How to Experience the Best of Tuscany in 8 Days

Rolling vineyards, medieval hilltop towns, Renaissance art, and world-famous cuisine—Tuscany and Florence uniquely blend history, culture and stunning scenery. Whether sampling a red wine, getting lost among the incredible architecture or indulging in mouth-watering gelato, there are unforgettable moments around every corner.

This comprehensive itinerary will guide you through the best of Tuscany and Florence. From the iconic sights of the Duomo di Florence and Ponte Vecchio to the charming Siena, San Gimignano, and Pienza. Along with planning tips on how to make the most of your time in the Italian countryside. This is an 8-day itinerary that can be easily modified for a weekend away to a multi-week trip. Prepare yourself for breathtaking landscapes, rich history, and a feast for all the senses. Let’s explore the heart of Italy!

Why Tuscany?

Italy is an incredibly diverse country with an attractive capital of Rome with all the Roman history and culture. The Alps and Dolomites are my natural draw to the mountains with the Alta Via 4 Trek being a highlight. Cities such as Venice attract people worldwide for its narrow canals. The southern regions of Naples and Sicily offer warmth and coastal towns. However, since doing a day trip to Florence from Rome in School, I’ve always wanted to return as an adult! The Tuscany countryside is beautiful and films such as Gladiator only add to the desire to visit. Renowned for being a wine region, the vineyards and medieval towns add to the laid-back lifestyle. Staying in an Agritourism (Accommodation on a working farm) is a wonderful experience and helps you appreciate the simpler things.

Itinerary

Tuscany Map

Planning Tips

What to see?

Controversially, the Leaning Tower of Pisa is not included on this list as I’ve had mixed recommendations about visiting. And this itinerary focuses more on South Tuscany instead of visiting Pisa, Lucca or the charming coastal towns. Florence is a must-see being the largest Tuscany city and ever popular with tourists flocking to see the history, and art plus indulge in the cuisine. Sienna is a medieval bricked city that has a magnificent Cathedral, the Piazza del Campo and Torre del Mangia to see. San Gimignano was my favourite town to visit with its ruined towers and the best gelato in the world! Finally, Val D’Orica and Pienza is a picture postcard of Tuscany and white tracks to explore among rolling hills.

Where to stay?

We stayed in Castlemuzio near Val D’Orica to start because the countryside views from the olive grove were very attractive. A 90-minute drive from Florence and many lovely towns surrounding it such as San Quirico d’Orcia, Pienza and Montepulciano. Hotels are available but for an authentic Italian experience, then stay in an Agritourism. This type of accommodation is on a family-run agriculture farm (a vineyard or olive grove) and has fresh products usually. Then we spent 2 nights in an apartment in Florence via AirBnB to give us easy access to the city. Florence has an abundance of accommodations for every budget, good transport links to Rome and an international airport.

Transport

The easiest way to navigate and fully explore Tuscany is by hiring a car. Public transport is limited and irregular for visiting the remote countryside towns. If you’re only staying in Florence, then you won’t need a car and could book a day tour to Siena, Pisa and other attractions. We used Zest to research the different rental companies and used AutoVia where we picked up from the Airport.
Tip – There is a free airport shuttle to the rental companies

When to visit?

The best time to visit would be Summer time but most places with swimming pools didn’t open them until June. So if you’re looking for a villa to relax by the pool then wait but be prepared for the higher prices and temperatures. We went in May which had a nice balance of warm sunny days and cheaper prices and fewer tourists too. Tuscany has things to offer all year around but be aware of Italian public and school holidays.

How long to visit?

The 8-day itinerary is adaptable for longer visits to explore northern Tuscany such as Pisa, Lucca or the Coastal towns. However, focusing on just Florence and then a long weekend would be enough. We felt that we covered most of the main sites in 2/3 days around the city. It’s easy to combine Tuscany with a trip to Rome as well!

The Itinerary

Day 1 – Castlemuzio

The start of our Tuscany adventure was rushed after oversleeping and needing to drop the car off at the Airport. Luckily it all worked out and before long we were boarding the flight to Florence (Amerigo Vespucci) Airport. Florence was sunny in early May when we arrived mid-morning and we quickly found the shuttle to the Car Rental. We had to queue for an hour to collect the rental car (VW T-Roc) and then hit the roads. I had the first challenge of navigating out of Florence and adapting to driving on the opposite side of the road. Soon we were away from the traffic and motoring towards the beautiful countryside of Val D’Orica for 90 minutes.

Castlemuzio

Castlemuzio is a small hilltop village near Pienza (12 min drive) and in the province of Siena. It’s a fortified and well-kept medieval settlement with stunning surrounding views of the famous rolling Tuscany hills and fields. We stayed in an Airbnb cottage in an olive grove downhill from the main town. This gave us space away from neighbours and amazing views of the scenery. Castlemuzio has minimal shops, cafes or restaurants which suit us for self-catering. We went to a supermarket in Siena when driving down to buy groceries to self-cater. Then popped into shops in Sinalunga near the motorway to stock up.

Day 2 – San Gimignano

The first full day to go explore and my number one destination to see was San Gimignano. The medieval walled hilltop town is known for its stone ruined towers such as the iconic Torre Grossa. I was first inspired to visit San Gimignano because of playing Assassin’s Creed 2. It took an hour to drive over and we found free parking outside town at Via Antonio Gramsci then walked 10 mins to the town entrance. Be prepared for lots of other tourists in the narrow streets! Shops are selling local produce and products along with many souvenir shops around. As you head to Piazza della Cisterna Square, you’ll find a long queue. My advice is to join it ASAP and then savour the delightful gelato of Gelateria Dondoli.

I recommend walking to Punto panoramic which offers fantastic views of the dozen towers and surrounding countryside. San Gimignano has Romanesque and Gothic architecture stules to appreicate. For lunch, we picked up slices of Pizza from the affordable and tasty RiccaPizza – San Matteo We ate them on the steps outside Duomo di Santa Maria Assunta basking in the sun. After hours of fun exploring the picturesque town, we said goodbye and drove back to Castlemuzio. The Airbnb had no WiFi (not deliberate when we booked) so we relaxed outside with our books and a glass of local wine. A homemade dinner eating Al Fresco with a vibrant sunset was a perfect end to the day.

Day 3 – Montepulciano

Cooking Class and Wine Tasting

For Roisin’s birthday, I gifted her a Cooking Class with the Chef at Tiberini in Montepulciano. This was located at Tiberini Vineyard where we spent the morning learning to cook authentic Pasta and Tuscan dishes. Professional chef (Samuel) and Grandma Dima supervised and guided our experience. It started by meeting the welcoming Tiberini family over an Espresso before starting to prep veg and slow cook the main course. Then the fun begins by making 2 different types of Pasta, an Egg Pasta Pici and a Flour-based Ravioli. It was incredible fun rolling out and making the pasta with light competition and sampling the wines from the vineyard as we cooked. It wouldn’t be an Italian cooking class without learning how to make Tiramisu!

Once the cooking was complete, we had a tour of the wine cellar and making process (unfortunately it was raining so not through the vines themselves). The Tiberini family enjoyed our cooking skills for lunch along with bottles of wine. The dishes were very flavoursome and (unbiased of course), my Spinach and Rocotta Ravioli was the best. Every dish was paired with a Tiberini wine to appreciate different flavour profiles and combinations. The owner of the Vineyard, Luca, was a wonderful host and very wise as he taught us about the laid-back Tuscan lifestyle and how to appreciate the simple things in life. After many glasses of wine and a great lunch, we brought several bottles and said farewell. This experience made my Best Travel Moments of 2024 and I would highly recommend the Tiberini vineyard!

Montepulciano

After the vineyard tour and cooking class, we went to see Montepulciano despite the rain and inbound storm. Montepulciano is a medieval and renaissance hilltop town known for its world-famous wine-making region. In particular, the Vino Nobile red wine is what the town produces best. The walk up the cobble streets is fairly steep towards the main square with wine shops seemingly everywhere. There are some great viewpoints of the vineyards all around Montepulciano that are worth seeing around town. The drive from Montepulciano was precarious due to a thunderstorm and torrential rain along the sweeping narrow roads but luckily quiet. We had another quiet evening after a long day out and cooked a simple homemade meatball dinner.

Day 4 – Pienza & Val D’Orica

Val D’Orica Gladiator Run

I was most excited about visiting Pienza to see Val D’Orica in full. The weather was perfect to get photographs of the landscape made famous by Russell Crowe in Gladiator. The plan was to drive the 10mins to Pienza and then run along the gravel tracks to the viewpoints and get some pics with our phones (No Fujifilm for this one). We jogged through the beautiful Pienza and found our way to the Corsignano Church before trail-running down to the famous photography spot. It was one of my favourite runs along the tracks with the green fields, cypress trees lining the roads, blue skies and hills in the distance. After the rain, however, we didn’t expect the track to turn to shoe-coating clay and turned the run into a trudging walk. Eventually, we reached the next road as the day warmed up and enjoyed a gentle pace back to Pienza.

Tip: Go Early for Gladiator Photos! We ran at 7:30 and beat the crowds there

Pienza

After our run, we got changed at the car and then walked back into Pienza for a much-needed café stop. La Posta has a prime location where we enjoyed coffee and pastries sitting outside for a reasonable price. The reviews aren’t great but our experience was good to people watch and soak in the sun. We walked around the small town and narrow streets before retracing our tracks of the run to get a view down towards the Gladiator spot and take photographs of the Val D’Orica valley. We didn’t stay too long as the rest of the day was a planned rest and recovery day around the cottage and Castlemuzio.

A hearty and healthy breakfast back at the Airbnb was necessary to refuel and we started to love the Bialetta Mokka pot coffee. The rest of the day was very relaxing where we lay on the sun lounges among the olive trees reading books. We enjoyed some Limoncello and Fanta in the afternoon while listening to music and taking things slower than I’m used to. Most of my trips are maximalist where I plan to make the most of each day whether hiking or in cities, so it was enjoyable to have a relaxing day (post 10K run). We wandered up the steep track from the olive grove to Castlemuzio to stretch our legs and then enjoyed another quiet evening of cooking, wine and relaxation.

Day 5 – Sienna

Sienna

Our last full day staying in Castlemuzio and there was one final place to visit in South Tuscany. Siena is a must-visit city and only an hour’s drive from Florence. The main attractions are Siena Cathedral (Duomo di Siena) and the fan-shaped Piazza del Campo with the gothic town hall and Torre del Mangia. Also, the Fortezza Medicea (walled fortress to walk around), Palazzo Salimbeni (gothic palace) and Fontanina Contrada dell’Oca (ancient fountain) are interesting things to see when visiting. There is an abundance of shops and an equal amount of tourist groups to fight past. Whilst we visited we didn’t go inside the Cathedral due to the long queues or up the tower but it’s a very pretty city to roam around.

The car park was under the train station which had very cheap parking for the day (only 2 euros!) with a 30 min walk into town after going up the escalators in the shopping centre all the way up. There is a supermarket and toilets in the shopping centre above which was convenient before heading into the city. For lunch, La Piccola Ciaccineria was chosen and delivered amazing pizza and ciaccine for cheap prices! We then walked to Gelateria Artigianale for ice cream and I was surprised it wasn’t more popular or had more reviews.

Giro D’Italia Cycling

The afternoon was spent at the side of a gravel track waiting… for context, I’m a road cycling fan and after we booked our Tuscany trip, I found there was a stage of the Giro D’Italia only 45 mins away. It was a “Strade Bianchi” stage which means instead of tarmac, the professionals would be racing along white gravel tracks. So I persuaded Roisin to spend the afternoon soaking up the sun and atmosphere with hundreds of other fans. We patiently waited and got fantastic photographs of the riders and the action. It was a full day out by the time we walked to the car and drove home to our cute cottage. The evening was a treat of wine with more Al Fresco dining outside before we started packing our bags to speed up the next morning’s check-out.

Day 6 – Florence

The day started with a 7Km run from Castlemuzio to Petroio and back along the road. It gave us great views of Castlemuzio and over to Pienza in the morning sun. After a last breakfast in the Airbnb, we packed up the remaining food and our bags into the rental car. We checked and cleaned the cottage before handing the keys back to the owner who gifted us a small sculpture made from olive tree bark (a challenge to transport home!). Then, we drove the 90mins along the motorways back towards Florence Airport to drop off the rental car back to AutoVia which was a simple process. Finally, we grabbed the bags and got the shuttle back to the airport terminal before buying tickets for a tram into the city. The tram was packed for the full 30min journey into the city centre as we finally arrived in Florence.

Florence

The first step was to drag the suitcase through the streets and over bridges to our Airbnb for the next few days. We stayed on the south side of the river with a 20min walk back to the central attractions. The studio flat had everything we needed for a base camp and before long we were ready to explore the wonderful city. It was 25 degrees to help cool off we headed to Gelateria dei Neri for delicious ice cream but not quite as good as San Gimignano! we booked an afternoon walking tour starting next to Basilica di San Lorenzo to learn about the history of Florence. but first I was desperate to see the Cathedral of Santa Maria del Fiore. The grand and imposing Cathedral with its famous Duomo and Tower is an absolute must-see.

Tip- Be aware of pickpockets, particularly around the Cathedral! With lots of groups of tourists taking photos, it’s a prime location for theft

Walking Tour

I enjoy free walking tours to learn about the history, and culture plus to pick up tips from a local guide. This tour, booked via GuruWalk, started next to Basilica di San Lorenzo and explained the origins of Florence with its connections to Rome and the influence of the Medici family. Next at the Cathedral of of Santa Maria del Fiore, we learnt about the construction of the ground-breaking Duomo, Cupola and, Bell Tower The tour showed local restaurants and medieval buildings to visit. The walking tour finished at the Piazza della Signoria with Palazzo Vecchio and the replica Statue of David outside. We learnt about the art history of the city and the secret tunnels connecting the city to Palazzo Piti via Ponte Vecchio. After the tour, we headed back to the apartment to cook leftover pasta with homemade bruschetta and tried to finish off the Limoncello.

Day 7 – Florence

Florence Morning Run

A new concept we tried was a running tour of Florence for the places we hadn’t seen on Day 6. Starting off along the river then chose to walk up the steep steps to Piazza Michelangelo for an incredible panoramic of the city skyline and very quiet compared to later in the day (stay tuned). Next, we crossed the river and headed towards the Basilica of Santa Croce for a photo stop. Then ran through Piazza della Signoria and up to the Cathedral which was quiet at 7:30. Next, we ran to Basilica of Santa Maria Novella before continuing up to Lidl to pick up some stuff and finished with a nice finish back over the river for a complete 10K.

Basilica of Santa Croce

After the run, we went to Wild Buns Bakery which serves mouth-watering Scandinavian pastries and breads. Plus it was opposite the apartment which helped keep the coffee warm for breakfast too. The plan for the day was to visit the Basilica of Santa Croce in the morning and then we had Duomo & Bell Tower tickets booked in the afternoon before dinner. First, we walked over the crowded Ponte Vecchio to the Basilica and weren’t turned away. There is a dress code to make sure you’re properly covered up which saw many tourists not get entry which was only 8 Euros. The Basilica is home to famous Tombs & Monuments such as Michelangelo, Galileo, Machiavelli, Alfieri, Rossini and Foscolo alongside Brunelleschi’s Pazzi Chapel and Donatello’s sculptures, a real gem of history. The Cloister and chapels are beautiful and worthy of a visit.

Cathedral of Santa Maria del Fiore

Afterwards, we went in search of lunch and avoided the hyped-up All’Antico Vinaio; instead, we went to La Schiacciata next door which had a much shorter queue, huge sizes and arguably better Schiacciata! We roamed the city until we collected the Duomo climb tickets, the Cathedral itself is free but to climb the Dumo or Bell Tower required tickets. I would recommend the Brunelleschi Pass (30 Euros or £25) which includes access to the Baptistery of San Giovanni, Giotto’s Bell Tower, Brunelleschi’s Dome, the Opera del Duomo Museum and the ancient Basilica of Santa Reparata.

Tip– Book the Cathedral tickets from the official website and a few weeks in advance as it books up fast! We were late so paid more via a 3rd company but still got to experience the unbelievable Cupola and city views.

The climb up the Dome (Cupola) is time allocated whereas the rest of the Piazza del Duomo attractions are valid until 3 days later. It is 453 steps and is only for physically capable people. However, the exercise to reach the viewing platform is the 2nd best view of Florence. The obvious viewpoints are the Bell Tower and the reverse view of the Cupola from the Tower puts the engineering masterpiece into scale. It’s a narrow walkway and even with limited visitors, it’s crowded at the top as seen above. Why stop climbing there after the Cupola climb when Giotti’s Bell Tower has 414 steps to scale next? Afterwards, we deserved a well-earned drink so we stopped at La Petite near Piazza della Repubblica. We had a delicious meal at La Bussola close by where I had the best Italian Pizza along with a lovely bottle of Montepulcino red wine.

Piazza Michelangelo

Instead of desert, as tempting as the Tiramisu was, we spontaneously decided to rush over to Piazza Michaelangelo in the hope of seeing the sunset over the city. We caught the sun setting over the river on the Ponte Vecchio before a fast hike up the hill to join the crowds. We managed to squeeze into a viewpoint and watched the pastel-coloured sky in the background of the landmarks- the best view in Florence! The photographs were incredible and felt most people had left too soon once the sun had dipped behind the hills. There were some live musicians on some nearby steps so we enjoyed the music, sunset and atmosphere of all the people gathered at the Piazza. On the way back to the apartment, we searched for a Hole in the Wall bar however we were too late unfortunately.

Day 8 – Florence

Our last day in Florence was a relaxing one which started with a long morning walk exploring the outer areas of Florence. For the second day, we dropped by the Wild Bun Bakery to try some different pastries from Day 7. Breakfast involved finishing off as much as possible before we packed the suitcase and bags before Check-Out. To not be weighed down, we dropped off the suitcase at a luggage store near the Train Station. Then we walked over to il Mercato Centrale Firenze to see the market and went in search of souvenir magnets. We scouted out the lunchtime restaurant before finishing off the souvenir shopping. To save on buying food at the airport, we bought Foccacia at L’Officina degli Antellesi which was only second to La Schiacciata. We had some spare time to kill so we visited a park to read our books in the sun.

Trattoria Za Za was the last restaurant before leaving and were glad we reserved as there was a long queue otherwise. I ordered a linguine mushroom dish with white wine and Roisin had a Ragu & Pici pasta with an Aperol Spritz. The flavours backed up the top ratings online and I would highly recommend it for Pasta! Afterwards, we fancied one last gelato to finish the trip so found Gelateria Artigianale La Sorbettiera. The best ice cream in Florence with its silky smooth and delicious with reasonable prices and a good selection! It was then that time of the trip to collect the suitcase from the storage, jump on a tram and head to the airport. Our 8 days in Tuscany were full of memories and a place I will be returning to for sure!

Budget

Italy is not the cheapest destination so be warned! It can add up very fast when tempted by the delicious food (see below how to spend your money) and incredible drink. And add on top all of the attractions and museums that could be visited, it’s easy to live a life of luxury and culture. The most expensive experience was the pre-booked Cooking Class in Montepulciano costing £150 each then the Florence Cathedral Duomo and Tower climb at £40 each. Our approach was to self-cater in the Agriturismo so we bought 6 days of food at Lidl in Siena. And whilst in Castlemuzio, we didn’t eat out at restaurants, instead got quick food to go and then enjoyed several lovely meals out in Florence.

The 2 Airbnb’s were good value at £50 a night each with the prices below for 2 people splitting the cost. The flights worked out reasonably well as we shared a 25kg Hold Bag for clothes. To get the best of Tuscany then a car rental is advised to give maximum flexibility. As mentioned, Zest is a helpful website to filter the options from global companies (Hertz, Enterprise or Europcar) to local Italian providers (AutoVia or Alamo). It cost us £120 for the 5 days with no additional cost for a 2nd driver with AutoVia and 50 euros to refill petrol.

Italian Cuisine

It wouldn’t be an Italian travel guide without mentioning the cuisine. I’d travelled to Venice & Dolomites before where I enjoyed my food but in comparison, the Tuscany food was streets ahead. The quality of the produce and the simplicity of the dishes were a refreshing contrast to other cuisines. Even the groceries from supermarkets were affordable and made into great homemade meals. We visited a famous wine region so rightfully had to try a few bottles which helped convert Roisin to liking red wine. Below is a summary of my favourite Food & Drink:

Not Quite Renaissance Art

Lessons Learnt

• Beauty – The main attraction for me was visiting Val D’Orica and seeing the rolling Tuscany hills around Castlemuzio. The weather was perfect with lots of sun and blue skies in May which added to the beauty. The hilltop towns were charming and I loved the medieval style. And there are jaw-dropping Cathedrals, Basilicas and Piazzas to admire and photograph.
• Food – As explained, the cuisine is on another level with the best pizza, pasta and ice cream I’ve ever had! It’s not the cheapest place for food but the quality is very high with many top-reviewed restaurants and places to eat, dine and drink.
• Running – A new one for 2024 was to do running tours of cities and landscapes. The Florence 10K run in the early morning gave a quiet tourist-free city to explore. And the Tuscany runs along the hills and tracks were relaxing and easily distracted by the panoramic views.
• History – Florence and Tuscany have a rich history and link to the Renaissance era. With so much art and culture linked to this period and still some Roman influence too. The history of the Medici family and the Cathedral of Santa Maria del Fiore was of personal interest.
• Relaxation – The aim of this trip was to relax and rest up but I learnt I’m not very good at having a day off! We only had Day 4 afternoon of reading, sketching and sunbathing but would happily do more if the accommodation had a pool and we had longer.

Final Thoughts

Tuscany has been a bucket list trip of mine for many years since playing Assassin’s Creed as a teen. And by making it a road trip with Roisin and then staying in a cute cottage with epic countryside views, it was perfect. The cuisine is first-class, there is so much to see and do in the Tuscany towns. Or kick back and relax at an Agriturismo with some wine and a book. Florence is one of my favourite cities I’ve visited with incredible history, architecture and culture.

Where is your favourite place to visit in Tuscany, Italy? I would love more recommendations for my next visit! If you’ve enjoyed this blog then please share it with others and subscribe to The Journal – monthly newsletter.