This ultimate itinerary takes you from the gorgeous seaside in Cinque Terre, to the bustling city of Florence, the dreamy Tuscan Countryside, and the beautiful mountainous region of South Tyrol!
Day 1 – Cinque Terre
Day 2 – Cinque Terre
Day 3 – Florence
Day 4 – Tuscan Countryside
Day 5 – Florence
Day 6 – Dolomites
Day 7 – Dolomites
Day 8 – Dolomites
I will start this with saying, we wish we had spent more time in Cinque Terre. However, we enjoyed this trip because we got to see diverse parts of Italy. From the seaside in Cinque Terre, the bustling city of Florence, the Tuscan Countryside, and the beautiful mountainous region of South Tyrol.
This was not my first trip to Italy, I studied abroad in Florence for a few months during College. I already had an idea of places I wanted to take my partner Greg to eat, but we were able to try new places and do different activities as I was not a broke college student this time just eating pizza and pasta for every meal!
Day 1: Travel to Cinque Terre
Day 1 – Travel Day: Pisa to Cinque Terre
We arrived late afternoon to Cinque Terre and had a beautiful seaside light dinner not far from the train station. We flew from Tampa-London-Pisa. We prefer to fly into the major airports and take the local airlines to our destinations when traveling in Europe.
Restaurant: Bar e Vini a Pié de Ma
After dinner, our Airbnb host kindly picked us up in Riomaggiore and drove us to our accommodations. This pic is from the backyard of the home! By far one of my favorite homes I have ever stayed in!
Day 2: Explore Cinque Terre
What we enjoyed in Cinque Terre:
Visiting all the Villages
We bought a Cinque Terre Day Pass which gives you access to foot trails and the trains between the villages. https://www.cinqueterre.eu.com/en/cinque-terre-card
Our Airbnb’s Dinner Party/Wine Tasting
You do not have to stay at the Airbnb to attend this! It was one of the most magical experiences, Emanuelle our host played live piano while we ate and drank around a table outside with new friends!
You can book it here: https://abnb.me/NSIXydr0G0
Hiking Around Cinque Terre
We hiked from our Airbnb into town, which was not for the faint of heart…I think we ended up walking 10+ miles this day because we were just so enthralled by the landscape!
Day 3-5: Florence and Tuscan Countryside
We took the train from Cinque Terre to Florence, we really enjoy the train rides because you can relax and view the scenery as you go from destination to destination. We took a high speed train which shortened the travel time immensely!
We stayed in a penthouse apartment across the street from the Mercato Centrale. It is a great central location for exploring the city!
What We Enjoyed In Florence:
Mercato Centrale – https://www.mercatocentrale.it/
It has tons of food options and shops with locally grown produce and cheese. There are even stalls where you can watch them make fresh pasta and mozzarella
All’antico Vinaio Firenze – https://www.allanticovinaio.com/
When I was living in Florence while I studied abroad, I went to this shop WEEKLY. It was our first food stop when we were in the city, it is just that good. Their sandwiches are unreal!!
Osteria Dell’Osso – https://osteriadellosso.it/#menu
One of our goals for our time in Florence was to have Bistecca alla Fiorentina. We had researched restaurants prior to traveling there, but when we smelled the steaks cooking from this restaurant (our apartment balcony was conveniently directly above it) we HAD to go. We split one giant steak and it was the best dinner we had in Florence. I will say this is not necessarily a -budget friendly- meal but it was worth every penny if you want to treat yourself!
Livio Pizzeria Napoletana – pizzerialivio.com
Visiting the Cathedrals
There are so many beautiful cathedrals throughout Florence, both the exteriors and interiors are detailed and remarkable!
Piazzale Michelangelo – Q778+52 Florence, Metropolitan City of Florence, Italy
I will forewarn you, it is a steep walk up to this, but the view is worth it! Grab a bottle of wine and head here to watch the sunset you won’t regret it.
The Biboli Gardens – https://www.uffizi.it/giardino-boboli/
The gardens provide one of the best views of Florence and are massive! It was a nice break from the bustling city streets.
What We Enjoyed in Tuscany:
Val D’Orcia: Cheese and Wine Tasting Tour from Florence
Since we did not rent a car this trip, we traveled mostly by train and foot. We wanted to do some wine tastings in the countryside, so against-our-norm we booked a tour that left from Florence:
We ended up really enjoying it, and this is perfect if you want to explore the countryside but do not want the headache of rental vehicles abroad! They gave us time to explore on our own which we loved and then we would do the wine tastings as a group.
Day 5-8: Dolomites
We took the train from Florence to the Dolomites. There is a bus transfer from the train station to take you into the villages or you can rent a vehicle. We stayed at the a wonderful Airbnb and the host met with us and provided us with tips on things to do and where to eat. We stayed in Val Gardena, but all the villages are so beautiful and have an assortment of accommodations.
What We Enjoyed in the Dolomites:
Biking Alpi di Suis
I recommend this for anyone planning to visit Alpi di Suis! It allows you to see so much more than you would on foot. 10/10 one of my all time favorite memories with Greg! There are tons of bike rental shops in each of the towns you can choose from.
Trying the Unique Cuisine
This is a Trio of Canederli dumplings. South Tyrol has unique cuisine and culture. Many people actually speak German in South Tyrol. It was once part of the Austro-Hungarian Empire, then was annexed to Italy in 1919, at the end of the World War I.
Visiting the Villages
Pictured below is Ortesei, but there are so many little villages to see in the Dolomites. We bought a shuttle pass which would take you through all the villages and take you on the ski lift up to Alpi di Suis! The prices vary depending what time you visit the Dolomites, we visited in the off-season and just prior to the ski season starting. You can find more information about the passes here:
On Day 8 we took the train from the Dolomites to Verona. Our flight departed from Verona-London. If you want to see more of the country, I recommend flying into one airport and then flying out of a different one as you make your way through the country!
Happy Exploring! – Morgan