Round trip Cinque Terre and Tuscany

9 days in

Cinque Terre and Tuscany

This 9 days´round trip takes you from Cinque Terre along the coast and to Pisa and romantic Florence. We discover the wineyards and bike between the hilltop villages in Tuscany. There are lots and lots of tourists that visit these amazing places and it can get really hot in the summer. Therefore, best time to visit is April-May and late September-October. In October the Mediterranean is still warm enough to swim in.


Highlights on this trip

  • Walk through the old town in Florence
  • Take a closer look at the Leaning tower of Pisa
  • Hike along Cinque Terre
  • Bike to the hilltop villages of Montepulciano and Pienza
  • Visit the magnificient dome of Siena
  • Visit San Gimignano with its towers


Day 1

Arrive in Pisa, drive to Monterosso (1,5 hours)

Day 2-3

Hiking in Cinque Terre

Day 4

Drive to Pisa and Florence (3 hours)

Day 5


Day 6

Drive to Montepulciano (1,5 hours)

Day 7-8

Discover Tuscany

Day 9

Drive to Pisa Airport (2 hours)

Leaving Italy.


Day 1

Arrive in Pisa and drive to Monterosso

Monterosso al Mare

From Pisa airport it is only a 1,5 hours drive to Monterosso, the most northern of the five Italian fishing villages known by the italian name Cinque Terre.

Cinque Terre means five countries or lands. The villages from north to south are Monterosso, Vernazza, Corniglia, Manarola and Riomaggiore. Monterosso is the only village with a beach (pebblestone) even though it is possible to take a swim also in the other villages except for Corniglia.

Staying in Cinque Terre means you park your car when you arrive and go by train, boat or hike along the Ligurian coast. There are several trains each day and you never have to wait for long. There are two parking areas in Monterosso, one in each part of the town (old town and new town). The cost for parking is 25 Euros for 24 hours (2019). 

Where to stay in Cinque Terre: You will stay here for three nights. We chose to stay in Monterosso because of the beach. We also figured it be a good thing to be at one end of the coast either in Riomaggiore or Monterosso.

Most of the places to stay in are small Bed & Breakfast and we stayed at Villa Accini. It is a simple but really nice small hotel. It has a lovely garden with lemon trees where you can have breakfast in the morning. It is about 5 minutes walk to the beach. 

Where to eat: This is a lovely thing about Cinque Terre! There are lots of really nice restaurants in most villages. 


The villages from north to south







Day 2-3

Hiking in Cinque Terre

View of Vernazza

The nice thing about hiking in this place is the mix of lovely views, the picturesque villages with its fishing boats and having great food. During daytime the fishing boats are "parked" along the streets in the villages.

Our first day started with breakfast in the garden surrounded by lemon trees at our Bed & Breakfast in Monterosso. We then had a pasta for lunch along the way in the village of Manarola and finally a fabulous tuna for dinner in Riomaggiore with views of the ocean before taking the train back to Monterosso.

Check out more about the hikes to do in Cinque Terre here.

Fishing boats during daytime

We actually spent three days in Cinque Terre but then we love to run and hike in the mountains. If you are not that keen into hiking and you are satisfied with just having seen the Cinque Terre villages an option is to stay for two nights in Cinque Terre and then continue to Florence on your third day.

Day 4

Pisa and Florence

Leaning tower of Pisa

Driving from Monterosso to Pisa is not far, 1,5 hours. Well in Pisa you should try to park the car close to the Leaning Tower because that is about what to see in Pisa besides the cathedral.

Depending on when you arrive it might be a good thing to have lunch in Pisa.

You then continue to Florence (1,5 hours). You will probably arrive in Florence late afternoon so you have a couple of hours to walk around in Old Town and feel the ambience of this historical town.

View of the Florence from Piazzale Michelangelo

Arriving in Florence you need a special permission to drive through the car free Old Town. You can get a permission through the hotel you choose to stay in or simply park your car outside Old Town. You will stay in Florence for two nights.

Where to stay in Florence: We stayed at a really nice and personal hotel Firenze Number Nine Wellness Hotel. From there it is only a few minutes walk to the cathedral Santa Maria del Fiore and Uffizi palace and Gallery. The staff at the hotel was very helpful and arranged with a guided tour and recommendations for lunch and dinner. The hotel also arranged with a permission to drive through Old Town and valet parking.

Where to eat in Florence: We had several nice lunches and dinners but it was difficult to find good options for vegetarian. Our impression was that there is much focus on meat in this region so we were a bit disappointed. Being in Italy and everything.

We had a great dinner at Ristorante la Giostra which was recommended by the hotel and a lovely Ossobuco at a typical Italian restaurant Vini e Vecchi Sapori which was recommended by our guide. We probably would not have chosen Vini e Vecchi Sapori without this recommendation since it almost right beside the cathedral. Too good to be true!

Day 5


Ponte Vecchio

Florence is so full of history. We usually prefer walking around by ourselves but this time we decided to go on a guided tour.

Since we are not that keen on walking in a large tourist group and also like to be able to ask questions we looked for a guide taking smaller groups. The hotel recommended and booked a guided tour for us with up to 8 people. This guided tour added a lot to our experience of Florence.

We learnt about the importance of the Medici family, how Florence was saved during World War II and much more.

You can easily spend a week visiting all the museums and hidden gems of this town. There are a few hot spots that most tourists visit. For a good reason! Just walking around in Old Town is an experience. Like in Rome Florence is like a museum in itself with its buildings and statues.

Check out more about what to do in Florence here.

Day 6

Drive to Montepulciano

View from Montepulciano

Driving south from Florence you have the choice between the faster highway E35 and Road SR222. Choose the latter one! You are not going far and it is lovely drive through the tuscanian landscape passing by little villages and wine yards.

Road SR222 takes you by Greve de Chianti. A lot of day tours from Florence go to Greve. We decided to just drive through and instead continued to the little hilltop village of Volpaia where we had lunch at Bar-Ucci. There are only two restaurants in the village and they are both just fine.

We then continued to our hotel close to Montepulciano. You will stay here for 3 nights.

Where to stay in Montepulciano: We found the cutest and loveliest Bed & Breakfast hotel just outside Montepulciano, Lupaia. It is also one of our favourite boutique hotels. This place has 12 rooms only and is probably always full. Each room has its own decorations and character. It is simply lovely and the staff is very helpful and friendly.

Where to eat in Montepulciano: We had dinner at the hotel twice. It was good, but if you are staying here for three nights it is probably a good thing to eat someplace else for one or two evenings. There are some restaurants in Montepulciano, Siena and also in Monticchiello.

Day 7-8

Discover Tuscany

Staying in Montepulciano is perfect if you want to visit cities like Siena, Montepulciano and Montalcino.

Siena is an Unesco World heritage and the city is of large historical importance in Tuscany. Siena once competed with Florence about beeing the most important city in Tuscany.

Arriving in Siena you park at a large parking just outside the old village. It is well signed how to get there. From there you take elevators to get to the centre of the village.

The cathedral in Siena is absolutely stunning with its black and white striped marmor.

Siena is also famous for its Piazza del Campo, a square formed like a shell where there is a horse race twice a year in August.

You also find several shops selling leather bags, shoes, belts by Italian designers in the pedestrian area of Siena.

The best thing we did in Tuscany was probably biking from one hilltop village to another during one day. It was very relaxing and exciting. Most of our bike tour was on unpaved roads. The distance between the hilltop villages is about 5-8 kilometres, perfect for a stop to have lunch or a cup of coffée or bear.

One day was well enough time to visit three hilltop villages: Pienza, Monticchiello and Montepulciano. Read more about biking between hilltop villages in Tuscany here.

Pienza is a lovely hilltop village that is a must to visit. Walk the narrow cobbled streets and enjoy the views of hills with cypresses and farms from Via dell Ámore. Don´t forget to buy some Pecorino cheese which is originally from Pienza. You can have dozens of different types of this famous cheese here. Pienza is also an Unesco World heritage.

If you arrive by car, there is a parking just outside the historical centre.

Montepulciano is another hilltop village to fall in love with. If you pass by, a third one is Monticcheillo. It is not big but great for a cup of coffee´ or ice-cream. Montalcino, finally, is famous for its wine - Brunello di Montalcine.

Day 9

Leaving Italy

If you are leaving Italy from Pisa Airport you have a 2 hours drive ahead of you. Depending on when you leave you might have time to visit the hilltop village San Gimignano that you pass on your way. San Gimignano is famous for its´ towers.

We chose to add a few more days in Tuscany to take part in the Ecomaratona Chianti Classico. It is a trail running competition with distances from 15 kilometres up to 42 kilometres along wineyards with the starting point in Castelnuovo Berardenga 15 kilometres from Siena. Read more about the Ecomaratona here.