Crafting a best of Italy itinerary is both very easy and very hard. To start, the three cities of Rome, Florence, and Venice are an obvious choice. But seeing everything in these cities is impossible, and visiting one museum after another will leave you exhausted and unable to absorb what you have seen. You’re better offer taking it slow and balancing days with a mix of sights and everyday activities, like lingering in piazze, tasting gelato, and enjoying aperitivo (happy hour). Using local travel cards like RomaPass, Firenzecard, and Venezia Unica will help you get the most out of your journey without wasting time in lines.

Rome is a convenient starting point for a three-city tour of Italy. Most transatlantic flights land directly in the Italian capital and tickets are less expensive than to Florence or Venice, which often require connecting flights. The 327 miles that separate the cities are covered by high-speed trains, which are the quickest and easiest way of getting between destinations. A Rome-to-Florence-to-Venice itinerary also allows you to travel from the most populated to the least populated city and from oldest to newest, which can facilitate appreciation and understanding of each.

colosseum during the day

Rome’s ancient amphitheater exceeds all expectations. Photo © Dreamstime.com.

Rome

Day 1

Walking is the best cure for jet lag, so after you settle into your room, head out for lunch and a stroll. The pizza al taglio parlors in the center provide a good introduction to Roman pizza. Point to the variety you like and have it wrapped up for takeaway. Grab a seat on the stone bench at the base of Palazzo Farnese and observe the comings and goings in the busy square. At the first sign of a yawn enter a bar and order an espresso. Although most Romans drink at the counter, outdoor seating is common.

Afterwards ride the number 23, 44, or 280 bus or 8 tram to Aventino and Testaccio. If it’s close to aperitivo (happy hour) order a cocktail at Porto Fluviale and enjoy the buffet that can double as dinner. The longer you resist sleep the easier it will be to adapt to Italian time.

Day 2

The Colosseum is a sight that cannot be missed. Walk to the ancient stadium, or ride Metro B to Circo Massimo and approach from the south. Skip the lines with your preordered tickets or RomaPass and spend an hour exploring the interior with the audio guide. Then head next door to the Roman Forum, where you can wander through ruins and get a feel for ancient Rome. To see more artifacts, climb nearby Capitoline Hill and visit the Musei Capitolino. Michelangelo designed the square outside the museum and there’s a great view of the city from the adjacent Vittoriano monument.

Walk down to the Jewish Ghetto for a taste of artichokes prepared in the Jewish style at Nonna Betta or the other kosher restaurants on Via del Portico D’Ottavia. Alternatively, ride the number 8 tram to the Piramide station and swap ancient for 19th-century history. Pay your respects to Keats in the Protestant Cemetery before heading to the covered Testaccio Market. Pick a stand and create an improvised picnic of a beef sandwich, cheese, and bread, all washed down with local wine served in plastic cups.

On the way back, explore the residential streets of Aventino and the shaded Giardini degli Aranci (Orange Garden) with a view of the Vatican. Return at night to Monte Testaccio via the Metro B to Piramide for dancing and Roman nightlife, or dine al fresco at one of the informal kiosks along the Tiber and let your feet have the night off.

Day 3

Zigzag along the pedestrian streets towards Campo De’ Fiori. Browse the market for household souvenirs and order pizza bianca from Il Forno on the northwestern corner of the square. There’s a flow of tourists on their way to Piazza Navona, but plenty of scenic side streets offer less crowded opportunities to reach the square. Choose one and admire the former athletic track with the help of a gelato from Frigidarium. Street musicians play near the fountains and there’s a lot of art on display. Avoid cafes with waitstaff out front recruiting tourists, and order an espresso at Antico Caffè della Pace.

The Pantheon is less than ten minutes away and free to enter. After visiting it, browse the boutiques along Via del Corso as you head towards the newly refurbished Spanish Steps, which you can climb to reach Villa Borghese. Escape the summer heat by cycling in the city’s biggest park or visiting the Borghese Gallery (advance reservations required).

Afterward, walk down to Piazza del Popolo and follow Via Ripetta to the Ara Pacis museum, then have dinner at Gusto. End your day by visiting the Trevi Fountain after dark.

statues and facade of Trevi Fountain

Trevi Fountain in Rome. Photo © Dreamstime.com.

Day 4

Walk or ride the Metro A to the Ottaviano station and follow the pilgrims to Vatican City. Remember to dress properly, and arrive early to the Vatican Museums where you can choose from several itineraries taking in the immense collection. Most visitors beeline to the Sistine Chapel, but there are less crowded parts of the museum.

Once you’ve gotten your fill of art, take the guided bus tour of the gardens before entering St. Peter’s Basilica. Light a candle and descend into the crypt to pay tribute to past popes, then make your way to the top of the cupola. The elevator only goes so far and you’ll need stamina to climb the highest structure in the city. If you arrive on Sunday morning you can join the faithful in the square below and receive the pope’s blessing.

The nearby streets of Borgo Pio and Borgo Vittorio have catered to pilgrims since the Middle Ages and are lined with eateries and souvenir shops. Follow one of these parallel streets to Castel Sant’Angelo. You can climb the castle and enjoy the view from the rooftop bar. Then walk or catch a bus to Trastevere and mingle with the crowds in Piazza Trilussa. Order cacao pepe pasta at Da Giovanni and explore the streets of this lively neighborhood packed with bars and clubs.

Optional: Add an Extra Day in Rome

Ride the train from Piramide station to Ostia Antica and walk along the well-preserved streets of an ancient city. Explore the baths, theater, shops, and villas to understand how the Romans once lived. Afterward, have lunch in the small medieval enclave near the entrance to the archeological site or take the train back and get off at the Magliana station to explore EUR. There are dozens of eateries along Viale Europa and Viale America, along with Fascist-era architecture and a man-made lake where Japanese cherry blossoms bloom in spring.

Via Appia Antica is closer to the center and can be reached on the 118 bus from Circus Maximus in 15 minutes or on foot in a little over twice that time. Rent a bike from the park office and then saddle up and set off on a leisurely trot down the first road that led to Rome.

Golden hour over the River Arno in Florence

The Arno River in Florence. Photo © Dreamstime.com.

Florence

Day 5

The journey from Rome to Florence on board Italo or Trenitalia trains takes less than two hours. Both operators run frequent departures from Termini station in the center of the city and Tiburtina slightly to the east. Depart midmorning so you can have lunch in Florence. There are taxis and buses waiting outside Santa Maria Novella station, but the historic center is small and flat enough to navigate on foot, with no two monuments more than 20 minutes apart.

If you’re driving, consider stopping in Assisi, burial site of St. Francis, or Siena. Florence’s historic rival is famous for its shell-shaped piazza, annual horse race, and enormous unfinished cathedral.

Once you’ve deposited your bags, find a small trattoria like Trattoria Sostanza and discover the difference between Florentine and Roman gastronomy. Order papa al pomodoro or the steak from Chianina cattle raised along the Tuscan coast. The two covered markets in the center are also good places to learn about local culinary traditions. The 2nd floor of Mercato Centrale is a food emporium, while downstairs you can sample tripe sandwiches, a Florentine specialty.

Work off your meal by hiking to Basilica San Miniato al Monte via the less traveled footpath, which has a panoramic payoff. Just cross the Pont alle Grazie bridge and follow the signs through the old city gate before turning right and up the grassy path. On the way back walk along the medieval walls to Forte Belvedere, where free outdoor exhibitions are organized, and enter the Pitti Palace gardens from the side entrance.

If there’s time catch the sunset over Ponte Vecchio from nearby Ponte Santa Trinità. Otherwise order an aperitivo at Volume or any of the bars with outdoor seating lining Piazza Santo Spirito. During the summer, head to the riverside beach where DJs spin lounge music until late.

Day 6

Start the day with an espresso at Café Rivoire and purchase a Duomo card for a tour of the cathedral. There are a lot of steps to climb up the Duomo, but the inside is nearly as impressive as the outside. (Note: It’s not for the claustrophobic.) Once you’ve reached the top, circle the terrace for a 360-degree view of the city. The card includes entry to the Campanile bell tower and newly renovated Museo dell’Opera, where you can learn how the Duomo was built. Just a few blocks away is the Piazza della Signoria in the center of the city and another steep climb to the top of Palazzo Vecchio.

Sample Florentine pizza at Cucina Torcicoda or a thick local steak at Mario’s before visiting the Museum of San Marco, which contains colorful frescoed cells where monks lived. Nearby and a couple of blocks north is the Accademia that houses the statue of David and only lets in 300 visitors at a time. That explains the line, which will require patience if you haven’t booked your tickets in advance.

Next pay homage to Michelangelo, who grew up in Florence and is buried inside Basilica di Santa Croce. Arrive a couple of hours before closing (5:30pm) if you want to get in. Then stop into nearby Vivoli for gelato. Try their crema de’ Medici (cream-flavored gelato). At night, wineries offer cellars full of local Tuscan vintages, and the happy hour cocktail of choice is Negroni served with cured meats and cheese. The Soul Kitchen and Winter Garden by Caino are both good options with happy hour appetizers that can easily substitute for a sit-down dinner.

front of basilica of santa croce

Basilica di Santa Croce in Florence. Photo © Dreamstime.com.

Day 7

Mornings are the only time to see the city’s Last Supper frescoes, which were painted inside Florence’s smaller churches like Cenacolo di Ognissanti and Cenacolo di Sant’Apollonia and are often overlooked by tourists. This is your opportunity to be alone with a masterpiece. Afterwards enjoy an enormous takeaway sandwich stuffed with Tuscan ham from All’Antico Vinaio.

Brace yourself for crowds and join the line at the Uffizi, home to works by Botticelli and other greats. After visiting the galleries, take a break in the museum bar overlooking Piazza della Signoria. The museum is considerably smaller than the Vatican Museums and you can see it all in a couple of hours. If the line is too long or you want to discover the city’s most underrated museum, head to the Bargello nearby and prepare to be blown away by another David with far fewer admirers.

For a caffeine pick-me-up stop into Ditta Artigianale, or pull up a lounge chair at Amble and start the evening with a cocktail. For dinner, the rustic Angiolino is a good choice for handmade pasta dishes, but if you want to sample Michelin-rated flavors and dine in a romantic interior reserve a table at La Bottega del Buon Caffè overlooking the Arno.

Optional: Add an Extra Day in Florence

Fiesole is a half-day excursion just outside the city with stunning views overlooking Florence. You can get there on the number 7 bus from the train station in around 20 minutes. During the summer there’s a musical festival and evening concerts are held in the ancient Roman amphitheater.

The hills around Florence are dotted with medieval villas where influential families retreated during hot Renaissance summers. There are finely furnished interiors and manicured gardens to explore with fountains, sculptures, and occasional views of the Duomo in the distance. Beyond these elegant homes is Tuscany and some of Italy’s most iconic landscapes. Use Enjoy or Car2Go, Florence’s car-sharing program, or rent a scooter from Walkabout or Tuscany Vespa Tours and motor down the SP 222 into Chianti country to sample the latest vintages from roadside vineyards.

If you prefer not to drive, board a regional train from SMN station to Lucca. An hour later you’ll be inside one of Italy’s best-preserved fortified towns and can cycle along the ramparts and climb medieval towers in the center. Soccer fans in town from September to June can walk or catch a bus to Artemio Franchi stadium. Home games are usually played on Sunday afternoons at 1pm and tickets are available at the gates. Make sure to wear purple.

gondola in the canal near the Rialto Bridge

The Rialto Bridge in Venice. Photo © Dreamstime.com.

Venice

Day 8

If you’re driving from Florence to Venice, consider a stop for lunch in Ferrara or Bologna, two cities that are famous for food. The latter is also on the same high-speed train line that connects Rome, Florence, and Venice, which makes it a convenient stop. Journey time by train to Venice is around two hours with several stops. Venice is the end of the line, and Santa Lucia station drops passengers off on the city’s doorstep. You can reach your accommodations on foot or via water taxi on the Grand Canal, which is more expensive but also more fun.

After you’ve settled in to your hotel, follow the yellow signs to St. Mark’s Square and take the secret tour of the Doge’s Palace to discover why they call it the Bridge of Sighs. Enter St. Mark’s Basilica next door and listen to the audio guide explain the mosaics.

Restaurants are expensive in Venice, but snacking at local bars is affordable and a chance to sample lagoon fish transformed into tapas-like appetizers called cicchetti. Try All’Arco across the Rialto Bridge and near the animated fish market. From there you can hitch a ride over the Grand Canal in a gondola and spend the evening in Campo Santo Stefano listening to Vivaldi.

Day 9

Purchase a ferry pass and go island hopping on the 4.1 or 4.2 vaporetto from Fondamente Nuove. Get a window seat or stand on deck for the best views. Get off at the first stop on Murano. From here, you can visit workshops and watch a glassblowing demonstration. Some require a small fee while others are free.

Continue on the 12 vaporetto from the Faro station to Burano. It’s a 45-minute ride past lagoon wildlife, and you can order fried calamari and cold beer at Fritto Misto near the main dock once you get there. Afterwards, circumnavigate the island on foot and put your camera to good use. Along the way are colorful houses and galleries where locals make and sell textiles and glassware.

Just north of Burano is the nearly uninhabited island of Torcello. There’s only one path to follow unless you decide to cross the Ponte del Diavolo (Devil’s Bridge) and follow the dirt trail to Santa Maria Assunta cathedral. On the way back stop at Locanda Cipriani, where Hemingway wrote and drank, before returning to Venice by vaporetto as the sun sets over the lagoon.

four people dressed in Carnivale costumes

Carnivale goers in Venice. Photo © Claudio D’Armini.

Day 10

If it’s a weekday morning, watch the fishmongers and greengrocers under the colorful Rialto market and shop for masks along the adjacent streets. Atelier Pietro Longhi is a good place for dressing up and getting into the Carnevale spirit. Head to any of the traditional bacari bars nearby and accompany every meal with prosecco from the Veneto region. If you don’t want to wander unknowingly past Marco Polo’s house or the oldest ghetto in Europe, spend a couple of hours with a certified guide who can provide an insider’s perspective on the city. Take a break inside the first pastry shop you see and sample as many delicacies as your appetite can handle. There’s a different sweet for every season, but burranei are baked all year long.

Hop a vaporetto to the Galleria dell’Accademia for a glimpse of Venetian Renaissance art. Alternatively, if you prefer contemporary canvases, keep going to the Guggenheim Foundation and Punta della Dogana at the very tip of Dorsoduro. Escape the narrow streets of the center and take a walk along the sun-drenched Fondamenta Zaterre promenade and stop for a gelato at Da Nico. Enjoy a cup or cone on the dock overlooking Giudecca and the southern lagoon. At night the squares near the university fill up. Campo Santa Margherita is the most animated in town, where you can listen to street musicians and join improvised parties spilling out into the square on weekends. If you haven’t tried risotto with fish, make your way to Osteria da Codroma.

Optional: Add an Extra Day in Venice

It’s difficult to tire of Venice, but if you long for a different landscape spend a morning cruising up the Brenta Canal on a boat tour with Il Burchiello and then take the train back to Venice. Ride a vaporetto out to the Lido and lie on the beach or rent a bike near the main landing and cycle along this narrow strip of an island to the wild reserve where Goethe was inspired and Mussolini played golf.

Back in Venice, do your own sailing with a boat from Brussa Is Boat. A license isn’t required but you will need to learn the rules of the lagoon. If that sounds too risky, try paddling through the city by kayak or riding a wakeboard.

If you happen to be in town during the Venice Biennale (May-November, odd-numbered years) art festival, visit the pavilions in the public gardens and installations set up around the city. All the gambling houses in the city have closed except one—you can still place bets at the Venice Casino and play familiar American table games or harder-to-master European games until 2am.

Back to Rome

Day 11

It takes a little over 3.5 hours to get back to Rome by train. Leave Venice early enough to enjoy a final meal in the capital. Take the subway, tram, or bus to Trastevere for a tasty farewell, and if you haven’t ordered amatriciana or carciofi alla romana this is the time to do so. Before heading off to the airport, climb the nearby Gianicolo Hill for one last look at the Eternal City and say your good-byes to Italy.


Excerpted from the First Edition of Moon Rome, Florence, and Venice.