10 days, 9 nights · Best for First-time travelers seeking Italy's Renaissance art, ancient monuments and coastal villages
Classical Italy Group Tour | Vacation Packages for 2026, 2027
Experience Rome, Florence, the Tuscan countryside and Venice as history, romance and breathtaking scenery come together for an unforgettable 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.
Stop 1Rome, Lazio
Rome
Ancient monuments, Vatican treasures and Trastevere trattorias
We base you in a premium four-star hotel near the historic center, steps from the fountains and markets that define Roman street life. Your guide walks you through the Colosseum and Roman Forum in the morning cool, then leads you past the Trevi Fountain and up Aventine Hill. A separate morning takes you inside Vatican City: the Museums' frescoed galleries, the Sistine Chapel ceiling, St. Peter's Basilica and Michelangelo's Pietà in white Carrara marble.
Between tours you explore Trastevere's cobbled lanes, shop for leather near Campo de' Fiori, and try suppli' at a corner fry shop. We arrange a welcome dinner the first evening at a traditional Roman restaurant, where the kitchen sends out carbonara made with guanciale and Pecorino Romano.
Arranged for you: Premium four-star hotel for three nights, guided walking tour of Ancient Rome including Colosseum, private guided tour of Vatican Museums and St. Peter's Basilica, welcome dinner at a traditional Roman restaurant, tour assistant airport transfer.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Rome
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Evening food walk in Testaccio Day Trips · Half day
Your guide leads you through the Testaccio market and its side-street osterie, stopping for trapizzino, maritozzo and cacio e pepe at three family-run spots.
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Borghese Gallery reserved entry Day Trips · Half day
We secure timed tickets to the Galleria Borghese and pair you with a guide who narrates Bernini's Apollo and Daphne, Caravaggio's Boy with a Basket of Fruit, and Canova's Paolina Borghese.
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Private cooking class in Monti Day Trips · Half day
A Roman chef teaches you to roll fettuccine, shape gnocchi and fry artichokes alla giudia in her apartment kitchen, then you sit down to the four-course lunch you made.
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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
Board your overnight flight from the United States to Rome and let the anticipation for your Italy vacation build! As you travel across the Atlantic, get ready for an unforgettable journey through Italy’s most iconic cities and scenic regions. Your Italian adventure is about to begin!
Benvenuti in Italia! After landing at Rome’s international airport, meet your dedicated tour assistant who will escort you to your first-class hotel nestled in one of Rome’s picturesque neighborhoods. Spend the afternoon exploring the city’s historic center. Consider visiting the lively Campo de’ Fiori market, famous for its fresh produce and local charm. In the evening, delight in a Welcome Dinner at a traditional Roman restaurant, sampling favorites like spaghetti alla carbonara or bucatini all’amatriciana. Overnight in Rome, ready for more discovery.
Start your day with a delicious breakfast at your Rome hotel before embarking on a guided walking tour of Ancient Rome’s most famous sites. Marvel at the Roman Forum, Palatine Hill, Imperial Forum, and explore the legendary Colosseum from the inside. Continue to the Arch of Constantine, the historic Circus Maximus, and Aventine Hill, then make a wish at the Trevi Fountain. Spend your afternoon shopping in Rome’s boutiques, visiting Castel Sant’Angelo, or indulging in classic Roman snacks such as suppli’ (fried rice balls with mozzarella). Enjoy another overnight stay in the heart of Rome.
Begin your day with breakfast, then immerse yourself in the wonders of Vatican City on a private guided tour. Discover the treasures of the Vatican Museums, including the Bernini Staircase, Candelabra Gallery, Tapestry Gallery, and the Gallery of Maps. Stand in awe before the frescoes of the Sistine Chapel and experience the grandeur of St. Peter’s Basilica, home to Michelangelo’s iconic Pietà. Use your free afternoon and evening to explore the Trastevere district, renowned for its authentic trattorias, artisan boutiques, and vibrant Roman nightlife.
Stop 2Florence, Tuscany
Florence
Renaissance art, Chianti vineyards and medieval hill towns
Your hotel sits in the historic center, a short walk from the Duomo's marble façade and the leather workshops of Oltrarno. A morning guide walks you past Brunelleschi's dome, through Piazza della Signoria to the Galleria dell'Accademia, where Michelangelo's David stands seventeen feet high in Carrara marble. You cross the Ponte Vecchio goldsmiths' bridge and climb to Piazzale Michelangelo for views over the terracotta rooftops.
We arrange a full-day excursion into Chianti, stopping in Siena's shell-shaped Piazza del Campo and the Gothic cathedral striped in black and white marble. At a family-run wine estate you walk the Sangiovese rows, tour the cellar and sit down to a Tuscan lunch with the estate's Chianti Classico and Riserva bottlings. Another day takes you to Pisa's Leaning Tower and baptistery, then west to the Cinque Terre coast, where five pastel villages cling to cliffs above the Ligurian Sea. A third day you visit San Gimignano's fourteen remaining medieval towers, walking lanes that have held their thirteenth-century profile.
Arranged for you: Centrally located hotel for four nights, guided walking tour of Florence including Duomo and Galleria dell'Accademia, full-day Chianti excursion with Siena and San Gimignano visits, wine estate tour and Tuscan lunch, Pisa and Cinque Terre day trip, dinner at Il Latini.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Florence
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Uffizi Gallery private morning tour Day Trips · Half day
We book a timed entry before the crowds arrive and pair you with a guide who walks you through Botticelli's Birth of Venus, Leonardo's Annunciation and Caravaggio's Medusa in the Tribuna room.
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Oltrarno artisan workshop visits Day Trips · Half day
A local guide introduces you to three working ateliers across the river: a bookbinder who makes marbled paper, a framemaker gilding in gold leaf, and a third-generation leather craftsman.
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Hot-air balloon over Chianti at dawn Day Trips · Half day
You lift off from a Chianti vineyard at sunrise, drift over stone farmhouses and cypress lines for an hour, then land for a prosecco breakfast in the estate's olive grove.
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Truffle hunting in the Tuscan hills Day Trips · Half day
A truffle hunter and his trained Lagotto dog lead you through oak woods outside San Miniato, digging for tuber magnatum, then the hunter's wife serves a truffle lunch at the family table.
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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
After breakfast, journey from Rome through the rolling hills of Umbria to the spiritual town of Assisi. Enjoy a guided walking tour of the Basilica of Saint Francis and the Basilica of Saint Clare, soaking up centuries of history and art. In the afternoon, transfer to Florence, Tuscany’s capital of art and culture. After check-in at your centrally located hotel, explore the city’s charming streets. Don’t miss a sunset stroll to the Ponte Vecchio. Cap off your day with an authentic Tuscan dinner at Il Latini, one of Florence’s most famous restaurants.
Art in Every Alley
Start your day with breakfast before joining a guided tour of Florence, the cradle of the Renaissance. Visit the awe-inspiring Cathedral of Santa Maria del Fiore, the Baptistery with its golden doors, Giotto’s Bell Tower, and the bustling Piazza della Signoria. Marvel at Michelangelo’s David at the Galleria dell’Accademia and stroll across the historic Ponte Vecchio. Spend your afternoon shopping for Italian leather, exploring Florence’s colorful markets, or relaxing in a local café. Overnight in Florence.
After breakfast, embark on a journey through the rolling vineyards of the Chianti region, renowned for its world-class wines. Discover Siena’s medieval charm with a guided tour of Piazza del Campo, the Cathedral, and historic churches. Visit a traditional Chianti wine estate to learn about local winemaking, sample top-rated wines, and enjoy a Tuscan lunch. Continue to San Gimignano, famous for its medieval towers and UNESCO-listed old town, before returning to Florence for a relaxing evening.
Enjoy breakfast, then set off for Pisa to see the iconic Leaning Tower and the architectural wonders of Piazza dei Miracoli, the Baptistery, and the Cathedral. In the afternoon, travel to the spectacular Cinque Terre, a UNESCO World Heritage Site known for its five pastel-hued fishing villages perched on dramatic cliffs above the Ligurian Sea. Return to Florence and, if time allows, visit Piazzale Michelangelo for sweeping views of the city skyline.
Stop 3Venice, Veneto
Venice
Grand Canal palaces, Byzantine mosaics and Verona's Roman arena
A private water taxi brings you from the mainland across the lagoon to your hotel on or near the Grand Canal. Your guide meets you in Piazza San Marco the next morning and walks you past the four bronze horses above the basilica entrance, through the gold-leaf mosaics inside, and up the bell tower for views across the terracotta domes. You cross the enclosed Bridge of Sighs into the Doge's Palace, where Tintoretto's Paradise covers an entire council-chamber wall and narrow stairs lead down to the prison cells that once held Casanova.
On the way to Venice you stop in Verona, where the same guide shows you the intact Roman Arena, still used for summer opera, and Juliet's balcony off Via Cappello. Between scheduled tours you shop for Murano glass on the Rialto, eat cuttlefish-ink risotto in a bacaro near the fish market, or take a gondola through the smaller canals that thread the Dorsoduro district. We arrange a farewell dinner your last evening at a local Venetian restaurant.
Arranged for you: Centrally located hotel for two nights, private water taxi arrival and departure, guided tour of Verona including Roman Arena, guided tour of Venice including St. Mark's Basilica and Doge's Palace, farewell dinner at a Venetian restaurant.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Venice
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Murano glassblowing demonstration and island visit Day Trips · Half day
A private water taxi takes you to Murano, where a maestro vetraio demonstrates lampworking and blowing techniques in his furnace workshop, then you tour the island's glass museum and lunch at a family trattoria.
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Gondola serenade at sunset Day Trips · Half day
A private gondola carries you through the smaller canals of Dorsoduro and under low bridges while a tenor and accordionist perform Venetian ballads from a second gondola.
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Cicchetti tasting walk Day Trips · Half day
Your guide leads you to four bacari near the Rialto market, where you stand at marble counters tasting baccalà mantecato, sardines in saor, polpette and sarde in saor paired with Veneto whites.
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Burano lace island and Torcello Day Trips · Half day
A water taxi takes you across the northern lagoon to Burano's brightly painted fishermen's houses and lace museum, then on to quiet Torcello to see the eleventh-century Byzantine mosaics in the basilica.
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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
After breakfast, travel to Verona, the romantic city immortalized by Shakespeare’s Romeo and Juliet. Enjoy a guided tour of the ancient Roman Arena, Juliet’s balcony, and the city’s charming historic center. In the afternoon, continue to Venice and arrive in style via private water taxi. Check into your hotel and spend the evening exploring Venice’s enchanting canals, unique shops, and lively piazzas.
Start your final full day in Italy with breakfast, then join a guided tour of Venice’s most iconic landmarks. Visit the stunning Piazza San Marco, climb St. Mark’s Bell Tower, admire the mosaics of St. Mark’s Basilica, and cross the famous Bridge of Sighs. Tour the Doge’s Palace, home to Tintoretto’s massive “Paradise” and the legendary prison of Casanova. Spend the afternoon discovering Venice’s hidden gems, shopping for Murano glass, or enjoying a gondola ride before gathering for a memorable Farewell Dinner at a local Venetian restaurant.
Day 10
Venice/Usa
Enjoy your final breakfast in magical Venice before taking a private water taxi to the airport. Board your flight home with a heart full of memories from your Italian vacation, from Rome’s ancient ruins to Florence’s Renaissance masterpieces, the vineyards of Tuscany, and the romantic canals of Venice. Arrivederci, Italia!
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
What will we see on this journey?
Over 11 days this journey brings you to Rome, Vatican, Cinque Terre, Florence, Pisa, San Gimignano, and Siena. Each stop is woven into the itinerary with time for the landmarks, the views, and the local flavor that make it special.
How do we get between the destinations?
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.
Is this package a good fit for our group?
It is built for groups traveling together, from friends and clubs to multigenerational reunions.
Is this package customizable?
It is. This itinerary is a sample built to spark ideas, and every element can be customized to your wishes and needs by your travel consultant. A minimum of 2 travelers applies.
When should we travel on this package?
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.