10 days, 9 nights · Best for First-time visitors seeking Italy's Renaissance art and ancient landmarks
Classical Italy Group Tour TO BE ELIMINATED DOUBLE
Experience Rome, Florence, Tuscany and Venice as ancient wonders, rolling vineyards and romantic canals create the ultimate Italian adventure.
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.
Stop 1Rome, Lazio
Rome
Ancient forums, Vatican treasures and neighborhood markets
We arrange three nights in the historic center, within walking distance of the Trevi Fountain and the Spanish Steps. Your guide leads a morning tour of the Colosseum, Roman Forum and Palatine Hill, then continues to the Circus Maximus and the Aventine. On a separate morning you visit the Vatican Museums and Sistine Chapel with skip-the-line access, moving through the Candelabra Gallery, the Tapestry Gallery and the Raphael Rooms before Michelangelo's frescoed ceiling.
Between tours you have time to explore Campo de' Fiori, where vendors sell flowers, vegetables and olive oil under market umbrellas, or to order cacio e pepe in a trattoria near Piazza Navona. A welcome dinner on your first evening introduces you to Roman antipasti, pasta and wine.
Arranged for you: Airport greeting and transfer, three nights' accommodation, daily breakfast, walking tours of ancient Rome and the Vatican with skip-the-line access, and a welcome dinner at a neighborhood restaurant.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Rome
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Private cooking class in a Roman kitchen Day Trips · Half day
Learn to make fettuccine, gnocchi and tiramisu with a chef in her home near Trastevere, then sit down to eat what you've prepared.
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After-hours tour of the Borghese Gallery Day Trips · Half day
View Bernini's Apollo and Daphne and Caravaggio's David with Goliath when the museum is closed to the public.
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Vespa tour through Rome's neighborhoods Day Trips · Half day
Ride behind an experienced driver through Monti, the Jewish Ghetto and along the Tiber to see the city as Romans do.
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Ancient and Old Rome Walking Tour, Skipping the line at Colosseum Guided Tours and Sightseeing · Tour in a DayUnlock the secrets of the Eternal City, skip the lines and step into the world of emperors, gladiators, and gods on this lively, story-filled Roman adventure.
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Full Day Rome Tour Guided Tours and Sightseeing · Tour in a DaySee Rome your way in one unforgettable day. Vatican treasures, Imperial ruins, and iconic monuments with the ease of a dedicated tour escort.
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Papal Audience in Saint Peter’s, Vatican City Guided Tours and Sightseeing · Tour in a DayWitness a truly unforgettable moment in Rome, attend a Papal Audience and receive the Pope’s blessing.
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Rome by Bicycles Tour with English Speaking Guide Guided Tours and Sightseeing · Tour in a DaySee more of Rome with less effort, cruise past iconic landmarks on a fun, guided bike ride made for everyone.
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Rome by Night Guided Tour Guided Tours and Sightseeing · Tour in a Day
See Rome at its most magical, an evening stroll through illuminated fountains, grand piazzas, and ancient ruins.
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Rome by Night guided Tour with Dinner & Show Guided Tours and Sightseeing · Tour in a Day
Fall for Rome after dark. Glowing landmarks, a romantic evening stroll, and dinner with live music to seal the moment.
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Rome: The Eternal & Ancient Rome Tour Combo Guided Tours and Sightseeing · Tour in a DayExperience the magic of the Eternal City with a full-day tour showcasing Rome’s most iconic historical sites.
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Rome: The Eternal City Tour Guided Tours and Sightseeing · Tour in a Day
Discover Rome’s most iconic monuments in comfort on this tour.
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Skip the Line: Vatican Museums and Sistine Chapel Guided tours Guided Tours and Sightseeing · Tour in a Day
Skip the lines and step straight into the Vatican’s greatest masterpieces. Museums, Sistine Chapel, and St. Peter’s Basilica with an expert guide.
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The Ancient Rome Tour Guided Tours and Sightseeing · Tour in a Day
Walk in the footsteps of emperors and gladiators, discover the power, passion, and innovation that shaped the world in Ancient Rome.
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The Ancient Rome Walking Tour, Skipping the line at Colosseum Guided Tours and Sightseeing · Tour in a Day
Experience the ancient highlights of the Eternal City with a guided walking tour that takes you through Rome’s most iconic landmarks.
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The Christian Rome & Catacombs Tour with Hotel Pick Up Guided Tours and Sightseeing · Tour in a DayJourney through Rome’s spiritual heart, explore ancient basilicas, sacred relics, and the origins of Christianity in the Eternal City.
Day by day in Rome
ROME
Board your overnight flight and leave the United States. Your Italian adventure has begun!
ROME
Benvenuti in Italia! Once you arrive at the airport, your meet and great assistant will meet and escort you to your first class hotel in one of Rome’s charming neighborhoods. After check-in, you will have time to explore Rome at your leisure for the remainder of the day. During this time, you may wish to visit one of Rome’s famous markets, the most historical of which is Campo de’ Fiori, located in the heart of Rome. In the evening, you will enjoy a Welcome Diner at a typical restaurant featuring delicious Roman dishes such as spaghetti alla carbonara or bucatini all’amatriciana. Afterwards, you will return to your hotel for the night.
ROME
After breakfast at your hotel, you will enjoy a walking tour of Rome’s famous ancient sites including the Roman Forum, the Palatine Hill, the Imperial Forum, and the Coliseum. During the tour, you will have the opportunity to explore the Coliseum from the inside.
The next part of the tour will feature the Arch of Constantine, the Circus Maximus, the Aventine Hill, and finally the Trevi Fountain, where you will have the chance to launch your own coin into the water of the fountain and secure your return trip to Rome one day. You will have the remainder of the day to shop at your leisure, see more sites such as Castel Sant’Angelo, or relax and enjoy a gelato or a typical Roman snack like suppli’(rice and mozzarella fried together into a ball).
ROME/VATICAN
After enjoying breakfast at your hotel, you will travel to the Vatican, the smallest country in the world located in the heart of Rome. Here, you will enjoy a private guided tour of the Vatican Museums. Inside the Vatican Museums you will find the largest collection of artwork in Europe, boasting more than 65,000 masterpieces. A few highlights include the Bernini Staircase from the 16th century, the Candelabra Gallery filled with statues and frescos, the Tapestry Gallery which dates back to the 16th and 17th centuries, the Gallery of Historical Maps made by Ignazio Danti, the Sistine Chapel commissioned by Pope Sixtus in the 15th century and decorated by Ghirlandaio, Perugino, Botticelli, and, of course, Michelangelo, St. Peter’s Basilica (which is the biggest church in the world) featuring several Papal Tombs, millions of skillfully crafted mosaics, and Michelangelo’s masterpiece "The Pietà". You will have the remainder of the day at your leisure to further experience the spirit of the colorful capital of Italy. We suggest a visit to Trastevere, one of Rome’s characteristic neighborhoods where you will have the opportunity to enjoy more exquisite cuisine in local trattorias, explore typical shops, and interact with the locals.
Stop 2Florence, Tuscany
Florence
Renaissance masterworks, Chianti vineyards and hill town ramparts
We hold four nights in the center of Florence, close to the Duomo and the Arno. A full-day walking tour covers Brunelleschi's cathedral, the bronze Baptistery doors, Giotto's bell tower, Piazza della Signoria and Michelangelo's David in the Galleria dell'Accademia. You cross the Ponte Vecchio, lined with goldsmiths' shops, and have time to wander the Oltrarno district or visit the Uffizi on your own.
On another day we drive through Chianti to Siena, where you walk the shell-shaped Piazza del Campo and see the black-and-white striped cathedral. After lunch you visit a Chianti estate for a tasting of Sangiovese, then continue to the towers of San Gimignano. A separate excursion takes you west to Pisa to see the Leaning Tower, the round Baptistery and the cathedral's mosaic-covered apse, then on to Cinque Terre to explore the five cliffside villages connected by coastal footpaths.
Arranged for you: Private transfer from Assisi with a stop for a guided walking tour of the Basilica of Saint Francis and the Basilica of Saint Clare, four nights' accommodation, daily breakfast, full-day walking tour of Florence with skip-the-line entry to the Accademia, full-day excursion to Siena, San Gimignano and a Chianti wine estate with tasting, and full-day excursion to Pisa and Cinque Terre with walking tour of Pisa.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Florence
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Private tour of the Uffizi Day Trips · Half day
Walk through the galleries with an art historian who explains Botticelli's Birth of Venus, Leonardo's Annunciation and Caravaggio's Medusa.
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Truffle hunting in the Tuscan hills Day Trips · Half day
Join a hunter and his dog in the woods near San Miniato, then taste the white truffles you find over tagliatelle and local wine.
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Market tour and cooking lesson Day Trips · Half day
Shop for vegetables, cheese and meat at Mercato Centrale, then prepare ribollita, pappardelle and cantucci in a chef's kitchen.
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Hot-air balloon over the Chianti countryside Day Trips · Half day
Lift off at dawn from a vineyard estate and float over cypress-lined roads, stone farmhouses and rows of Sangiovese vines.
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Accademia Gallery Guided Tour, Skip the Line with Advanced Reservation & Tickets Guided Tours and Sightseeing · Tour in a DayVisit one of the most important collections of art, including Michelangelo’s David, while skipping the long lines!
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Discovering Florence Walking Tour Guided Tours and Sightseeing · Tour in a DayDiscover the highlights of Florence on a guided walking tour that showcases the city’s most iconic sites and artistic treasures.
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Florence and Fiesole Hills Small Group Guided Sightseeing Tour Guided Tours and Sightseeing · Tour in a DayFlorence’s Renaissance icons, then a breath of Tuscan air, small-group sightseeing with panoramic Fiesole views and zero big-bus chaos.
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Florence Historical Center Walking Tour Guided Tours and Sightseeing · Tour in a DayMeet Florence in a single stroll. Renaissance palazzos, landmark churches, and UNESCO beauty with stories that make it all click.
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Florence Morning Guided Walking Tour Guided Tours and Sightseeing · Tour in a DaySee Florence’s greatest hits, Renaissance stories, iconic sights, and a surprise tasting that adds a delicious twist.
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Florence Tour Guided Tours and Sightseeing · Tour in a DayFall in love with Florence in a single day. Renaissance streets and churches, Uffizi masterpieces, and a Tuscan lunch to top it off.
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Florence, Tuscany, Cooking Class package with Typical Dinner Food and Wine · Tour in a DayImmerse yourself in the flavors of Tuscany with a hands-on cooking class at a top culinary school, where expert chefs will guide you in creating an authentic Tuscan dinner.
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Florence: Handmade Pasta Cooking Course with Lunch Food and Wine · Tour in a Day
Roll, cut, and taste Tuscany, make fresh pasta from scratch in Florence with local experts.
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Florence’s Art & Gourmet Private Walking Tour Guided Tours and Sightseeing · Tour in a Day
Taste and explore Florence like a local. Markets, secret bakeries, historic churches, and hidden corners on a private walk through the city’s heart.
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Guided Visit of Accademia & Uffizi Gallery Skip the Line with Advanced reservation & tickets included Guided Tours and Sightseeing · Tour in a Day
Two legendary museums, one seamless day. Skip the lines for Michelangelo’s David and Botticelli’s Birth of Venus with an expert guide.
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Guided Visit of Uffizi Gallery, Skip the Line with Advanced Reservation & Tickets Guided Tours and Sightseeing · Tour in a Day
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Horse Riding through the Tuscany Countryside guided Tour Guided Tours and Sightseeing · Tour in a DaySaddle up for an unforgettable Tuscan adventure as you spend the morning horseback riding through picturesque vineyards and olive groves surrounding a charming villa.
Day by day in Florence
ROME/ASSISI/FLORENCE
After enjoying breakfast at your hotel, you will travel from Rome, through the scenic countryside of Umbria, to the city of Assisi. Here, you will enjoy a guided walking tour of Assisi during which you will visit the Basilica of Saint Francis and the Basilica of Saint Clare. After your tour of Assisi ends in the late afternoon, you will travel to your new hotel in the heart of Florence. Once you check-in, you will have some free time to relax or explore the city independently. If you are interested, we suggest walking through the city center to the Ponte Vecchio bridge to get your first taste of the many flavors this famous Tuscan city offers. Afterwards, you will enjoy Dinner at the famous restaurant in Florence called Il Latini where you will experience delicious Tuscan cuisine for the first time.
FLORENCE
After enjoying breakfast at your hotel, you will take a guided walking tour of Florence, the birthplace of the Italian Renaissance and one of the world’s most iconic cities. You will visit the main sites of the city center including Brunelleschi’s Cathedral of Santa Maria del Fiore, the Baptistery and its famous entry doors made of bronze, Giotto’s Bell-tower, Piazza della Signoria, Loggia della Signoria, the Galleria dell’Accademia where Michelangelo’s “David” is on display, and the famous Ponte Vecchio. After the tour, you will have time to explore Florence on your own to witness its characteristic streets and visit its popular markets.
FLORENCE/SIENA/SAN GIMIGNANO/WINE TASTING
Today after breakfast you will travel through the picturesque area of Chianti production in the enchanting Tuscan countryside. You will first stop in the medieval city of Siena, famous for its Palio horse race. You will discover Siena’s enchanting atmosphere as you immerse yourself in the important sites of the city including the Church of St. Francis, the Church of St. Domenic, the Cathedral, and Piazza del Campo where the Palio is held each year. Next, you will leave Siena and visit a characteristic Chianti wine estate in the beautiful Tuscan countryside. Here you will learn about the production of Chianti wine first-hand from the proprietors and enjoy a light lunch with a wine tasting. Before returning to Florence, you will make one more stop at the hilltop town of San Gimignano, famous for its stunningly preserved towers and city walls. You will then travel back to your hotel in Florence where you will have the rest of the day at your leisure to explore more piazzas and/or churches (such as Piazza San Lorenzo or Santa Croce), or simply relax and enjoy an espresso or gelato in one of Florence’s many cafes.
FLORENCE/PISA/CINQUE TERRE
After breakfast you will travel once more through picturesque Tuscan landscapes, this time stopping in the unique city of Pisa. Besides its famous tower, Pisa is known for its university and its location on the Arno River. While in Pisa, you will admire the Leaning Tower in Piazza dei Miracoli, the Baptistery, and the Cathedral with its remarkable paintings, mosaics, and pulpit. After Pisa, you will leave Tuscany, travel to the seaside region of Liguria, and stop in Cinque Terre. This unique location is composed of a series of five villages featuring iconic colorful houses resting along the coast and suspended from steep cliffs surrounded by hills, creating one of the most breathtaking landscapes imaginable. After taking in these unforgettable panoramic views, you will return to Florence and have the rest of the day at your leisure to further explore the city and perhaps visit Piazzale Michelangelo to witness stunning panoramic views of the city.
Stop 3Venice, Veneto
Venice
Island palaces, Byzantine mosaics and canals without cars
We arrange two nights on or near the Grand Canal, reached by private water taxi from the mainland. On the way we stop in Verona for a guided walk through the Roman arena and past the so-called Juliet balcony, a fourteenth-century courtyard that draws its name from Shakespeare rather than history.
In Venice a full-day walking tour takes you through Piazza San Marco to see the gold mosaics inside the basilica, the view from the bell tower, the Bridge of Sighs and the Doge's Palace, where Tintoretto's seventy-foot canvas Paradise covers an entire wall. Between the tour and your departure you have time to cross the Rialto Bridge, order cicchetti at a bacaro in Cannaregio, or take the vaporetto to Murano to watch glassblowers shape molten silica into goblets and chandeliers.
Arranged for you: Private transfer from Florence with a stop in Verona for a guided walking tour of the arena and the historic center, private water taxi to your hotel, two nights' accommodation, daily breakfast, full-day walking tour of Venice with skip-the-line entry to St. Mark's Basilica and the Doge's Palace, and private water taxi to the airport.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Venice
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Private gondola ride at sunset Day Trips · Half day
Glide through narrow back canals and under arched bridges while the gondolier propels the boat with a single oar.
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Glassblowing demonstration on Murano Day Trips · Half day
Visit a historic furnace where a maestro shapes molten glass into vases and figurines using techniques unchanged since the Renaissance.
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Cicchetti tasting tour in Cannaregio Day Trips · Half day
Walk from bacaro to bacaro sampling small plates of marinated sardines, baccalà mantecato and polpette with local white wine.
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Ca’ Rezonico, the Doge’s Palace and St. Mark’s Basilica Shore Excursions · Tour in a DayImmerse yourself in the rich history and breathtaking beauty of Venice on this 5-hour tour, where you’ll explore iconic landmarks such as the Doge’s Palace, St. Mark’s Basilica, and Ca’ Rezzonico.
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Doge’s Palace and Gondola Ride Shore Excursions · Tour in a Day -
Murano and Burano Shore Excursions · Tour in a DayThis 4-hour tour gives you an up close and personal look at the stunning glass factories of Murano Island, as well as a tour of the brightly painted houses on Burano Island.
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San Giorgio, Murano Glass Factory and Gondola Ride Shore Excursions · Tour in a DayThis 5-hour tour allows you to explore a working Murano glass factory, takes you through stunning San Giorgio and lets you relax and unwind with a magical gondola ride through the canals of Venice.
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Tour Venice by Gondola Shore Excursions · Tour in a DayExperience Venice in the most iconic way, gliding through its enchanting canals aboard a traditional gondola.
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Venetian Costumes Tour Shore Excursions · Tour in a Day
Uncover Venice’s most elegant legacy, where master tailors, lavish fabrics, and palace-ready fashion shaped centuries of style.
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Venetian Lagoon Cruise Shore Excursions · Tour in a Day
See Venice the way it was meant to be seen, by water, gliding through the lagoon with postcard views at every turn.
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Venice and Jewish Ghetto Shore Excursions · Tour in a DayStep into Venice beyond the postcards. Discover the Jewish Ghetto’s living history, vibrant squares, and authentic neighborhood soul.
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Venice with Doge’s Palace and St. Mark’s Cathedral Shore Excursions · Tour in a DayFor travelers eager to experience Venice’s top sights, this 6-hour guided tour provides exclusive access to two of the city’s most iconic landmarks.
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Walking Tour of Venice Shore Excursions · Tour in a Day
Wander Venice’s legendary squares and secret lanes on a relaxed 4-hour walk filled with bridges, beauty, and unforgettable stories.
Day by day in Venice
FLORENCE/VERONA/VENICE
After enjoying breakfast at your hotel, you will travel to Verona, the town of Romeo and Juliet, located in the eastern region of Veneto. In Verona you will enjoy a guided walking tour of the town and see the important sites including the Arena and the famous Juliet balcony. When your visit in Verona concludes, you will travel on to the famous water town of Venice. Once there you will take a private water taxi to your hotel and check-in. You will then have the remainder of the day at your leisure to rest or to explore Venice on your own. We suggest strolling through the city’s narrow streets, called calli, and visiting any local shops that may interest you.
VENICE
Today marks your last full day in Italy and it will be dedicated to exploring one of Italy’s most famous jewels: Venice. After enjoying breakfast at the hotel, you will embark on a guided walking tour of Venice. The first stop will be the iconic Piazza San Marco with St. Mark’s Bell-tower, St. Mark’s Basilica, the Bridge of Sighs, and the Doge’s Palace. Inside the Doge’s Palace you will observe, among many other artworks, the largest oil painting in the world, “Paradise” by Jacopo Tintoretto, which measures 23 feet by 75 feet. During the tour you will also witness the prison in which Casanova was incarcerated before he escaped. After the tour you will have time for lunch on your own, the perfect opportunity to sample some of Venice’s delicious seafood. Then, for the rest of the afternoon you will be free to discover the heart of Venice on your own. You will then enjoy a final Farewell Dinner in one of Venice’s typical restaurants.
Day 10
Day 11
VENICE
After one last Italian breakfast, you will take a private water taxi to Venice Airport and board your flight back home to the United States. Arrivederci!
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.
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.
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Questions travelers ask
Where will we travel on this itinerary?
Over 11 days this journey brings you to Rome, Cinque Terre, Florence, Pisa, San Gimignano, Siena, and Assisi. Each stop is woven into the itinerary with time for the landmarks, the views, and the local flavor that make it special.
How will we get around during the vacation?
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.
What kind of traveler is this package for?
It suits travelers who enjoy the ease of an escorted experience, with sightseeing arranged and a group to share it with.
Can we customize this itinerary?
Absolutely. Every Trips 2 Italy itinerary is designed to inspire and can be tailored end to end, from the number of nights and hotel categories to the experiences along the way. A minimum of 2 travelers applies.
What is the best season for this itinerary?
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.