Start your trip in Rome and visit the legendary Colosseum. Admire the Sistine Chapel and stroll through the streets of its buzzing nightlife. See Michelangelo's 'David' sculpture in Florence, meander through piazzas and across the famed Ponte Vecchio bridge before exploring the colorful, seaside villages of Cinque Terre. Finish off in Venice, shopping for carnival masks and handblown art.

Highlights

  • Soak in the tradition and culture as you tour Rome's top cultural sites
  • Discover ancient legends and Rome's darker side at the Colosseum
  • Tour Florence's beautiful medieval piazzas & cathedrals
  • Discover the rugged nature and medieval villages of the Cinque Terre
  • Explore Venice’s canals & grand palaces

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Rome Rome
Day 2 Vatican Tour: Museums, Sistine Chapel & St Peter’s Basilica Rome
Day 3 Self-Guided Visit of the Colosseum and Forum Rome
Day 4 Half-Day Pizza Making & Wine Tasting Experience from Rome Rome
Day 5 From Rome to Florence Florence
Day 6 Historic Walking Tour of Florence Florence
Day 7 Self Guided Visit to Accademia Gallery & the Uffizi Florence
Day 8 Tuscany Day Trip: Siena & San Gimignano Florence
Day 9 From Florence to Cinque Terre Cinque Terre
Day 10 Sunset Cruise on the Cinque Terre Coast Cinque Terre
Day 11 From Cinque Terre to Venice Venice
Day 12 Self-Guided City Tour of Venice Venice
Day 13 Murano & Burano Half Day Excursion Venice
Day 14 Depart Venice  

Detailed Itinerary

Day 1: Arrive in Rome

Streets of Trastevere, Rome
Streets of Trastevere, Rome

Welcome to Rome, known as the City of the Seven Hills! According to legend, Rome was founded by brothers Romulus and Remus in 753 BCE atop Palatine Hill. As the long-time center of the powerful Roman Empire, you'll find nearly 3,000 years of architecture, history, and culture throughout the city. 

After arriving at one of Rome's airports, you'll transfer to your hotel in the historic center. Settle in and relax, then head out for a stroll and your first look at the Eternal City. The next few days will involve lots of sightseeing, so spend your first few hours enjoying some of the highlights. Suggested activities include:

  • Visit the Catacombs of Priscilla, which were originally used from the 2nd to 5th centuries as burial grounds for the elite families of Rome. After the entrance was blocked for centuries to protect against grave robbers, the catacombs were rediscovered in the 16th century. Visitors can see the original structures as well as paintings and artifacts from various time periods. 

  • Stroll through the tangle of narrow streets in Centro Storico, one of Rome's most historic districts, to see classical Roman and baroque architecture. 

  • Stop to see the Colonna di Marco Aurelio, a Doric column with a spiral of relief sculptures. It was erected in the 2nd century C.E. to celebrate the victories of the emperor Marcus Aurelius. 

  • Head to the Colle Aventino, one of Rome's famous seven hills. Stroll through the Roseto Comunale, the rose garden which sits on the site of a former Jewish cemetery. Then continue to Parco Savello (Orange Tree Park), where you can find the famous keyhole that gives visitors a direct view of the Vatican. Grab a cappuccino and snack from one of the adjacent cafes.

  • For an authentic market experience, stop by the Mercato dei Fiori, where locals shop for fresh vegetables, flowers, meats, and cheeses. Browse for authentic Italian pasta and other souvenirs, then take a break with coffee and a pastry at one of the many cafes surrounding the market. 

For dinner, head to the Trastevere neighborhood for some of the city's best trattorias.

Day 2: Vatican Tour: Museums, Sistine Chapel & St Peter’s Basilica

St. Peter's Square and the Vatican

Today you will visit the Vatican City museums and Sistine Chapel, as well as other top sights in a 3-hour guided tour of the city's incredible art and history. The Vatican is not only rich in history, but also in art, housing some of the most important Renaissance masterpieces in the world. You'll visit the Pio Clementio Museum, plus the Gallery of the Candelabra, the Gallery of Tapestries, and the Gallery of the Geographical Maps

Continue through the museums to the Raphael Rooms, where you can admire the frescoes before entering the incredible Sistine Chapel and St. Peter's Basilica. Your guide will help you experience the allure of Renaissance art by divulging secret details and untold stories throughout the tour.

The rest of the day is free for you to explore on your own. Stroll through the Centro Storico, the historic center, of Rome wander past iconic monuments and architecture such as the Spanish Steps and Trevi Fountain. Head over to Piazza Navona and admire the Fountain of the Four Rivers, designed by the iconic Italian sculptor, Bernini. 

Finish your evening with a stroll through the piazza, stopping for some pizza, gelato, and people-watching.

Day 3: Self-Guided Visit of the Colosseum and Forum

The Colosseum
The Colosseum

Dive into the history of the Roman Empire with a self-guided visit to the Colosseum, the world's largest amphitheater. Walking through the ancient amphitheater is like taking a trip back in time to the days of the Roman Empire. Learn about some of ancient Rome's most famous and illustrious citizens, such as Julius Caesar, Emperors Augustus and Nero, and the Flavian Emperors who built the Colosseum. 

As you approach the Colosseum, you will see the Outer Wall with 3 levels of arches. Near the Colosseum, stands the Arch of Constantine which was constructed to honor Emperor Constantine’s victory in the battle of Milvian Bridge in 312 AD. The Colosseum, the Roman Forum, and the Palatine Hill are all located very close to each other in the same archaeological area. 

Recommended Schedule

Best to start early in the morning! Give yourself 2-3 hours to visit the Colosseum- with a little extra time to go through security- and around 1 -2 hours to explore the Roman Forum & Palatine Hill. 

While many rush to visit the Colosseum first, the Palatine Hill is typically the least crowded of these three sites and offers an entrance with shorter lines. As it's not the typical order to visit- it might a good idea then to start your visit bright and early here. As you walk through Palatine Hill, make your way to the directly connected and incredible Roman Forum. Your entrance ticket serves for all three sites, so after making your way through the Roman Forum to see the impressive monuments, the exit will lead you right next to the entrance of the Colosseum. 

After all this exploring, venture to the nearby Monti neighborhood- less than a 10-minute walk- to tuck into a well-deserved meal.

Day 4: Half-Day Pizza Making & Wine Tasting Experience from Rome

Traditional Pizza Making

Today, head outside of Rome for a local pizza making and wine experience in the nearby town of Frascati. Known for its local products and wines since ancient times, Frascati can easily be reached on a 25-minute train ride from Rome. Take the morning to learn about the history of the town and the local food it's known for, such as slow-roasted pork and jug wine. You'll feel the sense of community as your local guide from Frascati takes you around and interacts with the local shop owners and artisans.

Visit one of the remaining wood-burning ovens in Frascati that fills the nearby piazza with an incomparable aroma. Enjoy the tranquility in this haven with views of Rome in the distance. Time to get cooking! The secret is in the simplicity- with just five ingredients you'll be able to make authentic pizza dough from scratch. Your Pizzaiolo is passionate about his craft and eager to show you the best way to make pizza. 

Your Pizza Maestro will walk you through the ingredients you need, and give you a step by step through the process- from kneading and flattening the dough to adding the perfect toppings. Pop it in the wood-burning oven as you begin to learn about the local Frascati wines from your expert guide. Paired together perfectly, you'll try a few before sitting down to enjoy your pizza fresh from the oven. 

Head back to Rome in the afternoon on the same train and take the rest of the day to explore the sights and sounds of the city. In the evening, check out the upscale Prati neighborhood, brimming with art nouveau architecture and trendy eateries. 

Day 5: From Rome to Florence

Ponte Vecchio across Arno at night
Ponte Vecchio across Arno at night

Take the morning to say your goodbyes to Rome and head to the city of Florence. 

Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo, a terracotta-tiled dome, and the Galleria dell'Accademia, which displays Michelangelo's 'David' sculpture. Make the most of your time at some of these spots:

  • Head to Studio Artemisia, located steps away from the Ponte Vecchio for a class in ancient fresco painting techniques
  • Visit the Chiesa e Museo di Orsanmichele, which served as the granary for the Sisters of San Michele in previous years
  • Take a walk through the peaceful Boboli Gardens to see the oval-shaped Isolotto, a small island surrounded by various sculptures and lots of greenery 

In the evening, stroll around the historic L-shaped Piazza della Signoria, located in front of the Palazzo Vecchio, for some people watching followed by dinner and drinks in the hip Sant'Ambrogio neighborhood.

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Day 6: Historic Walking Tour of Florence

Piazza della Signoria, a UNESCO site
Piazza della Signoria, a UNESCO site

Spend the day exploring the city's top sites, starting with a guided half-day walking tour. Stroll through the picturesque historic center where you'll find the most important squares and monuments: from the Piazza della Repubblica to the Palazzo Vecchio, you'll explore the beautiful squares and architecture that make Florence so picturesque. Soak in the atmosphere before heading over to the Ponte Vecchio, where you can admire the Arno River.

You'll then make a stop at the iconic Duomo, with its terracotta-tiled dome, where across the way Giotto's Bell Tower and the Baptistery with its bronze doors create an unforgettable scene. Finally, with Skip the Line entrance tickets in hand, you'll head to the Galleria dell’Accademia to see Michelangelo’s David. Your guide will share stories of Michelangelo and how this masterpiece came to be.

In the evening, head over to the trendy Piazza Santo Spirito for some pre-dinner aperitivos

Day 7: Self Guided Visit to Accademia Gallery & the Uffizi

Florence's Famous Ponte Vecchio Bridge
Florence's Famous Ponte Vecchio Bridge

Spend a day exploring Florence and discovering its famous museums on your own. Start with the Uffizi Gallery. See masterpieces by Leonardo da Vinci, Michelangelo, Caravaggio, Donatello, and others. However, keep in mind- it's closed on Mondays.

Start your day early and give yourself at least 3-4 hours for your visit to the Uffizi. The expansive art gallery has so much to offer but if you're in a hurry and just want to see the main masterpieces, still give yourself 2 hours. Audio guides with your tickets will be helpful to navigate this large museum. Booking online ahead of time gives you the chance to skip any potential lines. Plus, tickets include an entry time slot so you can plan your day accordingly. 

After a visit to this expansive collection, head to the top floor of the Uffizi for a stop at the Gallery's cafeteria. Offering beautiful panoramic views of the Florence city center, have a cappuccino and recharge your batteries before continuing on to your next stop. 

From there, head over to the Accademia Gallery. The Galleria dates back to 1784 when the Grand Duke of Tuscany, Pietro Leopoldo, reorganized the Academy of Arts of Design in Florence into the modern Academy of Fine Arts. The Galleria was specifically designed to house valuable works of art and its spectacular architecture is impressive in its own right. Remember- also closed on Mondays!

Among other masterpieces, the Galleria is home to one of the Renaissance's most iconic masterpieces, Michelangelo's David. This incredible 14 ft tall Renaissance sculpture, which depicts the Biblical hero, was created between 1501 and 1504 and became a symbol of the Florentine republic's strength during a time of massive political change. Much like David facing the mighty Goliath, the Republic was threatened at the time by stronger states, not to mention to Medici family regaining power.

Give yourself an hour to explore and admire the great works of art inside this gallery. Booking online ahead of time is always suggested. And with just one kind of entrance ticket, the museum streamlines and simplifies the process.

Day 8: Tuscany Day Trip: Siena & San Gimignano

Cathedral and Historic Center of Siena
Cathedral and Historic Center of Siena

In the morning, you'll head to the countryside to explore Tuscany. Your first stop will be the medieval village of San Gimignano, a UNESCO World Heritage Site located an hour away from Florence. Explore the beautiful squares, palaces, and churches of the city before taking a break with a coffee in a terraced cafe. 

In the afternoon, you'll visit nearby Siena, a medieval city brimming with historic sites. You can't miss the incredible main square, Piazza del Campo, which is surrounded by the Gothic Pubblico Palace, the Tower of Mangia, and the Gaia Fountain. From here, walk over to the 13th-century cathedral, Duomo di Siena, which dominates the skyline of the city. In summer months, the town comes alive with festivities, as the Palio takes place in July and August. This exciting horserace held twice a year in the main square of Siena ignites the town in a fervor. 

Finish the day with a visit to the medieval fortress town of Monteriggioni. The intact castle walls surround this town perched on a hillside, and are a sight to behold. Continue on to the Chianti Classico wine region to visit a typical Tuscan winery before returning to Florence for the evening.

Day 9: From Florence to Cinque Terre

Houses of Cinque Terre

Today, head by train or private transport to La Spezia, where the local train that connects to all five villages of Cinque Terre begins. 

Cinque Terre is a rugged strip of the Liguria coastline made up of five old fishing villages—Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. The coast, villages, and surrounding hillsides are all part of the Cinque Terre National Park and are a UNESCO World Heritage Site.

The region is renowned for its beautiful nature and by the abundance of Mediterranean plants that cover the scrubby hillsides that tumble down to the turquoise water. The historic villages and breathtaking beauty of the region make it a popular choice for travelers. The historic towns prohibit vehicles to preserve the traditional charm, so most travelers arrive by train that runs along the coast or by tour boat. 

The area's coastline hiking trails are some of the world's best, linking the small villages together on a beautiful footpath. The path from Riomaggiore to Manarola is called the Via Dell'Amore (Italian for Lover's Walk), and its midpoint—The Lover's Lock, a statue of two people kissing—is a favorite place for couples to copy the gesture for a photo. Bring a small lock to attach to one of the gates or rails on the way to seal your eternal love.

Day 10: Sunset Cruise on the Cinque Terre Coast

The Cinque Terre coastline

Take the morning to explore Cinque Terre on your own. Whether it's soaking in the sunshine on a beach, hiking through its breathtaking trails, or wandering around the colorful villages, be enchanted by this incredibly unique area. 

We recommend some of these activities to make the most of your day: 

  • The Cinque Terre has no shortage of churches—visit a few of them, including the Santuario di Nostra Signora di Montenero in Riomaggiore and the Church of San Giovanni Battista in Corniglia 
  • Explore the 13th-century Castello Di Riomaggiore, which dominates the Cinque Terre coastline. Built to protect the town from seafaring pirates, the castle is now simply a throwback to a different time, as well as a great place for photographs. Head inside the castle to see the museum exhibit of the centuries of town history
  • Walk up to the Torre Aurora, a medieval castle that stands on the intersection of Monterosso's Old Town and New Town 
  • Pay a visit to Cantina 5 Terre in Riomaggiore, the Cinque Terre's only major winery, to learn about how ancient traditions mix with modern-day production techniques to produce a unique and flavorful wine. Sample the wines, especially the local white, and enjoy a relaxing afternoon 

In the evening, head out onto the water to enjoy a small group sunset boat tour. Sit back and admire the views of the charming Cinque Terre fishing villages on a 2.5-hour route from Vernazza. You'll pass by grottos tucked into cliffsides, and admire the villages of Corniglia, Manarola, and Riomaggiore from the sea. 

Go for a dip in the water off the deck of the boat and toast your time on the Cinque Terre coast with a drink in hand as you watch the sunset.

Day 11: From Cinque Terre to Venice

Photo taken by Mick R
Photo taken by Mick R

Time to say goodbye to the Ligurian Coast of Cinque Terre. Head to the La Spezia train station and from there, you'll make your way to the other side of Italy, to the city of Venice. Settle in for about a 5-hour journey, with usually two train changes along the way. 

Venice in northern Italy is famous for both industry and tourism. With nicknames like "Queen of the Adriatic", "City of Water", and "The Floating City", it's clear that the city's myriad canals are its main draw. Stretching across 117 small islands in the marshy Venetian Lagoon along the Adriatic Sea, the city has long been a commercial and cultural hub thanks to its strategic placement. Silk, grains, spices, and art were traded through the Middle Ages, making Venice very wealthy.

Venice is well known for several artistic movements, particularly from the Renaissance period. The city's many musicians, like Antonio Vivaldi and others, played important roles in the shaping of symphonic and operatic music. Numerous artists have called Venice home, and their work continues to draw visitors worldwide. 

The city is also famous for its many beautiful historic attractions, such as the Piazza San Marco and San Marco Basilica, the Grand Canal, and the ornate Doge's Palace. The Lido de Venezia is a popular luxury destination that attracts actors, critics, and other cinema industry celebrities.

Take the evening to explore the Cannaregio district. This area of Venice, known for holding the Jewish Quarter is the perfect place to simply walk through admiring the unique, iconic architecture. Cannaregio has plenty of artisanal shops to explore and not to mention a plethora of delicious restaurants and lively bars to stop in for dinner and drinks.

Day 12: Self-Guided City Tour of Venice

Traditional Venetian carnival masks
Traditional Venetian carnival masks

We'd recommend starting at the center of it all in St. Mark's Square, or Piazza San Marco. Take a moment to breathe in the sights and sounds of this famed square before getting a deeper look inside the impressive buildings and architecture that surround it. 

Admire the impressive Basilica San Marco from outside before venturing in. While admission is free, there is a skip-the-line fee that can be purchased online to avoid lining up in busy months. Be sure to wear appropriate clothing entering inside. Marvel at the incredible mosaics that adorn the inside of the building. If you're up for it, you can climb the campanile, the bell tower of the Basilica that offers incredible views! Here, we'd recommend buying tickets ahead of time online. 

From here, turn your attention to Doge's Palace, also located in St. Mark's Square. This almost 600-year-old building has served many purposes over the course of time but always continued to remain an impressive symbol of Venetian history. Most notably, it was the home to the Doge, the ruler of Venice, and the center of government during the Venetian Republic.  Before entering for a visit of the incredibly lavish interior of the palace (buy your admission tickets online to save yourself time!), walk over to the Grand Canal side of the palace for a look at another iconic spot in Venice- the Bridge of Sighs. This ornate Baroque-style bridge connected the palace with its first-floor prison and was used to transfer its prisoners.

Having seen the highlights of St. Mark's Square, it's time to make the 10-minute walk to Rialto Bridge. As you explore Venice on foot, you'll surely cross one of the four bridges that span the Grand Canal. The Rialto Bridge is the oldest and arguably most well-known. Linking the districts of San Marco with San Polo, the bridge gives amazing views of both sides of the canal. 

A little further down along the Grand Canal you'll find the Rialto Market. This iconic food market is buzzing with local life and flavors. Overlooking the canal, you can stroll around this lively epicenter of daily Venetian life and culture seeing and tasting the local products that make up its incomparable cuisine. Note that the market shuts down around midday and is closed on Sundays and Mondays. 

To round out your day, head to another of the four iconic bridges crossing the Grand Canal, the Ponte dell'Accademia. The vantage point from this bridge offers an incredible view of Venice and the canal it spans. Take a moment to admire this picture-perfect setting before heading to a nearby bar to finish off your day with a glass of wine and Cicchetti- the Venetian version of tapas.

Day 13: Murano & Burano Half Day Excursion

Colorful homes in Burano
Colorful homes in Burano

When in Venice, a visit to its lagoon and neighboring islands is a must! These picturesque villages offer a getaway from the city of Venice and a unique look into the local life and culture nearby. This morning, head out for a half-day tour of Venice's famous neighbors—the islands of Murano and Burano.

Board your motorboat in the center of Venice and make your way first to Burano, about 45 minutes away. Along the way, your guide will offer insights about the spectacular Venetian lagoon and the various islands it contains. Arrive first at Burano and have free time to explore the island. Traditionally a quiet fishing village, it's known for its exquisite lacemaking and the colorful houses that adorn its canals. You'll be sure to leave with a camera roll full of photos, as this charming island is incredibly postcard-worthy.

From there, return to your boat and head over to the island of Murano. Murano is famous for its colorful glass-making. Visit a glassblower to see a demonstration and learn about the history of glass-making on Murano and the process behind it. Marvel at the intricate pieces, and peruse Murano's many local shops to see the many forms of this delicate craft for yourself. 

After spending the better part of your morning enjoying the sights and sounds of the unique islands, return to Venice by boat in time for lunch at one of its many delicious local eateries.

In the afternoon, explore Venice on your own with one of these options to make the most of your time: 

  • Discover art at the Peggy Guggenheim Collection Modern Art Museum, and La Biennale di Venezia Art Museum
  • See an opera show at the Teatro La Fenice 
  • Browse textiles, craft shops, unique boutiques, and galleries in the bohemian San Samuele district

Day 14: Depart Venice

Farewell, Venice!

Your exploration of Italy will end after breakfast, with a transfer to the airport to catch your flight home or to your next destination.

Map

Map of Rome, Florence, Cinque Terre, & Venice - 14 Days
Map of Rome, Florence, Cinque Terre, & Venice - 14 Days