This 16-day itinerary travels through all the highlights Italy has to offer. Start off in Florence, strolling along cobblestone streets and across the famed Ponte Vecchio before venturing to the coast and exploring the colorful villages of the Cinque Terre. From here, head south to Rome to discover the Eternal City, delving into the history of the Colosseum and admiring the breathtaking Sistine Chapel. Finish up with some beach time and relaxation along the Amalfi Coast. 

Highlights

  • Tour Florence's beautiful medieval piazzas & cathedrals
  • Discover the rugged nature and medieval villages of the Cinque Terre
  • Visit the Vatican Museum, Sistine Chapel, and Colosseum in Rome
  • Spend time enjoying sunshine, fresh seafood, and medieval villages on the Amalfi Coast
  • Take a day trip to the island of Capri to see how Ancient Romans spent their summer

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Rome, Travel to Florence Florence
Day 2 Florence Self-Guided City Tour Florence
Day 3 Tuscany Day Trip: Siena & San Gimignano Florence
Day 4 Self-Guided Visit to Accademia Gallery & the Uffizi Florence
Day 5 From Florence to Cinque Terre Cinque Terre
Day 6 Wine Tasting in the Cinque Terre Cinque Terre
Day 7 Sunset Cruise on the Cinque Terre Coast Cinque Terre
Day 8 From Cinque Terre to Rome Rome
Day 9 Self-Guided Visit of the Colosseum and Forum Rome
Day 10 Early Morning Vatican Experience Rome
Day 11 Rome to the Amalfi Coast - Pompeii en Route Amalfi Coast
Day 12 Capri Day Trip Amalfi Coast
Day 13 Vespa Tour of the Amalfi Coast Amalfi Coast
Day 14 Free Day on the Amalfi Coast Amalfi Coast
Day 15 From the Amalfi Coast to Rome Rome
Day 16 Depart Rome  

Detailed Itinerary

Day 1: Arrive in Rome, Travel to Florence

Florence Duomo
Florence Duomo

Welcome to Italy! Arrive in one of Rome's two international airports, then transfer to the train station for a 1.5-hour ride on the high-speed train en route to Florence. Once in the city, transfer to the city center to check in to your hotel. If there's time after you arrive, head out to explore the city on your own. 

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 this first day at some of these spots:

  • Head to Studio Artemisia, located steps away from the Ponte Vecchio, for a class in ancient fresco painting techniques.
  • 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, dinner, and drinks in the hip Sant'Ambrogio neighborhood.

Day 2: Florence Self-Guided City Tour

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

Spend the day strolling the streets of Florence and exploring this incredible city with a self-guided itinerary. All together, the route is just a couple of miles, but if you take your time to enjoy the sites along the way, you'll find it to be a full-day experience.

Start your day at the iconic Duomo, the earlier the better! Also known as the Cathedral of Santa Maria del Fiore, Florence’s Duomo is the third-largest church in the world. Entrance into the main sanctuary is free, but keep in mind there is a modesty dress code. There is often a line to get in, so give yourself an hour to properly visit this iconic spot. 

From there, make the 5-minute walk over to the Mercato Centrale, on the second floor of the San Lorenzo market. There, you'll be able to stroll through the stalls of local goods and grab a morning coffee to start your day.  Give yourself an hour or two to soak in the sights and smells, and to buy some traditional leather goods as souvenirs. After, the nearby Piazza della Republica is the perfect place to soak in the atmosphere and architecture of Florence's city center. 

Take a moment to pass through the Piazza della Signoria, where replicas of famous statues, including that of Michelangelo's David, line the square. These works of art give the piazza an incomparable air of elegance- soak it in before stopping for lunch nearby.

Across this same piazza, you'll find the entrance to the Uffizi Gallery. Even if you decide not to peruse the expansive art collection, you can cross through its famed courtyard, Piazzale degli Uffizi, to make your way to the Ponte Vecchio. This famed bridge is now dotted with jewelry shops and is an iconic sight in Florence's cityscape. Cross the bridge, stopping to admire the views along the Arno River that passes quietly underneath. 

End your day with a visit to Piazzale Michelangelo. It's a bit of an uphill climb or a quick taxi ride away. This spectacular viewpoint offers an incredible view of all of Florence and is the perfect place to watch the sunset before you head over to Piazza Santo Spirito for some pre-dinner aperitivos. 

Day 3: 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 an hour away from Florence. San Gimignano is known for its unique towers that dominate the village skyline. In the Middle Ages, noble families built these as a refuge when battling neighboring villages. While most of these across Tuscany were torn down when the villages came under Florentine control, San Gimignano's were left standing. 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 horse race, 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 4: 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, home to masterpieces by Leonardo da Vinci, Michelangelo, Caravaggio, Donatello, and others. However, please keep in mind that it is closed on Mondays.

Start your day early and give yourself at least 3-4 hours to truly see the Uffizi. The expansive art gallery has so much to offer! If you're in a hurry and just want to see the main masterpieces, still give yourself 2 hours. The Uffizi is home to Botticelli's Birth of Venus as well as La Primavera, both not to be missed during your visit. Other masterpieces in the Uffizi include the works of Caravaggio, both Medusa and Bacchus. Tickets include an entry time slot so you can plan your day accordingly. Audioguides you can include with your tickets will be helpful to navigate this large museum.

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

Head over to the Accademia Gallery. Give yourself an hour to explore and admire the great works of art inside this gallery. With just one kind of entrance ticket, the museum streamlines and simplifies the process.

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, this important site is also closed on Mondays!

Among other masterpieces, the Galleria is home to one of the Renaissance's most iconic works of art, Michelangelo's David. This incredible 14-foot tall Renaissance sculpture, which depicts the Biblical hero, was created between 1501 and 1504. It 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, as well as the Medici family's regaining of power.

Afterwards, head to the nearby Piazza San Marco, a hub for Florentines coming and going into the city center, and the perfect place to sit back and relax with a glass of wine in hand at ones of its cafes after a full day of explorations.

Day 5: From Florence to Cinque Terre

Today, you'll leave Florence behind and travel to Cinque Terre. Upon arrival, check into your hotel and spend the rest of the afternoon exploring your new surroundings. 

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 natural surroundings and its abundance of Mediterranean plants, covering 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 well-preserved towns prohibit vehicles so as not to destroy the traditional charm, and most travelers arrive by the 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.

In the evening, head over to Monterosso al Mare and pop into one of the village's several enotecas, local wine bars, to cheers your first night on the Cinque Terre coast with a glass of wine in hand.  

Day 6: Wine Tasting in the Cinque Terre

Wine Tasting in Cinque Terre
Wine Tasting in Cinque Terre

Start the day today with a guided hike up to a Riomaggiore vineyard, where your expert guide will explain the region's tradition of wine-making. Here, each family owns a small piece of terraced vineyard on the steep cliffs above the village. The family lots, which pass down from generation to generation, have been terraced and cultivated in the same way for centuries. The locals take a lot of pride in growing their own family wine and taking care of the delicate grapevines the same way their ancestors did. 

The town and vineyard both enjoy sweeping views over the coastline and surrounding hills. Learn about this region’s centuries-old techniques as you walk through the rows of grapes. The focus here is on making high-quality wine without using any chemical products, and the results are the pride of the Cinque Terre region.  

Enjoy a tour of the vineyard, then sample two local wines to experience the delicate fruit flavors for yourself, and see how organic wine-making makes a difference in flavor. Nibble on traditional Ligurian focaccia bread as you learn more about the production of the specific vintages and take in the views from the vineyard. 

After the three-hour tour, head back to town to find a family-owned cafe for lunch, then spend the rest of the afternoon exploring the rest of the Cinque Terre villages, easily accessible through the network of boat and train lines that ferry locals and travelers from town to town.

There will be plenty of time in each village to learn about its past, explore its individual charms, and buy gifts before returning to your home base for the evening.

Day 7: Sunset Cruise on the Cinque Terre Coast

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, you'll find plenty to be enchanted by in this 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 on 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 winery in Riomaggiore, 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 to your time on the Cinque Terre coast as you watch the sunset.

Day 8: From Cinque Terre to Rome

Pathway along the sea
Pathway along the sea

After a relaxing breakfast, it's time to say goodbye to the Cinque Terre coast and head to Rome. Head to the train station and make your way to Italy's capital, typically changing trains in Pisa and Florence. Your journey should be around 3 hours. Once arrived, head to your hotel to settle in and explore your new surroundings. 

According to legend, Rome was founded by brothers Romulus and Remus in 753 BCE atop Rome's Palatine Hill. The long-time center of the powerful Roman Empire, Rome boasts nearly 3,000 years of architecture, history, and culture. These days, Italy's capital is considered one of Europe's top cities thanks to its ancient monuments, incredible art masterpieces, and cosmopolitan vibe. Its a center for fashion as well, with a buzzing food culture and a growing nightlife scene. 

Be sure to visit the Mouth of Truth, Bocca della Verità, widely recognized from the film Roman Holiday. Movie buffs and visitors alike flock to this monument, as legend has it any liar that dares to stick their hand in the mouth of this giant marble mask will lose it. For dinner, head to the Trastevere neighborhood for some of the city's best trattorias.

Day 9: 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 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. For centuries, Palatine Hill, regarded as the founding site of Rome, housed the Roman nobility while the Roman Forum was the center of daily life. Today, the impressive buildings and archaeological ruins are not to be overlooked during your visit. 

As you approach the Colosseum, you will see the Outer Wall with 3 levels of arches. Near the Colosseum, stands the Arch of Constantine, constructed to honor Emperor Constantine’s victory in the battle of Milvian Bridge in 312 CE. 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 and 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 is a good idea to start your day 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. 

Eating Nearby

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

Day 10: Early Morning Vatican Experience

St. Peter's Square and the Vatican
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 tour will start at the Vatican, entering the Museums at 8 am and giving you a one-hour head start on the rest of the crowds. See the Pio Clementio Museum, Gallery of the Candelabra, Gallery of Tapestries, and Gallery of the Geographical Maps. 

Continue on to the magnificent Raphael Rooms, ending in the breathtaking Sistine Chapel with Michelangelo's Genesis ceiling frescoes and his Last Judgement altar fresco. Finally, end the tour at St. Peter's Basilica and Square, experiencing the magic of Renaissance art while learning the secret details and little known stories of these masterpieces. 

The rest of the day is free for you to explore on your own. Stroll through the Centro Storico, the historic center, of Rome and 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 around the piazza, stopping for some pizza, gelato, and people-watching.

Note: Early Vatican visit not available Wednesdays and Vatican closed entirely on Sundays

Day 11: Rome to the Amalfi Coast - Pompeii en Route

Ancient street in Pompeii
Ancient street in Pompeii

In the morning, you'll leave Rome and head south to the Amalfi Coast. Take the train to Naples before heading by private transfer to your final destination of the Amalfi Coast, but before you arrive, you'll make an incredible stop. Visit the ruins of Pompeii, a bustling seaside city that was buried underneath 13-20 ft (4 to 6 m) of ash and volcanic debris after the 79 CE eruption of Mount Vesuvius. The ash, which killed many of the city's residents, acted as an archaeological time capsule by preserving many of the city's original buildings and features completely intact. 

The city was lost for 1,500 years following Mount Vesuvius' eruption before its accidental rediscovery in 1599. Items of all kinds from jars to furniture were frozen in time, and even those unfortunate citizens of the empire, unable to flee the oncoming ash, were perfectly preserved. A stroll through Pompeii's ancient streets will show off preserved villas, shops, public buildings, and plazas, giving you an insider's look into life 2,000 years ago.

After the excursion to Vesuvius, you'll continue on to the Amalfi Coast, where you'll check in to your hotel and settle in for the evening.

Day 12: Capri Day Trip

Busy port on Capri
Busy port on Capri

Spend the day enjoying the sunshine and clear blue waters of Capri Island. Known locally as the "Pearl of the Mediterranean," the ancient Greeks called it the "Isle of Sirens." Capri sits on the south side of the Gulf of Naples and has been a popular vacation destination for millennia. The ancient Romans, in fact, built summer villas here for the Empire's VIPs.

In the morning, you'll head out to catch a hydrofoil to Capri. Visit the Marina Grande and Marina Piccola harbors, walk along the Belvedere of Tragara (a villa-lined promenade with panoramic views), and explore the ruins of ancient Roman villas.

Then head up the hill to Anacapri to see the Piazzetta and Augustus' Garden, and enjoy the best views of the Faraglioni Rocks. Should you choose, you can later return to the water and explore the Grotta Azzurra, the famous "Blue Grotto," which is located inside a hollowed sea cave. Afterward, we recommend spending the remainder of the afternoon soaking in the sunshine on the beach, before taking the ferry back in the evening.

Day 13: Vespa Tour of the Amalfi Coast

Zip along the Amalfi Coast on a Vespa
Zip along the Amalfi Coast on a Vespa

Just south of the Gulf of Naples lies the Sorrentine Peninsula, featuring the 24 miles (40 km) of Italy's famed Amalfi Coast. This entire region is one of the most storied and beautiful parts of the country, boasting a long history dating back to ancient Rome. Notable citizens of the empire were the first to come here to build seaside villas. There's no better way to explore this singularly gorgeous stretch of coastline than on two wheels—particularly those attached to a Vespa.

This full-day Vespa tour begins and ends at your accommodation along the Amalfi Coast. The pebbly beaches and clifftop views made it a prime destination for Europe's literati and aristocracy from the 17th century onward. From the Amalfi Coast, you'll zip along with your experienced driver to the charming fishing villages whose homes are resplendent with bright colors. The tour finishes with a ride along the stunning coastline, famous for its terraced lemon groves and vineyards, after which you'll return to your accommodation. 

All in all, the route follows 46 miles (75 km) of some of the most incredible coastal landscapes on Earth. Even better, you'll get to stop along the way for tours and, should you choose, to relax on the beach and take a dip in the water. No need to worry if you've never been on a Vespa: your expert guide and driver will take care of zipping along the coastline so you can sit back and enjoy the ride.

Head to the village of Amalfi to finish off your day with fresh seafood and a Delizie al Limone, lemon delight, for dessert to cap off your day.

Day 14: Free Day on the Amalfi Coast

Enjoy your day on  the Amalfi Coast
Enjoy your day on the Amalfi Coast

Today, you are free to explore and enjoy the leisurely coastal pace of life. Go for a walk on the Lemon Path in the town of Minori, or try your hand at windsurfing or kayaking near the shores of Praiano. You can see artisanal ceramics manufacturers in the town of Vietri, or go for a half-day hike on the Path of the Gods. Of course, simply lazing on the beaches of Positano, Vettica Maggiore, and Centra is also an excellent option. 

Other suggestions include: 

  • Visit the beautiful Villa Cimbrone and Terrace of Infinity in Ravello.
  • Check out Praiano's nightlife at the Africana and Music on the Rocks nightclubs.
  • Rent a kayak and explore emerald green grottos, tiny hidden beaches, and impressive sea caves. 
  • Enjoy a quiet day in the serene town of Atrani, far away from the hustle and bustle of the larger villages. 
  • Explore the Fiordo di Furore, Italy's only fjord.
  • Visit the Cloister of San Francesco in Sorrento, an oasis of tranquility that's located steps away from the town's historic Sant'Antonino piazza. 
  • Enjoy nature in the Ferriere Valley Nature Reserve, famous for its postcard-perfect fishing villages and bucolic countryside crisscrossed with hiking trails.

For dinner head to a family-run restaurant for the best Italian pizza paired with a glass of the perfect local wine.

Day 15: From the Amalfi Coast to Rome

Ancient Roman ruins at sunrise
Ancient Roman ruins at sunrise

After a relaxing breakfast, it's time to say goodbye to the Amalfi Coast. After transferring to Naples, catch a 1.5 hour high-speed train back to Rome, then check in to your hotel. 

Spend the rest of the afternoon exploring the city's highlights and making the most of your time in the Eternal City.

  • Hop on a tour boat to explore the city banks from the Tiber River.
  • Walk through the ornate rooms of the Galleria Borghese and explore the splendid frescoes, stories, and masterful techniques behind one of the world's most beautiful art museums. End the tour with a peaceful stroll around the Villa Borghese gardens, enjoying its beauty and calm far from the chaos of the city.
  • Enjoy the sunshine in the orange groves of the Giardino degli Aranci, on the city's Aventine Hill 

Day 16: Depart Rome

Farewell, Rome!
Farewell, Rome!

Time to say goodbye to Italy—for now! After one last Roman breakfast, you'll transfer to the airport for your flight home. Safe travels!

Map

Map of Florence, Cinque Terre, Rome, & Amalfi Coast - 16 Days
Map of Florence, Cinque Terre, Rome, & Amalfi Coast - 16 Days