Tour of Tuscany - Italia Espresso
The Tuscany motorcycle tour has it all! From bustling Florence to the quiet, walled hill town of Assisi; from the terraced vineyards of Chianti to enchanting town of Lucca; from the best wines of Southern Europe to the best espresso.
Tuscany enchants with its winding roads, hillside villages surrounded by olive groves, country lanes, and such historic cities as Voltera, Florence, and Siena. This area of Italy is the quintessential “Bel Paese.” Our tour takes in the best sweeping roads, divulging the region’s treasures.
Starting from Bologna, we ride through the Apennines Mountains passing many quaint Tuscan villages before arriving at the picturesque city of Siena. We touch Umbria to explore the narrow streets of hilltop Assisi and continue along the rolling hills of the Val d'Orcia. A stop in the tiny Republic of San Marino, host of the motorcycle Grand Prix. Next is Florence and then Montalcino, Pienza and the splendid Chianti region. The city of Lucca is our "waving goodbye" point before returning to Bologna. And should the land and architecture fail to inspire, the food and wine certainly will.
Tour overview
Road description
The whole tour runs on asphalt.
Highlights
Riding in Tuscany, San Marino, Assisi, Siena, Chianti region, San Gimignano
Countries:
Italy, San Marino
Route
Mileage: 1.700 km (1.100 miles)
Mileage: 180 - 300 km (110 - 190 miles).
Tour starts / ends
Bologna, Italy
Rest days
1; Florence
Accommodation
Comfortable, very nice hotels.
Day by day
Previous
Next
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Arrival to Bologna
Welcome to the colourful and beautiful city of Bologna!
We'll meet you at the airport and take you to your hotel. At 4 PM, we'll meet for the introductory briefing and in the evening go for a welcome dinner at a traditional Italian Trattoria.
Bologna - Siena
Our second riding day begins in Bologna, where we leave the city’s graceful porticoes behind and ride south into the heart of the Italian countryside. The road soon winds through forested hills and open farmland, revealing glimpses of stone villages and distant ridgelines.
As we cross from Emilia-Romagna into Tuscany, the landscape softens into rolling vineyards, olive groves, and cypress-lined lanes typical of the Chianti region. The final stretch carries us through gentle curves and sun-warmed valleys before we arrive in Siena, its medieval towers rising above the terracotta rooftops.
Siena - Assisi
Setting out from Siena, we follow winding roads that carry us eastward across the gentle hills and golden fields of southern Tuscany. The route passes through quiet villages and vineyards, the landscape dotted with cypress trees and rustic farmhouses.
As we approach Umbria, the terrain grows more dramatic, with rolling hills giving way to wooded valleys and river gorges. The town of Assisi emerges on a hillside, its pale stone basilicas and medieval streets rising gracefully above the surrounding countryside. Arriving in the afternoon, we are greeted by the serene charm and spiritual atmosphere that have made Assisi a timeless destination.
Assisi - San Marino
Leaving Assisi, we ride southeast through the gentle hills and patchwork fields of Umbria, the morning light casting a warm glow over olive groves and vineyards. The road soon begins to climb as we approach the Apennines, winding through forested slopes and small, perched villages.
Each curve reveals glimpses of distant valleys and rugged ridgelines, building anticipation for the day's destination. By afternoon, we reach San Marino, where the medieval towers of Monte Titano rise dramatically above the countryside, offering sweeping views and a sense of history etched into every stone street.
San Marino - Florence
Departing San Marino, we wind down from Monte Titano’s heights, the morning air cool and clear as the road dips into the fertile plains below. The route carries us across Emilia-Romagna’s countryside, past farmsteads and sleepy hamlets, before turning west toward the wooded slopes of the Apennines.
The ride is a mix of smooth curves and sweeping vistas, each bend revealing another postcard view of rural Italy. As we cross back into Tuscany, the scenery softens into golden fields and olive-dotted hillsides. By day's end, Florence awaits—its terracotta rooftops, graceful bridges, and the majestic Duomo glowing in the afternoon light.
Rest day in Florence
Spend the rest-day in the fabled city of Florence and see all the attractions that are on offer. Start with a stroll to the Cattadrale di Santa Maria del Fiore, or Duomo, with its famous, colorful, towering cupola.
Then take a walk over the city's famous Old Bridge, the Ponte Vecchio. If art interests you, the Galleria Degli Uffizi houses the greatest collection of Renaissance art in the world. And don't miss Michelangelo's 'David' at the Galleria dell'Accedemia.
Florence - Lucca
Leaving Florence behind, we follow quiet backroads that soon lead us deep into the Tuscan countryside. The ride unfolds across rolling hills toward San Gimignano, where stone towers rise above the vineyards like sentinels from another age. Continuing south and west, the road twists toward Volterra, its medieval walls and hilltop views offering the perfect pause to soak in the landscape.
From there, we descend toward the plains and the city of Pisa, pausing to glimpse its iconic Leaning Tower before turning north once more. The final stretch to Lucca is a joy—gentle curves bordered by olive groves and poplar-lined lanes—until the ancient walls of the city appear, welcoming us with their timeless charm.
Lucca - Bologna
Departing Lucca, we ride north through the last folds of Tuscany’s hills before crossing into Emilia-Romagna. The road climbs gently into the Apennines, weaving through chestnut forests and mountain villages where time seems to linger. As we descend toward Modena, the landscape opens into fertile plains dotted with vineyards and farmhouses.
This region is the beating heart of Italian motoring, and a short detour near Bologna offers the chance to visit the Pagani Museum—a shrine to artistry and engineering that celebrates the spirit of speed. From there, a final stretch of smooth, flowing roads leads us back into Bologna, where the day ends surrounded by history, food, and the hum of Italian passion.
Flight home from Bologna
Depart Bologna.
Use any extra time for a true Italian expresso or just relax and enjoy the vibrant city.
Day by day
Day 1: Arrival to Bologna
Welcome to the colourful and beautiful city of Bologna!
We'll meet you at the airport and take you to your hotel. At 4 PM, we'll meet for the introductory briefing and in the evening go for a welcome dinner at a traditional Italian Trattoria.
Day 2: Bologna - Siena
Our second riding day begins in Bologna, where we leave the city’s graceful porticoes behind and ride south into the heart of the Italian countryside. The road soon winds through forested hills and open farmland, revealing glimpses of stone villages and distant ridgelines.
As we cross from Emilia-Romagna into Tuscany, the landscape softens into rolling vineyards, olive groves, and cypress-lined lanes typical of the Chianti region. The final stretch carries us through gentle curves and sun-warmed valleys before we arrive in Siena, its medieval towers rising above the terracotta rooftops.
Day 3: Siena - Assisi
Setting out from Siena, we follow winding roads that carry us eastward across the gentle hills and golden fields of southern Tuscany. The route passes through quiet villages and vineyards, the landscape dotted with cypress trees and rustic farmhouses.
As we approach Umbria, the terrain grows more dramatic, with rolling hills giving way to wooded valleys and river gorges. The town of Assisi emerges on a hillside, its pale stone basilicas and medieval streets rising gracefully above the surrounding countryside. Arriving in the afternoon, we are greeted by the serene charm and spiritual atmosphere that have made Assisi a timeless destination.
Day 4: Assisi - San Marino
Leaving Assisi, we ride southeast through the gentle hills and patchwork fields of Umbria, the morning light casting a warm glow over olive groves and vineyards. The road soon begins to climb as we approach the Apennines, winding through forested slopes and small, perched villages.
Each curve reveals glimpses of distant valleys and rugged ridgelines, building anticipation for the day's destination. By afternoon, we reach San Marino, where the medieval towers of Monte Titano rise dramatically above the countryside, offering sweeping views and a sense of history etched into every stone street.
Day 5: San Marino - Florence
Departing San Marino, we wind down from Monte Titano’s heights, the morning air cool and clear as the road dips into the fertile plains below. The route carries us across Emilia-Romagna’s countryside, past farmsteads and sleepy hamlets, before turning west toward the wooded slopes of the Apennines.
The ride is a mix of smooth curves and sweeping vistas, each bend revealing another postcard view of rural Italy. As we cross back into Tuscany, the scenery softens into golden fields and olive-dotted hillsides. By day's end, Florence awaits—its terracotta rooftops, graceful bridges, and the majestic Duomo glowing in the afternoon light.
Day 6: Rest day in Florence
Spend the rest-day in the fabled city of Florence and see all the attractions that are on offer. Start with a stroll to the Cattadrale di Santa Maria del Fiore, or Duomo, with its famous, colorful, towering cupola.
Then take a walk over the city's famous Old Bridge, the Ponte Vecchio. If art interests you, the Galleria Degli Uffizi houses the greatest collection of Renaissance art in the world. And don't miss Michelangelo's 'David' at the Galleria dell'Accedemia.
Day 7: Florence - Lucca
Leaving Florence behind, we follow quiet backroads that soon lead us deep into the Tuscan countryside. The ride unfolds across rolling hills toward San Gimignano, where stone towers rise above the vineyards like sentinels from another age. Continuing south and west, the road twists toward Volterra, its medieval walls and hilltop views offering the perfect pause to soak in the landscape.
From there, we descend toward the plains and the city of Pisa, pausing to glimpse its iconic Leaning Tower before turning north once more. The final stretch to Lucca is a joy—gentle curves bordered by olive groves and poplar-lined lanes—until the ancient walls of the city appear, welcoming us with their timeless charm.
Day 8: Lucca - Bologna
Departing Lucca, we ride north through the last folds of Tuscany’s hills before crossing into Emilia-Romagna. The road climbs gently into the Apennines, weaving through chestnut forests and mountain villages where time seems to linger. As we descend toward Modena, the landscape opens into fertile plains dotted with vineyards and farmhouses.
This region is the beating heart of Italian motoring, and a short detour near Bologna offers the chance to visit the Pagani Museum—a shrine to artistry and engineering that celebrates the spirit of speed. From there, a final stretch of smooth, flowing roads leads us back into Bologna, where the day ends surrounded by history, food, and the hum of Italian passion.
Day 9: Flight home from Bologna
Depart Bologna.
Use any extra time for a true Italian expresso or just relax and enjoy the vibrant city.
Pricing
| Motorcycle | Price for the RIDER * Based on sharing a double / twin room |
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4.760 € |
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4.970 € |
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5.040 € |
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5.390 € |
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5.460 € |
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5.740 € |
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| Your own motorcycle | 4.330 € |
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| Passenger | 3.640 € |
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580 € |
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Book a single room with your tour. |
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7.50 % |
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Purchasing trip cancellation insurance allows customers to receive a refund for a tour when a customer must cancel a tour for reasons covered by this insurance. Trip cancellation insurance costs 7,5% of the total listed price of the tour, including supplements like motorcycle upgrades, single room requests, and passenger costs. |
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175 € |
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VIP & Super VIP Insurance For a fixed cost of 25 EUR per day VIP Insurance lowers your security deposit for the motorcycle, while Super VIP Insurance reduces your security deposit to zero (0 EUR) and costs 40 EUR per day. VIP and Super VIP Insurances are available on all our tours and rentals of 7 days or more. Riders must have at least 2 years of riding experiences and must be at least 25 or less than 75 years old to obtain VIP or Super VIP Insurance. Riders with less than 2 years of riding experiences are responsible for full motorcycle value. See the chart below:
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280 € |
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VIP & Super VIP Insurance For a fixed cost of 25 EUR per day VIP Insurance lowers your security deposit for the motorcycle, while Super VIP Insurance reduces your security deposit to zero (0 EUR) and costs 40 EUR per day. VIP and Super VIP Insurances are available on all our tours and rentals of 7 days or more. Riders must have at least 2 years of riding experiences and must be at least 25 or less than 75 years old to obtain VIP or Super VIP Insurance. Riders with less than 2 years of riding experiences are responsible for full motorcycle value. See the chart below:
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Tour of Tuscany - Italia Espresso includes:
- Late model motorcycle with lockable hard luggage plus a Third party liability insurance and Comprehensive vehicle insurance.
- Experienced guide on a motorcycle.
- Support van for luggage, souvenirs, and 1 or 2 passengers.
- 8 nights' accommodation in quality, mostly 4**** hotels.
- 8 breakfasts in the hotel.
- 6 dinners, mostly in traditional local restaurants.
- Guided tour of Florence with a local guide.
- Arrival and departure transfers between the airport and the touring hotel.
- Extensive tour app.
- GPS with all the daily routes uploaded.
Not included in the price:
Air ticket, dinners on rest days, most lunches, drinks, gasoline, personal spending, tips.
Tour Cancellation Insurance: more information HERE.
Our clients say
1.) Mitja and Jure were excellent as the guides. They were very organized and thorough with all the many details. They clearly enjoy what they do and helped make the tour a lot of fun. Mitja also demonstrated a lot of patience with a couple difficult situations.
Testimonials
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SMTours d.o.o., Trpinčeva 37a 1000 Ljubljana, Slovenija, EU
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