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Our ultimate Italy itinerary – Pisa, Florence, Rome & Tuscany

There are so many cool places to see in Italy, it can be difficult to choose just one for a city break. More and more people are opting for multi-destination Italy itineraries, visiting multiple places by train within a 2-week period. This is a great way to see as much of Italy as possible in a short space of time, taking in true Italian culture, checking out the top historical sites and getting a taste of both city and country life.

We’ve put together a 2-week Italy itinerary that takes you on an adventure to some of the top Italian cities, from Pisa to Rome, with a countryside stop in between. It covers plenty of sightseeing, but not so much that you return home tired – it’s a holiday after all!

2 week Italy holiday itinerary - Travel plan

Pisa, Italy – Rome, Italy 14 day trip

Pisa: 2 nights

Start your Italy itinerary by flying into Pisa or a nearby airport. You’ll find cheap flights from across the UK to Pisa’s nearby airport and it’s a great place to start your trip due to the relaxed atmosphere compared to the larger cities, easing you into the vibe of city life. Pisa is relatively small but has world famous sites that draw visitors and make it one of the most popular tourist cities.

Spend your time in Pisa visiting sites such as the Leaning Tower of Pisa, the Battistero and Duomo, National Museum of San Matteo and much more. Pisa is also a great introduction to Italian food. You’ll find quaint restaurants that aren’t too touristy or busy and everything in the town is within walking distance, giving you plenty of time to relax. Check out our ‘cheap and free things to do in Pisa’ article for inspiration on planning your 2 days in the city.

Shows the leaning Tower of Pisa

TRAIN – 1 hour (Pisa Central Railway Station to Firenze Santa Maria Novella Station) Ticket cost = £8-9 per person

Florence: 3 nights

2 week Italy holiday itinerary - Florence

Florence is capital of the Tuscany region and arguably the number one must-see city in the north. Similar to a lot of Rome’s historic cities, the main attractions here consist of famous churches and historic monuments and ‘Piazzas’. We’d recommend spending 3 full days of sightseeing in the city, checking out attractions such as the Duomo, Palazzo Vecchio, the Baptistery of San Giovanni and the Central Market. The city is best explored on foot so we’d advise on bringing some good walking shoes or trainers, joining a walking tour on your first day and then looking at the remaining sites in detail for the remainder of your stay. We suggest Walks of Italy.

Florence is also excellent for live performances. Stop by an evening Opera or Theatre show for a traditional Italian show – it may be difficult to understand but the venues, stages and overall experience are still worth checking out. We recommend buying tickets to the nightly Opera at St Mark’s Anglican Church. The church is a beautiful venue and the performances even appeal to those who aren’t Opera regulars. It’s a truly authentic part of Italian culture and the singers are excellent.

As there’s so much to see in Florence, we recommend doing as much as you can in those 3 days but stopping off for regular café breaks so you don’t tire yourself out. Make Bar Pasticceria Cucciolo the first stopping point on your agenda. Their pastries and cakes are some of the best in the city.

BUS – 1 hour 30 minutes – from Firenze Santa Maria Novella Station (Florence) to Stazione Ferroviaria Siena (Siena). You can then catch a bus to your hotel in Chiani or stay a night in Siena.

Alternatively, rent a car for 4 days and drive to Tuscany yourself

Tuscany wine country: 5 nights

After a full week on your Italy itinerary doing lots of sightseeing, the Tuscany wine country can be a great place to relax and re-build your energy before continuing with action-packed days in Rome.

Spend 4 days in Tuscany in a secluded villa with a swimming pool overlooking the wineries and farmlands of rural Italy. Enjoy slow walks and relax in the sun during the day and indulge in hearty Italian food and wine on an evening. We’re confident you’ll love the peace and quiet away from the busy cities and will enjoy a different side of Tuscany. We recommend staying in the rural Chianti region as a base but taking time to visit other small towns and regions for the day. The cities of Siena and Lucca make great day trips.

Shows the vast countryside of Tuscany

Siena Siena is an architectural beauty of a town deep into the Tuscany countryside. Gothic buildings and monuments are spread throughout the town and it’s a lot more tranquil than the large Italian cities, but with the same rich history. Siena is a great place to stay if you prefer an active town over the countryside but is also a must-see day trip for those staying in a countryside villa. If you’re visiting Siena in August, be sure to watch the famous II Palio Horse Race, where the whole city turns into a race track and flocks of people descend on the town to spectate.

2 week Italy holiday itinerary - Siena

Lucca Similar to Siena, Lucca is a beautiful place to stay in its own right or to explore in a day trip from the countryside. It’s a small medieval town with charming Piazza’s, cobbled streets and small cafes and restaurants offering locally sourced specialities. As well as being nice to look at and stroll at your leisure, Lucca has a number of museums, picturesque towers and monuments to photograph. We recommend joining a walking tour for a morning of sightseeing and then getting involved in a cooking class or food tour in the afternoon. If you love wine and Italian food, Lucca can be one of the best places to experience traditional cooking. Check out Extra Virgin Cooking Class. Lucca is a must-see stop on your Italy itinerary!

2 week Italy holiday itinerary - Lucca

Rome: 3 nights

In our opinion, we left the best until last, simply down the sheer volume of historic and infamous sites on offer in Rome. It’s a city which will take you back in history, exploring places such as the Roman Fort, Colosseum, Vatican City and a plethora of beautiful churches, monuments and intricate ‘Piazza’s’. Needless to say, Rome is also excellent for food.

Shows the Trevi Fountain in Rome

We recommend checking out our 3-day itinerary for Rome here. It takes you to many of the must-see attractions, with a small amount of quiet time to shop, relax and visit a spa at your leisure.

As well as the usual sightseeing in Rome (which will probably be the highlight of your trip), spend your last day shopping in the cities markets, designer fashion boutiques and high streets stores. Leaving your shopping until last means that you won’t be carrying lots of bags throughout the rest of your Italy itinerary.

2 week Italy holiday itinerary - Rome monuments

Fly out from Rome back to the UK. There are plenty of cheap flights from Rome Fiumicino airport to most UK airports.

Italy is bigger than the UK so seeing all of the country in a short trip would be impossible. Tuscany is the most popular area of the country to visit and a natural beauty full of history. Staying in this region and then venturing south to Rome means you won’t spend a great deal of time travelling as everything is close by.

Feel free to substitute one of our Italy itinerary destinations or change the amount of nights you stay if there’s somewhere else in the area that you’d prefer to visit – some people prefer rural Tuscany over the cities and vice versa. Browse our Tuscany travel tips below to help your tour live up to its full potential.

Travel tips for your trip:

  • A lot of people forget that the Tuscany region has a coastline of white sand beaches and opt to stay in the countryside. If you enjoy a relaxing beach visit on holiday, drive or take a local bus to the Viareggio coastline for a fun day in the sun
  • If you’re opting for exploration over relaxation in rural Tuscany, we’d recommend renting a car on departure from Florence and driving to the countryside yourself, choosing to stay in one place or spending a couple of nights in multiple small towns. Car rental can be quite a bit more expensive than public transport but it gives you a lot of freedom. A car isn’t needed for the busy cities of Pisa, Florence and Rome, everything can be reached on foot or by bike
  • If wine tasting is hovering near the top of your agenda, the Chianti region is the best place to experience it. We recommend Chianti Wine Tour.
  • Food in Tuscany is excellent but as with any destination with lots of restaurant options, do your research and find top rated and ‘cheap eat’ restaurants off-the-beaten-track. Tripadvisor is your best friend in this department


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