Siena Tours

Leave Siena aboard a luxury minivan and head east into the heart of Italy?s picturesque Chianti region to start your Chianti wine-tasting and castles trip. Passing through the captivating countryside, you'll see the cypress trees and olive groves that typify this beautiful part of Tuscany. Soon enough, you'll notice impressive castles, fortified farm houses and towers that bear testimony to turbulent wars between the once opposing republics of Siena and Florence.

Perched high on a forested hill sits the enchanting Castello di Brolio -- your first Chianti castle visit of the day. Learn about its importance during medieval battles, and about the fascinating Ricasoli family who have owned the castle since the 11th century. With your friendly and knowledgeable guide, explore the Castello di Brolio vineyards where the world-famous red Chianti wine is said to have originated. Then, enjoy a photo opportunity amid the gorgeous surroundings.

Continue to Castello di Meleto, another impressive Chianti castle with 15th-century fortifications and a distinctive cylindrical tower. Surrounded by sun-kissed fields, the castle is now a famous winery, boasting large vineyards and a wine-tasting room. With your guide, tour the castle grounds before savoring a glass of Black Rooster Chianti Classico -- the winery's most prestigious red wine.

Once you?ve worked up an appetite, head to a traditional Tuscan farm for lunch and enjoy platters of locally produced food and fine wines. After this delicious feast, continue to one of the countryside?s many quaint medieval villages and spend time exploring at leisure. Your guide will happily recommend local coffee bars or interesting sights for you to see.

The last stop of the day is at another Chianti winery, where you'll meet the local producer and hear about the lifestyle of the charismatic Chianti folk. Visit the cellars and gardens before enjoying a relaxing ride back to Siena.

Your small-group tour begins in the afternoon with a comfortable drive in a luxury minivan from Siena to Chianti -- a region of Italy famous for its beautiful vineyards and landscapes shaped into works of art by the combined actions of nature and man. Arrive first in the village of Castellina in Chianti, and enjoy a gelato (own expense) as you walk through its medieval alleyways and town center with your guide.

From here, enjoy the drive to a Chianti wine estate, where you'll tour the grounds and wine cellars while learning about the winemaking process. Sit down and savor a tasting of Black Rooster Chianti Classico wine and olive oil (included).

Then head to Monteriggioni, a perfectly preserved medieval town with a complete ring of walls and turrets built in the 13th century. It was Siena?s main bastion of defense against the armies of Florence during the Middle Ages, and today it is a quiet hamlet. Enjoy leisure time here to explore the charming city on your own.

In the late afternoon, arrive in San Gimignano and explore this romantic town of towers. You'll have free time to enter its impressive church, the Collegiata di San Gimignano, or explore the Civic Museum (entrance fees at own expense). Alternatively, shop in the artisan boutiques for leather goods and hand-painted pottery; sample the fruits of the soil in the food shops and wine bars; or discover the town?s many hidden beauties.

After your time in San Gimignano, head out of town to a nearby rustic farmhouse, where you'll be treated to a classic Tuscan dinner, accompanied by tastings of Vernaccia (the famous white wine of San Gimignano) and red Chianti wine. Your Tuscan dinner, consisting of cured meats, home-grown vegetables and cheeses, will be served on a terrace overlooking the cultivated fields and the ?skyline? of San Gimignano?s towers during sunset. As your tour comes to an end, meet your guide back at the minivan for the relaxing return journey to Siena.

Leave Siena in the morning and set off in a comfortable, air-conditioned minivan toward the famous wine hills of Montalcino in Italy?s Tuscany wine region. The first stop is at a small, traditional winery, where you'll walk among the vineyards, explore the cellars, and enjoy your first Brunello di Montalcino wine tasting of the day.

Next, arrive in Montalcino, the hilltop town that gives its name to the region and its wines. Here, you'll have the opportunity to walk around the walls of the fortress where brave soldiers of the Republic of Siena made their last stand to Florence during battles in medieval times. Explore this captivating town independently and visit the town?s stores, taste the famous Brunello wines, or simply enjoy the incredible views overlooking the valley below.

After your visit to Montalcino, continue your drive to a family-run winery, where you?ll be introduced to the owners and winemakers themselves. Visit the farm before sitting down to enjoy a traditional Tuscan meal (included) accompanied by delicious wines produced in this region.

After lunch, consisting of antipasti, pasta or risotto, desert, coffee and wine tastings, visit the stunning, ancient Benedictine abbey of Sant'Antimo, a special place radiating tranquility, set in a fabulous landscape. With your expert guide, explore the inside of the abbey and learn about its fascinating history. You may get the chance to witness the monks singing Gregorian chants as you enjoy the serene natural surroundings.

In the afternoon, head to a third winery, where you'll get a detailed explanation of the wine-making processes, learn about the tools used, discover how the vines are cared for, and learn about the long aging process in oak barrels that gives these wines their distinctive flavor. After visiting the cellars and getting to know the winemakers you can sit down for a last tasting of this 'Nectar of the Gods', before enjoying a relaxing ride back to Siena.

Leave Siena in the morning and head northwest by comfortable minivan toward San Gimignano. On your way, stop at the medieval Fortress of Monteriggioni, a captivating Tuscan hill town that is one of the few whose medieval city walls remain completely intact. Walk around the stone walls encircling this charming town and learn about the area?s interesting history from your guide.

From Monteriggioni, continue to the beautiful hill town of San Gimignano -- undoubtedly the highlight of your trip. Walk down the Via Francigena strip that runs through the town as your guide explains the history of this ancient pilgrimage road said to link Rome to Canterbury in England. Learn how in bygone times, Christian pilgrims would travel between cities in Italy, Switzerland, France and England on this road.

After tracing the pilgrim's steps down Via Francigena, you'll have time for independent sightseeing in San Gimignano. This gorgeous, UNESCO World Heritage-listed town is as famous for its medieval architecture as it is for its scenic views. See beautiful monuments in Piazza del Duomo, or search the local shops for quality saffron spice that the town produces, known locally as ?red gold.? Perhaps check out Palazzo Communale and climb up Torre Grossa (own expense). The climb is steep but worthwhile -- simply for the panoramic views of Tuscany from the top!

Break for lunch at a traditional, family-run farm just outside of San Gimignano, and indulge in a Tuscan feast! Your friendly Italian hosts will treat you to scrumptious platters of home-grown delicacies prepared with organic saffron, accompanied by chilled Vernaccia white wine.

In the afternoon, enjoy a scenic drive farther south to Volterra. The fascinating Tuscan city is renowned for its alabaster -- the translucent stone used for centuries to create vases, lamps and other works of art. On the way, visit an authentic alabaster workshop and watch an artisan craftsman at work. In Volterra itself, you'll have approximately one hour to spend at leisure to explore the picturesque streets before returning to Siena.

Meet your friendly guide in central Siena and head out of town in a comfortable minivan on one of Tuscany's panoramic roads, passing through the characteristic clay hills known as the Crete Senesi. Arrive first in the beautiful town of Pienza, which was entirely planned out by Pope Pius II, the humanist pope, to be the ideal Renaissance town.

Pienza is rightly considered the gem of the Val d?Orcia region; the town and the entire Val d?Orcia are World Heritage Sites. You'll have time to spend at leisure here, so make the most of it by shopping or exploring the pretty alleyways of this small town at your leisure. As you leave Pienza, enjoy the fantastic views of Tuscany?s famous picture-perfect scenery.

Your next stop is a local dairy farm, where you?ll feast on a wholesome and refreshing lunch (included) of fresh ingredients mostly produced on the farm. You?ll also enjoy a tasting of Italy?s salty Pecorino cheese, hear about the cheese-making process, visit the farm?s animals and learn about the lifestyle of the area.

In the afternoon, travel to Montepulciano, one of Tuscany?s biggest hill towns, located on a steep hill overlooking the amazing landscape of the Tuscany-Umbria border. With your guide, take a short walk around town to see the Piazza Grande at the top of the hill. You?ll then have free time to visit the town?s many stores, palaces or churches. Head to a family winery to enjoy a tasting of Montepulciano?s renowned wine and tour of the wine cellars before your relaxing ride back to Siena.

To begin your walking tour of Siena, meet your friendly guide in Siena's famous Piazza del Campo, a gorgeous square that represents day-to-day life of this medieval city and is widely considered one of the most beautiful squares in Europe.

Explore Siena?s UNESCO World Heritage-listed Old Town by foot and listen as your guide points out Palazzo Tolomei, which is said to be the oldest private palace in Siena. See the imposing stone tower of Palazzo Chigi Saracini, a palace erected in the mid-12th century by the powerful Marescotti family. Currently, this building is the seat of the prestigious Accademia Musicale, founded in 1923. Next, walk to the magnificent Basilica of San Domenico and admire its Gothic architecture constructed entirely in brick.

Continue your tour to one of the most spectacular cathedrals in Italy, the Siena Duomo (Siena Cathedral), named locally as Il Duomo. After skipping the entrance line with your skip-the-line ticket, your guide will escort you into this breathtaking cathedral to see impressive masterpieces by Donatello, Bernini and Michelangelo. Admire the exquisite Gothic architecture; walk through nave arcades with Renaissance busts of popes and emperors; and marvel at the unique black-and-white-striped bell tower.

After your tour, you?ll leave feeling truly enchanted.

Discover Tuscany?s famed natural beauty on this full-day tour from Siena! Your private hiking tour starts in the morning with a comfortable 40-minute drive by luxury minivan from Siena to the heart of Chianti. Chianti is a Tuscan region world-renowned for its picturesque vineyards and landscapes typified by lush green hills and olive groves.

Following your expert guide, unleash your inner adventurer on a scenic, leisurely-paced walk through the gorgeous Chianti countryside. Stop along the way to enjoy gelato or coffee (own expense) at a local caf?. At the end of the hike, your friendly guide will lead you to a spot where you can relax and enjoy a picnic of cured meats, locally grown vegetables, breads and cheeses, accompanied by a glass of wine.

After the picnic, you'll be picked up by air conditioned minivan and driven to San Gimignano, a colorful medieval hill town surrounded by vineyards that produce one of Tuscany?s most popular white wines, Vernaccia. Explore the town's breathtaking UNESCO World Heritage-listed city center, famous for its medieval architecture and panoramic views over Tuscany. Stroll down the Via Francigena path as your guide explains the history of this ancient pilgrimage road, said to link Rome to Canterbury in England.

After tracing the pilgrim's steps down Via Francigena, you'll have time for independent sightseeing in San Gimignano. See beautiful monuments in Piazza del Duomo and go inside the impressive cathedral (own expense), or browse the local shops for quality saffron spices that the town produces. In the late afternoon, meet your guide back at the minivan for the relaxing return journey to Siena.

Note: This hiking tour is suitable for those in good physical condition, and who have experience with long walks. Although the walking trails in Chianti are open to everyone, remember that the area is natural and unspoiled, so the ground can be uneven and, in some places, steep and narrow.

Leave Siena early in a luxury minivan with your guide, and set off to the Chianti hills, enjoying views of beautiful forests, rows of vineyards and pretty medieval hamlets. Your first stop is the walled village of Castellina in Chianti, where you'll explore the town and its covered medieval walkway with your guide. See the fascinating Castle of Castellina, which dates to the 15th century and was built by the order of Lorenzo il Manifico, a popular Florentine statesman in medieval times.

Next, head to the beautiful town of Greve in Chianti, famous for its triangular-shaped piazza and for being the home of famous sailor Verrazzano. Have leisure time here to sample wines (additional cost) or visit the local boutiques and market stalls.

From Greve, you'll take a short drive over to Montefioralle, a village that claims to be the birthplace of Amerigo Verpucci, the famous cartographer who gave his name to the Americas. Enjoy a walk along Montefioralle?s cobbled streets and take in the breathtaking views.

Just outside of this beautiful village is a family-run winery, where you'll enjoy a delicious Tuscan lunch, consisting of cured meats, home-grown vegetables and cheeses, and enjoy a wine tasting of the famous Black Rooster Chianti Classico. While you eat and drink, learn from your friendly guide about the region?s customs and traditions. Then visit another, larger winery, where you?ll be guided through the process of wine production and visit the wine cellars. Hear more about Chianti?s famous red wines, including how they are made and the differences in flavor of the various blends and grapes.

Your last stop before returning to Siena is the beautiful Abbey of Passignano, where you?ll admire the glorious landscapes of the surrounding countryside. The abbey, whose existence has been documented from the beginning of the 11th century, was once one of the most powerful castles of the Val di Pesa.

Meet your guide in central Siena and after listening to a comprehensive safety briefing, put on your helmet, hop on your bike and set off on your way. Following your guide, cycle through Siena?s pretty streets to Piazza del Campo -- the city's UNESCO World Heritage-listed square. Soak up the laid-back atmosphere that abounds, and hear how the square has been used in films ? most notably how it featured in the James Bond film Quantum of Solace.

Enjoy plenty of stops throughout your ride to soak up the sights and relax. Hop off your bike in Piazza del Duomo and then pose for photos in front of Siena Cathedral ? Tuscany?s Gothic masterpiece! Pass though Siena?s atmospheric Old Town, pedaling past quaint pavement-side cafes where the Sienese spill out onto the streets drinking their coffees.

Continue cycling to Porta San Marco, Siena?s famous terracotta arch, and then meander past Porta Camollia ? an intriguing medieval gateway that once served as the entrance to the city for visiting pilgrims. Hear about the Contrade of Siena, the city?s 17 neighborhoods, and learn about their different personalities as you cycle through the streets.

After two hours on your bike, head back to the center of town with your guide and finish your tour at the start point.

Meet your host in central Siena and stroll to a private kitchen in the center of town to start your 4-hour Tuscan cooking class. All utensils and equipment are provided for your session, and under the careful eye of your host you?ll learn all about the culinary secrets of Tuscany.

?Eat local? is a theme that Tuscans don?t really consider; it?s a concept that?s ingrained in their heritage thanks to the region?s rich abundance of quality ingredients. The countryside around Siena teems with produce: lush olive groves, fragrant sage and rosemary bushes, and hills blanketed with heaving grape vines.

Using these key ingredients, help your host prepare an antipasto feast of breads, cheeses and cured meats ? a staple dish in Tuscan restaurants and caf?s. Prepare toppings for bruschetta (grilled bread, topped with tomatoes, basil and olive oil) and put together plates of crostini (crispy thin slices of white bread drizzled with extra virgin olive oil).

Learn about Tuscan pici -- a doughy and flavorsome type of egg pasta -- and then make some for yourself. Mix the ingredients and knead the dough before rolling and cutting it into distinctive thick spaghetti strands, and cooking it with a sauce.

Toward the end of your session, sit down with your host and group to eat your creations! The dishes are paired with quality Tuscan wine ? carefully selected by your host to complement and accentuate the flavors of the food. Before leaving, your host will give you a recipe card so that you can re-create the food yourself at home to impress friends and family!

Meet your guide and tour escorts at your hotel, put on your helmet and get acquainted with your quintessentially Italian mode of transport ? a beautiful Vespa scooter! After a safety briefing and a few practice sessions to get used to the Vespa?s automatic gears, follow the lead of your guide and set off on your way. Alternatively, hop on behind one of your tour escorts if you prefer not to drive yourself.

Following your guide, take a leisurely drive through the area of Monteriggioni. Then, head into the luscious Chianti hills of Tuscany, passing along quiet countryside lanes that meander through medieval villages and flower-filled fields. If you?ve chosen to share your scooter with a traveling companion, there will be plenty of breaks factored in to stop and switch drivers, or to simply stretch your legs while soaking up the views.

Half-way through the day, stop at a Chianti winery in the heart of the region to learn all about winemaking in Tuscany. Explore the vineyards and cellars with your guide, and then taste several local wines, including prestigious varieties such as Chianti Classico, Gallo Nero and Super Tuscan.

After your wine-tasting session, sit down inside the winery and enjoy a traditional Tuscan lunch of cured meats, mild cheeses, freshly baked bread and olives, while chatting with your guide about life in the idyllic Chianti region. Spend some free time here relaxing in the sunshine before driving back into Siena.

Your Vespa tour finishes in the late afternoon back at your Siena hotel.

Leave your central Siena hotel in the morning and travel east to Cortona, a stunning little hilltop town of ancient origins. The setting for the 2003 rom-com Under the Tuscan Sun, Cortona boasts a wealth of picture-perfect medieval architecture making it a perfect place to spend your morning. Sightsee at leisure or join a walking tour (own expense), seeing sites like Santa Margherita Sanctuary ? built to commemorate the patron saint of the city ? and the imposing Palazzo Communale. Enjoy a walk and stroll around the city walls.

After your tour, relax with some free time in the town to do as you please. Perhaps find a piazza-side caf? for lunch (own expense) or stroll around the narrow lanes admiring the sun-bleached stone buildings. Meet back up with your guide at a pre-arranged time to leave Cortona by coach.

Continue your tour traveling south into Umbria to visit Assisi, an enchantingly beautiful hill town, best known for its links to St Francis ? a wealthy merchant?s son who chose to embrace poverty and preach on the streets of the town.

Follow in St Francis? footsteps on a walking tour around Assisi, ambling along winding streets and alleyways and ending up in the spectacular Basilica di San Francesco. See both the upper and lower basilicas -- one lavishly ornate and the other minimalistic and sober in line with St Francis? teachings. The church is also famous for its Giotto frescoes, and your guide will point out these medieval depictions of St Francis? life in the town. Finish your afternoon in Assisi with a visit to Santa Maria degli Angeli Church -- a little-known place where St Francis is said to have realized his vocation.

Return to your coach for the journey back through the picturesque Tuscan hills to Siena, where you'll arrive in the late afternoon.

Leave central Siena bright and early, and travel north out of the city toward Tuscany?s capital, Florence. After a brief stop here to pick up fellow passengers, continue traveling west in the direction of the coast. Pass out of the lush Tuscan countryside into Liguria and head into the Cinque Terre National Park ? a UNESCO World Heritage Site that lines the Italian Riviera?s coast.

Meaning ?five lands,? the Cinque Terre is precisely that, but a whole lot more scenic than its name suggests. Five sun-baked fishing villages cling to the area?s dramatic sea cliffs, separated only by wind-gnarled vineyards and olive groves; it?s the rugged face of the Italian Riviera at its picture-perfect best.

Hop off your coach at the village of Manarola and explore its streets on a stroll around the village. Meet your guide at the pre-arranged time and hop on the train to travel north to Vernazza -- a village once favored by Italian nobility and naval forces. Amble around the pretty streets at leisure, and then hop aboard your sightseeing boat (or train if the weather is bad) to the village of Monterosso. Sit down for lunch in one of its charming seaside trattorias, and admire views over its turquoise bay as you eat. The rest of your time in Monterosso is spent at leisure, so why not head to one of its beaches for a swim?

Your last stop is Riomaggiore, the area?s southernmost village, and on arrival here, your guide will show off its delights on a stroll around. A winemaking village that dates back to the 13th century, Riomaggiore is often considered the highlight of the Cinque Terre, with its candy colored houses and secluded beaches. After exploring Riomaggiore, board your train to La Spezia and then board your coach for the journey southeast back to Siena. Your tour finishes around 9pm in the evening at the start point.

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