a day for the details

Day 16TAORMINA (GIARDINI NAXOS or surroundings); SAVOCA and FORZA D'AGRÃ’, CATANIASee this day

Day 17

Catania

Enjoy your final breakfast in Catania before concluding your grand tour of Italy and Sicily. Depart with lasting memories of ancient ruins, breathtaking coastlines, vibrant cities, and authentic Italian culture.

Why plan with Trips 2 Italy?

Designed around you by Italian-born planners

Guides, drivers and boats for your party alone

Hand-selected hotels in every destination

Local English-speaking guides who know their city

Met at the airport, private transfers throughout

Testimonials

Hear from travelers who have planned Italy with us

They took the time to understand our preferences and designed an itinerary that was comfortable, personalized, and enjoyable. They offered thoughtful recommendations while never being pushy.
“Li and EtienneCustom Italy journey
We missed our connecting flight in Munich. I had just got through customs and was looking up the number to call when Trips 2 Italy called me. They told me exactly what to do and they already knew what flight we had been rebooked on.
“The Valdez familyRome, Florence and Venice

Ready to make it yours?

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Questions travelers ask

What destinations does this package visit?

Over 17 days this journey brings you to Amalfi, Amalfi Coast, Capri, Naples, Positano, Ravello, and Sorrento. Each stop is woven into the itinerary with time for the landmarks, the views, and the local flavor that make it special.

How is transportation handled on this trip?

Transportation is arranged as part of the itinerary, with comfortable train segments between the cities and vehicle transfers where they serve you best. Every connection is planned for you, so you can focus on the scenery instead of the logistics.

Who will enjoy this itinerary most?

It suits travelers who enjoy the ease of an escorted experience, with sightseeing arranged and a group to share it with.

Can we tailor this trip to our wishes?

Yes. This sample itinerary is a starting point, and every Trips 2 Italy package is fully customizable. Your travel consultant will adjust the destinations, hotel category, pace, and experiences to fit your plans. A minimum of 2 travelers applies.

When is the best time to take this trip?

The package is available all year around on request. Late spring through early fall is prime time on the coast, with warm seas and long evenings, while April, May, September, and October pair gentle weather with quieter towns.

Keep exploring

Italian Peninsula and Sicily 17 Day Escorted16 nights · 8 stops · 0 experiences added