TUSCANY ROADTRIP ITINERARY FROM FLORENCE OR ROME

The day came when I finally visited Tuscany! I had long longed for this dreamy destination after seeing so many movies that feature it: Under The Tuscan Sun, Life is Beautiful, Stealing Beauty, etc and just word out there about how wonderful it is.

ESSENTIALS FOR YOUR TRIP TO TUSCANY

Transport / As this is a road trip, you’ll need a car! I use DiscoverCars for all international car hires.

Connect / You’ll need mobile data while you are in Italy and particularly to guide you on Google Maps while driving, I always recommend using an eSIM (there’s absolutely no need for a physical one!) – here’s some eSIM options for Poland.

Get Insured / Unfortunately, things can and do go wrong when you travel. World Nomads offers coverage for more than 150 activities as well as emergency medical, lost luggage, trip cancellation and more.

TUSCANY ROADTRIP ITINERARY: HOW TO GET TO AND AROUND TUSCANY

The best way to get around Tuscany is with a car as there are so many small towns to visit not easily reachable with other forms of transportation, so for my visit to Tuscany I planned a roadtrip itinerary which came out just perfect. I recommend you book a car using DiscoverCars, get full insurance, and avoid Goldcar and any other brands that are ridiculously cheap and not international. I’ve heard horror stories from them. On my trip to Tuscany I got Alamo and it was perfect, you’ll be fine with any other well known brands such as Avis, Budget, Europcar, Enterprise, Hertz, National, etc.

Most Tuscany roadtrip itineraries start from Florence which is in Tuscany. This makes a lot of logical sense, but for me any trip to Italy is an excuse to visit Rome, so I decided to start from Rome instead. If you want to start from Florence, this itinerary also works, just skip the Rome days. To fly to Rome or Florence, check out Skyscanner for the best prices.

TUSCANY ROADTRIP ITINERARY: DAILY BREAKDOWN

Day 1: Rome

DEPARTING FROM ROME: SUMMARY

Experience / Here’s some tours and tickets you could book for your day(s) in Rome:
Priority Access Colosseum, Roman Forum & Palatine Tour
Vatican Museums, Sistine Chapel, and Basilica Tour
Borghese Gallery Guided Tour with Tickets
3-in-1 Fettuccine, Ravioli, and Tiramisu Cooking Class
Capitoline Museums Experience with Multimedia Video

Stay / These are the best rated hotels between Rome and Florence for your first night:
Relais Il Chiostro di Pienza $$$
Palazzo Bandino $$$
Fonteverde Lifestyle & Thermal Retreat $$$
BiancoCancello $$
Hotel Sant’Antonio $$

Eat / My top recommendations for each meal for the day you’ll be here:
Brunch/Breakfast: Roscioli Caffè Pasticceria
Lunch: Osteria Bonelli
Dinner: Felice a Testaccio
Dessert: Giolitti

The recommendation for day one is to arrive to Rome in the morning, leave luggage on storage either in the airport or Termini train station and spend the day exploring Rome. This itinerary includes 2 full days in Rome (one at the beginning and one at the end) so if is your first time I would recommend adding 2 more days either at the beginning or the end of the itinerary in Rome.

To give you an idea of what I did this day in Rome, I walked from Termini station to the Colosseum, Roman Forum & Palatine Hill, followed by a visit to the Musei Capitolini. After that, walked down to Piazza Venezia and went inside the Vittorio Emanuele monument to see the exhibitions. Then I walked around the hipster neighborhood of Rome, Monti, and visited the Monti designer market and some of its vintage stores.

As you will be pressed on time this day I recommend that you book tickets to museums you want to visit in advance: Colosseum, Roman Forum & Palatine Hill, Musei Capitolini (includes a tour of the museum), see other Rome attractions you might want to book here.

And if you only have one of each meal in Rome this day, make it these:

• Dessert: Giolitti – Indulge in some of the best gelato in Rome at this iconic gelateria, serving locals and tourists since 1900.
• Breakfast/Brunch: Roscioli Caffè Pasticceria – Start your day at this elegant spot offering artisanal pastries, perfectly brewed coffee, and a great atmosphere. Perfect for a true Roman morning.
• Lunch: Osteria Bonelli – This hidden gem is loved by locals for its authentic Roman dishes like cacio e pepe and saltimbocca. Affordable, hearty, and utterly delicious.
• Dinner: Felice a Testaccio – Treat yourself to an unforgettable dinner at this historic restaurant, famous for its traditional Roman cuisine and exceptional service.

We then picked up the rental car booked using DiscoverCars from Fiumicino, as my dad was joining me on this trip and he was arriving via plane in the evening. You could pick up your rental from the centre of Rome as well, whatever feels more convenient to you.

This itinerary is designed so as to spend the next day in Florence which is a 3hr drive from Rome so it is ideal to sleep somewhere in the middle so you have less of drive the following day. We stayed at a lovely B&B called BiancoCancello in Sacrofano which was on the way. The B&B was amazing and exceeded all of our expectations but it was too close to Rome, so I would recommend you choose a location a bit more in the middle between Rome and Florence or a bit closer to it. For hotels in Rome, read on as I’ll recommend some at the end of this post where a night in our Rome is part of our last stop.

Here’s some hotels mid way between Rome & Florence, some of them already in Tuscany!

• Relais Il Chiostro di Pienza $$$: Located in Pienza, this charming historic hotel offers elegant accommodations with stunning views of the Val d’Orcia.
• Palazzo Bandino $$$: A luxurious agriturismo in Chianciano Terme, featuring wellness facilities, vineyards, and a peaceful countryside setting.
• Fonteverde Lifestyle & Thermal Retreat $$$: Nestled in San Casciano dei Bagni, this high-end spa resort offers thermal pools and panoramic views of rolling hills.
• BiancoCancello $$: A boutique retreat blending modern luxury and rustic charm, located in a serene countryside setting ideal for relaxation.
• Hotel Sant’Antonio $$: A rustic hotel near Montepulciano, offering comfortable rooms and an authentic Tuscan experience.

Day 2: Florence

FLORENCE: SUMMARY

Experience / Here’s some tours and tickets you could book for your day(s) in Florence:
Cathedral & Brunelleschi’s Dome Ticket & Audio App
Entrance Ticket to Pitti Palace
Timed Entrance Ticket to Michelangelo’s David
Skip-the-Line Uffizi Small Group Tour

Stay / These are the best rated hotels in Florence:
Hotel Brunelleschi $$$
Villa Cora $$$
The St. Regis Florence $$$
Numa Rodo $$
Hotel Pendini $
Hotel Spadai $$

Eat / My top recommendations for each meal for the day you’ll be here:
Breakfast/Brunch: Dolce e Dolcezze
Lunch: Mercato Centrale
Dinner: Trattoria Sostanza
Dessert: Gelateria dei Neri

We arrived in Florence in the morning, checked in at Numa | Rodo parked the car in a garage nearby and started exploring! If this is your first time in Florence I would add an extra day to it.

What we did during this day was to visit the Duomo (or Cathedral of Santa Maria del Fiore) then crossed the Ponte Vecchio, then went to Pitti Palace & its Boboli Gardens, followed by a shopping visit to Officina Profumo-Farmaceutica di Santa Maria Novella & the Santa Maria Novella Piazza & Church. We had been to Uffizi Gallery & the Accademia Gallery to see the David by Michelangelo in a previous trip, these are not to be missed when in Florence.

If you are wondering where to eat in Florence, here’s some food recommendations:

• Breakfast/Brunch: Dolce e Dolcezze – Start your day at this charming pastry shop offering high-quality pastries, cakes, and classic Italian coffee.
• Lunch: Mercato Centrale – Enjoy a variety of delicious options at this central market, perfect for any meal.
• Dinner: Trattoria Sostanza – Indulge in the famed Florentine bistecca at this renowned trattoria.
• Dessert: Gelateria dei Neri – Treat yourself to some of the best gelato in Florence at this popular gelateria.

We then headed back to Numa | Rodo for a fabulous sleep. We chose this hotel as it’s only meters away from the Duomo, hence very central which is essential for a short visit and has a beautiful view of the Duomo. Despite its location, the rooms are spacious and tastefully decorated to the utmost detail.

If that hotel is booked or out of your budget, here’s others for you to consider:

• Hotel Brunelleschi $$$: A luxurious boutique hotel located near the Duomo, offering refined rooms and excellent service.
• Villa Cora $$$: An opulent 19th-century villa with elegant accommodations, a stunning pool, and panoramic views of Florence.
• The St. Regis Florence $$$: A lavish hotel overlooking the Arno River, known for its exquisite design and impeccable service.
• Numa Rodo $$: A chic and contemporary hotel steps away from the Duomo, blending stylish interiors with modern amenities.
• Hotel Pendini $$: A charming hotel in Piazza della Repubblica, featuring cozy rooms and a warm, welcoming atmosphere.
• Hotel Spadai $$: Centrally located with modern design, offering comfortable accommodations close to Florence’s main attractions.

Day 3: San Gimignano and Volterra

SAN GIMIGNANO AND VOLTERRA: SUMMARY

Experience / Here’s some tours and tickets you could book either to reach these towns or in them:

From Florence:
Florence: Pisa, Siena, San Gimignano, and Chianti Experience

In San Gimignano:
San Gimignano: Torre Grossa and Duomo Tickets
San Gimignano: Wine and Oil Tasting with Tuscan Appetizers
San Gimignano: Truffle Hunting with Lunch & Wine Tasting

In Volterra:
Volterra: Fresh Pasta Cooking Class at a Tuscan Farmhouse
Tuscany: Volterra Truffle Hunting
Volterra: Pizza Cooking Class in a Tuscan Farmhouse
Volterra: Private Picnic in the Tuscan Countryside

Stay / These are the best rated hotels in San Gimignano, Volterra & surroundings:
Agriturismo Il Segreto di Pietrafitta $$$
Relais Santa Chiara Hotel $$$
Villa Palagetto $$
Hotel Volterra In $$
Podere Benintendi $$
Hotel San Lino $$

Eat / My top recommendations for each meal both for San Gimignano & Volterra:

Siena
Breakfast: Pasticceria Armando e Marcella
Lunch: Cum Quibus Ristorante
Dinner: Ristorante Bel Soggiorno

Volterra
Dinner: Ristorante Enoteca Del Duca
Breakfast: Pasticceria Migliorini
Lunch: Osteria La Pace

We woke up in Florence, said arrivederci to the Duomo and headed to San Gimignano. If you haven’t heard of it, San Gimignano is a small walled medieval hill town known as the Town of Fine Towers. It get this name for its medieval architecture particularly the unique in the preservation of about a dozen of its tower houses, which with its hilltop setting and encircling walls make it visibly enticing.

The main thing to do in San Gimignano is to walk around and appreciate its architecture and shops, try some wild boar salami, eat gelato (I recommend Dondoli in the main square), drink Vernaccia de San Gimignano visit the Duomo and climb up the Torre Grossa. You can buy tickets for the Duomo and Torre Grossa here.

After, we headed to Volterra. When we asked someone in San Gimignano what they thought about Volterra they said it was “un paese misterioso” (a mysterious place). It might be because we visited in low season and during sundown but I couldn’t agree more. This town dates back from Etruscan times and has Roman and medieval influence as well. There is a lot to do here. You should visit the Piaza dei Priori & Palazzo dei Priori, the Duomo (Cathedral of Santa Maria Assunta), the Guarnacci Etruscan Museum, the Etruscan Acropolis, the Medicean Fortress and Porta a Selci (you won’t be able to get inside the fortress as it’s a high security prison but you can watch the architecture from outside), the Roman Amphitheater and its surrounding archeological area. Also, you’ll see many items made from alabaster stone in many store fronts as using alabaster is an ancient tradition in Volterra which exists since Etruscan times. You can window shop and buy some souvenirs to take home.

Another lovely thing to do in either of these towns is go truffle hunting or do a cooking class. You can book a truffle hunting experience from San Gimignano or from Volterra. You can also book a wine tasting in San Gimignano and either a pasta or pizza class from Volterra, and even a private picnic!

And here’s some food recommendations for both towns:

San Gimignano

• Breakfast: Pasticceria Armando e Marcella – This quaint pastry shop offers a variety of freshly baked goods and excellent coffee. It’s a local favorite for starting the day on a sweet note with Tuscan-style breakfast options.
• Lunch: Cum Quibus Ristorante – An elegant Michelin-starred restaurant offering elevated Tuscan cuisine. Enjoy dishes like truffle pasta and creative reinterpretations of local flavors in a refined yet welcoming atmosphere.
• Dinner: Ristorante Bel Soggiorno – Feast on traditional Tuscan dishes with panoramic views of the rolling hills. Their handmade pasta and bistecca alla Fiorentina are perfect for ending your day on a high note.

Volterra

• Dinner: Ristorante Enoteca Del Duca – Savor fine Tuscan dining with a focus on seasonal ingredients and an extensive wine list. Known for its romantic ambiance and exquisite dishes like guinea fowl and truffle specialties.
• Breakfast: Pasticceria Migliorini – With stellar reviews and a reputation for delicious pastries and coffee, Pasticceria Migliorini is a favorite for breakfast in Volterra. Their freshly baked croissants, cakes, and traditional Italian sweets are paired perfectly with expertly brewed espresso or cappuccino. It’s a cozy and authentic spot to start your day.
• Lunch: Osteria La Pace – This rustic trattoria offers hearty Tuscan fare, including wild boar dishes and handmade pasta. The warm and friendly service makes it a great midday stop.

After Volterra, we headed to our accommodation for the night: Podere Benintendi. This was one of my favorite accommodations in this trip because it was so unique! It’s located close to Certaldo a medieval hamlet in the heart of the Val d’Elsa which is incredibly charming and worth spending a few hours in. It is also where the famous Italian writer Boccaccio (author of Decameron) was born.

Bocaccio was a great fan of Dante Alighieri, and our room in Podere Benintendi was inspired after Dante! Some of his books were displayed as well as a drawing of his unequivocal face profile on one of the walls and a quote from Dante’s Paradiso on the other. The room has unique pieces of decoration such as an amazing chair-nigh-table-and-lamp piece of furniture.

Should Podere Benintendi not be available, here’s other great choices in the area:

• Agriturismo Il Segreto di Pietrafitta $$$: A stunning farmhouse near San Gimignano offering luxurious accommodations, an infinity pool, and breathtaking countryside views.
• Relais Santa Chiara Hotel $$$: A charming boutique hotel located near San Gimignano, featuring elegant rooms, a beautiful garden, and an outdoor pool.
• Villa Palagetto $$: A charming agriturismo with rustic accommodations, set among olive groves and vineyards near San Gimignano.
• Hotel Volterra In $$: Located in Volterra’s historic center, this boutique hotel offers stylish rooms and a convenient location.
• Podere Benintendi $$: A delightful countryside retreat close to Certaldo, featuring comfortable rooms, a pool, and panoramic views.
• Hotel San Lino $$: A cozy hotel in Volterra’s medieval center, offering a mix of modern comforts and historical charm.

Day 4: Siena

SIENA: SUMMARY

Experience / Here’s some tours and tickets you might like to book:
Siena Cathedral and Piccolomini Library Entry Ticket
Siena: Walking Tour and Skip-the-Line Duomo Tickets
Siena: Palazzo Pubblico Entry Ticket
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Siena: Horseback Adventure in the Tuscan Countryside
Siena: Small Group Cooking Class in Chianti Farmhouse

Stay / These are the best rated hotels in Siena & surroundings:
Borgo San Luigi $$$
Grand Hotel Continental Siena $$$
Hotel Athena $$$
Palazzo Ravizza $$
Hotel Santa Caterina $$
Hotel Duomo $$
Villa Scacciapensieri $$

Eat / My top recommendations for each meal for the day you’ll be here:
Breakfast: Bar Pasticceria Nannini
Lunch: Osteria Boccon del Prete
Dinner: Ristorante Tre Cristi
Dessert: La Vecchia Latteria

I woke up in Podere Benintendi, peeked through the window and couldn’t believe my eyes! Podere Benintendi is located at the top of a hill and in that foggy morning, we were sitting above the clouds. The view was unbelievable and I felt so blessed of having been able to experience it. After documenting that enchanting morning through photos and videos, we went to the lobby for breakfast which was extremely complete with lots of home made delicacies and many options to choose from. We then spent the morning exploring the estate as there is a lake, an aromatic herb garden, and nice quaint corners with sculptures or fun details spread allover. There’s also a pool, a gym, a billiard room and a shop where they sell their self branded wine, limoncello, marmalade and olive oil at very competitive prices.

Unfortunately, all good things must come to an end and it was time for us to leave Podere Benintendi and visit Siena. We spent most of our time exploring Siena’s Cathedral and surroundings. It is possible to purchase a joint ticket to visit Siena’s Cathedral, crypt, baptistery, museum, and Piccolomini Library. You can also opt for a walking tour of the city. Other things to visit are the Santa Maria della Scala museum, the epic Torre del Mangia and Palazzo Publico, the Piazza del Campo and the Basilica Cateriniana where St. Catherine’s head is kept. You can buy tickets to the Palazzo Publico which hosts the Civic Museum here, a 13th-century building home to impressive wall-to-wall fresco paintings. If you are looking for more unique experiences you can also try horse back riding or a cooking class.

When it comes to eating in Siena, depending which meal you are having, try out these places:

• Breakfast: Bar Pasticceria Nannini – Start your day at Bar Pasticceria Nannini, a legendary café in Siena known for its delightful pastries and coffee. Try their ricciarelli (traditional almond cookies) or a buttery cornetto with a creamy cappuccino to fuel your day of exploring.
• Lunch: Osteria Boccon del Prete – This charming osteria offers authentic Tuscan dishes like handmade pici pasta with cacio e pepe or wild boar ragù. It’s a perfect spot to enjoy a relaxed midday meal in a cozy atmosphere near the Duomo.
• Dinner: Ristorante Tre Cristi – For an elegant evening meal, Tre Cristi offers refined Tuscan cuisine with a modern twist. Their seafood dishes and wine selection are exceptional, making it an ideal choice for a memorable dinner in Siena.
• Dessert: La Vecchia Latteria – Indulge in authentic Italian gelato at this beloved gelateria. Their flavors are rich and natural, with highlights like pistachio, hazelnut, and local seasonal options.

After a full day of Siena exploring, we reached our accommodation for the night: Borgo San Luigi. Borgo San Luigi is a luxury hotel set in a 17th century estate just 5 minutes away from the medieval town of Monteriggioni and 25 mins away from Siena by car. Our room at Borgo San Luigi was spacious and had a terrace overlooking the estate which is 60.000sqm. During the evening, we enjoyed delicious Tuscan cuisine in the in-house restaurant La Bianca located just a short walk from your room. Food is delicious and served at very reasonable prices.

Should Borgo San Luigi not be available, here’s other great choices in the area for all budgets:

• Grand Hotel Continental Siena $$$: A luxury 5-star hotel in the heart of Siena’s historic center, offering elegant rooms, exceptional service, and fine dining.
• Hotel Athena $$$: Located within the city walls, this upscale hotel features panoramic views, spacious rooms, and an on-site restaurant.
• Palazzo Ravizza $$: A historic boutique hotel with charming accommodations, a lovely garden, and views of the Tuscan countryside.
• Hotel Santa Caterina $$: A cozy and elegant hotel near Porta Romana, offering classic rooms and a peaceful garden with views.
• Hotel Duomo $$: A centrally located hotel offering comfortable rooms and proximity to Siena’s top attractions, including the Duomo.
• Villa Scacciapensieri $$: A tranquil retreat just outside Siena, with beautiful grounds, a pool, and classic Tuscan charm.

Day 5: Val D’Orcia | Chiusure, San Quirico D’Orcia, Montalcino & Monticchiello

VAL D’ORCIA: SUMMARY

Experience / Here’s some tours and tickets you might like to book:
From Rome: Highlights of Tuscany Day Trip with Lunch & Wines
From Florence: Val D’Orcia Tour with Wine Tasting
Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

Stay / These are the best rated hotels in Val D’Orcia
Il Torrino Monticchiello $$$
Adler Spa Resort Thermae $$$
Castello di Velona Resort $$$
Locanda in Tuscany $$
B&B Daria Monticchiello $$

Eat / My top recommendations for each meal for the day you’ll be here:
Lunch: Trattoria Toscana Al Vecchio Forno (San Quirico d’Orcia) / Osteria Osticcio (Montalcino)
Dinner: Ristorante Daria / Osteria La Porta (Monticchiello)

After enjoying a wonderful breakfast at Borgo San Luigi, we spent the morning exploring its beautiful grounds, admiring the ivy covered 17 century buildings as well as its impressive entrance flanked by cypress trees.

We hopped into our car to continue our road trip now entering Val D’Orcia. Our first stop was Chiusure a small town in Siena’s Crete Senesi. The purpose wasn’t really to visit the town itself but to admire the views from the drive as these are meant to be the best views of Tuscany (and they were, in my opinion). Also most people come to Chiusure to visit the Abbey of Monte Oliveto Maggiore, which is up a hill a few hundred metres from the center of the village. The Abbey is an active monastery and has beautiful frescoes by Luca Signorelli – Michelangelo’s teacher – in the Cloister. There are also frescoes by the Sienese painter, Antonio Bazzi, called “Il Sodoma” (“The Sodomite”).

We continued to and then reached San Quirico D’Orcia a walled town in Val D’Orcia. The town has many beautiful churches to visit as well as an Italian symmetrical garden called Horti di Leonini. Lastly near this town you’ll find the famous bunch of cypress trees that you see in all photographs from Tuscany which are an icon of Val D’Orcia.

Our town hopping spree continued to Montalcino, which I would consider an absolute must. Montalcino is a 14th-century town also located in Val d’Orcia. It stands out immediately thanks to its military layout and imposing fortress and it is characterised by narrow, steep streets. Once there you’ll also be able to benefit from incredible views of the valley. As for things to do, the Diocesan Museum of Sacred Art conserves one of the richest collections of painting and wooden sculpture by the Sienese school. Amongst the churches in town, I recommend the 14th-century Church of Sant’Agostino, the Neoclassical cathedral, the Sanctuary of the Madonna del Soccorso and the Church of Sant’Egidio – the church “of the Sienese”. The town hall is also unique with its slender structure being flanked by a tall functioning bell tower. You might also want to do a wine tasting here (includes lunch)

Montalcino is also famous for its wine production, particularly the Brunello. The countryside around Montalcino also produces honey, extra-virgin olive oil, meats and cheeses, all of which can be enjoyed in some of the characteristic restaurants and wine bars in the area. Nearby Montalcino, it’s worth visiting the splendid Abbey of Sant’Antimo, a monumental structure dating to the 12th century, one of the best examples of French Romanesque architecture in Italy.

Here’s two options for lunch on this day:

Lunch Option 1: Trattoria Toscana Al Vecchio Forno (San Quirico d’Orcia) – Located in the heart of San Quirico d’Orcia, this charming trattoria serves up authentic Tuscan dishes in a cozy setting. Their pici all’aglione and slow-cooked meats are highly recommended.

Lunch Option 2: Osteria Osticcio (Montalcino) – Enjoy lunch with breathtaking views of the countryside. This restaurant is known for its exceptional pasta dishes, hearty soups, and a stellar wine selection featuring Brunello di Montalcino.

Our last stop for the day and our home for the next two days was Monticchielo. Monticchielo is a small medieval town with just 200 inhabitants close to Pienza, where time seems to have frozen and which has also not been discovered by tourists. I stayed in Monticchielo two nights in B&B Daria Monticchiello, and used it as a base to explore the nearby towns. With little tourists, peace and calm can be achieved in Monticchiello where at night the only sound to be heard is that of silence. Or perhaps, the locals singing as they rehearse for the Teatro Povero, the town’s theatre for which its plays are written, directed and performed by Monticchiello’s inhabitants.

B&B Daria Monticchiello used to be the home of Daria’s, its owner, family. It dates from 1890 and has been renovated beautifully with great taste, lots of pastel colors and nice touches. Our room also had those touches, plus a beautiful view of the town as the property is located in the highest point of the town. The bathroom was spacious, with a hydromassage tub and a view. Guests can use the kitchen of the B&B where there is coffee, water and snacks available for guests at all times. In the winter months one can relax by the fireplace while in the warmer months one can sit in the outside terrace to admire the views. There’s also a hot tub in the garden and free parking right at the property itself.

Now B&B Daria Monticchiello is probably the less exciting part of Daria’s ventures as she also owns Ristorante Daria, which is one of the best ones I’ve been to in Tuscany, not only said so by myself but also by The Telegraph & Goop. It’s in Ristorante Daria where you are served breakfast if staying at B&B Daria Monticchiello and where I would encourage everyone to have dinner. The restaurant is beautifully decorated, and food is of such high quality that it could easily compete with the best restaurants in my home town, London. Daria is an absolute rockstar, she’s kind and chic and comes by as an obviously strong and busy woman. Guests can also choose to do a cooking class with one of the chefs of Ristorante Daria, Daniele.

The days where Ristorante Daria is closed, Osteria La Porta is also surprisingly good. Apparently it used to be owned by Daria as well.

Now should B&B Daria be booked make sure to try these options next:

• Il Torrino Monticchiello $$$: A charming and luxurious property in the picturesque village of Monticchiello, inside a tower! It offers stunning views, elegant accommodations, and a serene atmosphere.
• Adler Spa Resort Thermae $$$: A luxurious wellness retreat with natural thermal pools, a full-service spa, and elegant rooms amidst rolling hills.
• Castello di Velona Resort $$$: A unique 5-star resort housed in a medieval castle, featuring a world-class spa, thermal pools, and breathtaking views.
• Locanda in Tuscany $$: A charming inn with traditional Tuscan decor, gourmet dining, and a relaxing pool area surrounded by stunning scenery.

Day 6: Castelo Banfi, Pienza & Monticchiello

CASTELO BANFI & PIENZA: SUMMARY

Experience / Here’s some tours and tickets you might like to book:
Castelo Banfi Winery Tour
Pienza: Typical Gourmet Lunch at Ancient Tuscan Farmhouse

Stay / Castello Banfi

Eat / My top recommendations for each meal for the day you’ll be here:
Lunch: Castello Banfi
Dinner: Trattoria La Buca delle Fate (Pienza)

We woke up at B&B Daria Monticchiello and had breakfast at Ristorante Daria. You can basically order what you want as it’s not a buffet and everything is made to order. We were then to leave Monticchiello to visit an exciting destination: Castello Banfi.

If you are a wine lover, Castello Banfi may ring a bell. It’s one the largest wine producers in Italy and Europe, with over 3000 hectares of land. The owners of the winery, the Mariani’s, first purchased the land and later purchased the Poggio Alle Mura medieval castle that can be traced back to the Etruscans with part of it going back up to the Middle Ages. Today, the castle serves as a hotel, enoteca and restaurant.

We visited Castello Banfi to take their winery tour and 5 course wine paired lunch at their restaurant, La Taverna. I really enjoyed the tour. Having done wine tours in Bordeaux, France and the Douro, Portugal this was a completely different experience mainly due to the unique process required to make the Brunello di Montalcino DOCG and also due to the scale of such large winery. It was very interesting to see so much technology integrated to the wine making process. Lastly, the 5 course paired lunch was marvelous. We tried fantastic wines, Rosso and Brunello di Montalcino as well as other delicious ones, and had five star quality food. They were able to make a vegan version of the 5 course lunch with a mix of both complex and simple dishes with outstanding flavors, and always with the Tuscan touch. You have to be prepared to eat and drink a lot, though.

I did not actually stay at Castello Banfi during this trip as, frankly, I was tired of changing hotels every night and decided to use Val D’Orcia as the place where to stay in the same hotel two nights and I chose B&B Daria Monticchiello for that. Although I obviously don’t regret my decision, I would have loved to stay at Castello Banfi’s wonderful estate as it is out of a Tuscan dream. If your trip allows staying one night here, then don’t hang around and book it. You won’t regret it.

After our big lunch we took our full bellies to Pienza which we hadn’t had a chance to visit yet. Pienza is another tiny village in Val D’Orcia also located in the top of a hill and hence offering extraordinary views. Pienza is widely known as the “ideal city of the Renaissance”, a creation of the great humanist Enea Silvio Piccolomini, later Pope Pius II. He shaped the city as what he thought the Utopian city should be, hiring architect Bernardo “il Rossellino” who completed the Cathedral, the Papal or Piccolomini Palace, the Town Hall, and the central square where these buildings stand. The square is one of the places you must visit but also check out Pieve di Corsignano, a romanesque church dating from the 7th century (romanesque details added later on the 12th century). Pienza is also the city of cacio (cheese). The Pecorino of Pienza is a worldwide renowned cheese made from sheep’s milk which makes a perfect souvenir from this charming village. If you decide not to go to Castelo Banfi, you could have lunch in Pienza at a Tuscan farmhouse.

Days 7 & 8: Rome

ROME: SUMMARY

Experience / Here’s some other tours and tickets you might like to book:
Castel Sant’Angelo Skip-the-Line Entry & Optional Audioguide
Rome: Trastevere or Jewish Quarter Street Food Tour
Rome: Hop-On Hop-Off Panoramic Open Bus Ticket

Stay / This is where I stayed this time:
Suites Giulia

Eat / My top recommendations for each meal for the day you’ll be here:
Breakfast: Santi Sebastiano e Valentino (Monti District)
Lunch: Bha Ghetto Milky (Jewish Ghetto)
Dinner: Alfredo alla Scrofa (Via della Scrofa) / Pierluigi (Campo de’ Fiori)

Our Tuscany Road Trip had come to an end and it was time to return to The Eternal City, Rome. We woke up at B&B Daria Monticchiello said goodbye to this special town which had rewarded us so much over the last two days and hit the road.

We arrived in Rome around noon to our accommodation for the last night of our trip: Suites Giulia. We stayed in a two bedroom suite with a fully equipped kitchen, living room and spacious bedrooms and bathrooms, even with a walk-in closet! From the bedrooms, there is an amazing view of the nearby Museo di Arte Sacra San Giovanni dei Fiorentini. The suite has crisp, minimalist decoration and it immediately feels like a home away from home. It even has a washing machine!

All Suites are located in Rione Regola, a fairly high end neighborhood just by Campo dei Fiori and Piazza Farnese which also has various cute wineries, restaurants and antique shops to choose from; including the popular restaurant Pierluigi usually frequented by celebs. It’s also just besides the Tevere river, Ponte Vittorio Emanuele II, the Ponte and Castel Sant’Angelo and just 10 mins walking from the Vatican.

Rome Tours you might be interested in:

TUSCANY ROADTRIP ITINERARY: MAP OF CITIES AND TOWNS VISITED

Link to map shown below.

TUSCANY FAQ

WHEN IS THE BEST TIME TO VISIT TUSCANY?
The best time to visit Tuscany is during the spring (April to June) and autumn (September to October) when the weather is pleasant, and the countryside is at its most vibrant. These periods are also less crowded than the peak summer months. I visited in October and it was absolutely incredible

DO I NEED A CAR TO TRAVEL AROUND TUSCANY?
While it’s possible to visit some towns using public transport, having a car is highly recommended for exploring Tuscany. It gives you the freedom to visit hidden gems, remote wineries, and small villages that are not easily accessible by train or bus. As mentioned above you can use DiscoverCars for your car rental.

HOW MANY DAYS SHOULD I SPEND IN TUSCANY?
A week is ideal to experience Tuscany’s highlights, but if you’re short on time, 4–5 days can still give you a taste of the region. For a more in-depth exploration, consider staying 10–14 days.

WHAT ARE SOME MUST-SEE TOWNS IN TUSCANY?
Be sure to visit Florence, Siena, Pisa, and San Gimignano for their iconic attractions. Smaller towns like Pienza, Montepulciano, and Montalcino are perfect for experiencing authentic Tuscan charm and wine tasting.

CAN I VISIT TUSCANY AS A DAY TRIP FROM FLORENCE?
Yes, you can visit towns like Siena, Pisa, and San Gimignano as day trips from Florence, especially if you don’t have a car. Here’s the best rated tour from Florence.

IS TUSCANY EXPENSIVE TO VISIT?
Tuscany can be tailored to different budgets. While luxury villas and fine dining are available, there are also affordable agriturismos (farm stays), budget-friendly trattorias, and free activities like exploring medieval towns or hiking in the countryside.

WHAT ARE SOME UNIQUE EXPERIENCES IN TUSCANY?

• Hot air balloon rides over the Tuscan hills.
• Cooking classes to learn traditional Tuscan recipes.
• Exploring thermal baths like Bagno Vignoni.
• Truffle hunting in the countryside.

IS ENGLISH WIDELY SPOKEN IN TUSCANY?
In major cities and tourist areas, many locals speak English. However, in smaller towns or rural areas, English may be less common, so learning a few basic Italian phrases can be helpful and appreciated.

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