Tuscany Road Trip: 10 Day Itinerary
Florence (3 Days), Siena (3 Days), Montepulciano (4 Days)
This is a sample itinerary which is completely customizable, ask us how.
Highlights
- Tour Florence's beautiful medieval piazzas & cathedrals
- Enjoy a wine tasting in the Tuscan city of Siena
- Discover Montepulciano and its famous wine
- Wander through the cobblestone streets of Cortona
- Travel back in time visiting the town of San Gimignano and Monteriggioni
Daily Itinerary
Day 1: Tuscany Road Trip Starts from Florence
Benvenuti a Florence
Spend the day relaxing and settling in to Florence, or head out for a relaxing stroll and dinner downtown.
If you wish to get stuck into some sightseeing we recommend these spots on a Tuscany road trip:
- Studio Artemisia, located steps away from the Ponte Vecchio for a class in ancient fresco painting techniques
- Mercato Centrale, a 19th-century open-air market, to browse for a wide selection of vegetables, fruits, meats, and cheeses, and a variety of lunch spots
- Boboli Gardens to see the oval-shaped Isolotto, a small island surrounded by various sculptures and lots of greenery
In the evening, stroll around the historic L-shaped Piazza della Signoria, located in front of the Palazzo Vecchio, for some people watching followed by dinner and drinks in the hip Sant’Ambrogio neighborhood.
Overnight: Florence
Day 2: Historic Walking Road Tour of Florence
Florence Road Trip By Foot
Spend the day exploring the city’s top sites, starting with a guided half-day walking road tour. Stroll through the picturesque historic center where you’ll find the most important squares and monuments in your Tuscany road trip:
- Piazza della Repubblica
- Palazzo Vecchio
- Ponte Vecchio
- Duomo
- Giotto’s Bell Tower and the Baptistery
- Galleria dell’Accademia to see Michelangelo’s David
- Piazzale Michelangelo
- Piazza Santo Spirito for some pre-dinner aperitivos.
Overnight: Florence
Day 3: Cooking Class in Florence
Florentino Feast
After a leisurely morning in Florence you’ll meet your host for a traditional Italian cooking class. You’ll be greeted with a prosecco and tasting board before a three-hour hands-on Italian cooking class. You’ll learn to cook four dishes from scratch, including a side or dessert. Observe the chef’s different tricks and techniques to cook Italian family recipes perfectly.
The best part of the class is, of course, in the end, when you’ll enjoy your freshly-made dinner in traditional Italian style.
Overnight: Florence
Day 4: Road Trip to Siena, Afternoon Wine Tasting
After breakfast, hit the road for the 1.5- hour drive to your accommodation in the UNESCO World Heritage city of Siena.
Make the most of your time in Siena with some recommended activities on your Tuscany road trip like:
- National Archaeological Museum of Siena
- Metropolitan Opera Museum
- Learn about the ceramics manufacturing process and shop for gifts at the Ceramiche Bianco e Nero di Staccioli
In the afternoon, head to a local wine school in the center to sample a variety of Tuscan classics paired with regional appetizers while learning about the region’s most essential and traditional wines and the history embedded in each glass.
Overnight: Siena
Day 5: Road Trip to San Gimignano & Monteriggioni
Siena’s Stunning Surrounds
Visit the neighboring UNESCO village, San Gimignano. A quintessentially Tuscan town comprised of medieval buildings perched atop one of the iconic hills that dot the countryside.
On the way back from San Gimignano, stop at the impressive medieval fortress of Monteriggioni. The intact castle walls surrounding this town perched on a hillside are a sight to behold. Take in the views before continuing on your Tuscany road trip to Siena.
Overnight: Siena
Day 6: Road Trip to Volterra
Venture over to Volterra from Siena
Today you’ll continue to explore the surroundings of Siena, venturing into the town of Volterra, a hilltop town about an hour from Siena.
This walled town has deep roots in Etruscan history, and to this day visitors can still see parts of its protective walls and ancient gates to enter the town.
This part of the road trip can be self-guided or we can pair you up with a local tour guide to talk you through the historic importance of the sites and local traditions such as:
- Palazzo dei Priori, whose bell tower offers impressive views
- Volterra Cathedral to see the marbled entrance and unique ceiling
- Roman Theater, an archaeological site of ancient ruins
- Artisanal shops showing off the cities famous alabaster production.
Overnight: Siena
Day 7: Road Trip From Siena to Montepulciano With a Stop in Pienza
Magnificent Montepulciano
Time to head further into the Tuscany countryside, visiting the famous village and surrounding wine region of Montepulciano stopping in the village of Pienza which stands atop a high hill above the Orcia Valley. The charming town is known as the “ideal city of the Renaissance”.
Continue to the historic village of Montepulciano, which sits along a ridge and is surrounded by walls and fortifications. Montepulciano is famous for its Renaissance buildings, churches, and historical Corso main street which leads through town, ending at the Piazza Grande.
This part of the road tour can be self-guided or we can pair you up with a knowledgeable local guide to talk you through the sites and traditions such as:
- Palazzo Comunale, the castle-like town hall with an iconic clock bell
- The spartan 15th-century Duomo, whose unfinished facade stands out from the surrounding buildings
- Palazzo Cappelli and Gothic Palazzo Neri Orselli, home to the civic museum, to see regional and national art.
Overnight: Montepulciano
Day 8: Wine Tasting in Montepulciano
The heart of Tuscan wine
A tour of wine tasting during your Tuscany road trip is one of the most wonderful ways to experience locale wine in a beautiful location. It is ancient wine cellars the town holds, where the wine bottles age to perfection. Go back in time in this centuries-old cellar, which holds vast barrels full of the town’s namesake red wine.
The tour wouldn’t be complete without a local lunch to pair with your wine tastings, enjoyed in your beautiful surroundings.
Back in Montepulciano, visit the Church of Sant’Agnese, dedicated to Montepulciano’s patron saint, and don’t miss the recognizable 16th-century Chiesa di San Biagio, which rests on a hill below the town.
Overnight: Montepulciano
Day 9: Walking Road Trip to Cortona
Charming Cortona
Just a 40-minute by-road drive away from the town of Montepulciano sits Cortona. This village was made more famous in recent years thanks to the book and movie, Under the Tuscan Sun. But although it is more well-known these days, Cortona still holds on to its authentic Tuscan charm.
A 2-hour tour guided tour will ensure you fall in love with this postcard-worthy town.
Learn about the historical significance of the sites and monuments and road trip to the most picturesque spots with your guide before enjoying a leisurely afternoon with museums and artisanal shops aplenty.
Overnight: Montepulciano
Day 10: Drive to Florence, Depart
After one last cappuccino head to the airport for your next destination during your Tuscany road trip. Arrivederci, Firenze!
Palermo, Two Nights
Walking tour of Palermo
Discover the iconic sights of Palermo on a private guided tour with an expert guide. On this private VIP experience, our expert guide will meet you at your hotel before taking you on a journey of discovery through the most glorious parts of Palermo. As a part of this special day, you will have the chance to see all of Palermo’s main attractions and stunning Baroque architecture, including Piazza Politeama, Teatro Massimo, the Quattro Canti, the Cathedral, the Martorana, Piazza Pretoria, the Palatine Chapel, the Norman Palace and the popular markets. During your cultural walk, there will be plenty of time to ask your private guide questions and learn more about the history of Palermo and its charming culture.
Excursion to Monreale
Overlooking the Golden Valley (Conca d’Oro) on top of Mons Regalis, the medieval village of Monreale is known for its magnificent Cathedral, which features some of the most beautiful religious mosaics of the 12th century. The Cathedral is considered to be one of the best examples of Norman architecture in Sicily and is a joy to discover on this small-group day trip from Palermo. As well as the Cathedral, you will have time to explore the abbey cloister, which boasts more than 200 intricate double columns decorated in glass mosaic.
Segesta, Erice, Marsala and Selinunte, Two Nights
Excursion to Segesta and Erice
Enhance your sightseeing experience of Sicily on an enriching full-day excursion to Erice and Segesta. First, you can delight in the medieval majesty of Erice, a walled town that reigns over the picturesque harbor of Trapani, where you can delve into the historical wonders of one of Sicily’s most in-demand destinations. Through the eyes of your expert guide, you will become acquainted with the city and its key landmarks on an in-depth history tour with the chance to also hike along the coastal reserve.
Next, you will discover Segesta, one of the major cities of the ancient indigenous Elymian people. Here you can visit the Doric temple, which dates back to the late 5th century BC. It was built on a hilltop just outside of the ancient city and has a commanding view of the surrounding area. If anyone needed yet more proof that the Greeks had a good eye for where to build, Segesta would lay any doubts to rest once and for all! Indeed, the setting of the temple is simply beautiful as completely unspoiled rolling green countryside stretches right down to the glistening aquamarine sea.
Wine tasting in Marsala and Selinunte
On this VIP excursion you will be picked up by our private driver at your hotel and leave for Marsala, which was once known as Lilibeo and was founded by refugees fleeing the destruction of Mozia. It was conquered by the Romans at the end of the First Punic War and became a luxurious town featuring glorious palaces and thermal baths. The Arabian settlers called the ancient city Mars-Alì (“the harbor of Alì” or “the big harbor”), but it is now known as Marsala. The modern city is known for its world-famous Marsala wine, as well as for the landing of Giuseppe Garibaldi in 1860. On our private adventure, you will discover all the best sights, including the Archaeological Museum and the Salt Road with the Salt Pans. You will also stop in a winery for Marsala wine tasting before reaching Selinunte, an ancient Greek city in the widest archaeological park of Europe. It was founded in the 7th century BC but was destroyed in 409 BC by the Carthaginians allied with Segesta, its eternal rival. The two most important areas you’ll visit are the Eastern Hill with the ruins of three temples, and the Acropolis where Greek and Punic ruins are still visible.
Agrigento, One Night
Valley of the Temples tour
Immerse yourself in Sicily’s Greek past with this tour of Agrigento’s Valley of the Temples (entry included).
The UNESCO-protected Valley of the Temples is one of Sicily’s most important archaeological sites and is a joy to discover if you have an interest in history or simply want to learn more about Sicily’s turbulent past. This tour experience takes you to the sacred site, where an expert guide will treat you to a guided walk through the Valley.
As a part of your tour, you will see the Temple of Hera, the Temple of Concordia, the Temple of Herakles, the Temple of Zeus and the Sanctuary of Chtonian Deities (Temple of Castor and Pollux). During the tour, your guide will discuss the temples’ construction and tell you about their on-going preservation.
Syracuse and Pantalica, Two Nights
Private walking tour of Syracuse Enjoy a private tour around the historical center of Syracuse with this VIP experience on the ancient island of Ortygia. This private walk begins at the ancient Greek Apollo Temple and leads you to Cathedral Square, which boasts beautiful limestone buildings and Baroque architecture. From here, you will visit the Arethusa Fountain, which is steeped in legend and mystery – your guide will tell you all its secrets! The tour concludes with a visit to the Jewish Quarter and Archimedes Square, where you can admire the Fountain of Diana, which was built in a Neoclassical style and is one of the most recognizable landmarks of Ortygia. Naturalistic excursion to Pantalica One of the most impressive archaeological sites in Sicily and a UNESCO World Heritage Site is the rocky necropolis of Pantalica, in eastern Sicily. This site is somewhat off the beaten track but certainly worth a visit on your complete Sicily vacation. Pantalica is a prehistoric site dating back to the late Bronze Age (from the 13th to the 8th century BC) and is famous for its necropolis, which features thousands of tombs dug into the overhanging walls of the Anapo Canyon. Pantalica is also famous for its breathtaking natural vistas and unusual wildlife. In fact, it is part of the revered Anapo Valley Nature Reserve, which is a paradise for trekking.
Taormina and Mount Etna, Two Nights
Full-day Mount Etna Jeep tour with wine tasting and lunch
Scale the slopes of Italy’s famously active Mount Etna on this full-day 4×4 Jeep tour from Taormina. As a part of this unique experience, you will travel up rugged mountain tracks in an off-road vehicle and trek by foot to a stunning lookout point with views of lava flow basins and cave tubes created by the 2002 eruption. After descending from the volcano, you will enjoy a decadent and authentic Sicilian lunch of handmade cheeses, cured meats, pasta and dessert served with local wine.
VIP Taormina tour, featuring the Greek Theater
Today you will discover Taormina’s historic secrets and modern delights on a two-hour private tour. This guided experience allows you to explore the highlights of this charming city, including Palazzo Corvaja, the Santa Caterina Church and Vicolo Stretto, which is the narrowest street in town. As a special addition to this Taormina tour, you will enjoy “skip the line” entry to the ancient Greek Theater, which boasts magnificent views of Mount Etna and Giardini Naxos. There is no better way to discover this unassuming city’s treasured attractions!
Catania, Two Nights
VIP Catania walking tour The scent of fresh lemons and oranges and the harmonized landscape of Mount Etna’s cliffs rolling into the glistening sea set the backdrop for the sublime city of Catania. And on this exclusive tour experience, you will have every opportunity to discover the best of Catania, including Piazza del Duomo, the Amenano Fountain, Castello Ursino, Teatro Massimo, Palazzo Biscari, Saint Agata Dome, Via Etnea, Piazza Stesicoro, which features a Roman Theater, and finally the Bellini Garden. Catania street food experience With our hand-selected local guide, who you can be sure knows where to find only the best Catania cuisine, you will begin this food-tasting experience with a historical overview of the city, including the intricate alleys and squares of Catania’s old town, the ancient central market of Catania, Piazza Duomo, Via Etnea (the main street) and Piazza Stesicoro. But, of course, the most important part of this Catania food tour will be the opportunity to taste no less than 15 popular street foods that the city is famous for: arancino, cipollina, pizzetta, fresh fish, meatballs, local cheese, olives, cannolo with ricotta, cassatella, granita and much more!Palermo, Two Nights
Walking tour of Palermo
Discover the iconic sights of Palermo on a private guided tour with an expert guide. On this private VIP experience, our expert guide will meet you at your hotel before taking you on a journey of discovery through the most glorious parts of Palermo. As a part of this special day, you will have the chance to see all of Palermo’s main attractions and stunning Baroque architecture, including Piazza Politeama, Teatro Massimo, the Quattro Canti, the Cathedral, the Martorana, Piazza Pretoria, the Palatine Chapel, the Norman Palace and the popular markets. During your cultural walk, there will be plenty of time to ask your private guide questions and learn more about the history of Palermo and its charming culture.
Excursion to Monreale
Overlooking the Golden Valley (Conca d’Oro) on top of Mons Regalis, the medieval village of Monreale is known for its magnificent Cathedral, which features some of the most beautiful religious mosaics of the 12th century. The Cathedral is considered to be one of the best examples of Norman architecture in Sicily and is a joy to discover on this small-group day trip from Palermo. As well as the Cathedral, you will have time to explore the abbey cloister, which boasts more than 200 intricate double columns decorated in glass mosaic.Segesta, Erice, Marsala and Selinunte, Two Nights
Excursion to Segesta and Erice
Enhance your sightseeing experience of Sicily on an enriching full-day excursion to Erice and Segesta. First, you can delight in the medieval majesty of Erice, a walled town that reigns over the picturesque harbor of Trapani, where you can delve into the historical wonders of one of Sicily’s most in-demand destinations. Through the eyes of your expert guide, you will become acquainted with the city and its key landmarks on an in-depth history tour with the chance to also hike along the coastal reserve.
Next, you will discover Segesta, one of the major cities of the ancient indigenous Elymian people. Here you can visit the Doric temple, which dates back to the late 5th century BC. It was built on a hilltop just outside of the ancient city and has a commanding view of the surrounding area. If anyone needed yet more proof that the Greeks had a good eye for where to build, Segesta would lay any doubts to rest once and for all! Indeed, the setting of the temple is simply beautiful as completely unspoiled rolling green countryside stretches right down to the glistening aquamarine sea.
Wine tasting in Marsala and Selinunte
On this VIP excursion you will be picked up by our private driver at your hotel and leave for Marsala, which was once known as Lilibeo and was founded by refugees fleeing the destruction of Mozia. It was conquered by the Romans at the end of the First Punic War and became a luxurious town featuring glorious palaces and thermal baths. The Arabian settlers called the ancient city Mars-Alì (“the harbor of Alì” or “the big harbor”), but it is now known as Marsala. The modern city is known for its world-famous Marsala wine, as well as for the landing of Giuseppe Garibaldi in 1860. On our private adventure, you will discover all the best sights, including the Archaeological Museum and the Salt Road with the Salt Pans. You will also stop in a winery for Marsala wine tasting before reaching Selinunte, an ancient Greek city in the widest archaeological park of Europe. It was founded in the 7th century BC but was destroyed in 409 BC by the Carthaginians allied with Segesta, its eternal rival. The two most important areas you’ll visit are the Eastern Hill with the ruins of three temples, and the Acropolis where Greek and Punic ruins are still visible.Agrigento, One Night
Valley of the Temples tour
Immerse yourself in Sicily’s Greek past with this tour of Agrigento’s Valley of the Temples (entry included).
The UNESCO-protected Valley of the Temples is one of Sicily’s most important archaeological sites and is a joy to discover if you have an interest in history or simply want to learn more about Sicily’s turbulent past. This tour experience takes you to the sacred site, where an expert guide will treat you to a guided walk through the Valley.
As a part of your tour, you will see the Temple of Hera, the Temple of Concordia, the Temple of Herakles, the Temple of Zeus and the Sanctuary of Chtonian Deities (Temple of Castor and Pollux). During the tour, your guide will discuss the temples’ construction and tell you about their on-going preservation.Syracuse and Pantalica, Two Nights
Private walking tour of Syracuse Enjoy a private tour around the historical center of Syracuse with this VIP experience on the ancient island of Ortygia. This private walk begins at the ancient Greek Apollo Temple and leads you to Cathedral Square, which boasts beautiful limestone buildings and Baroque architecture. From here, you will visit the Arethusa Fountain, which is steeped in legend and mystery – your guide will tell you all its secrets! The tour concludes with a visit to the Jewish Quarter and Archimedes Square, where you can admire the Fountain of Diana, which was built in a Neoclassical style and is one of the most recognizable landmarks of Ortygia. Naturalistic excursion to Pantalica One of the most impressive archaeological sites in Sicily and a UNESCO World Heritage Site is the rocky necropolis of Pantalica, in eastern Sicily. This site is somewhat off the beaten track but certainly worth a visit on your complete Sicily vacation. Pantalica is a prehistoric site dating back to the late Bronze Age (from the 13th to the 8th century BC) and is famous for its necropolis, which features thousands of tombs dug into the overhanging walls of the Anapo Canyon. Pantalica is also famous for its breathtaking natural vistas and unusual wildlife. In fact, it is part of the revered Anapo Valley Nature Reserve, which is a paradise for trekking.Taormina and Mount Etna, Two Nights
Full-day Mount Etna Jeep tour with wine tasting and lunch
Scale the slopes of Italy’s famously active Mount Etna on this full-day 4×4 Jeep tour from Taormina. As a part of this unique experience, you will travel up rugged mountain tracks in an off-road vehicle and trek by foot to a stunning lookout point with views of lava flow basins and cave tubes created by the 2002 eruption. After descending from the volcano, you will enjoy a decadent and authentic Sicilian lunch of handmade cheeses, cured meats, pasta and dessert served with local wine.
VIP Taormina tour, featuring the Greek Theater
Today you will discover Taormina’s historic secrets and modern delights on a two-hour private tour. This guided experience allows you to explore the highlights of this charming city, including Palazzo Corvaja, the Santa Caterina Church and Vicolo Stretto, which is the narrowest street in town. As a special addition to this Taormina tour, you will enjoy “skip the line” entry to the ancient Greek Theater, which boasts magnificent views of Mount Etna and Giardini Naxos. There is no better way to discover this unassuming city’s treasured attractions!Why Travel with Bellarome
Personalized Travel Services
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