How To Experience Tuscany – A 2 Day Cruise Stop

The last time we were in Italy, we only got the chance to see Rome and the town of Tivoli. That short visit kept us wanting to explore more, particularly Tuscany, having read and seen so much of its beauty.  We finally booked a Western Mediterranean cruise over a year ago with Tuscany as one of the destinations, counting down the days with excited anticipation. Still, we knew we had to plan well how to experience Tuscany to get the most out of our two-day stop.

We boarded our ship in Civitavecchia, Rome, and sailed towards Tuscany for our first stop. With so much to offer, we had to decide how to be able to take in as much of the place without being rushed, and still hit our must-see and must-do lists.

After considering what we will see in our other cruise stops, we decided on San Gimignano and Pisa. Florence’ Uffizi Gallery and other exciting treasures deserve another trip back.

The Picturesque Rolling Hills of Tuscany

It was a 2-hour scenic drive from the port city of Livorno (where our ship docked) to the medieval town of San Gimignano.  The misty weather added an ethereal beauty to the rolling hills of the countryside dotted with vineyards and charming houses.  It gave us a glimpse of the wonderful experience ahead of us.

Along the way, we were awed by views of cypress trees lining up the winding roads leading to private villas, scenes straight out of paintings, and much envied Instagram posts.

San Gimignano – Tragedy of the Past, Fortune of Today

It was raining when we finally arrived at the hilltop town of San Gimignano, but nothing can dampen our excitement. We anticipated the weather, and we came prepared. While some people in our group brought umbrellas, we decided to wear rainproof jackets instead. The jackets allowed us more flexibility and freed our hands to be able to take pictures.

The city rose to prosperity in the 14th century.  Its affluent families built towers (around 70 at one point) to flaunt power and wealth. These wealthy families later on turned into warring factions, and as a result, the thriving commerce and industry went elsewhere and left, leaving its narrow streets and disintegrating towers untouched.  The town has been made a national monument, with its dozen or so medieval towers still standing serving as a living testament of what it used to be.


We entered the old walled city through the southern gate of Porta San Giovanni and strolled through the slightly uphill path of Via San Giovanni. The street is flanked by terraced houses that have been converted into cafes and tourist shops while retaining most of its original exteriors.


From Via San Giovani, we headed to the Piazza Della Cisterna. The Square’s pavement is a beautiful herringbone pattern of brick with a bit of a slope. At the center is an octagonal travertine well built in the late 12th
century.  We spotted a gelato shop by the corner and stopped by for a scoop of Italy’s world-famous gelato.


We then found ourselves in the center of Piazza Duomo, with three impressive medieval buildings facing one another. It felt like a place where time stood still. We sat by the bench-lined walls of one of the buildings and soaked in the view, enjoying the tranquil setting without the usual crowd.


On our way back to the bus, we did a bit of window-shopping and bought small souvenir items. There are shops selling leather products, copies of artworks, and other handicrafts. We focused on spending the remaining time looking for fascinating details of centuries past instead.


Fattoria San Donato – An Authentic Farm-to-Table Experience

Our tour group then headed to Fattoria San Donato, a 900-year old farm and winery that still operates to this day.

We were warmly welcomed by the head of the Fenzi family who now owns the farm. He gave us a mini-tour of their winery, peppered with anecdotes about its history.

After our tour, he led us to the old house where a generous spread of mouth-watering antipasti and a variety of wines awaited us.


He explained how everything was prepared with ingredients from their farm and other small neighbouring farms, with recipes handed down through generations. He educated us with the best wine pairings for each food, from appetizer to dessert. Couldn’t have a more authentic farm to table experience!


The trip will not be complete without buying something to remind us of our enjoyable experience. We bought a few items from the farm’s store – a bottle of wine, a can of extra virgin olive oil, and balsamic vinegar. We will enjoy these later with freshly baked Italian bread and pasta when we are back home.


Pisa – More Than Just the Leaning Tower

We headed to the city of Pisa the next day– about an hour bus ride from Livorno. Pisa is another Tuscan treasure, with the Square of the Miracles as its centrepiece. It is home to a trinity of masterpieces – the circular Baptistery, the 13th-century Cathedral, and of course, the Leaning Tower.

On our way, we drove through roads lined with uniquely shaped trees. We were intrigued by what they were as we don’t see them in North America.  Called “umbrella” pine as their shape implies, they are common in Italy. Their edible nuts are used in making pesto sauce and other dishes. Anything with pesto will now make us feel nostalgic for our Italy trip.


The first building we entered at the Square was the Baptistery. It has a simple interior, but we were surprised at its impressive acoustics. An analysis of the sound inside the circular, marble structure suggested that renaissance architects designed it to emulate a church organ. The resulting flawless acoustics was either an incredible coincidence or the work of genius! We were lucky to hear it with a demonstration. We recommend that you check the schedule of the short performance to take this into account when you visit.


We explored the Cathedral next, a remarkable example of Romanesque architecture with its elegant marble façade and bronze doors. The exterior also shows Moorish-inspired arches and details.  Its interiors brim with bronze and gilded statues, paintings, and religious mosaics. The pulpit is regarded as one of the great masterpieces of Giovanni Pisano (sometimes called the only true Gothic sculptor of Italy). It was interesting to learn that it was not as popular before and was even considered an eyesore.


No visit to the Square will be complete without taking a picture of the Leaning Tower in the background.  It is the most famous structure, but we were surprised to find the Baptistery and Cathedral equally, if not more, fascinating.


It was indeed an excellent decision to visit during an off-peak season. Our tour guide mentioned that during summertime, the crowd could be tenfold that you could hardly enjoy the experience.

Tuscany – Memorable and Captivating

Tuscany stole our hearts; its beauty is beyond words. It deserves another visit to explore the other areas and immerse ourselves longer in the Tuscan way of life and its rich history.

Is Tuscany in your bucket list or have you already experienced it?  Please let us know your thoughts and stories about this incredible place by leaving your comments below. If you enjoyed reading our post, please share the joy with your family and friends.

Comments (18)
June 22, 2022

I’ve been to Italy a couple of times and I absolutely love the culture and the people. Pisa, I only visited through the airport but on both stays I visited Lucca. A fantastic little renaissance old town with almost magical architecture and ambience.

On the latest trip we stayd at Lucca for a week and then went to Tuscany through Florence. We stayd on a Villa/Mansion that was located near Lucignano. Visited several small towns nearby but the one that really stood out was Cortona. The views from the top were spectacular. Would love to live in a small old town like that one day.

    June 23, 2022

    Hi Jukka,

    Great that you had the chance to visit several places there as well. Indeed, the spectacular landscape and the richness of the culture, ambiance and architecture contribute to the lure of the Tuscan countryside. We surely would love to live there as well.

Ivan Brozincevic
June 22, 2022

Great website! Thanks for sharing your experience from your trip to Tuscany. I have never been there, but I’m planning to pay it a visit next year. After seeing these pictures, I can’t wait to see how it’s like there. Thanks again!

    June 23, 2022

    Hi Ivan,

    Glad to know you liked our website. Yes, our Tuscany experience left an indelible mark on our memories. We are sure it will be on you as well when you visit next year. Let us know.

June 10, 2022

wow after reading this article I don’t know I should say that wont to move to Itlay or just visit. Probably I will start with visiting Tuscany, eating good food, and admiring beautiful places and art. Definitely I will give it a go. Thanks for sharing

    June 11, 2022

    Yes, definitely Tuscany is one of the regions that you should visit. It was great for us. It will surely be great for you as well.

June 10, 2022

Beautiful pictures! Looks like an amazing trip! 🙂

    June 11, 2022

    Thank you. Yes, it was an amazing trip.

June 9, 2022

I’m loving and enjoying your travel blog very much! This post about Tuscany and Pisa is brilliant!

I watched the movie – Under The Tuscan Sun – when it was first released. And I just watched it again last week! The movie is beautiful! The scenery is magnificent! It made me want to visit Tuscany. And your blog post makes me want to do it even more!

And the photos of the food! Oh my! The gelato has me wanting to get one right away after writing this comment.

And the farm to table spread. Wow! I want to have that too! It’s inspiring me to prepare all that this weekend and have a dinner like that with my family.

Thank you for this inspiring post. I look forward to reading more about your travels.

    June 9, 2022

    Hi Timotheus,

    Yes, Tuscany has been on our bucket list for some time, also inspired by the same book and movie. Our trip exceeded our expectations!

    The gelato was sinfully delicious! We learned that the shop we bought it from had been winning world championships. And indeed, the farm-to-table experience was authentic. They even guided us on how to progress on the antipasti spread and pair with the right wine the Tuscan way.

    Do you have any travel plans to Italy in the near future? If you do, we highly recommend including Tuscany.

June 9, 2022

Hi buddy,

Your article made me live visualization about your tour.In Tuscany, I like dramatic landscapes and historic cities. Even my sister recommended for a tour, But  I am not interested in any tours. But after seeing your article it makes interest  to move to Tuscany.Thanks for giving the recommended article,And keep creating more articles for the viewer’s use.


    June 9, 2022

    Thank you for your comments.  Glad to know that our post visualized for you what a Tuscany tour can look like.  Let us know if you have any questions or need further information that can hopefully help you with your decision.  We will try to provide answers as much as we can.

June 9, 2022

I hear Italy has real wonderful and intertaining tourist attraction places and I’m looking forward to go there not so long from now to take a vacation. Hopefully I’ll be able to get to Tuscany as well and hope to go see the walls the buildings the cathedral and all those ancient stuff. 

Here in Africa tourists don’t really come to see such nice looking buildings from the 12th century, here its all about caves and paintings and I would like to see something different  now from those way back centuries 

    June 9, 2022

    Hi Donny – Yes Italy is rich with interesting attractions.  It has so many regions and Tuscany is only one of them.  And Tuscan on its own has a lot to offer.  Wish you can have the chance to visit one of them.  

    Africa though seems to offer a lot to tourists as well and it is one of those destinations that are on our bucket list.  What country or attraction in Africa would you recommend?

June 8, 2022

Wow what an amazing collection of photographs and memories! Reading through this article I really felt as though I was there with you, right down to the rain on that first day!
I have never visited Tuscany and I will definitely be bookmarking this page to refer back to if I ever get there!
Thank you so much for letting me into your life and sharing your travels.

    June 8, 2022

    Hi Jo,

    Yes, indeed Tuscany is beautiful and so much to offer. Due to our limited time, we think we just scratched the surface and we also hope to visit the region again in the future. Which part of our short visit resonated with you most?

June 8, 2022

I’m in Aww, what such Beauty just in the pictures. Reading this wonderful article brought tears to my eyes and such Thankfulness to my heart for all the Beauty that God has made and preserved for us to enjoy and experience. Thank you so much for sharing! I would love to go there one day.


    June 8, 2022

    Hi Renea,

    Thank you for your comments. We are glad you liked the article as well as the pictures which we took and shared. Yes, we have so much to enjoy and experience in this world. Do you have plans of travelling soon? If you have further questions to help you decide, do let us know and we will try our best to answer them.

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