Planning Your Ultimate Trip to Italy
Italy holds a cherished place in the popular imagination thanks to its history and architecture, from Ancient Rome to the Renaissance, as well as its unique cuisine and natural beauty. The following itineraries take both geography and timing into consideration, allowing you to make the most of your trip by grouping sights that are closer together or easier to travel between.
If you have limited time and want a quick taste of why Italy is so special, start with our five-day itinerary recommendations for just one city or region. One of our recommendations for a full week in Italy efficiently combines the country’s capital city of Rome with the Amalfi Coast, a nearby region chock full of enticing sights. The other lets you spend more time in two distinct cities – Venice and Florence - each a beloved destination for different reasons. For more 7-day itinerary ideas, see here.
With a bit more time, you can combine these two shorter itineraries, making it a 10-day trip across three amazing Italian cities – Rome, Florence, and Venice – with some time on the Amalfi Coast as well. For more 10-day trip ideas, see here.
If you have two weeks at your disposal, add on another region, such as the Lakes Region near Milan and the Cinque Terre, or swap Venice and Florence for Sicily, a huge island with a history and culture all its own. Given Sicily’s size, number of attractions, and possible day trips from its main cities, you’ll need multiple days to take it all in. A longer trip is the perfect way to experience it. For more two-week trip ideas, see here.
In 5 Days: Stick to One City or Region
- A perfect mix of Ancient Roman and Renaissance highlights in Rome
- Food tour of Roman delicacies
- Pompeii, Mt. Vesuvius, and seaside towns of the Amalfi Coast
If you have less than a week in Italy, it makes sense to pick one city or region and stick to it. That way, you can come away inspired and enriched, with a true understanding of a specific part of Italy and excitement for a return trip.
On this 5-day itinerary in Rome, highlights will include a guided tour of the Colosseum; a visit to the Vatican Museum and its priceless works of art, including the Sistine Chapel; and a boat tour of the Tiber River. You’ll also get the chance to taste Roman delicacies and learn about the culinary heritage of the Eternal City. That way, you’ll be experiencing all the best of what Rome has to offer, including history, art and architecture, food, and culture.
If you opt for this 5-day itinerary on the Amalfi Coast instead, you’ll make Naples your base. You'll explore Naples itself, drive around the region to see the ancient Roman towns of Pompeii and Herculaneum, and hike up the active volcano of Mt. Vesuvius (that destroyed those two cities in the infamous eruption of 79 AD). On day three, you’ll set out to explore the photogenic towns of the Amalfi Coast, like Amalfi and Positano, and see for yourself why this region has been a cherished getaway for centuries.
In 7 Days: The Best of Italy
- Art, architecture, history, and culture in three major cities
- A boat tour of Venice's Grand Canal
- A wine tour of the Tuscany Region
With a full week in Italy, you have the time for a road trip through Tuscany. Discover Renaissance buildings and museums like the Uffizi in Florence, before driving to the medieval city of Siena. It's perfectly located for short day trips to the hilltop villages of San Gimignano & Monteriggioni. Tuscany is a world-renowned wine region, so you will savor visits to a couple of wineries to taste the local specialties. In Montepulciano, you will learn about making and tasting typical full-bodied red wines in a spectacular rural setting. Alternatively, you could stay in an agriturismo near Pisa on a week-long self-drive trip.
If this is your first time in Italy however, the classic route through Rome, Florence, and Venice is a must. In this compact yet comprehensive 7-day itinerary, you’ll start in the capital city with a full day of sightseeing, including historic highlights like the Colosseum and the Vatican Museum with the Sistine Chapel, leaving enough time to taste some of Rome’s distinctive culinary delights as well, including traditional Italian pizza and gelato. You'll split up your two full days based in Florence equally between the city itself and the coastal towns of the Cinque Terre, using your first day to take a tour of the walkable city center, filled with beautiful art and architecture. On day two, you'll travel to the coast and spend your day exploring the five villages. Enjoy activities such as hiking, wine tasting, or relaxing on the beach. In Venice, a unique and popular city, it's nice to find your own way around with a self-guided tour of the city's canals and monumental buildings, including the Grand Canal and Basilica San Marco in the main Piazza San Marco square!
In 10 Days: Three Classic Cities and the Amalfi Coast
- A mix of art, architecture, history, and food in Italy's "big three" cities
- Explore the Veneto islands of Murano, Burano, and Torcello
- A tour of the Blue Grotto of Capri and a sunset boat trip along the coast
- Roman highlights and extensive time at the Vatican Museums
With 10 days in Italy, you can trace the history of the ancient world in Rome, see Renaissance masterpieces from the likes of Leonardo and Michelangelo in Florence, and travel south to the Amalfi Coast, exploring Naples, the island of Capri, and towns like Amalfi and Positano or the buried cities of Pompeii and Herculaneum.
You’ll start with full days in Florence and a whirlwind of sights and tastes. Take in the masterpieces of the Galleria dell’Accademia, home to Michelangelo’s David; the Uffizi, an entire universe of Renaissance paintings; and the 15th-century Pitti Palace. Enjoy Florentine delicacies on your self-guided tour, stopping at tiny gelaterias and coffee shops, and trying truffle panini and focaccia. On day two, you’ll head into the hills, sipping wine at a Tuscan vineyard in the Chianti region, and touring small towns like San Gimignano, known for its many towers, and Siena, home of the famed Palio horse race.
In Rome, visit highlights like the Colosseum and the Roman Forum, including the ancient Roman street Via Sacra with its Temples of Vesta, Antonino, and Faustina. Your second day will include extensive time at the Vatican Museums, giving you a chance to marvel at the Sistine Chapel and see countless other masterworks of the Renaissance age. The afternoon will include a tour of many of the city’s notable landmarks, including the Trevi Fountain, where you can throw a coin over your shoulder and make a wish to return to Rome, and the Piazza Navona. On your last day in the capital, learn how to make pizza like an Italian, paired with the perfect regional wine.
On the Amalfi Coast, you’ll get the chance to explore the island of Capri, known for its luxurious villas and the natural wonder known as the Grotta Azzura or Blue Grotto. You’ll take in the towns of the Amalfi Coast by land and sea, as you enjoy a sunset boat tour along this iconic stretch of coastline, ending in Positano for a romantic dinner. If you’re interested in ancient history, you can opt to swap out your day on Capri for a visit to Pompeii, where you’ll explore this ancient Roman city buried in the 79 AD eruption of Mt. Vesuvius, and learn about how archaeologists and scientists recovered and preserved the city and continue to monitor the active volcano.
In 14 Days: Major Cities and a Whole New Region
- Feel the romance in Verona
- With a local guide discover the cave-like labyrinth underneath Orvieto
- Visiting the coastal towns of Amalfi, plus Capri's Blue Grotto
- A full week exploring dynamic cities and Greek temples in Sicily
With two full weeks in Italy, you can build on the previous itinerary by adding a new region like Umbria and Verona as an alternative to Venice, or swapping out two of the cities for the island of Sicily, which could easily fill two weeks of your trip all by itself, with its dynamic cities, Greek and Roman ruins, and a cuisine all its own.
Rome awaits you at the beginning of a two-week trip from the south to the north. Be sure to visit the main sites. including the Colosseum and a guided tour of all parts of the Vatican City. Moving north out of the capital, you reach the Umbria region, a lesser-known but equally beautiful area that neighbors Tuscany. The wine and views are excellent, but the secret to Orvieto, a jewel of this region, is underground. A local guide will take you under the town, exploring some of the 440 caves, and when you resurface you'll enjoy wine tasting to round out your day.
Travel onward to Florence and begin with a historic walking tour, then learn how to prepare fresh Italian pasta during a cooking class with a local chef. This experience is a lot of fun and, at the end, you'll sit down to taste the delicious dishes you made. Finally, you'll take a day trip to the Tuscan countryside through the wine region and spend time in Siena and San Gimignano.
Verona is your last stop and a great base from which to explore the Dolomites and Venice. After seeing the Roman Arena and Juliet's balcony at Casa di Giulietta, spend a day outdoors touring the Dolomite mountain villages. Take in the panoramic views on a funicular cablecar that reaches more than 10,000 feet! This is sure to be the highest point, and a highlight, of your trip.
Your second option for a two-week trip in Italy is to swap out two of the three major cities for time spent in Sicily, as in this itinerary, which starts in Rome before making its way south to Italy’s largest island.
You’ll start with three days exploring Rome, the Eternal City, including enduring sights like the Colosseum, the Roman Forum, and the temples to various Roman gods along the Via Sacra. You’ll stop at famed sights like the Trevi Fountain and the Piazza Navona, and spend several hours exploring the masterpieces of the Vatican Museums, including the Sistine Chapel. A cooking class will give you a new taste of the city, as you learn to make cherished Roman pasta specialties like Cacio e Pepe, Carbonara, and Amatriciana.
Your three days on the Amalfi Coast will be full of many man-made and natural wonders, including photogenic cliffside towns like Amalfi and Positano, where pastel houses seem to tumble down towards the water. You’ll follow footpaths that will give you epic views out onto the water from the hills, including the Lemon Path in the town of Minori, and the Path of the Gods, linking Agerola and Nocelle. On your second day, you can choose to explore the island of Capri, with natural wonders like the Faraglioni Rocks and the Grotta Azzura or Blue Grotto, or you can instead drive to the Ancient Roman towns of Pompeii and Herculaneum, buried by a volcanic eruption in 79 AD, and finish with a dramatic hike up the volcano itself, Mt. Vesuvius.
A quick flight from Naples will have you to Sicily in no time, ready to explore the island for a full week. From your first home base, the regional capital of Palermo, you’ll experience architecture from the Roman, Byzantine, Arab, and Norman eras in a guided tour of its main sights. You’ll visit the Palazzo Reale, the 12th-century Duomo or Palermo Cathedral, and the Monreale Cathedral, a Norman structure on the slopes of Monte Caputo.
The next day, you’ll journey to Taormina, a seaside resort town with a preserved Roman amphitheater, and hike up Mt. Etna, Europe’s largest active volcano. You’ll also have a chance to explore the Baroque town of Noto, and enjoy a whole day devoted to the city of Syracuse, a center of ancient Greek life and now a UNESCO World Heritage site for its incredible ruins. On your last day, in Sicily’s second-largest city of Catania, you’ll explore the Castle of Ursino and take pictures at the Elephant Fountain, a symbol of the city.