How To Plan Your Multi-City Dream Trip To Italy

The best ways to spend 10-14 days in Italy — from must-sees to hidden gems

By Journy Admin

3 August 2018

Italy: a high-heeled boot of culinary wonders, Renaissance art, Roman and Etruscan ruins, and breathtaking mountains, beaches, and cities. It's no wonder visitors fall in love with the country. Though this city in Europe is just two-thirds the size of California, Italy offers so much in so little space. Each city offers an intoxicating (and delicious) glimpse into a different aspect of Western history.

There are endless options when it comes to visiting Italy for a 10-14 days. Here, we break down a few of our most popular itineraries for exploring the country, whether it's your first time looking to visit all the must-see sights, a honeymooner looking to enjoy the beaches and romantic views of Southern Italy, a culinary aficionado looking to enjoy the best of Tuscany and hunt for white truffles in Alba, or a movie and celebrity buff hoping to wave to the Clooneys at Lake Como.

Plan My Trip To Italy

The Essential Italy Itinerary, For First-Timers:

Venice, Florence, Tuscany, and Rome in 10 days (option to add 2 days in Cinque Terre)

Treasures Of Southern Italy, For Food And Beach Lovers:

Rome, Naples, Pompeii, Capri, Positano, Sicily, Amalfi, and Salerno in 12 days (option to add a day in the Cilento Coast for a cooking class or food tour, or for a stay on Ischia Island)

Culinary Tour From Tuscany To Piedmont:

Florence, Tuscany, and Alba in Piedmont

Central And Northern Italian Highlights:

Florence, Tuscany, Cinque Terre, Crema, Lombardy, Bergamo, Pisa, Lake Como OR Lake Garda, Dolomites, and Milan

If you need travel tips and help deciding on where to go and how long to spend in each place, schedule a free consultation call here.

The Essential Italy Tour: Venice, Florence, Tuscany, Rome

This itinerary features ten days of culture, history, and cuisine—all curated from our experts. From start to finish: explore magical Venice and its melancholic lagoons, then on to Renaissance Florence and the picturesque surrounding Tuscan countryside, and finally end in Rome — La Città Eterna.

Below is an example of what our experts and hand-selected private guides might put together for you with a combination of the must-sees and the behind-the-scenes glimpses of Italian life.

READ MORE: Visit Italy With Kids: A Complete Guide

Venice (3 Nights)

Venice Sample Day 1:

Rialto Bridge, Venice | Rebe Adelaida

Begin your first day the best way we know how: exploring the famous Rialto Market. Visit its many shops and fish market, and the hidden bacari and cicchetti spots, some of which have been around for centuries. We recommend an intimate small group tour to get to know the city the way the locals' do: through its cuisine. The tour will take you from the market, to the best cicchetti spots, to one of the last non-touristy neighborhoods in the city—Cannaregio.

In the early evening, visit the jewels of Venice—St. Mark's Basilica and Doge's Palace, with an intimate small group, after hours. That's right, get an in-depth guided tour of Doge's Palace as other visitors filter out, and then an intimate tour of St. Mark's Basilica after it has closed. This tour brings you up close to the majesty of St. Mark's Basilica in serenity and tranquility.

Finish your night with a drink at Harry's Bar!

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Tuscany & Rome

Plan My Trip

Venice Sample Day 2:

Spend the morning on a walking tour of the best of Venice. Meet your private guide and visit some incredible sights and hidden gems like the Rialto Bridge, while learning history and culture from a top Venice tour guide.

*Sample Tour Itinerary: Visit Ca' Rezzonico, an 18th Century Palace with works by Tieppolo and Tintoretto. Stop in the oft-overlooked Basilica di Santa Maria Gloriosa dei Frari. As you walk, pass the very picture worthy Boat of Fruits and Vegetables, and shop for real Venetian masks at Ca' Mancana. Then, make your way over the Punta della Dogana bridge to see an incredible view of the Santa Maria della Salute Basilica, before you head to the church to enjoy its beauty from the inside.

In the afternoon, visit the Peggy Guggenheim Museum, one of the most incredible art collections in the city. Continue your afternoon getting lost in the winding streets of the city, and let yourself go phone free to really experience it!

At sunset, meet your gondolier. Enjoy an hour long private gondola ride with the gondolier serenading, a lazy ride through the canals, and a glass of Prosecco, what more could you need?

Venice Sample Day 3:

Burano, Venice | Lopez Robin

On your third day in Venice, get a tour of the islands and lagoon that make this city so unique ecologically. First, visit Murano, the famous glass island, and take in a demonstration of the glass blowing. Then you'll head to colorful and picturesque Burano island where Venetian lace is made. Be sure to stop in the Lace Museum to learn the intricacies behind the craft, and pick up some lace to bring home! Enjoy lunch on Burano and then head to some of the lesser known islands in the afternoon including the less touristy Mazzorbo (a walk across a bridge from Burano) and Torcello. On Mazzorbo, a visit to Venissa winery is a must. Enjoy a tour of the winery and tasting of the unique golden wine from the Dorona di Venezia grape. Round out the day with dinner on Torcello island before you head back.

--> TRANSPORTATION TO FLORENCE: Take the 2 hour and 5 min high-speed train to Florence

Want an itinerary just like this customized to you? Talk to an Italy expert and get a FREE, no-obligation travel offer with your travel route, flights, transportation, and hotels.

Florence (2 nights)

Florence Sample Day 4:

Florence at sunset | Mark Tegethoff

You'll start in Florence with some of the biggest hits. Take a guided (small group or private) round trip tour, skipping the lines to visit to the Accademia to see Michelangelo's David, followed by a tour of the Duomo, and learn the incredible story of Brunelleschi's design of the dome. You'll also learn about the beautiful baptistry and Gates of Paradise. Continue the tour with a stroll through Piazza della Signoria and Piazza della Reppublica, ending with a walk across the famous Ponte Vecchio. This tour provides not only skip-the-line access to the best sights in Florence, but allows for in depth discussion (and question time) of the history and events that surround each site.

Florence Sample Day 5:

Kick off day two in the terracotta Renaissance city with stroll through the San Lorenzo Leather Market (so many goodies!), with a stop at the small but powerful Medici Chapel, and a visit to the endless culinary delights found at the Florence Central Market. Be sure to stop at Da Nerbone for some classic Florentine street food.

Spend the afternoon at the Uffizi Gallery with a guided tour of the world's most incredible collection of Italian Renaissance art followed by a behind the scenes visit to the Palazzo Vecchio.

Tuscany (2 Nights)

Tuscany Sample Day 6:

San Quirico d'Orcia, Siena, Tuscany, Italy | Luca Micheli

Get out of the city and head to your beautiful villa in the Tuscan countryside. You will spend the afternoon exploring wineries and small towns in the pastoral rolling hills. The all day excursion includes visits, tastings and tours to small towns and at vineyards in Montalcino, Pienza, and Montepulciano. This day can be tailored to your liking if you prefer certain wineries and towns! Your private driver will pick you up and drop you off at your accommodations. For dinner, your driver will take you to the town of Panzano in Chianti to enjoy a once-in-a-lifetime meal that celebrates the Tuscan bistecca!

Tuscany Sample Day 7:

After a good night's rest you'll be ready to head off again, this time, to visit the incredible city of Siena. Explore the town with or without a guided tour, and see the site of the Palio (the ancient horse race), the Duomo, the Piccolimini Library, and more, with time to pop in shops and explore as well.

Then, head to a secluded winery in the countryside for a paired lunch of delightful seasonal Tuscan fare. In the afternoon, you'll visit San Gimignano, one of the most beautiful Medieval hilltop towns in all of Tuscany. You'll be driven back to Florence in time for dinner in the city.

TRANSPORTATION TO ROME: 1 hr 20 min high-speed train to Rome

READ MORE:Eataly NYC’s Olive Oil Expert Shares His Insider Guide To Tuscany​​​

Rome (3 Nights)

Colosseum, Rome | Dennis van den Worm

Rome Sample Day 8:

Get your bearings in the incredible city of Ancient Ruins and noisy traffic with a walk through the main sites and attractions. You'll visit the most impressive works of Roman architecture: the Colosseum, the Palatine Hill, and the Roman Forum with a Private tour guide. Then, meander through the c streets to visit the Pantheon, Trevi Fountain and Spanish Steps. We can recommend plenty of stops for lunch or gelato along the way!

Rome Sample Day 9:

Vatican Museums | Jonathan Singer

Begin the day early with a skip-the-line guided tour of the Vatican museums before it's open to most tourists. The collection is huge, so you'll want to take your time. The tour includes a visit to the Sistine Chapel and tour of St. Peter's Basilica. The early hour means the crowds are few and you can enjoy a work of art seemingly to yourself!

Spend the rest of the day getting lost in the myriad delights of the city. Make your way from the Vatican across the Sant'Angelo bridge and to the bustling and grand Piazza di Navona followed by Campo de' Fiori and its market. Then make your way to the neighborhood of Trastevere to get a glimpse of a different Rome, with its winding alleys and outdoor bars and restaurants.

Rome Sample Day 10:

On your last day in Rome, begin with a stroll through the Villa Borghese gardens before you tour the Galleria Borghese and its many works by Bernini, Caravaggio, and Raphael. Enjoy a lunch with a view of the city from the park before you spend a leisurely afternoon exploring the more locals' side of Rome in Monti- known for its vintage and local designer clothing shops and great cafes. In the evening, wrap up your whirlwind of an Italian adventure with none other than a hands-on pasta making class and dinner!

READ MORE:The Journy Guide To Rome​​​

Optional Add-Ons After Florence:

Option 1: Cinque Terre (2 Additional Nights)

Vernazza, Cinque Terre | Anders Jildén

Cinque Terre is just a short 2.5 hour train ride from Florence. While you can certainly do it as a long day trip, we recommend spending at least 2 nights there to truly appreciate it. One of the most common questions we get is, "What town should I stay in when visiting Cinque Terre?"

Cinque Terre (a national park) consists of 5 towns. All are great options depending on what you’re looking for, especially considering they are just 5 minutes from each other via the Cinque Terre Train, which connects La Spezia with the 5 towns.


Known to be the most beautiful with a church built on water, a castle, and a gorgeous waterfront and harbor with a little beach section. This is also the most famous village in Cinque Terre, and therefore often crowded. You’ll find many restaurants and bars in the village center.


The town is one street, a harbor, a beach, castle, and a few restaurants — it's closest to the main city of La Spezia (just 10 minutes by train — you’ll want to avoid driving in Cinque Terre as the streets are very narrow and the villages themselves are closed to traffic) for easy access to anything you might need.


Manarola, Cinque Terre | Marc Zimmer

Where the most famous pics of Cinque Terre are taken from — like Riomaggiore, but more grown-up. It has a tiny harbor for swimming. It is also located among the famous terraced vineyards, which makes it the perfect spot for wine-lovers to do a tasting.


The largest town in terms of having the most hotels, restaurants, wine, and artisan shops. Monterosso also has the best and largest beaches of the Cinque Terre villages. Those concerned about climbing the steep steps of Cinque Terre towns should also consider staying here as the landscape is more flat.


The only village not on the sea. Located on a hill above the Mediterranean, it’s nearly impossible to reach by car. You’ll arrive by train and then take a small bus that will take you to the village square (or you can also walk a steep 382 steps). Travelers choose Corniglia for the gorgeous view of the sea and other parts of Cinque Terre and for the peace and quiet — this is the least crowded and busy village to stay in.

Option 2: Capalbio / Maremma (1 Additional Night)

Capalbio And Maremma

If you’re traveling in the summertime, you may want to spend an extra day in Tuscany to explore the Tuscan coast. Capalbio and Maremma are two charming beach areas just a short hour long drive from the heart of Tuscany. Both areas have beach clubs where you can pay a small fee for a lounge chairs, lounge beds, and umbrellas and have lunch with your toes in the sand.

Treasures Of Southern Italy: Rome, Naples, Pompeii, Capri, Positano, Amalfi, Ravello, Salerno

Positano | Ricardo Gomez Angel

While Northern Italy boasts Renaissance Florence, The Last Supper in Milan, the Italian alps and rich and hearty fare and bold wines, Southern Italy may beat the north in its vibrancy, culture, beaches, and dare we say it… even cuisine?

The below is a 12 day adventure through the best of Southern Italy. From the must-see attractions in Rome to off-the-beaten path destinations on the Amalfi Coast, we have you covered. You'll leave Italy with olive oil in your veins and a Mediterranean sunset in your soul.

Rome (2 Nights)

Rome Sample Day 1:

Start your Southern Italian adventure with a bucket list Rome walking tour. Your tour guide will take you first to explore the Colosseum, Palatine Hill and Roman Forum before you make your way into Centro Storico. There you'll encounter the jaw dropping Pantheon and Trevi Fountain, and end at the Spanish Steps with your guide illuminating the history and culture of Rome for you along the way.

Rome Sample Day 2:

Spend the morning diving deeper into the amazing culture of the Citta Eterna with a Food Walking Tour of Trastevere, Campo de' Fiori, and the Jewish Ghetto. Each location represents a different aspect of the unique Roman cuisine, and will bring you closer to daily life in Rome as well.

Spend the afternoon shopping, visiting Piazza del Popolo and its imposing churches, and walking through the English gardens of Villa Borghese.

In the evening: No trip to Rome would be complete without seeing the splendor of the Vatican. We take you on a small group guided tour after hours (available only on nights with extended hours) of the Vatican Museums and Sistine Chapel.

After your late night Vatican City Tour, we’ll arrange a dinner for you at one of Rome's best trattorias.

--> TRANSPORTATION TO NAPLES: 1 hr 10 min train

Naples (2 Nights)

Naples | fabio scarcella

Naples Sample Day 3:

Spend the day with a small group tour exploring and learning about the most historic and beautiful sights of Naples, interspersed with stops for street food, wine, salumi, treats, and of course, pizza. You'll get a rundown of the most interesting and delicious aspects of city with knowledgeable and entertaining tour guides.

Optional Pizza Add-On:

If, like us, you are pizza fanatics, we offer an add-on for a private driver to take you from Rome to Naples with a pit stop in Caiazzo (on Sundays only). Or, a driver to take you from Naples (we know, this sounds crazy) to Caiazzo for dinner. This tiny town is home to Pepe in Grani — the (often disputed) best pizza anywhere. But if pizza didn't ignite a fiery debate, what would it be? We recommend you dine at Pepe in Grani to give your two cents, you won't be disappointed.

Naples Sample Day 4: Pompeii

Pompeii Archaeological Park | Andy Holmes

Head out with your private driver to explore life as an ancient Roman through the city frozen in time, Pompeii. Your guide will teach you about daily life in the city, showing you the granary, marina, marketplace, and more. Then, he'll take you on to the unfairly overlooked Herculaneum for more incredible Roman ruins and a different perspective. You'll enjoy a relaxing picnic lunch on Vesuvius with enough time to enjoy a hike across the foothills of the active volcano to follow.

--> TRANSPORTATION TO CAPRI: 40 min. ferry to Capri

Capri (2 Nights)

Capri Sample Day 5:

Punta Tragara Hotel, Capri | @puntatragarahotel

Nothing gets you from hectic city to luxury island getaway quite like a day tour on a private speed boat. So hop on board and let the city melt away from view. Once you've settled into your hotel, spend the full day exploring the island, touring the beautiful city of Capri and Ana Capri. Your driver will scoop you up and first head off in a convertible to the Blue Grotto. Then wind through the cliffs of the island and make your way to Ana Capri. There, you'll take the funicular up to Monte Solara to take in breathtaking views of the Amalfi Coast and Mediterranean Sea. The day continues with a tour of the gardens and art at Villa San Michele. Explore Ana Capri on your own a bite and find a spot to grab a bite. Then, it's off to the main town of Capri, and the center of town, the Chiazza- where the glitterati are chased down by the paparazzi. Enjoy the glamorous window shopping and busy cafes. Then you'll head on to visit the botanical Augustus Gardens- and the views of the Faraglioni limestone sea stacks. End the day back at the Marina Grande, with another incredible view from the island.

“What makes you guys different is how you personally take care of your customers. You feel that each person that works on your plan ends up becoming your friend. And the trips are very well planned. They personalize your plan exactly how you want it. You know it’s not cut and pasted from other sources, but written for you."


Florence, Rome, & Venice

Plan My Trip

Capri Sample Day 6:

Faraglioni Rocks, Capri | @tanya_vasilenko

After a day of touring the island, you'll be more than ready to dive into those crystal blue waters. Your private boat driver will meet you at the Marina Grande's Bar Gabbiano for a quick breakfast and cappuccino before you board the local traditional Gozzo boat. Gianni (subject to availability) will take you around Tiberius' Leap, over to the White Grotto for a pristine swim under the Faraglioni rocks. Then, enjoy a lunch at a waterfront restaurant or a picnic on board! In the afternoon, laze about on the boat while Gianni tours you around on the water. Later, you'll enjoy the Blue Grotto again, but this time after the busy time of day, when it will be all yours! A perfect day at sea? We think so.

--> TRANSPORTATION TO POSITANO: 50 min high-speed ferry to Positano

Amalfi Coast: 5 Nights With Positano As A Home Base To Explore

Positano | Sander Crombac

Amalfi Coast Sample Day 7: Positano

It's time to head to the mainland Amalfi Coast! After a leisurely morning at your hotel, hop a ferry to Positano. A porter will bring your things up the dizzying steps of this beautiful town to your impeccable 5 star hotel (either Il San Pietro, Hotel Villa Franca, Il Sireneuse). After you get settled in, explore Positano's famous ateliers of sandals and airy linen beach wear. Then grab a water taxi and head to Da Adolfo- Positano's "old school hippie" beach club about a five minute boat ride away. Don't let the shabby-chic look fool you though, this beach club is one of the best. And the food at the club is divine. For a more "clubby" atmosphere, with equally incredible dining, head to OneFire beach. Everyday at 4:30 pm, Piccolino hosts "watermelon time" a party centered around the juicy fruit and juicy Piccolino's dance moves. There is nothing quite like this place.  For a more refined experience, we recommend Treville Beach Club- adjacent to Da Adolfo.

In the evening we'll reserve a table for you (and driver or boat transportation if necessary) to one of our favorite restaurants on the coast.

Amalfi Coast Sample Day 8 — Sentiero Degli Dei + Emerald Grotto

Sentiero delgi Dei | @rhoff27

Your driver will pick you up early (to beat the heat), and bring you to the beginning of Sentiero degli Dei, aka the Path of the Gods. This footpath in the mountains was the only road on the Amalfi Coast until the late 19th century, so while it may seem like an enjoyable hike now, just imagine the donkeys and people lugging ricotta from Agerola down to Positano as you walk, and you'll appreciate that windy Amalfi Coast highway a little more. Option to start in Agerola or begin in Praiano.

Note: The vertical steps up to the path from Praiano are not for the faint of heart (or glutes), but a killer workout. Alternatively, starting from Agerola means a more leisurely walk, mostly downhill.

Either way, you'll enjoy spectacular views of the coast and Capri. After the early hike (you'll be back by 10/11), you'll want to head back to the hotel for a change. In the afternoon, we'll take you on a private boat to your some of the more beautiful spots along the Amalfi Coast. The Emerald Grotto, which rivals Capri's Blue Grotto is not to be missed. We'll stop at a beautiful seaside restaurant for a late lunch or cocktail and then stop to visit the Furore beach. This little spit doesn't get the best rays as it's in a hidden fjord, but it's so picturesque, it's worth a visit.

In the evening, we'll take you to dinner in the tiny village of Montepertuso, above Positano. Alternatively, enjoy an incredible meal in neighboring Praiano.

Amalfi Coast Sample Day 9: Positano + Ravello

Spend the morning soaking up Positano, shopping for ceramics and getting lost in the tiny back streets. Then, it's time to pack up and head to Ravello — the beautiful town in the mountains above Amalfi. Spend the afternoon exploring the villas and gardens of Ravello at Villa Cimbrone, Palazzo Avino, and relaxing at one of the finest hotels on the Amalfi Coast.

Amalfi Coast Sample Day 10: Ravello To Furore winery + Bacco + Amalfi OR Valle Delle Ferriere + Amalfi

Cantine Marisa Cuomo | @amandadruk

In the morning, you'll be picked up by your driver, first with a stop in Amalfi for breakfast. Then you'll head on to award-winning Marisa Cuomo winery in the mountain town of Furore. The tour offers an incredible glimpse into the beauty and difficulties of wine-making on those slopes. Then, your tasting will be over a multi-course lunch at Hostaria di Bacco- an incredible restaurant with stunning views owned by the same family. Your driver will then bring you back to Amalfi for an afternoon of exploring--the incredible Cathedral, a visit to the paper museum, and the many incredible shops in town.

If wineries aren't your thing, we offer a private walking tour to the Valle delle Ferriere- a beautiful hike through the woods that ends at waterfall.

And If another four hour hike isn't your thing, we offer an Amalfi lemon tour. Beginning wandering through the shops of Amalfi, followed by an easier hike through the organic lemon groves, and ending with a fabulous lunch at an organic lemon farm. You'll learn from your guide what sets these lemons apart!

Amalfi Coast Sample Day 11: Cetara, A Hidden Gem

Cetara | @jess_tren

Spend your last day on the coast touring some of the lesser known areas of this beautiful region. Your driver and tour guide for the day, Emiliano (subject to availability), will pick you up at your hotel and take you to see some of the best hidden gems! You'll head to Cetara, one of the last towns on the coast, to visit a century old lemon orchard, and then explore this quaint fishing town. A visit to a colatura di alici (fish sauce) factory will elucidate the ancient methods this town still uses to create their local delicacy. Then you'll enjoy a lunch at one of the best restaurants that is often overlooked. After lunch, continue on to Minori to visit the best preserved Roman Villa on the coast, you'll also make a stop at a local amazing bakery. Finish the afternoon with a visit to little known Atrani and its cathedral. Emiliano will either take you back to your hotel for your last night or bring you to a restaurant we recommend. An epic finish to an epic week!

Amalfi Coast Sample Day 12: Salerno

Salerno | _M_V_

Your driver will pick you (and your bags) up from your hotel in Ravello and you'll head towards the underappreciated city of Salerno. On the way, you'll stop to visit tiny fishing village Cetara, and Vietri sul Mare, where the Solimene ceramics factory creates the most beautiful ceramics on the coast. Then, you'll get to Salerno. Check in to your hotel and explore the old town of this city. The churches are magnificent, the food scene is vibrant, and the old town has a charm and warmth that is hard to find in Naples.

READ MORE:The Journy Guide To The Amalfi Coast and Capri​​​

Depart Day 13:

Transportation to the airport from Ravello or Salerno.

Optional Add-On Options:

Spend an additional day or two on any of these activities:

  • Road trip to the Cilentano Coast: Tour a buffalo farm where the best buffalo mozzarella in the world is made and visit Greek ruins at Paestum.
  • Spend a day at an Agriturismo for a cooking class or wine class.
  • Purchase a train ticket to Pisa to see the Leaning Tower of Pisa.
  • Spend an extra day in Salerno for a food tour or visit to the botanical/medical museum (the world's oldest medical school).
  • If you have 2 extra days to spend, we’d recommend a stay on Ischia island — a larger and much less touristy island in the bay of Naples.

Planning  a trip to Italy? Leave the planning to Journy. We'll build the perfect, custom itinerary for you with with hotels/Airbnbs, restaurants, tours/activities, in-destination transportation, and everything in between.

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