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Italy: Tuscany, Lucca to Siena

This is the Tuscany bike tour that independent-minded cyclists dream of. On this Self-Guided Bicycling Vacation, you’ll ride from Lucca to Siena inn to inn at your own pace, traversing the rolling vineyard-draped hills and cypress-lined lanes that have long inspired travelers. Much of your route follows the ancient pilgrim’s way of Via Francigena, delivering you to enchanting hill towns brimming with medieval treasures. Visit Leonardo’s hometown of Vinci. Marvel at sprawling manses along the elite Villa Way. Ride into the renowned wine region of Chianti. Along the way, indulge in welcoming lodgings that place you at the heart of the famed towns of Lucca, San Gimignano, and Siena, and savor the rustic charms of an authentic country agriturismo far from the crowds.

Tour Highlights

  • Stay in the heart of San Gimignano and Siena, two of Tuscany’s most beloved UNESCO World Heritage sites.
  • Cycle the Via Francigena, the ancient pilgrimage route to Rome, admiring Tuscany’s rolling hills, vineyards, cypress-lined byways and hilltop towns.
  • Explore Lucca as you wish, strolling its cobbled pedestrian streets and riding the ramparts of its wide Renaissance walls.
  • Discover the charms and the castle museum of the small town of Vinci, birthplace of Leonardi da Vinci
  • Stroll the cobbled lanes of historic Siena, lingering in its scallop-shaped Piazza del Campo, visiting its striking cathedral and browsing priceless collections of medieval art.

What to Expect

This tour is rated moderate for riders of analog bikes and easy-to-moderate for riders of E-bikes. It offers a combination of easy terrain and moderate hills and is ideal for beginning and experienced cyclists. Rides are on designated bike routes along quiet country roads; you spend a small percentage of time on dedicated bike paths. The traffic will be somewhat busier when entering and exiting larger towns such as Lucca and Siena. Routes often follow flat river valleys and then ascend to rolling hills. Please verify your bike selection for this tour as it is not always possible to change bikes once you arrive on tour. Travel with your friends and family—we can accommodate multiple guests on this self-guided vacation. Our 24/7 support system is available as needed.

  • Daily Mileage: 3 - 40 miles|
  • Biking: 1 - 4 hours
Activity Moderate Moderate
Cycling
Bar Graph Beginner - Experienced
Cyclists
24/7 Support System 24/7 Support
System

Average High /
Low Temperature (°F):

Apr68º/46º

May75º/53º

Jun84º/58º

Jul89º/63º

Aug88º/63º

Sep81º/58º

Oct69º/51º

Average
Precipitation:

Apr2.2 in

May2.9 in

Jun2.2 in

Jul1.6 in

Aug3.0 in

Sep3.0 in

Oct3.5 in

Air Package

Tour Only

Roundtrip international airfare Check
Detailed information for your independent travel to/from arrival and departure airports Check
One night in Lucca and one night in Florence in conveniently located hotels with daily breakfast Check
5 nights in boutique hotels and a small country estate Check Check
6 meals: 5 breakfasts, 1 dinner Check Check

Road Bicycle (Carbon frame)

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Step-Through (Mixte Hybrid) Comfort Bicycle

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Step-Over (Diamond) Comfort Bicycle

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Electric-Assisted Bicycle (E-bike) 5

Electric-Assisted Bicycle (E-bike)

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Self-Guided Biking Packages Include:

Custom VBT bike, helmet, and bike bag

Welcome orientation and bike fitting with local host

Luggage transfers

Ride with GPS and daily route notes

VBT Road Book with destination information

24/7 support system

Flat kit and multi-tool

Your choice of VBT branded gear for your adventure

Itinerary

Sat, Apr 22 to Sun, Apr 30 - 2023

Show Itinerary:

Depart home for Italy. The particulars of your arrival overseas are detailed with your flight itinerary.

Upon arrival at the Pisa airport, make your own independent travel arrangements to the nearby city of Lucca. For details, refer to your VBT Handbook.

If any flight delays cause you to arrive a day later, please contact Redpoint Global Support (see contact information in this document) to advise of your delay and they will contact your hotel.

VBT provides you with city information that includes recommendations for what to see and do in Lucca. Enjoy the rest of the day relaxing or roaming the atmospheric old-world warrens. Perhaps stroll to Piazza dell’Anfiteatro, a scenic square where an ancient amphitheater once stood. Visit one of the beautiful “101 Churches.” Or stroll along the medieval walls, restored into a lovely pedestrian park overlooking the red roofs of the Old City. Lucca’s pedestrian-friendly streets make exploring a pleasure.

Enjoy dinner tonight on your own in one of Lucca’s many excellent restaurants or intimate trattorias.

Meet your VBT Local host at 1:00 p.m., along with any other VBT guests arriving on the same day, for your Welcome Orientation in the lobby of the Hotel Ilaria & Residenza dell’Alba. Your Local host will be carrying a VBT sign and/or wearing a VBT garment.

Lucca (meaning “marsh”) was named for the wetlands on which it was built in the 1300s. The city prospered from silk production and trade. Women once dyed the fabrics in the canal that still today runs along the modern-day Via del Fosso. Later, bankers took over and wealthy families erected their lavish villas in the surrounding countryside. Today, about 10,000 Lucchesi live within the ancient city walls while about 80,000 live outside.

If you would like ample time to browse Lucca’s numerous beautiful churches, fascinating museums and café-lined piazzas, you can enjoy a short riding option. Pedaling along the ramparts of the Renaissance-era walls—refashioned for pedestrians and leisure cyclists with wide pathways—you enjoy marvelous views over the city’s red roofs and bell towers.

Your longer option follows an easy and unpaved bike path along the scenic Serchio River. You trace part of an ancient pilgrimage route that will reappear on your map throughout the week. In medieval days, devout followers walked this path from Canterbury, England, to the Holy See in Rome—though it was known more commonly as the Via Francigena, “the road that comes from France.” After a few miles, you join the gentle rolling piedemontana route at the foothills of the Apuan Alps. Not far from here, Michelangelo personally chose the blocks of marble from which he carved his most iconic sculptures.

Later, arrive at Lake Massaciuccoli, a shallow lagoon hosting more than 100 species of permanent and migrating birds. Over millennia, this unspoiled lake and wetlands have been shaped by shifting rivers and sediments and, more recently, human reclamation. While here, you might visit the remains of an ancient Roman villa and perhaps hear the echoes of a Puccini opera in the breeze—the great composer lived nearby and frequently hunted on the lake’s shores. You return to Lucca on a slightly different route.

What To Expect:

Lucca’s city walls — 5 km (3 miles)

This very easy and scenic ride follows the top of Lucca’s Renaissance city walls, built by the Medici family over the span of 100 years. You can ride it as many times as you’d like, seeing something new each time in the city below or the surrounding countryside. (Ride it once according to our directions, and the second time in the opposite direction. Repeat as you wish!). On a clear day, the peaks of the Apuan Alps are visible in the far north/northwest.

Lucca to Oasi Lipu Nature Preserve and Oasi Lipu Nature Preserve to Lucca — 50 km (31 miles)

This easy ride departs Lucca on bike lanes until you reach the outskirts of town. Then you join a flat, well-packed gravel path for about 5 km (3 miles) and country roads lead to the eastern side of Lake Massaciuccoli. Return on the same route, but you follow a road instead of a bike path for the last 5 km (3 miles). Expect some traffic as you ride in and out of Lucca.

Included Meals: Breakfast

Today you cycle east out of Lucca along the Via Francigena bike path. The ancient way is marked by big iron crosses that pointed pilgrims toward Rome in medieval times. It was Archbishop Sigeric who first walked from Canterbury to Rome, in the year 990. But he only documented his return journey to Canterbury. Today’s pilgrims typically follow in his footsteps toward Rome—as you do today.

Your scenic ride traces stunning vineyards and olive groves, passing by the Via delle Ville, or Villa Way. If you’d like, you may leave today’s main route to detour down this scenic byway and visit the magnificent Villa Torrigiani, one of many stately mansions built by wealthy families in the 16th and 17th centuries.

Continue on winding, gently rolling roads past olive groves and through the charming towns of the Valdinievole Valley. Soon, you cycle into the scenic Fucecchio Marsh, the largest inland marsh in Italy, stretching almost 4,500 acres. More than 200 bird species nest in this World Wildlife Fund region, such as herons, egrets, cranes and black storks. The area also boasts a rich human history, with its canals and port systems built by the Medicis and other powerful families.

Ride’s end delivers you into the bucolic countryside surrounding the town of Vinci, the birthplace of renowned artist Leonardo. Your hotel—an authentic agriturismo estate—is just one mile from the town center and its Castello dei Guidi, a former castle that now hosts a museum dedicated to Leonardo da Vinci. Settle in and enjoy your agriturismo’s pool and grounds or stroll or cycle into Vinci on a signed walking path. Dinner is included this evening at your agriturismo, a true Tuscan feast of home-grown products with olive oil, fresh vegetables and wine.

What To Expect:

Lucca to Vinci — 63 km (39 miles)

.

Included Meals: Breakfast, Dinner

Ride out of Vinci and head south on tranquil country roads into the spectacular Arno River Valley. You cross the river into historic San Miniato, a lovely village straddling three hills with spectacular views of the valley. The Tower of Frederick II that dominates the town was originally built in the 13th century, and was rebuilt in 1958 after it was bombed by the Germans during World War II.

Today’s rewarding route leads you deep into the Tuscan countryside. Some of Italy’s most stunning hilltop medieval towns here have mysteriously been left off the mainstream tourist map, leaving you free to explore them free of crowds. You pass through the hamlet of Corrazzano, then start climbing a ridge flanked by the hill towns of Castelfalfi and Montaione, a pair of lovely villages that were down on their luck until German investors invested in them. Continue a gradual climb to the 15th-century San Vivaldo Monastery, a Franciscan complex renowned for its 18 chapels containing splendid statuary depicting the Passion of Christ. Take advantage of the serenity here to enjoy a break.

Soon, you reach the highest point of the day, then enjoy a thrilling descent toward San Gimignano, passing through the rustic village of Castagno Val d’Elsa along the way. You may see San Gimignano long before you arrive; its soaring towers are visible from miles away. Its small medieval center—a UNESCO World Heritage site—once brimmed with 76 towers, erected in a 14th-century building frenzy by competing families. Today, only 13 remain.

What To Expect:

Vinci to San Gimignano — 65 km (40 miles)

Today’s ride takes you initially mostly downhill to the Arno River Valley. You cross the river with some traffic through a slightly industrial area. Remaining relatively flat with a few ascents and descents after San Miniato, the route has less traffic. Later, you begin a long gradual climb of about 13 km (8 miles) to the highest point of about 1,600 feet. After, a rolling then continual descent winds through stunning scenery of forest and wide-open distant views to the south until you arrive at the base of San Gimignano, its 13 towers soaring above. Pedal up to the hilltop town on winding streets and ride carefully or walk the last few hundred feet to your hotel, located on the cobbled pedestrian main street.

Included Meals: Breakfast

Immerse yourself more deeply into the rich and storied Tuscan landscape today as you trace the historic route between San Gimignano and Siena, two of Tuscany’s seven UNESCO World Heritage sites. On this magnificent ride, you experience the Tuscany of your dreams, winding through rolling emerald hills with sweeping vistas of distant hilltop towns, olive groves and lines of cypress trees.

Along the way, you may pause as you wish to fulfill your curiosity and follow your inspiration. It’s worth your while, however, to visit two particular sites. The Cistercian Abbey of Abbadia a Isola, in the village of the same name, was mentioned in the travel diary of Sigeric, that erstwhile pilgrim from Canterbury. During medieval times, it enjoyed protection from Siena and served as an inn for the devout making their way to Rome. Today, it is an austere and magnificent version of its former self. Its 11th-century Lombard-style church houses a 15th-century marble baptismal font and a 16th-century fresco.

Nearby, the walled medieval jewel of Monteriggioni rests on the plateau of a low hill. With its remarkably preserved wall and 14 watchtowers, it resembles a regal crown sitting astride the Tuscan hills. Built in 1213 by Siena as a fortress to face down the Florentines, it too was an important stage for pilgrims walking the Via Francigena. Merchants laid their heads here as well, and as you roam its atmospheric streets, it’s easy to imagine the bustle of commerce and transit during centuries past.

Later, you pedal into Siena, the sublime embodiment of a medieval city. Its inhabitants pursued their rivalry with Florence right into the area of urban planning. The entire city, built around the Piazza del Campo, was created with an eye toward aesthetics, so as to complement the surrounding landscape. Throughout the centuries, the Sienese have vigilantly preserved their city’s Gothic appearance.

Your hotel is located in the quietest part of the city, the contrada della Pantera (the Panther district)—only a few steps from a typical chiesa del cavallo (horse church). You can find these unique places of worship only here: churches where horses are received and blessed before the city’s famous Palio race. This evening, enjoy stunning sunset views over Tuscany from the hotel’s lovely west-facing gardens. Dinner is on your own in one of the many local trattorias in the heart of the city.

What To Expect:

San Gimignano to Siena — 59 km (36 miles)

Roll out of San Gimignano on a beautiful country road with rolling terrain past the Abbey of Abbadia a Isola to the small hilltop town Monteriggioni, a good lunch stop. You will find some traffic entering and exiting Monteriggioni. Exiting the way you came, you continue on parts of the Via Francigena through mixed countryside of oak forest and open agricultural land and into the outskirts of Siena, where traffic will become more frequent. A last ascent brings you to the western side of the city. You enter Siena through the Porta San Marco.

Included Meals: Breakfast

Follow your desires today, perhaps visiting the magnificent Gothic cathedral, the Duomo of Santa Maria Assunta. Be sure also to marvel at the 13th and 14th-century palazzos surrounding the Piazza del Campo and ascend the 500 steps of the bell tower of the Palazzo Pubblico for breathtaking views of Tuscany’s broad and beautiful landscapes.

If you would like to explore more of those landscapes on two wheels, grab your bike and head out into the famed Chianti region. You follow the Via Chiantigiana, a panoramic road that runs north-to-south across vineyards and through hilltop villages such as Castellina. Chianti is most beloved for its namesake wine. Its complex hilly territory comprises a collection of valleys—the Pesa, Greve, Elsa and Arbia—reaching out in different directions. This spectacular region was the subject of lengthy disputes between Florence and Siena until 1555, which explains the numerous castles, towers and fortified villages you ride past today.

Back in Siena, discover the city at your own pace. Siena’s Gothic appearance was developed between the 12th and 15th -centuries. During this period, the work of Duccio, the Lorenzetti brothers and Simone Martini set the stage for developments in Italian and, more broadly, European art. And even as the Renaissance of art, architecture, science and ideas swept the rest of Europe, the people of Siena clung to many of their medieval Gothic structures.

This evening, after day-trippers have gone, take a stroll through the various rioni (the territories within each contrada, or district) or through the quiet Duomo district. There is nothing quite like roaming these hushed medieval streets under the soft glow of lamplight.

Siena’s famous Palio horse race takes place every year on July 2 and August 16. A celebration of a miraculous apparition of the Virgin Mary, it first took place in 1656. From 1701, it was run in honor of the Madonna dell’Assunta, the patroness of Siena. The race’s history is strictly connected with the origins of Siena’s contrade, or districts. Each contrada is an institution in itself, with its own government, coat of arms, emblems and colors, festivities, patron saints and more. Today only 17 contrade exist, 10 of which participate in the race. During the month of July, you are likely to witness some of the festivities and decorations.

Today’s Ride Choices

Optional Walk: Siena morning walk from Hotel Athena — 2 km (1 mile)

What To Expect:

Siena to Castellina in Chianti through Porta Romana and Castellina to Siena — 29 km (18 miles)

Depart Siena through the city center, skirting its main pedestrian thoroughfare. Exercise caution with the city traffic. After the town of Quercegrossa, begin a gradual climb of about 10 km (6 miles) through the small towns of Capanno and Fonterutoli.

Siena morning walk from Hotel Athena Optional Walk: — 32 km (20 miles)

A short morning loop walk from your hotel provides a window into Siena as a local. Avoiding the more touristed areas but still full of views and landmarks, you trace the city walls with views over the outskirts, turn into a city park, and pass by small bars where you can grab an espresso standing up like the locals.

Included Meals: Breakfast

Enjoy breakfast at your hotel. Check-out is at 10:00 a.m. After, you make your own way to Florence, the cultural capital of Renaissance Italy; for details, refer to your VBT Handbook.

VBT provides you with city information and recommendations for what to see and do in Florence. Your hotel is perfectly situated to take advantage of all the city has to offer. Don’t miss exploring the signature of the city, the Duomo, with its soaring Brunelleschi dome. Next door lies the Baptistery with its massive copper Gates of Paradise designed by Ghiberti. Nearby, at the Piazza della Signoria, you can admire more sculptures including a replica of Michelangelo’s David. But the real thing awaits you a little farther north at the Galleria dell’Accademia. In the evening, relax in one of the city’s many fine restaurants and sample the best of la cucina fiorentina.

Included Meals: Breakfast

After an included breakfast* this morning, allow yourself a minimum of three hours prior to your flight departure to get to Florence Peretola Airport. This timeframe includes approximately 30 minutes (taxi) to maximum one hour of travel (on public transportation) and around two hours of recommended pre-flight check-in time.

*For guests with early-morning departures, breakfast at the hotel may not be available. Please check with the front desk to verify the times that breakfast is served.

Included Meals: Breakfast

Italy: Tuscany, Lucca to Siena 9

Download PDF Itinerary:

Air Package (PDF) Tour Only (PDF)

Mon, Apr 24 to Sat, Apr 29 - 2023

Show Itinerary:

We suggest arriving in Italy at least one day prior to the start date as your tour begins at 1:00 p.m. Make your own independent travel arrangements to Lucca. For details, refer to your VBT handbook.

Meet your VBT Local host at 1:00 p.m., along with any other VBT guests arriving on the same day, for your Welcome Orientation in the lobby of the Hotel Ilaria & Residenza dell’Alba. Your Local host will be carrying a VBT sign and/or wearing a VBT garment.

Lucca (meaning “marsh”) was named for the wetlands on which it was built in the 1300s. The city prospered from silk production and trade. Women once dyed the fabrics in the canal that still today runs along the modern-day Via del Fosso. Later, bankers took over and wealthy families erected their lavish villas in the surrounding countryside. Today, about 10,000 Lucchesi live within the ancient city walls while about 80,000 live outside.

If you would like ample time to browse Lucca’s numerous beautiful churches, fascinating museums and café-lined piazzas, you can enjoy a short riding option. Pedaling along the ramparts of the Renaissance-era walls—refashioned for pedestrians and leisure cyclists with wide pathways—you enjoy marvelous views over the city’s red roofs and bell towers.

Your longer option follows an easy and unpaved bike path along the scenic Serchio River. You trace part of an ancient pilgrimage route that will reappear on your map throughout the week. In medieval days, devout followers walked this path from Canterbury, England, to the Holy See in Rome—though it was known more commonly as the Via Francigena, “the road that comes from France.” After a few miles, you join the gentle rolling piedemontana route at the foothills of the Apuan Alps. Not far from here, Michelangelo personally chose the blocks of marble from which he carved his most iconic sculptures.

Later, arrive at Lake Massaciuccoli, a shallow lagoon hosting more than 100 species of permanent and migrating birds. Over millennia, this unspoiled lake and wetlands have been shaped by shifting rivers and sediments and, more recently, human reclamation. While here, you might visit the remains of an ancient Roman villa and perhaps hear the echoes of a Puccini opera in the breeze—the great composer lived nearby and frequently hunted on the lake’s shores. You return to Lucca on a slightly different route.

What To Expect:

Lucca’s city walls — 5 km (3 miles)

This very easy and scenic ride follows the top of Lucca’s Renaissance city walls, built by the Medici family over the span of 100 years. You can ride it as many times as you’d like, seeing something new each time in the city below or the surrounding countryside. (Ride it once according to our directions, and the second time in the opposite direction. Repeat as you wish!). On a clear day, the peaks of the Apuan Alps are visible in the far north/northwest.

Lucca to Oasi Lipu Nature Preserve and Oasi Lipu Nature Preserve to Lucca — 50 km (31 miles)

This easy ride departs Lucca on bike lanes until you reach the outskirts of town. Then you join a flat, well-packed gravel path for about 5 km (3 miles) and country roads lead to the eastern side of Lake Massaciuccoli. Return on the same route, but you follow a road instead of a bike path for the last 5 km (3 miles). Expect some traffic as you ride in and out of Lucca.

Today you cycle east out of Lucca along the Via Francigena bike path. The ancient way is marked by big iron crosses that pointed pilgrims toward Rome in medieval times. It was Archbishop Sigeric who first walked from Canterbury to Rome, in the year 990. But he only documented his return journey to Canterbury. Today’s pilgrims typically follow in his footsteps toward Rome—as you do today.

Your scenic ride traces stunning vineyards and olive groves, passing by the Via delle Ville, or Villa Way. If you’d like, you may leave today’s main route to detour down this scenic byway and visit the magnificent Villa Torrigiani, one of many stately mansions built by wealthy families in the 16th and 17th centuries.

Continue on winding, gently rolling roads past olive groves and through the charming towns of the Valdinievole Valley. Soon, you cycle into the scenic Fucecchio Marsh, the largest inland marsh in Italy, stretching almost 4,500 acres. More than 200 bird species nest in this World Wildlife Fund region, such as herons, egrets, cranes and black storks. The area also boasts a rich human history, with its canals and port systems built by the Medicis and other powerful families.

Ride’s end delivers you into the bucolic countryside surrounding the town of Vinci, the birthplace of renowned artist Leonardo. Your hotel—an authentic agriturismo estate—is just one mile from the town center and its Castello dei Guidi, a former castle that now hosts a museum dedicated to Leonardo da Vinci. Settle in and enjoy your agriturismo’s pool and grounds or stroll or cycle into Vinci on a signed walking path. Dinner is included this evening at your agriturismo, a true Tuscan feast of home-grown products with olive oil, fresh vegetables and wine.

What To Expect:

Lucca to Vinci — 63 km (39 miles)

.

Included Meals: Breakfast, Dinner

Ride out of Vinci and head south on tranquil country roads into the spectacular Arno River Valley. You cross the river into historic San Miniato, a lovely village straddling three hills with spectacular views of the valley. The Tower of Frederick II that dominates the town was originally built in the 13th century, and was rebuilt in 1958 after it was bombed by the Germans during World War II.

Today’s rewarding route leads you deep into the Tuscan countryside. Some of Italy’s most stunning hilltop medieval towns here have mysteriously been left off the mainstream tourist map, leaving you free to explore them free of crowds. You pass through the hamlet of Corrazzano, then start climbing a ridge flanked by the hill towns of Castelfalfi and Montaione, a pair of lovely villages that were down on their luck until German investors invested in them. Continue a gradual climb to the 15th-century San Vivaldo Monastery, a Franciscan complex renowned for its 18 chapels containing splendid statuary depicting the Passion of Christ. Take advantage of the serenity here to enjoy a break.

Soon, you reach the highest point of the day, then enjoy a thrilling descent toward San Gimignano, passing through the rustic village of Castagno Val d’Elsa along the way. You may see San Gimignano long before you arrive; its soaring towers are visible from miles away. Its small medieval center—a UNESCO World Heritage site—once brimmed with 76 towers, erected in a 14th-century building frenzy by competing families. Today, only 13 remain.

What To Expect:

Vinci to San Gimignano — 65 km (40 miles)

Today’s ride takes you initially mostly downhill to the Arno River Valley. You cross the river with some traffic through a slightly industrial area. Remaining relatively flat with a few ascents and descents after San Miniato, the route has less traffic. Later, you begin a long gradual climb of about 13 km (8 miles) to the highest point of about 1,600 feet. After, a rolling then continual descent winds through stunning scenery of forest and wide-open distant views to the south until you arrive at the base of San Gimignano, its 13 towers soaring above. Pedal up to the hilltop town on winding streets and ride carefully or walk the last few hundred feet to your hotel, located on the cobbled pedestrian main street.

Included Meals: Breakfast

Immerse yourself more deeply into the rich and storied Tuscan landscape today as you trace the historic route between San Gimignano and Siena, two of Tuscany’s seven UNESCO World Heritage sites. On this magnificent ride, you experience the Tuscany of your dreams, winding through rolling emerald hills with sweeping vistas of distant hilltop towns, olive groves and lines of cypress trees.

Along the way, you may pause as you wish to fulfill your curiosity and follow your inspiration. It’s worth your while, however, to visit two particular sites. The Cistercian Abbey of Abbadia a Isola, in the village of the same name, was mentioned in the travel diary of Sigeric, that erstwhile pilgrim from Canterbury. During medieval times, it enjoyed protection from Siena and served as an inn for the devout making their way to Rome. Today, it is an austere and magnificent version of its former self. Its 11th-century Lombard-style church houses a 15th-century marble baptismal font and a 16th-century fresco.

Nearby, the walled medieval jewel of Monteriggioni rests on the plateau of a low hill. With its remarkably preserved wall and 14 watchtowers, it resembles a regal crown sitting astride the Tuscan hills. Built in 1213 by Siena as a fortress to face down the Florentines, it too was an important stage for pilgrims walking the Via Francigena. Merchants laid their heads here as well, and as you roam its atmospheric streets, it’s easy to imagine the bustle of commerce and transit during centuries past.

Later, you pedal into Siena, the sublime embodiment of a medieval city. Its inhabitants pursued their rivalry with Florence right into the area of urban planning. The entire city, built around the Piazza del Campo, was created with an eye toward aesthetics, so as to complement the surrounding landscape. Throughout the centuries, the Sienese have vigilantly preserved their city’s Gothic appearance.

Your hotel is located in the quietest part of the city, the contrada della Pantera (the Panther district)—only a few steps from a typical chiesa del cavallo (horse church). You can find these unique places of worship only here: churches where horses are received and blessed before the city’s famous Palio race. This evening, enjoy stunning sunset views over Tuscany from the hotel’s lovely west-facing gardens. Dinner is on your own in one of the many local trattorias in the heart of the city.

What To Expect:

San Gimignano to Siena — 59 km (36 miles)

Roll out of San Gimignano on a beautiful country road with rolling terrain past the Abbey of Abbadia a Isola to the small hilltop town Monteriggioni, a good lunch stop. You will find some traffic entering and exiting Monteriggioni. Exiting the way you came, you continue on parts of the Via Francigena through mixed countryside of oak forest and open agricultural land and into the outskirts of Siena, where traffic will become more frequent. A last ascent brings you to the western side of the city. You enter Siena through the Porta San Marco.

Included Meals: Breakfast

Follow your desires today, perhaps visiting the magnificent Gothic cathedral, the Duomo of Santa Maria Assunta. Be sure also to marvel at the 13th and 14th-century palazzos surrounding the Piazza del Campo and ascend the 500 steps of the bell tower of the Palazzo Pubblico for breathtaking views of Tuscany’s broad and beautiful landscapes.

If you would like to explore more of those landscapes on two wheels, grab your bike and head out into the famed Chianti region. You follow the Via Chiantigiana, a panoramic road that runs north-to-south across vineyards and through hilltop villages such as Castellina. Chianti is most beloved for its namesake wine. Its complex hilly territory comprises a collection of valleys—the Pesa, Greve, Elsa and Arbia—reaching out in different directions. This spectacular region was the subject of lengthy disputes between Florence and Siena until 1555, which explains the numerous castles, towers and fortified villages you ride past today.

Back in Siena, discover the city at your own pace. Siena’s Gothic appearance was developed between the 12th and 15th -centuries. During this period, the work of Duccio, the Lorenzetti brothers and Simone Martini set the stage for developments in Italian and, more broadly, European art. And even as the Renaissance of art, architecture, science and ideas swept the rest of Europe, the people of Siena clung to many of their medieval Gothic structures.

This evening, after day-trippers have gone, take a stroll through the various rioni (the territories within each contrada, or district) or through the quiet Duomo district. There is nothing quite like roaming these hushed medieval streets under the soft glow of lamplight.

Siena’s famous Palio horse race takes place every year on July 2 and August 16. A celebration of a miraculous apparition of the Virgin Mary, it first took place in 1656. From 1701, it was run in honor of the Madonna dell’Assunta, the patroness of Siena. The race’s history is strictly connected with the origins of Siena’s contrade, or districts. Each contrada is an institution in itself, with its own government, coat of arms, emblems and colors, festivities, patron saints and more. Today only 17 contrade exist, 10 of which participate in the race. During the month of July, you are likely to witness some of the festivities and decorations.

Today’s Ride Choices

Optional Walk: Siena morning walk from Hotel Athena — 2 km (1 mile)

What To Expect:

Siena to Castellina in Chianti through Porta Romana and Castellina to Siena — 29 km (18 miles)

Depart Siena through the city center, skirting its main pedestrian thoroughfare. Exercise caution with the city traffic. After the town of Quercegrossa, begin a gradual climb of about 10 km (6 miles) through the small towns of Capanno and Fonterutoli.

Siena morning walk from Hotel Athena Optional Walk: — 32 km (20 miles)

A short morning loop walk from your hotel provides a window into Siena as a local. Avoiding the more touristed areas but still full of views and landmarks, you trace the city walls with views over the outskirts, turn into a city park, and pass by small bars where you can grab an espresso standing up like the locals.

Included Meals: Breakfast

Enjoy breakfast at your hotel. Check-out is at 10:00 a.m. Depending upon your final destination, it may not be possible to depart for the U.S. on the last day of the tour. Please check airline schedules carefully. If you plan to schedule return flights immediately following the tour’s conclusion, please call your airline directly for specific check-in requirements. Your VBT Handbook provides suggestions on onward travel options from Siena.

Included Meals: Breakfast

Italy: Tuscany, Lucca to Siena 9

Download PDF Itinerary:

Air Package (PDF) Tour Only (PDF)

Accommodations (Please Note: Days are based on the Air Package Itinerary. Accommodations may vary depending on departure date. )

Reviews
1 out of 2 (50%)
4.5 out of 5 stars.
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We took 4 of our children and their spouses and it really was the best trip ever! We loved everything about it. The routes were challenging but worth it. We loved the self guided. Tuscany is truly amazing and the best way to see it is on a bike. One of the highlights of our trip was going to the Montese Cooking school near San Gimignano, I highly recommend it. All the hotels were wonderful except one but it was the only one in the area. I would not rate it moderate compared to the 6 other VBT trips we…

Brower, Draper, Utah

Italy: Tuscany, Lucca to Siena

Dates & Prices

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Air Package

9 days, includes round-trip international airfare and additional hotel nights with included breakfast.

Single Supplement: From $695

Sat, Apr 22 - Sun, Apr 30, 2023

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$3,695

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Sat, Apr 29 - Sun, May 7, 2023

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Sat, May 6 - Sun, May 14, 2023

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Sat, May 13 - Sun, May 21, 2023

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Sat, May 20 - Sun, May 28, 2023

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Sat, May 27 - Sun, Jun 4, 2023

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Sat, Jun 10 - Sun, Jun 18, 2023

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Sat, Sep 9 - Sun, Sep 17, 2023

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Sat, Sep 16 - Sun, Sep 24, 2023

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Sat, Sep 23 - Sun, Oct 1, 2023

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Sat, Sep 30 - Sun, Oct 8, 2023

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Sat, Oct 7 - Sun, Oct 15, 2023

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Sat, Sep 3 - Sun, Sep 11, 2022

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Sat, Oct 1 - Sun, Oct 9, 2022

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6 Days. Includes Self-Guided bike vacation only.

Single Supplement: From $445

Mon, Apr 24 - Sat, Apr 29, 2023

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Mon, May 1 - Sat, May 6, 2023

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Mon, May 29 - Sat, Jun 3, 2023

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Mon, Jun 12 - Sat, Jun 17, 2023

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Mon, Sep 11 - Sat, Sep 16, 2023

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Mon, Sep 18 - Sat, Sep 23, 2023

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Mon, Sep 25 - Sat, Sep 30, 2023

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Mon, Oct 2 - Sat, Oct 7, 2023

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Mon, Oct 16 - Sat, Oct 21, 2023

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Mon, Sep 5 - Sat, Sep 10, 2022

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For more information, call: 800-245-3868

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