0 In Europe

Two Weeks in Italy

Welcome to my Itineraries series! This is the third installment of day-by-day trip recaps to help you plan your next adventure. Click here for 2.5 Weeks in Mexico, Belize and Guatemala and here for two weeks in Portugal.

This month’s topic is two weeks in Italy. As with all of the places in my Itineraries series, you could spend much more time than this in Italy and never run out of things to do, see and – most importantly – eat. But two weeks is a great start, giving you enough time to visit multiple cities and regions.

two weeks in italy itinerary travel guide
Manarola, Cinque Terre

I hope this sample itinerary helps you plan your dream trip to Italy.

Two Weeks in Italy: Areas Visited


Budget-Friendly Boat Ride Venice Italy
Grand Canal, Venice


piazzale michelangelo self-guided walking tour Florence Italy
Piazzale Michelangelo, Florence


a day trip to lucca, italy
Piazza dell’Anfiteatro, Lucca


two weeks in italy itinerary travel guide
Piazza del Campo, Siena

Val d’Orcia

val d'orcia road trip travel guide Monticchiello
Monticchiello, Tuscany

Cinque Terre

two weeks in italy itinerary travel guide
Vernazza, Cinque Terre


bosco verticale milan two weeks in italy itinerary travel guide
Bosco Verticale, Milan

Two Weeks in Italy: Flight Details

Our home airport is about an hour away in Syracuse. Since it’s relatively small, it’s not common to find good international flights departing directly from there. More often than not, we buy our “main ticket” from a New York City airport and then separately buy flights between Syracuse and NYC.

That said, for this trip we happened to find cheap United flights right from Syracuse (SYR) to Milan (MXP) connecting through Newark (EWR). It’s always nice to have your flights linked as one journey in case there are any delays along the way, and having just one stopover is the dream! (Ok, non-stop is the dream, but I try to keep my expectations realistic when it comes to flying.)

The Temple of San Biagio Montepulciano
The Temple of San Biagio in Montepulciano

Two Weeks in Italy: Itinerary

Day 1

Fly out.

Day 2

Land at Milan Malpensa in the morning.

Don’t settle in yet, though – today you’re heading right to Venice!

two weeks in italy itinerary travel guide


MXP to Milan: Take the Malpensa Express to Milan Central train station. The journey costs 13 euro and takes just under an hour.

Milan to Venice: We used the Trenitalia website and app to plan all of our train trips. I’ll share some tips at the end of this post to help you stick to your budget and not be surprised by last-minute price increases.


We stayed in a small apartment at Casa Baseggio in the Cannaregio neighborhood. Cannaregio is beautiful and quiet while still being centrally located enough to walk everywhere. Other than being a little chilly at night, we enjoyed the guesthouse and the hosts let us leave our luggage there the next day until our train out of the city.


  • Digging in to our first gelato of the trip – a treat we strived to enjoy daily
  • Taking in panoramic city views from the rooftop of T Fondaco dei Tedeschi
  • Sampling typical Venetian cicchetti: small plates or bar snacks
cicchetti two weeks in italy itinerary travel guide

Day 3

Spend the day in Venice and take a late afternoon or evening train to Florence.

two weeks in italy itinerary travel guide


  • Starting the day with coffee and books at sullaluna
  • Enjoying a budget-friendly boat ride down the Grand Canal
  • Getting lost among the increasingly picturesque streets of the city, partly on purpose and partly because it’s inevitable in Venice!
  • Revisiting the T Fondaco dei Tedeschi rooftop, this time for sunny views
t fondaco dei tedeschi venice
two weeks in italy itinerary travel guide


We again used Trenitalia to get from Santa Lucia Station in Venice to Santa Maria Novella Station in Florence. Don’t forget to check the end of this post for my Italy train tips to help you know what to expect to pay for tickets.


In Florence we stayed at Hotel Accademia. Visiting during shoulder season allowed us to book this hotel which would usually be out of our price range. While it didn’t have as much character as some of our other accommodations, we enjoyed our stay here and it’s in a convenient location – walkable to everything and just a few minutes from Santa Maria Novella Station.

Day 4

Spend the day in Florence.


  • Visiting some of the city’s many beautiful landmarks like the Ponte Vecchio, Piazza del Duomo, Piazza della Signoria, and Piazza di Santa Croce
  • Having lunch at Osteria Vini E Vecchi Sapori, one of my favorite meals of the trip. Stop by in advance to reserve a table if you can.
  • Crossing the Arno River to enjoy the quieter, less touristed Oltrarno neighborhood
  • Visiting the Abbazia di San Miniato al Monte followed by sunset at the Piazzale Michelangelo
  • Reuniting with my friend Niccolò after many years and enjoying a delicious dinner together. There’s nothing better than the opportunity to enjoy food in a new country with a local!

Click here for my self-guided walking tour of Florence.

self-guided walking tour Florence Italy Santa Croce
san miniato al monte self-guided walking tour Florence Italy

Day 5

Day trip to nearby Lucca.

a day trip to lucca, italy


Lucca is an easy day trip from Florence, but be sure to look up train times in advance. Depending on which train you take, the journey from Santa Maria Novella to Lucca can vary from a direct route taking an hour and twenty minutes to a route with one to two stops lasting almost three hours. When we visited, there were several direct routes per day. These options aren’t currently showing up on Trenitalia and after doing a little digging, this may be due to track work.

a day trip to lucca, italy


  • Starting the morning in Florence at the Thursday morning flower market in Piazza della Repubblica along Via Pelliceria
  • Ordering handmade gnocchi to go from the FN Pasta Fresca stand at Mercato Centrale
  • Walking along the 16th- and 17th-century ramparts that have surrounded Lucca’s historic center for hundreds of years
  • Visiting Piazza dell’Anfiteatro, Lucca’s uniquely shaped oval square
  • Climbing the Guinigi Tower
  • Soaking up the sun in Piazza San Michele
  • Enjoying our daily gelato from La Bottega del Gelato
  • Returning to Florence and having delicious panini for dinner from All’Antico Vinaio
a day trip to lucca, italy

Click here for my full post on day tripping to Lucca from Florence.

Day 6

Pick up your rental car – you’re heading to the countryside!

La Cappella della Madonna di Vitaleta


We used Rentalcars.com to compare prices and make our reservation. The morning we picked up our car, we used Florence’s light rail to reach the rental agency in the Oltrarno.

If you have the capability of using data on your cell phone, having easy GPS access will be hugely helpful at this point. We thought we had a pretty good understanding of how to get onto the highway heading south toward Siena, but we got turned around almost immediately. Road signs in another language don’t help!

If using cell phone data isn’t an option, you can usually include a GPS with your car rental. That said, it’s not always easy to familiarize yourself with a new device like this at a moment’s notice, and it can be a pricy addition.


We based ourselves at Agriturismo Pacifico in Montepulciano and we loved it. I highly recommend experiencing an agriturismo, or farmhouse guesthouse, while in Italy. Our room was comfy and the property was lovely. There are a lot of beautiful villages you can choose to base yourself in while in Tuscany – I’m not sure you can go wrong! I did a basic search of options on or near our road trip route and chose the one that looked best for us price and ratings-wise.

Agriturismo Pacifico Montepulciano
Arriving at our agriturismo


  • Breaking up our drive from Florence to Montepulciano with a visit to Siena
  • Walking from the Porta al Prato to the Piazza Grande to enjoy sunset after arriving in Montepulciano. We didn’t actually realize when we started how long and uphill this walk would be, but it was worth it. We realized later there is a small shuttle bus that will take you to the top of town as well!
two weeks in italy itinerary travel guide
Siena’s Torre del Mangia
two weeks in italy itinerary travel guide
The Duomo Di Siena
val d'orcia road trip travel guide montepulciano
Sunset in Montepulciano

Day 7

Spend the day in the Val d’Orcia.

val d'orcia road trip travel guide san quirico d'orcia
San Quirico d’Orcia


  • The whole day! Click here for my full post on a road trip through Italy’s Val d’Orcia.
  • Visiting Pienza, the Cappella di Vitaleta, San Quirico d’Orcia, Montalcino, Monticchiello, and the Temple of San Biagio
  • Returning to Montepulciano and having a fun and delicious dinner at La Vineria di Montepulciano
val d'orcia road trip travel guide pienza
two weeks in italy itinerary travel guide
The Cappella di Vitaleta, or Vitaleta Chapel
La Vineria Montepulciano

Day 8

Spend another day in the Val d’Orcia.

val d'orcia road trip travel guide bagno vignoni
The main square of Bagno Vignoni


val d'orcia road trip travel guide Bagni San Filippo
Bagni San Filippo

Day 9

Drive back to Florence to drop off your rental car before continuing on to Cinque Terre.


Head to Santa Maria Novella Station to take the train to La Spezia. La Spezia is the southern gateway to Cinque Terre, and you change trains here to continue on to the five villages. While at the station, we purchased 2-Day Cinque Terre Treno MS Cards, allowing us unlimited train travel between La Spezia and Levanto (this includes the five villages) as well as access to the national park’s hiking paths. We then hopped on the next train to Corniglia, the cost now covered by our cards.

two weeks in italy itinerary travel guide
Vernazza, Cinque Terre


We stayed at this Airbnb and loved it. The hosts, who own a bar down the street where you can enjoy a coffee and pastry for breakfast, were very kind. And while the room is tiny, it has one of the most picturesque views you could ask for!

two weeks in italy itinerary travel guide


  • Hiking the red trail or “high path” from Corniglia to Manarola
  • Visiting Riomaggiore for more postcard harbor views
two weeks in italy itinerary travel guide
Excited to reach Manarola after a steep and sweaty hike
riomaggiore cinque terre two weeks in italy itinerary travel guide
Riomaggiore, Cinque Terre

Day 10

Enjoy the day in Cinque Terre.

monterosso al mare cinque terre two weeks in italy itinerary travel guide
Monterosso, Cinque Terre
vernazza cinque terre two weeks in italy itinerary travel guide
Vernazza, Cinque Terre
corniglia cinque terre two weeks in italy itinerary travel guide
Corniglia, Cinque Terre


  • Hiking the blue trail/coastal path from Monterosso to Corniglia by way of Vernazza
  • Heading back to Manarola for wine and a beautiful sunset
manarola cinque terre
Manarola, Cinque Terre

Day 11

Take the train from Cinque Terre to Milan. Spend a few hours exploring Milan before catching your flight home tomorrow.

milan duomo two weeks in italy itinerary travel guide
The Duomo di Milano


We took a train from Corniglia to Milan Central, changing once in Levanto.


We stayed at Enjoy Milano, which was perfect for a short overnight. It’s a quick ten-minute walk from the Central Railway Station, which made our early start the next morning a little bit easier.


  • Visiting the Galleria Vittorio Emanuele II, a stunning 19th-century landmark with arched iron and glass ceilings
  • Seeing the Bosco Verticale, or Vertical Forest. These two apartment buildings are covered in thousands of trees, shrubs and flowering plants to improve air quality by absorbing and converting carbon dioxide, increase biodiversity, moderate interior temps, block noise pollution, and combat dust.
  • Taking in the imposing and beautiful Duomo di Milano, or Milan Cathedral
Galleria Vittorio Emanuele II Milan Italy
The Galleria Vittorio Emanuele II

Day 12

Fly home.


In hindsight, heading straight to Venice after landing in Milan made a long overnight journey even longer. Navigating an immediate train trip after flights, lack of sleep, Customs, and the hour-long train ride into the city felt like a lot. For this reason I would recommend staying at least one night in Milan before moving on, even if it’s largely to rest.

val d'orcia road trip travel guide montalcino

Similarly, in trips since Italy I’ve made sure our last full day doesn’t include travel. Our train from Cinque Terre to Milan was delayed, so we didn’t have as much of a relaxing afternoon in Milan as I was hoping for. Our early flight the next day made the delay seem even more frustrating than it would have otherwise.

Train Tips

While planning our trip to Italy, I knew we’d predominantly be traveling by train. I used the Trenitalia website to get a general idea of availability, routes and pricing. To allow ourselves flexibility, I didn’t want to buy anything in advance and lock us into specific times. Unfortunately I didn’t realize that in some cases, tickets are priced much higher when you buy them last minute. This was a major bummer when we arrived in Milan after an overnight flight and immediately paid more than twice what we were expecting to for our tickets to Venice.

Avoiding higher rates:

Depending on the train, some rates stay the same whether you buy tickets months in advance or on the same day, while others get much more expensive when you buy them last minute. When you’re looking online, the price of Regionale trains will likely not fluctuate, while the Frecciarossa and Eurocity trains will get more expensive if you wait.

Often times there are both Frecciarossa and Regionale options for the same trip, but the Regionale option is likely to take longer and involve train changes. (We could have paid less to take a regional train from Milan to Venice, but it left later in the afternoon, took an additional hour and involved a stopover.)

More often than not, the Frecciarossa routes that get more expensive are for longer journeys, whereas shorter journeys are likely to have a set price. We bought our ticket from Florence to Lucca – a shorter regional route – about 15 minutes before getting on the train, and the rate was the same as it would have been had we bought it in advance. 

My advice would be: leave the shorter trips open ended to allow yourself flexibility for day trips, but look in advance to see if you can save yourself money by booking early on some of your longer journeys. And if booking in advance still doesn’t make sense for your longer journeys, at least you’ll know to expect to pay more and it won’t be a surprise in the moment.

two weeks in italy itinerary travel guide

There’s also the option of utilizing Italo trains (run by a private company) instead of Trenitalia (the primary government-run train operator). From glancing at their website, it’s also a good idea to book in advance for many Italo journeys.

Extend Your Stay

Interested in adding a couple of days to round out your trip to an even two weeks? There are a lot of options! Here are a few ideas we considered before finalizing our itinerary:

  • Giving ourselves more time in Milan
  • Visiting Bologna, Modena or Parma
  • Expanding our Tuscany road trip to include San Gimignano and Volterra
  • Spending time on the Lerici coast visiting Portovenere, San Terenzo, Lerici, Fiascherino, Tellaro and Ameglia

Have you been to Italy? What would you add to this itinerary? Let me know in the Comments!

siena two weeks in italy itinerary travel guide

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