Tour of Italy Itinerary
Italy attracts millions of visitors each year and it’s a country we love to return to. In winter, the Italian Alps attract outdoor enthusiasts in droves. When spring and summer arrive the Italian lakes, historic cities and blooming countryside offer so much to visitors. From our many trips to Italy, we’ve pulled together 14 nights that represents what we feel is the best first timers tour of Italy itinerary.
If you’re thinking you want to travel by train we encourage you to use out tips in this post and make the bookings directly yourself. It was much easier than we initially imagined to pull it together.
While our suggested Tour of Italy itinerary doesn’t begin to cover all Italy offers, it’s a great ‘starting point’. Italy by train is a relaxing and affordable way to explore this southern European country.
A Few Basics for Your Tour of Italy Itinerary
Our 14 night (13 day) Tour included: Venice ( 3 nights), Florence ( 2 nights), Siena, Tuscany ( 2 nights), Rome ( 3 nights), Sorrento/Amalfi Coast (3 nights) and Fuiminco (near Rome airport) (1 night).
You could start your tour further south but we like the idea of ending a trip in a more relaxed part of a country. So, we flew into Venice and then out of Rome.
How to Get to Venice Italy
Within Europe flights are competitive to/from multiple cities so best to search for your preferred route directly. We flew from Edinburgh to Venice with EasyJet (3 hrs). There are multiple route options to choose from using Skyscanner or your preferred search app.
Transfer to city. Our airport transfer was at night by a classic Wooden boat, passing through the lagoon and along the famous Grand Canal. You have to take this more expensive option at least once! It’s amazing!
Where to Stay in Italy
We decided that we would mix Air B&B and Booking.com as we worked up our itinerary. These were all recommended and in Rome, Florence and Naples our views were fabulous. With so much of Italy being near the coast, it’s worth paying a little more for a coastal views from a roof top terrace if you can.
Venice – Ca’barba 24, Venice (Expedia)
Florence – Santa Croce Terrace, (Air B&B) Via Giuseppe Verdi, 6.
Rome – Penthouse Cardello (Booking.com) Via del Cardello 16.
Naples – Corso Italia, (Air B&B), 250 piano 5, fabbricato U, interno 21, Sorrento.
Fiumicino – Intorno al Fico Hotel (Expedia). Via delle Carenarie 81 D, 00054
How to Book Train Travel within Italy
Don’t panic or stress about train travel to get around Italy. It’s easy to reserve tickets, fast and efficient and takes you into the heart of each city. Book your tickets with Italia Rail using the fast speed option for most journeys.
We used regional trains for day trips to Pisa, Naples to Pompeii and again no issues at all. Travelling by train in relaxing and the perfect way to sample lots of delicious Italian foods by having a picnic on each leg of your journey!
Day 1 – Venice
Morning: Get orientated with a Free Walking Tour starting at Campo Santo Apostoli, 4455 Strada Nuova.
This comprehensive walking tour covers northern Venice and is highly recommended. You’re not just walking around central sites you’ll easily discover strolling around on your own.
Afternoon: Head to Saint Mark’s Square. Entering what locals call San Marco square was breathtaking. Take time to admire the Basilica, with its golden mosaics and the precious marble, especially the red porphyry. Check out the Clock Tower, and the 324 feet high Bell Tower.
This square can be busy, is too expensive, and sometimes it’s under water, but it is the heart of the city and a great place for a coffee or drink. You may need to compete with the pigeons for your croissant!
Book a tour of the unique Doge’s Palace, a seat of government and the center of city political life dating back to the 14th century. It is a fascinating insight into how life was in this city.
Then take a moment at the Bridge of Sighs one of 400 or so in Venice but the one considered to be the most romantic.
Why not take a sunset Gondola ride through crumbling water streets where life spills out onto the water at every turn. Yes it’s expensive! but a lasting memory.
After a busy day, head to an Osteria (wine bar with light meals). They are dotted all over the city, so check those out closest to where you are staying on Open Table or via your hotel.
Day 2 – Venice
Morning: To get a change of scene from the city’s hustle, get yourself on local water ferry, called vaporettos. You will see the Cathedral of Santa Maria Assunta on Torcello a largely uninhabited island.
Next, continue to Burano island, ablaze with colour. Here you will find a selection of shops perfect to browse in.
Walk over the bridge to the island of Mazzorbo and park yourself on the grassy area in the sun! It’s the perfect way to relax before lunch back in Burano.
Afternoon: In September when we visited Venice had the historic annual Regata Storica. Venice has hosted this historic gondola race and ceremonial pageant down the Grand Canal since the 13th century.
Thousands congregate to catch a glimpse of the beautiful boats and brightly coloured participants who compete for the King of the Oar title in traditional Venetian costumes.
A good place to view this is from the Hotel Londra Palace, Riva degli Schiavoni, 4171, 30122, or stand at Punta della Dogana.
Day 3 – Florence
Morning: If you’re staying in Central Venice it is not a long walk (it took us 15 mins) to the Venezia SL rail station. Alternatively grab a taxi to the station to depart for Florence (or Firenze as the Italians call it).
Again no issues with the trains! On arrival, it was pouring with rain, giving us an excuse to head to a local cafe for a delicious pizza and glass of red wine.
As you continue on YOUR best of italy tour, do make time to sit, east and enjoy the flavors that only come to life in authentic Italian back street restaurants!
Afternoon: Batteries recharged, we got our brollies out and explored this enthralling city center before getting ready for cooking class. Book in advance with Eating Europe, located at Piazzo Santo Spirito 50125 or a well reviewed cooking class.
As part of the class, we visited the market, bought produce, cooked it up and ate dinner as a group. Highly recommended! Bring bottle of water and comfortable shoes to walk around the market to shop before cooking.
Day 4 – Pisa
Our Tour of Italy Itinerary continues with a day trip to Pisa.
Morning: Leaving around 8am from Florence’s Santa Maria Novella train take a regional train (there are 2-5 an hour) to Pisa (around 1 hour). Use the highly recommended and reliable Trainline.com Site or App to help identify the service schedule and prices.
Named after a Greek city (from where it’s believed the first inhabitants came from), its tower has earned it world recognition. It has a title of one of the seven wonders of the medieval world. It continues to fascinate day travellers and specialist engineers. Buy Tickets at the Official Tower of Pisa Ticket Site 20 days before your visit.
There is a time slot for each ticket so make sure you get there in time to join the queue for your entrance. There are lockers for any backpacks as you can’t take these on the climb up.
It is a funny feeling climbing the winding stairs at an angle. The views from the top are great – beware when the bells ring out! It is loud 🙂
Afternoon: Its late afternoon when you return to Florence so take it easy. If you enjoy a steak, head to a recommended restaurant to try the ginormous Steak Florentine (T-bone steak). As a vegetarian you’re never short of options with pasta and salads, not to mention great pizza!
Evening just before sunset is also a great time to walk back to the riverside or around the square where people are gathering enjoying what’s left of the day.
Day 5 – Siena
As the cities of Florence, Pisa and Siena are so close together they make a great choice for a long weekend. Read our Florence, Pisa and Siena Post for how to enjoy days between these cities This is an affordable itinerary with great tips on using local trains and where to stay in Pisa.
Morning: The bus service from Florence Central Bus Station to the center of Siena is easy. Take the Rapida, line 131R, since it is a non-stop service, taking just over an hour.
The bus has adequate storage for luggage. 1-way tickets were 8-10 Euros (we bought ours at the station before boarding) Remember to validate your tickets before getting on the bus. Check the latest Florence to Siena timetables online.
Siena is stunning, set on three hills, arriving here feels like going back in time. You’re encased in stunning, medieval architecture.
Afternoon/Evening: Honestly just wander around this beautiful city. The massive medieval Piazza del Campo dates from the 1300s with its nine segments still evident.
These originally represented the Nine who governed. It’s a perfect place to sit, sip and get orientated to the city. A couple of times a year, the Il Palio horse races take place – an annual ritual that has been happening here since the 16th century.
Also, make sure to see the Cathedral. It was a beautiful building to walk through and the attention to detail is fascinating. If you like a top-down view, climb the 400 steps of the Torre del Mangia.
Day 6 – Tuscan Wine Tour
In our humble opinion, it’s not a tour of Italy without a Tuscan Wine Trip. This was a fantastic day as we toured and tasted the best of Tuscan reds. Book via Grape Tours from Siena.
Honestly, we could have easily spent a week touring around, exploring this gorgeous landscape, delicious wines and farm fresh foods, so if you have the time, try a couple of tours!
I was surprised to see kiwi fruit growing at vineyards which really are small farms with so much fresh produce, beyond wine, to sample!
Day 7 – Rome
Morning: Catch an early train to Rome Termini Station from Siena. The journey time to Rome is approx. 90 minutes. Two metro stops later and we were at our accommodation, next to the Colosseum.
Afternoon and Evening: Stroll around central Rome, taking in the top sights including Trevi Fountain, Spanish Steps, Piazza Navona.
It’s fun to wander around, find a spot for a refreshing Prosecco and celebrate arriving in the City of Seven Hills or Eternal City.
Day 8 – Vatican City
The tiny country of Vatican City is essential to include in any Tour of Italy Itinerary and we have visited more than once and always seen something new!
Morning/Afternoon: Bring your passport! We took the subway station from our apartment to Cipro – the Vatican stop. The journey took 20 minutes. We decided to go at dawn before tourists turned up and it was definitely worth it, watching life get going in St Peter’s Square.
After a coffee, we had to join the long queue but since we had pre-booked tickets, we got into the ‘faster line’. Once at the gate, we were directed to the Customer Care desk. We presented our voucher and OUR PASSPORTS. Remember The Vatican is a separate country!
We then had to clear security and head upstairs for our guided tour at the Meeting Desk which is located at Cash Desk 15. The admin was a bit of a hassle so I think good to share:)
The Galleries of the Vatican Museum house incredible art and having headphones/guide helped us understand a lot in a short period of time. We finished our tour ends in the spectacular Sistine Chapel.
Last but not least, visit St. Peter’s Basilica, with its over-the-top richness of design. You can book tickets directly via The Official Vatican Visit Site.
Evening: We walked over to the Trastevere area of Rome. Cobbled streets, small bars and small authentic restaurants line the streets with many churches on corners. It’s a lovely part of the city.
There is a little bar Chocolata Vino that serves chocolate shots on Vicolo Del Cinque near Piazza Santa Maria. It’s a lot of fun!
Day 9 – Ancient Rome
Morning: Tour of Forum and Colosseum with Guide. We booked via Coopculture. If you do this, you need to collect your tickets 30 minutes before your tour.
We loved the 3 hours tour around Ancient Rome. Most of us learnt about the Romans at school but there’s nothing like seeing it first hand.
Having a local guide transport you back to the days of the Roman legions, is time well spent. Don’t miss Circus Maximus, site of Ben Hur style races, the Roman forum, and the postcard perfect Colosseum.
For a last night in Rome, visit the Pantheon. All lit up, it is the perfect spot for dinner while admiring the technical skills that designed this back in 126 AD! How incredible that the building has the same diameter as height – 43.5 meters.
This, together with the 16 granite columns that form the facade, can only be appreciated in person in my humble opinion. Icons of Italian life are buried here from kings to renaissance star, Raphael.
Day 10 – South to Sorrento, Capri and Amalfi Coast
Late Morning: Head back to Roma Termini station to head to Sorrento (via Naples). From Napoli Garibaldi station take the Circumvesuviana train to Sorrento. FYI; this is Stop #2 on the Circumvesuviana route and can be busy.
An option is to exit Napoli Centrale Station and walk 8 minutes to the Porta Nolana station which is the first station of the Circumvesuviana line. Doing this will almost guarantee a seat and an overhead luggage spot (secure).
Our Air B&B was a 5 minute walk from the Sorrento Train station but we were met by the owner and driven there.
Late Afternoon/Evening: Enjoy a classic walk along Corso Italia and Via San Cesareo. Stop off for an aperitif in Piazza Tasso in Sorrento. Afterwards, enjoy a leisurely dinner in one of the many restaurants in the historic centre, many of which feature local cuisine and seafood.
Day 11- Capri Island
This is an All Day Tour. You will leave Marina Grande port at your appointed time (we left at 9am) and take a ferry to the island of Capri, 6km out to sea and an original Roman site.
Sit on the left side of the boat for the best views! We had a slight problem as our pre-booked boat was unexpectedly cancelled, but we got transferred onto another within about 30 minutes.
On arrival, stay on the boat for an ‘around the island’ ride which included the ‘blue grotto’. We didn’t go in as there were hoards of tourists and well it’s only a cave! Instead get off at the harbour and take a bus tour to Capri town.
The Monte Solaro chair lift was a great way to get to the highest point of Capri (1932 feet). There is a restaurant at the top where we had a refreshment and admired the incredible views before returning down.
The newsagent shop at the entrance of the Marina Grande is open all hours, and was helpful regarding transport and options. It was busy and it might be an option to stay overnight in Capri to enjoy the island once the day trippers have left.
We returned on a late afternoon Ferry to Sorrento. I suggest buying an open return ticket to give you flexibility.
Day 12 – Amalfi Coast Tour
It is totally worth booking an all-day private tour to experience the best of one of the most beautiful coastlines in the world.
We booked with Amalfi Coast Destination and the van and driver were great. Note: you will need to pay cash for this tour at the end of the day.
The Tour: From Sorrento, you will make several stops along the way at the best viewing spots for memorable pics. Next, you will join with the Amalfi Drive, a famous windy 163 state road.
We followed the winding one-way road into the heart of Positano, a stunning village of seaside villas, with the most colorful plants all around. (Glad I wasn’t driving!)
It’s good to get out of the car and enjoy a pleasant walk along the narrow streets leading down to the waterfront area. Countless outdoor cafes, gorgeous hotels, and Mediterranean boutiques make Positano such a magical location.
Amalfi
From Positano, climb up the main road high above and head south east towards Amalfi passing by other fishing villages – Praiano, Furore and Conca Dei Marini.
Once in Amalfi, explore Piazza Duomo ( central Square ) dominated by the magnificent Cathedral of St. Andrew. There is the statue of Flavio Gioia considered the inventor of the sea compass for navigation. The aroma of lemons fills the air!
Day 13 – Sorrento to Rome
The last full day of our Tour of Italy Itinerary! Where did the time go! Head back to the Sorrento Circumvesuviana Train Station and buy a 1-way ticket to Naples Centrale.
It is possible to store bags at the station until you return in the afternoon for your train to Rome. Left luggage in Napoli Centrale is managed by KiPoint. It is located at the ground level by platform 5.
The Circumvesuviana train goes to Pompeii Scavi/Villa dei Misteri stop/ Station. The ancient city of Pompeii is only 16 miles (35 minutes) from Naples, making it a perfect half-day activity. Since Pompeii has little shade bring lots of sunscreen and water.
Visit to Pompeii
Pompeii is one of Italy’s most famous attractions. It is almost unbelievable that this was once an entire Roman town before it was smothered under volcanic ash in 79 AD.
Now a UNESCO World Heritage Site, Pompeii lies close to the southern slopes of Vesuvius (Mount Vesuvius, Vesuvio), the volcano whose eruption destroyed the town.
Whether you choose to walk around the ruins or book an official guide, it is definitely worthwhile reading up about the history behind Pompeii before you visit.
Until you visit, it is hard to imagine the scale. However, it was a whole town that was buried so perhaps it is not so surprising to learn that the ruins of Pompeii cover around 440,000 square metres. It would take at least three days to explore these both fascinating and poignant completely.
Check out the Official Pompeii Website for details of tickets and tours. Close to Pompeii is the neighbouring sister site called Herculaneum also UNESCO and also buried by the mighty Vesuvius.
It is much smaller than Pompeii so if you are rushed for time, try and visit this site instead – it will still give you the feel of a town destroyed and uncovered.
Vesuvius
Vesuvius itself is another major tourist attraction Ruby visited whilst on her cultural triangle tour of this area. The view of the inside crater from the top is incredible with breath-taking views across the fallen cities.
Return by Train to Naples
After visiting Pompeii, make your way back to Naples for a last night of what we hope was a brilliant Tour of Italy itinerary. Trains run to Rome Termini from here so it’s an easy start in the morning for your last day of this Tour of Italy Itinerary.
How to Get from Naples to Rome Airport
From Naples Train stations, its a straight forward ride via fast trains to Rome.
Next, you will transfer to The Leonardo Express Airport train. This is a dedicated airport train taking 30 minutes with a frequency of every 15 minutes. There are shuttles to the local hotels running most of the day but check in advance for arrangements for your chosen home. Some incurring a charge for the shuttle.
We suggest you pick a final night’s hotel in Fiumicino near the airport. This way you can have an evening to experience a coastal suburb of Rome but be close enough for an early flight the next morning. Day 14 and you will be Homeward Bound with incredible memories from your own Tour of Italy itinerary!
Wrap Up: Tour of Italy Itinerary
We know! 2 weeks hardly scratches the surface of any best of Italy itinerary. There are literally hundreds of world class sites to visit. Did you know that Italy has the most UNESCO destinations in the world?
The Island of Sicily is a perfect spot for a relaxing few days if you have time to squeeze in 5-7 more days in Italy. We have a great guide to a 6-day trip to Taormina and Palermo in Sicily. It’s a quick flight from Naples or Rome.
If you are looking for a romantic low key getaway late summer, around September, the Amalfi Coast has it all. Buon Viaggio!
