Spectacular Trails from Chianti to the Italian Riviera & Historic Siena
Immerse yourself in two of Italy's most enchanting regions on this perfectly paced walking adventure from Tuscany to the Italian Riviera. Follow scenic trails through Tuscan vineyards and cypress-dotted valleys, exploring historic hill towns and sampling fine Chianti wines along the way. Marvel at the medieval wonders of Siena and San Gimignano with their ancient ramparts and towers. Then journey to Liguria's spectacular coast to hike cliff-side paths that connect the Cinque Terre's picturesque seaside towns. With fragrant lemon groves and stunning sea views, this is la dolce vita at its best!
Immerse yourself in two of Italy's most enchanting regions on this perfectly paced walking adventure from Tuscany to the Italian Riviera. Follow scenic trails through Tuscan vineyards and cypress-dotted valleys, exploring historic hill towns and sampling fine Chianti wines along the way. Marvel at the medieval wonders of Siena and San Gimignano with their ancient ramparts and towers. Then journey to Liguria's spectacular coast to hike cliff-side paths that connect the Cinque Terre's picturesque seaside towns. With fragrant lemon groves and stunning sea views, this is la dolce vita at its best!
Explore hilltop towns in the heart of Chianti and follow dramatic coastal trails in the Cinque Terre
[Description] => Explore hilltop towns in the heart of Chianti and follow dramatic coastal trails in the Cinque Terre
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Experience a "Gateway to the Middle Ages" through the splendor of Siena, San Gimignano, and Monteriggioni
[Description] => Experience a "Gateway to the Middle Ages" through the splendor of Siena, San Gimignano, and Monteriggioni
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Sip fine wines, feast on regional culinary delights, and enjoy tranquil stays at charming hotels
Welcome to Italy! Arrive in Florence this afternoon and meet your trip leader for an orientation. Explore the Benedictine church of San Miniato al Monte, with its splendid Romanesque architecture and sweeping views of the city, before heading south to the hilltop town of San Casciano. Enjoy a scenic drive on the Via Cassia, an ancient Roman road, then set off on a hike past olive orchards and vineyards to the 15th-century home of a local Tuscan family. Here you'll sample olive oils and savor a delicious country dinner.
Accommodation: The Hotel Executive
Activity: 2 hours/2-3 miles hiking
Transportation: 1-hour private van transfer
Meals: Dinner
Chianti Wines & Walks
Day 2
Rise for a journey through bucolic rolling hills to Greve, the wine capital of Chianti. Here you'll sample some of the region's most celebrated reds and take a picturesque hike to the hilltop village of Lamole. Lunch on local delights and continue on foot to Volpaia, a medieval hamlet famed for its Chianti Classico wine. Rest up tonight in your charming hotel in the historic town of Radda.
Accommodation: Hotel Palazzo Leopoldo
Activity: 3-4 hours/5 miles hiking
Meals: Breakfast, Lunch, Dinner
Vineyard Trails to San Polo in Rosso
Day 3
Begin the day with a short transfer to San Giusto in Salcio, a pretty Romanesque church just south of Radda in Chianti. From here, you'll follow vineyard trails to the fortified medieval estate of San Polo in Rosso, where a refreshing picnic lunch awaits. Continue walking via enchanting rural villages back to San Giusto in Salcio. Return by van to Radda and sample more Chianti wines before exploring the town at leisure. Tonight, dinner is on your own at the hotel or local restaurant .
Accommodation: Hotel Palazzo Leopoldo
Activity: 3-4 hours/5 miles hiking
Meals: Breakfast, Lunch
Explore Enchanting Siena
Day 4
Journey to the captivating city of Siena for a special guided tour of its historical wonders, including UNESCO-listed Piazza del Campo and the Duomo. Next, enjoy free time to explore the city's beautiful cobblestone streets and charming restaurants. In the afternoon, visit the walled city of Monteriggioni, known as "Gateway to the Middle Ages" for its fortified ramparts and watchtowers. Later, transfer to your hotel set in a 15th-century villa in Poggibonsi.
Accommodation: Hotel Villa San Lucchese
Activity: 4 hours/2-3 miles hiking
Meals: Breakfast, Dinner
Hike to San Gimignano
Day 5
Start the day with a drive to Colle Val d'Elsa, known for its fine Italian crystal, then follow scenic trails to the romantic hill town of San Gimignano. This UNESCO World Heritage wonder, known as "medieval Manhattan," is beloved for its 11th-century towers, labyrinthine streets, and fresco-adorned Duomo. Explore town before heading back to your hotel.
Accommodation: Hotel Villa San Lucchese
Activity: 4-5 hours/6 miles hiking
Meals: Breakfast, Lunch, Dinner
Journey from Carrara to Cinque Terre
Day 6
Rise for a drive to Carrara, world famous for its ancient marble quarries that rise like snow-capped peaks above the town. After lunch, breathtaking coastal scenery awaits in the UNESCO-listed Cinque Terre and the pretty seaside town of Levanto. Enjoy a tasty dinner in town and get ready to explore the Italian Riviera over the next two days.
Accommodation: Hotel La Giada del Mesco
Transportation: 2.75-hour private van transfer
Meals: Breakfast, Lunch, Dinner
Explore Trails in Cinque Terre
Day 7
Take a short train ride to Monterosso al Mare, one of the five towns that make up the Cinque Terre. Perched on cliffs above the Ligurian Sea, these breathtakingly beautiful seaside villages are a bucket-list must - and perfect for hikers. Take in amazing coastal scenery on a stunning trail that links the neighboring villages of Vernazza, Corniglia, Manarola, and Riomaggiore. Alternatively, you can enjoy a scenic train and boat ride from village to village. Return to Levanto for dinner on your own tonight.
Accommodation: Hotel La Giada del Mesco
Activity: 5 hours/5-6 miles hiking
Meals: Breakfast, Lunch
Coastal Path to Monterosso
Day 8
Starting at the hotel, follow a meandering coastal trail back to Monterosso. Along the way you'll pass lemon groves and old hilltop farmhouses, and enjoy splendid views of the Ligurian Sea. Reward yourself with a refreshing gelato and explore the town at leisure. Take a train back to Levanto and celebrate your Italian adventure with a farewell dinner in town.
Accommodation: Hotel La Giada del Mesco
Activity: 3-4 hours/3-4 miles hiking
Meals: Breakfast, Dinner
Depart from Pisa
Day 9
Bid farewell to Italy as you transfer back to the airport in Pisa.
Dreaming of an adventure designed exclusively for you? With insider access and decades of experience, our travel experts create custom tailored adventures that are perfect for families, couples, and large groups. MT Sobek's custom adventures are designed to our exacting standards and led by our award-winning adventure guides.
When to start planning? Earlier is always better when designing a custom trip. More time allows for better availability of preferred accommodations, guides and your desired activities. Ideally, start the conversation with us at least 6 months before you want to travel. If you are looking for a custom trip that departs within three months, chances are greatly diminished in securing requested accommodations and the best guides.
*Custom trips require a 25% non-refundable deposit once an itinerary is agreed upon.
The best people to immerse you in a destination are the ones who live there, which is why we feature local Adventure Guides on our trips. Here are a few that you might meet on this adventure.
Silvia G.
Silvia was born and raised in Venice, and now lives in the Tuscany region of central Italy. While she is an architect by training, with an MA in History of Architecture, Silvia has more than 20 years of experience as a professional trip leader. She lived in Toronto, Canada, for over a decade and, since then, she has led both walking and bicycle trips throughout Europe. Now she guides trips in Tuscany and southern Italy—sharing her passion for her country with MT Sobek travelers. Silvia speaks Italian, English, and French.
Chiara P.
Chiara was born in Trieste and grew up in Milan where she achieved her degree in languages before changing her focus to geology. She then worked for a non-profit medical organization, as well as a multinational advertising agency. Having been initiated into different cultures at a relatively young age, Chiara developed a curiosity and passion for travel, and has been guiding with enthusiasm ever since.
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Welcome to Italy! Arrive in Florence this afternoon and meet your trip leader for an orientation. Explore the Benedictine church of San Miniato al Monte, with its splendid Romanesque architecture and sweeping views of the city, before heading south to the hilltop town of San Casciano. Enjoy a scenic drive on the Via Cassia, an ancient Roman road, then set off on a hike past olive orchards and vineyards to the 15th-century home of a local Tuscan family. Here you\'ll sample olive oils and savor a delicious country dinner.
Rise for a journey through bucolic rolling hills to Greve, the wine capital of Chianti. Here you\'ll sample some of the region\'s most celebrated reds and take a picturesque hike to the hilltop village of Lamole. Lunch on local delights and continue on foot to Volpaia, a medieval hamlet famed for its Chianti Classico wine. Rest up tonight in your charming hotel in the historic town of Radda.
Begin the day with a short transfer to San Giusto in Salcio, a pretty Romanesque church just south of Radda in Chianti. From here, you\'ll follow vineyard trails to the fortified medieval estate of San Polo in Rosso, where a refreshing picnic lunch awaits. Continue walking via enchanting rural villages back to San Giusto in Salcio. Return by van to Radda and sample more Chianti wines before exploring the town at leisure. Tonight, dinner is on your own at the hotel or local restaurant .
Journey to the captivating city of Siena for a special guided tour of its historical wonders, including UNESCO-listed Piazza del Campo and the Duomo. Next, enjoy free time to explore the city\'s beautiful cobblestone streets and charming restaurants. In the afternoon, visit the walled city of Monteriggioni, known as "Gateway to the Middle Ages" for its fortified ramparts and watchtowers. Later, transfer to your hotel set in a 15th-century villa in Poggibonsi.
Start the day with a drive to Colle Val d\'Elsa, known for its fine Italian crystal, then follow scenic trails to the romantic hill town of San Gimignano. This UNESCO World Heritage wonder, known as "medieval Manhattan," is beloved for its 11th-century towers, labyrinthine streets, and fresco-adorned Duomo. Explore town before heading back to your hotel.
Rise for a drive to Carrara, world famous for its ancient marble quarries that rise like snow-capped peaks above the town. After lunch, breathtaking coastal scenery awaits in the UNESCO-listed Cinque Terre and the pretty seaside town of Levanto. Enjoy a tasty dinner in town and get ready to explore the Italian Riviera over the next two days.
Take a short train ride to Monterosso al Mare, one of the five towns that make up the Cinque Terre. Perched on cliffs above the Ligurian Sea, these breathtakingly beautiful seaside villages are a bucket-list must - and perfect for hikers. Take in amazing coastal scenery on a stunning trail that links the neighboring villages of Vernazza, Corniglia, Manarola, and Riomaggiore. Alternatively, you can enjoy a scenic train and boat ride from village to village. Return to Levanto for dinner on your own tonight.
Starting at the hotel, follow a meandering coastal trail back to Monterosso. Along the way you\'ll pass lemon groves and old hilltop farmhouses, and enjoy splendid views of the Ligurian Sea. Reward yourself with a refreshing gelato and explore the town at leisure. Take a train back to Levanto and celebrate your Italian adventure with a farewell dinner in town.
Bid farewell to Italy as you transfer back to the airport in Pisa.
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Activity Level
This trip is rated activity level 3. Easy to moderate walking and hiking for 3-5 hours per day on gently rolling terrain, vineyards and cliffside trails. Cultural touring of historic sites includes walking on cobblestone streets. Learn more about activity levels here.
Activity Snapshot
Day 1
2 hours/2-3 miles hiking
Day 2
3-4 hours/5 miles hiking
Day 3
3-4 hours/5 miles hiking
Day 4
4 hours/2-3 miles hiking
Day 5
4-5 hours/6 miles hiking
Day 7
5 hours/5-6 miles hiking
Day 8
3-4 hours/3-4 miles hiking
Accommodations
Ideally located hotels and villas providing all the comforts of a 4 or 5 star equivalent accommodation. Some lodging equipped with spas and swimming pools.
Occupying a former royal residence built in the 16th century, this elegant hotel is just a 7-minute walk from Santa Maria Novella train station and 9 minute on foot from the Santa Maria Novella. The traditionally furnished, warmly decorated rooms feature flat-screen TVs, free Wi-Fi and minibars.There's a restaurant, a cocktail lounge and a library reading room.
This elegant hotel is set in a 14th-century Tuscan building, and is nestled in Chianti's vineyards. Guestrooms offer old-world charm and feature free Wi-Fi, room service and flat-screen TVs. Amenities include a restaurant and a fitness room, as well as a spa with a heated indoor pool and hot tubs.
Set on beautifully landscaped grounds, this elegant hotel offers down-to-earth guestrooms with free Wi-Fi, satellite TV and safes. Some have canopy beds, whirlpool tubs, exposed beams and/or sitting areas. Other amenities include 2 outdoor pools, a tennis court and a restaurant with a terrace. There's also a landscaped garden, a library and a bar, plus a wine cellar. Wine tastings and massage services are available.
In a stone villa on a hillside overlooking the Ligurian Sea, this relaxed hotel has 12 cozy guestrooms offering minifridges, flat-screen TVs and free Wi-Fi, as well as balconies with sea views. Room service is available. Other amenities include a bar, a terrace, and an infinity pool, both with panoramic sea views.
Weather
Tuscany likely to be warm, with lots of sunshine, and temperatures on the 70's and 80's. Italy's west coast boasts a warm, coastal Mediterranean climate, with dry summers. There is often a pleasant sea breeze in summertime.
May
Sep
Cinque Terre
High
Low
High
Low
Cinque Terre
72
58
77
62
Florence
High
Low
High
Low
Florence
76
54
80
58
Pisa
High
Low
High
Low
Pisa
72
52
79
58
FAQs
Who will meet me on arrival?
An MT Sobek representative will meet you at the airport on the morning of Day-1, and transfer with you to our hotel in Florence. Early and later arrivals will need to get to the hotel on your own.
Can I wear trail shoes/cross training shoes on this trip?
Proper trail shoes or lightweight hiking boots are appropriate for this trip. Please be sure your shoes have a good sole, and will be comfortable on varying terrain - vineyards, cobblestone, hiking trails, and roads.
How challenging are the hikes on this trip?
Most experienced hikers will consider this trip to be on the easier side. However, if you are more of a walker, you may feel challenged by 3 - 5 hours on your feet. Come in good physical condition, and expect an active, outdoorsy experience.
Can you accommodate my diet?
In Italy, it is easy to accommodate most diets - vegetarian, vegan, even gluten-free. Please let us know your dietary restrictions are in advance, so that we can make the appropriate arrangements.
Do you offer this trip in the summer?
We have selected the months of May and September as the daytime temperatures are mild, the weather mostly sunny, and the colors of spring and autumn are at their peak. June through August can be both hot and overly crowded with tourists.
Can I fly out of any nearby airport?
At the end of your trip, transfers will be provide to both the Pisa and Florence Airports. If you are flying out of Milan, we will provide information on how to get to the Milan Malpensa Airport from the train station in Levanto.
What is the minimum age for this trip?
The standard minimum age for this trip is 18, but check out our private trip options for families and groups with younger guests.
How much time is recommended for Tuscany and Cinque Terre?
To make the most out of a trip to Tuscany and Cinque Terre, we recommend 9 days. This allows you to start in Florence and end in Pisa, with a stop in Siena along the way, plus enjoy two days hiking spectacular coastal trails. This is the best way to get an insider feel for the destination.
Can you hike the five towns of Cinque Terre?
Yes, you can hike between the five towns of Cinque Terre. There is a system of trails that connect the towns, providing a picturesque way to explore this beautiful coastal region. Our first hike in Cinque Terre starts in Monterosso al Mare, and follows a scenic trail that links the neighboring villages of Vernazza, Corniglia, Manarola, and Riomaggiore.
What is the most scenic hike in Cinque Terre?
One of the most scenic hikes in Cinque Terre is the stretch between Monterosso and Vernazza, which hugs a steep hillside overlooking the Mediterranean Sea, and passes through vineyards. Is that hike included on this trip? Yes!
