The Best 9 Day Casual Itinerary For Italy: Tuscany, Cinque Terre, and Rome

The Best 9 Day Casual Italian Itinerary

Written by: Travel With Wally

Home Base: Pisa

Destinations: Florence, Cinque Terre, Siena, Pisa and Rome

Recently my dear friend came to visit me in Pisa. Aren’t friends simply amazing? I love my friends. I hold them close even when I am far away. I have to sheepishly admit that I am not always the best at communication with my far-away friends, but you know what? We always pick up right where we left off. We still love each other, care about each other, and think of each other.

I was so incredibly excited when my friend Sabrina told me she wanted to come and visit. I was so happy to have not just our first visitor but it was also one of my closest friends!

But then came the planning, which is both fun and stressful for me. Do you have that experience? Sometimes it is hard to put yourself in the shoes of a visitor. The things I now take for granted are actually incredible sights and experiences for a first-time visitor. I had to stop and rewind to when we first arrived in Italy. Where did I want to go first? What did I want to see? Do I want it to be a fast-paced, see all that you can Italian itinerary, or a more casual experience.

I don’t know if it happens to you, but when we move somewhere new it is always a bright new beginning full of opportunity and adventure. You get to explore new places and discover your new surroundings. But then I become complacent, numb to the greatness of our surroundings. That’s why it is so refreshing to have visitors remind you of what is so special.

I am trying very hard to keep Andrew and me busy discovering new places and experiences. We are the weekend warriors of travel. Even in places we have been before such as Florence, there are always museums to see, shops to visit, tours to experience. When we lived in San Diego, people that lived less than 5 miles from the ocean told me they never go to the beach. I am adamant that this won’t happen to us during our short 3-year stint in Italy. An epic Italian itinerary isn’t so difficult to manufacture after all.

Of course, traveling every weekend isn’t exactly feasible, especially on a student’s and teacher’s budget. But maybe once or twice a month, we can do that, right? I hope so.

Sabrina coming to visit was such a wonderful gift. Not only did we get to reconnect, but I got to rediscover many of the places I had already been to through the eyes of a first-time visitor. It was so much fun! I also learned and found new things that are close to us but I never knew existed (hello, spa!)

Days 1 & 2: Florence

The only input I had been given on what she wanted to do was a pasta class. Okay, I can handle that, those are everywhere! I booked a class in Florence on Airbnb. It wasn’t anything fancy but it was still fun and positively scrumptious. There was even a church across the street where musicians serenaded with song.

We made our dough using two ingredients, flour and eggs.

It’s amazing how simple ingredients can be kneaded into such delightfully tasty meals. Our pasta dough slowly turned into dishes such as ravioli, cappelletti, and taglietti. At the end of our class our group enjoyed our creations with homemade sauces and delicious wine. It was a warm and memorable experience.

Did Someone Say Cheese? Day 2

Another activity I wanted to share with Sabrina while in Florence was centered around wine and cheese. Our friendship had grown over the years while chatting and sharing wine and charcuterie boards in San Diego. So, really, how could she come to Italy and not indulge in Italy’s claims to fame?

I wanted to jump into the full experience, something that would allow us to experience the countryside, to see the countless vineyards scattered across the Chianti hillsides. I found this on Airbnb. The tour that I chose was named “The Secret of Wine and Cheese in a Winery.”

I had not used the Airbnb experiences option before this trip, but after the pasta class and wine and cheese tour, I highly recommend checking it out when planning a trip.

On Saturday we woke up after a late night of exploring Florence after dark. Of course it also included some wine. (If you ever have the chance, explore Florence after the sunsets.) Well, we slowly woke up and got ready for a day that would turn into a trip highlight.

After meeting our driver and other group members (including Leo the dog,) we clambered into the van and continued to the Chianti region of Tuscany. There were a total of five group members, which I loved. Small groups are so much more personal. You can get to know everyone, including the guides, much better than in a large tour group. It was such a pleasure to get to know other people from other countries, with a variety of backgrounds, but a shared passion for adventure.

Our first stop was an organic winery where we met our tour guide. He was excited to meet Leo, as he was the first dog to join the tour. Leo was welcomed with open arms and partook in all of the day’s activities.

When I think of a typical winery, I think of quaint little farms surrounded by vines dripping with grapes. But in reality, large production wineries are, well, big. Which makes sense after seeing it. Trucks filled with the day’s harvest of grapes come in and empty their bounty into vats that then separate the grapes from the vines and leaves. Then they are carried on to undergo other treatments to become one of Italy’s favorite wines.

Grapes being separated from leaves and vines

There are areas for many different types of wine production including prosecco, whites, and of course, reds. Chianti wine is named after the region in which it is produced, and not an actual variety of grape. The wines are continually checked and have specific time lines that must be followed before being bottled.

I learned that younger wines tend to have a more tart taste while the older ones smooth out their flavors. Also, our guide was clear that you should try your best to drink the most local wines that you can. This is due to the preservatives.

Preservatives are added to wines that will travel to far-off locations, such as Chiantis headed for the States. The wines that are provided to local markets and groceries tend to have fewer or even no additives, due to the probability of more timely consumption.

At the winery we were given glasses of their prosecco, a white wine, and several reds. They even have a delightful olive oil that I fell in love with. The pours were generous and the conversation rich.

Then it was back into the van. Little did we realize, the glasses of wine had just begun.

Our tour guide, stopped in one of the vineyards and we ate up the views. Tuscany truly is as beautiful as the pictures suggest. Down a short hill was an old farmhouse where we were warmly greeted and hosted for lunch.

Sabrina pointed out how wonderful it was to be having such an experience in such a place. It wasn’t fancy, it was real, it was local, it was authentic. We were being invited into a local’s home.

Another glass of prosecco, okay, maybe two.

Relaxing, soaking up the Tuscan sun.

And then it was time to eat. Do you like cheese? We walked into a smorgasbord of cheeses, bread, olive oil, melon, prosciutto, and fresh tomatoes. Sabrina and I looked at each other and smiled. We were in our idea of heaven. The wine continued to flow while we excitedly sampled the numerous cheeses. Hard, soft, flavored with truffle, pepper, and numerous others. Then came a surprise course of fresh pasta. I was about to start rolling across the floor like a puffer fish full of cheese. But it wasn’t over! Gelato and espresso appeared with a glass of dessert wine.

My mouth is watering while I write, it was such an exemplary experience.

The sun was starting to fall to the horizon and it was time for us to head back to reality, to awaken from our dream. At that point, the only reminder of it being reality was a full stomach and smiles.

Homeward Bound

We arrived in Pisa on the evening of our second day. The home base of our Italian itinerary. Tired and happy we were greeted by Andrew and Wally at the train station. After dropping off our luggage, we went out to drink some much-needed coffee. Did I mention that we also LOVE coffee? Gosh, aren’t Sabrina and I just a perfect match? I think so.

Day 3: Cinque Terre

As both of us are lovers of the sea, I knew this was a must see for Sabrina. She just didn’t know it yet. It was automatically added to our Italian itinerary

Cinque Terre sits along the Ligurian Sea in the province of Liguria. Just north of La Spezia.

You can find out more about Cinque Terre, hiking, and how to get there HERE

There are, you guessed it, five villages. All part of a world UNESCO site and National Park. They are simply stunning, each in their own way. They consist of Manarola, Vernazza, Corniglia, Monterosso, and Riomaggiore.

The villages reach into the crevices and up the sides of the ocean cliffs and are surrounded by vineyards and country spotted by villas clinging to the steep cliff sides. Originally fishing villages, they are now primarily funded by tourism, and it is not hard to see the allure.

Originally we had thought we would hike between the villages, but due to personal reasons, we opted for the train and ferry instead. We also had added to our pack of travelers–our friend Mustafa was joining us. Four years in Pisa, and yet to visit Cinque Terre? That is just not acceptable in my book. He had to come.

We also brought our trusty side-kick, Wally the dog. Cinque Terre is very dog friendly, as are the trains, trails, and ferries. We try to include him in all possible Italian itineraries.

We exhausted ourselves by wandering the various villages. Stopping for coffee in each location was a must, and we were able to find our new daily dietary requirement, cheese.

How do you like to enjoy your fine cheeses? I have developed a preference for jams and honey on a crispy cracker. Oh how my midwestern friends must be rolling their eyes.

My favorite village is the one most overlooked by tourists for its small size and more difficult accessibility. It is the village of Corniglia, the middle of the five, sitting above the sea. It lacks easy sea access, and therefore the ferries do not have a port to stop at. From the train station you must climb a long switchback of stairs to reach the top.

Because of these added difficulties, and the small size of Corniglia, it is not as heavily frequented. I love the lack of large crowds and the small winding streets. Being able to hike in on the vineyard-lined trail is also a very special experience.

Four villages in, and we were drained of energy. We decided to leave Manarola for her next visit. Back to Pisa we went.

Day 4: A day in Pisa

Needless to say, we’d had wonderful but long tiring days. So it was nice to have a relaxing start to our morning before venturing out for a slow day in Pisa.

It was Monday and Andrew had to work, so Sabrina, Wally, and I headed out the door towards more coffee. Because we were headed towards the Leaning Tower, I wanted to bring her to one of my favorite coffee spots in town, Filter.

Some days I miss the variety of coffee sizes and flavors that can be found back in the U.S. And Filter is able to deliver these. I was excited to get on board the fall-themed wagon and get a classic pumpkin spice latte. Filter definitely has a leg up on Starbucks in regards to this specialty coffee. YUM!!

After a delicious little brunch accompanied by excellent conversation, we headed on towards the tower. You can’t visit Pisa and not visit the Leaning Tower! Plus Wally is a huge fan of the grass by the Baptistery. Lucky for us the drizzly weather was deterring many tourists from the site and we were able to enjoy the view of the Field of Miracles without the crowds.

It truly is beautiful. The white marble and the Roman arches create for a glorious site across the three structures. Tower, cathedral, baptistry. The Field of Miracles.

Free and affordable things to do in Pisa, Field of Miracles

Gelato break! One of my favorite gelaterias in Pisa is located near the tower and is adjacent to a beautiful park. It has a sister shop even closer to the tower but I have yet to visit the smaller location. Rufus hosts several freshly made flavors of gelato, including my favorite, pistacchio.

Check out my list of favorite Gelaterias in Pisa HERE

Sabrina and I enjoyed our cones on what had become a drizzly afternoon. We discussed what activities we would like to do later in the day as well as the following day. We were both tired from our previous days of adventure, and weren’t sure if my plan of going to Siena the next day was what we wanted. Then she came up with a great idea.

A spa day! I had never gone to a spa, other than a random massage here and there for various injuries. Maybe going to the beach is like a natural spa with the exfoliating sand and soaking in a giant salt water bath. But I was intrigued by the idea of the real deal.

And so we began to search for a nearby spa. To our surprise there was a glamorous spa only one town away from Pisa. Pools fed by local hot springs, luxurious massages, and rejuvenating treatments? We couldn’t resist. I was giddy with excitement,

Looking for more free and affordable things to do in Pisa? Check out our post!

Day 5: The Spa

San Giuliano Terme is a small village just North of Pisa. It is a short 10 minute train ride away, making it easily accessible for those of us without cars. Andrew and I had previously ventured through the small downtown on our way to a nearby hike.

Little did we know that we were also passing the very spa where Sabrina and I would enjoy a very pleasurable afternoon in the near future. Are you waiting to hear the downfall, the disappointment? Well, the closest we get to that is one lost credit card. Sorry!

The great thing about a casual Italian itinerary is that it can be easily modified. Instead of Siena, we opted for the SPA and pushed Siena back a day.

The spa is Bagni di Pisa. It has a plethora of treatments, pools and even retreats. It is mostly frequented by locals and those partaking in the retreats. They have family-friendly treatments, couples massages, and even an option to simply enjoy the pools for the day.

To our surprise, we were even able to get a somewhat self-service scrub and mud treatment, which was included in the price. Score!

Another great discovery we made there was the bar. We never imagined that we would walk into the bar for lunch and be wowed by red velvet chairs, mosaic ceilings, and just pure class. The bartender was so kind and fun. He served us his pick of white wines followed by delectable cocktails to be enjoyed by the pool.

This Midwestern farm girl was out of her element, but in the best way. Spoiled and loving it. My mom called me while we were at lunch and laughed at the thought of her daughter lolling around at a luxurious spa. It wasn’t so long ago that I was covered in mud and picking cold potatoes out of the ground.

Day 6: Siena

Oh how I love Siena. It is old, it is charming, it is beautiful. A day in Siena is nothing short of perfection. Other than perhaps the crowded shopping streets, but even then, it is easy to find quiet alleyways that lead you back and forth throughout the medieval city.

Going to Siena was always on my to-do list for our Italian itinerary for Sabrina’s visit. I just knew that Sabrina would enjoy it and have a wonderful time. I think I was right. With a midday start, we headed to the hilly and medieval city. The train brought us to Empoli, where we caught another train to Siena.

On our previous trip to Siena, Andrew and I had focused on exploring the city. We avoided the main streets and headed toward the areas that were a little bit more secluded or off the beaten path. We had also had Wally with us and wanted him to enjoy his time as well.

This time around, we focused on shopping! We barely made it to the Duomo as we were distracted by leather shops, stationary stores, and tasty restaurants. This was a bit more of an indulgent trip than before. I mean, Christmas is coming, we needed to find gifts…

The leather in Tuscany varies in quality, but the good quality leather is buttery soft and sewn into bags, jackets, wallets, and more with expert craftsmanship. Sabrina purchased two beautiful backpacks as gifts for her family, and I picked up some leather-bound notebooks.

To find out about how to have the perfect day trip to Siena, click HERE

Oh does time fly, it just slips through the cracks and you don’t even realize it is gone until it is too late. Needless to say, we missed our train.

Days 7-9: Rome

Rome, what can I say. It really is a magical city that has it all. History, food, shopping, nightlife, oh and did I mention history? It is so old! Around every corner is something ridiculously old and stunningly beautiful. The ancient Romans really knew what they were doing when it came to infrastructure and art.

I just don’t think I can write enough about how much we loved Rome. Andrew was able to accompany us on our Roman holiday, and we had a blast.

Our little trio arrived in Rome via the train, a mere 3 hours from Pisa, midday. I was in no way impressed with our first glances of the city. But train stations tend to never be in the heart of the city, surrounded by beauty. They seem to be shoved to the outskirts and surrounded by the city’s grime. I suppose that makes sense, but it is still too bad for first impressions.

We stowed our bags and searched out some much needed lunch. I am sure you have heard the term “Hangry” which simply translates into “angry when hungry”. And I unfortunately fall into that category, luckily Andrew has learned to read the early signs and knows when we need to find food even before I do.

We found a quirky little restaurant not too far from the station and enjoyed a pizza and a bottle of wine. How very Italian of us, right? If you didn’t notice, we really jumped into the stereotype for this trip.

Unfortunately I cannot recall the name of the restaurant we ate at, but don’t worry, there are so many choices, you are sure to find something delightful.

Looking back I may have changed the order of operations for this part of our great Italian itinerary. We had stored our bags at a kiosk in order to explore a bit before heading to our hotel as we had arrived prior to check-in. I should have thought about the fact that there isn’t always a lot to do around public transportation stations.

I think I would have gone straight to our hotel location and found some lunch. Then by the time we were finished it would have been time to check-in, rest for a minute, and then head out for some exploration.

Lesson learned? I am impatient and a worrier, I knew that already, not something I love about myself but it’s just a fact. (I am working on it.)

Public transportation in Rome has a reputation, and not a good one. They only have two metro lines, their buses catch on fire, and buses are notorious for being late (if they even show up at all.) Luckily, we were staying near one of the metro stops near the Vatican.

Our hotel was a self check-in and located maybe two blocks from Vatican City on a quiet and very cute little street. I had been crossing my fingers that my budget-friendly find would be worthy of our visitor and I think that other than a lack of privacy, it was worthwhile.

Note: Something interesting and sometimes frustrating that I have learned about hotels in Italy, is that they do not always have people manning the desks or even working. We have had several occurrences where we had to communicate our arrival time in order to be greeted by the hosts. And these are hotels, not Airbnb’s.

We settled in, took a little rest, and then headed out to do a bit of exploring. We didn’t go far on our first day, but that doesn’t mean we didn’t see a lot. The Vatican is beautiful and St. Peters Square offers wonderful views.

The Tiber River flows through the city and hosts beautiful bridges connecting its banks. There is a bike path that follows the banks of the river, a local friendly way to get close to nature. Andrew and I walked along part of the river gazing at the bridges and enjoying the fall air.

The next couple of days were going to be packed full of sight seeing and unforgettable experiences.

We had so many wonderful experiences in Rome that I have compiled a list of our top recommendations and notes about lessons learned. I hope that this can be helpful for your Roman holiday.

Top recommendations in Rome

To See: Of course the main attractions are a must. These include the Colosseum, Trevi Fountain, The Pantheon, The Vatican, etc. But just like many Italian cities and villages, it can be just as rewarding to wander the side streets. You can find ivy-covered buildings housing adorable cafes, twinkle lights hanging across the street, and just a quieter atmosphere away from the touristy hustle and bustle.

One of our favorite places that we visited was the Trastevere neighborhood. A trendy yet quaint neighborhood that reminded us of other smaller villages we have visited. At night it becomes full of young people who are ready for a fun night out. This wasn’t quite our scene, but during the day we had a lovely time.

To Tour: The Colosseum dungeons at night. This is the only tour that we did. We were signed up for a daytime tour, but it was overbooked and we got one of the last spots on the 9:20PM tour. It was AWESOME!! You are brought down to the bottom level of the Colosseum which dates back nearly 2,000 years!

Parts of the building have been restored but largely it holds its original stone work. It is incredible that something that was built so long ago and in under 10 years, could still be standing.

It was humbling to walk where the gladiators and enslaved people walked, where animals were housed, and history was built. The wooden stage rotted away long ago, but you can still imagine the stands filled with fans, both rich and poor, cheering over the fates of the fighting men below.

To Eat: Giggetto. I cannot say enough good things about this restaurant. It is located in the Jewish quarter next to the old mosque. It was recommended to us by a local cab driver. It has Andrew’s favorite caccio e Pepe, fantastic seafood risotto, suppli, fish cakes, and fried artichokes. When you go inside there is an employee trimming fresh artichokes for the meals. So you know it’s fresh!

Find the menu and other information HERE

Shopping:

High End: If you are looking for high-end shops, then you will want to head toward the area around the Spanish Steps. We didn’t spend a lot of time here, we were a bit out of our comfort zone, not to mention our price zone. I didn’t even stop to look at the menus in this area for fear of what I call “Price Fainting.”

Leather: As we traveled, Sabrina was looking for souvenirs and simple gifts for her family and friends back home. When she discovered the beautiful leather that is available in Italy, that is what she gravitated towards. She is going to have some very happy recipients back stateside. I have to admit that the leather goods are truly beautiful.

Rome is full of beautiful leather shops. The front of the shops tend to have the cheaper and lower quality leather and as you move toward the back you will find the higher quality and even more beautiful items. I highly recommend adding a leather shop or two to your casual Italian itinerary.

One of our favorite finds was actually directly next door to where we were staying on Borgo Strada. But you can find them in various places across the city including the Jewish Quarter.

Tips:

Pre-book your tickets!!! I learned my lesson in this area. Rome is busy, it is crowded, there are always tourists. If you want to visit places like the Vatican/Sistine Chapel or the Colosseum, then I HIGHLY recommend that you pre-book your tickets.

We didn’t get to see the interior of the Vatican, which really made me sad. We are part of the lucky few that can return to Rome, but for many this is a once in a lifetime experience and I don’t want you to miss out. You can book tickets for the Vatican and the Colosseum online, this includes tours. The Vatican even has a happy hour tour!

Vatican Tickets: HERE

Colosseum Tickets: (Usually also include Roman Forum/Palatine Hill) HERE

Be ready for ticket scalpers that want to sell you tickets at an inflated rate. You will also come across people coming up to you and trying to sell you useless trinkets, selfie sticks, lighters, etc. Just say, NO. They will keep trying, but walking away and saying no will let them know you aren’t going to give in. Don’t give in, stay strong! For some reason, they tended to gravitate towards Andrew and try to get him to buy things. So perhaps men are targeted more than women–at least that was how it worked out for us.

Ask your cab drivers for recommendations. We were taking a taxi from the colosseum to the Trastevere neighborhood and asked for a lunch recommendation. It turned out to be one of the best restaurants we have been to in Italy. Located in the Jewish quarter.

Saying Goodbye

Early on Sunday morning, we had to say goodbye to Sabrina. I was going to miss her, but I knew I was lucky to have had those nine days together. Goodbyes are always hard, but it gives us a chance to have another hello in the future.

Travelling and experiencing Tuscany, Cinque Terre, and Rome with Sabrina was an incredibly special experience for me. I will always remember it and I learned a lot about what is just outside our door. That is something I love about having guests. They introduce you to what you may have overlooked.

I hope that you can take some of these adventures and make them your own. This Italian itinerary is just one of many that can belong to you. Italian holidays and adventures are waiting for you.