Italy Tuscany & Cinque Terre Walking
Florence, Italy to Pisa, Italy
Highlights:
- Explore hilltop towns in the heart of Chianti and follow dramatic coastal trails in the Cinque Terre
- Experience a "Gateway to the Middle Ages" through the splendor of Siena, San Gimignano, and Monteriggioni
- Sip fine wines, feast on regional culinary delights, and enjoy tranquil stays at charming hotels
Important Trip Details:
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.
Minimum Age: 16
- Adventure and Active
- Culinary and Cooking
- Walking
- Wine
Day: 1, duration: 1
The Hotel Executive
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 minutes 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.
Day: 2, duration: 2Hotel Palazzo Leopoldo
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.
Day: 2, duration: 2Palazzo San Niccolo
The romance of a 15th century palace with original frescoes and architectural details takes you back through history as you step out onto the main square. Modern rooms continue the theme with Tuscan terracotta flooring, beamed ceilings, and marble showers. In the historic vaulted cellar, a heated indoor swimming pool, whirlpool, massage services, and sauna. Enjoy the sights of Radda in Chianti from this regal hotel.Day: 4, duration: 2
Villa Sabolini
Located in the Tuscan hills outside Siena and near Colle di Val D'Elsa, Villa Sabolini was once an elegant 15th-century residence and later became an Archiepiscopal Seminary. Today the Villa is a 4-star hotel whose 40 rooms are surrounded by an Italian garden, and finely furnished with canopy beds, cotto floors, and marble bathrooms. The restaurant serves traditional dishes made with local ingredients inspired by the seasons.Day: 4, duration: 2
Hotel Villa San Lucchese
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.
Day: 6, duration: 3Hotel La Giada del Mesco
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, all with panoramic sea views.
Chiara Pigni
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.

Daniele Cavazzoni
Daniele grew up in a farmhouse deep in the Tuscan countryside, where his family spent their days making Pecorino sheep cheese and exploring the Italian regions. He got a Master's degree in Natural Sciences at the University of Siena in 2009 and started working as nature guide around the Indian Ocean and the African Savannah, before coming back to his beloved homeland. As a passionate birdwatcher, he always keeps an eye on the sky during his walks, and enjoys the discovery of new places.

Marco Favalli
Marco was born in Nairobi, Kenya. At the age of 13, already passionate about nature, he moved with his family to the northeast of Italy. His career in guiding and conservation was launched in Trieste where he graduated with a degree in natural science in 1998. He then worked on wildlife research projects and became a professional Nature Guide. He is excited to show you the wonders of Italy!
Inclusions
Expertise and services of our experienced adventure guides
All accommodations as noted in the itinerary
All breakfasts, almost all lunches and dinners as noted in the itinerary
Snacks and water between meals
Additional regional guides and experts where necessary
Comprehensive Trip Planner with detailed pre-trip information
Private guided tours at historic sites, museums, wineries and other select attractions as noted in the itinerary
Special events and other select attractions as mentioned in the itinerary
All gratuities at hotels and restaurants
Equipment and experienced guides for activities as described in the itinerary
Park and other entry fees (unless otherwise noted in the Trip Planner)
Fares for trains, ferries and other modes of travel as listed in the itinerary
Select transfers as mentioned in the itinerary
Baggage transfers and porterage
Exclusions
International airfare, airport taxes, and excess baggage fees
Alcoholic beverages (MT Sobek provides wine at select events)
Gratuities for MT Sobek guides and guide-drivers
Travel Protection Program
Personal expenses
Reason #01
This perfectly paced adventure blends active hiking and cultural immersion, getting you to the heart of Tuscany and the Cinque Terre.
Reason #02We have been refining our hiking adventures in Italy for over 40 years building an unrivaled team of local guides and genuine connections.
Reason #03We seek out genuine experiences, from family-run restaurants and biodynamic farms, to wineries and historic hotels, so you can enjoy every moment.
ActivitiesLeisurely hiking for 3-5 hours per day on gently rolling terrain. Cultural touring with stops at historic sites and wineries.
LodgingIdeally located hotels and villas providing all the comforts of a 4 or 5 star equivalent accommodation. Some lodging equipped with spas and swimming pools.
ClimateTuscany is likely to be warm, with lots of sunshine, and temperatures in 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.
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.
What is the best time to hike Cinque Terre?The best months to hike Cinque Terre are May, early June and September as the daytime temperatures are mild, the weather mostly sunny, and the colors of spring and fall are at their peak. April and October can also be stunning, but there is more chance of rain. July and 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.
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!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.
At MT Sobek, sustainability isn’t just a principle; it’s woven into the very fabric of how we operate. We don’t simply observe the world’s unique cultures and fragile ecosystems—we take an active role in their preservation. Supporting organizations dedicated to environmental conservation and community well-being is part of our DNA. Over the years, we have contributed over half a million dollars to conservation efforts and volunteered hundreds of hours to initiatives like Yosemite Facelift. Our programs work to ensure that the wild and beautiful places we visit will continue to thrive, with a special emphasis on sustainable practices and positive social impact. From funding reforestation projects to supporting local artisans, our commitment to sustainability goes hand-in-hand with unforgettable adventure.
Day: 1, duration: 1
The Hotel Executive
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 minutes 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.
Day: 2, duration: 2Hotel Palazzo Leopoldo
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.
Day: 2, duration: 2Palazzo San Niccolo
The romance of a 15th century palace with original frescoes and architectural details takes you back through history as you step out onto the main square. Modern rooms continue the theme with Tuscan terracotta flooring, beamed ceilings, and marble showers. In the historic vaulted cellar, a heated indoor swimming pool, whirlpool, massage services, and sauna. Enjoy the sights of Radda in Chianti from this regal hotel.Day: 4, duration: 2
Villa Sabolini
Located in the Tuscan hills outside Siena and near Colle di Val D'Elsa, Villa Sabolini was once an elegant 15th-century residence and later became an Archiepiscopal Seminary. Today the Villa is a 4-star hotel whose 40 rooms are surrounded by an Italian garden, and finely furnished with canopy beds, cotto floors, and marble bathrooms. The restaurant serves traditional dishes made with local ingredients inspired by the seasons.Day: 4, duration: 2
Hotel Villa San Lucchese
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.
Day: 6, duration: 3Hotel La Giada del Mesco
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, all with panoramic sea views.
Chiara Pigni
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.

Daniele Cavazzoni
Daniele grew up in a farmhouse deep in the Tuscan countryside, where his family spent their days making Pecorino sheep cheese and exploring the Italian regions. He got a Master's degree in Natural Sciences at the University of Siena in 2009 and started working as nature guide around the Indian Ocean and the African Savannah, before coming back to his beloved homeland. As a passionate birdwatcher, he always keeps an eye on the sky during his walks, and enjoys the discovery of new places.

Marco Favalli
Marco was born in Nairobi, Kenya. At the age of 13, already passionate about nature, he moved with his family to the northeast of Italy. His career in guiding and conservation was launched in Trieste where he graduated with a degree in natural science in 1998. He then worked on wildlife research projects and became a professional Nature Guide. He is excited to show you the wonders of Italy!
Inclusions
Expertise and services of our experienced adventure guides
All accommodations as noted in the itinerary
All breakfasts, almost all lunches and dinners as noted in the itinerary
Snacks and water between meals
Additional regional guides and experts where necessary
Comprehensive Trip Planner with detailed pre-trip information
Private guided tours at historic sites, museums, wineries and other select attractions as noted in the itinerary
Special events and other select attractions as mentioned in the itinerary
All gratuities at hotels and restaurants
Equipment and experienced guides for activities as described in the itinerary
Park and other entry fees (unless otherwise noted in the Trip Planner)
Fares for trains, ferries and other modes of travel as listed in the itinerary
Select transfers as mentioned in the itinerary
Baggage transfers and porterage
Exclusions
International airfare, airport taxes, and excess baggage fees
Alcoholic beverages (MT Sobek provides wine at select events)
Gratuities for MT Sobek guides and guide-drivers
Travel Protection Program
Personal expenses
Reason #01
This perfectly paced adventure blends active hiking and cultural immersion, getting you to the heart of Tuscany and the Cinque Terre.
Reason #02We have been refining our hiking adventures in Italy for over 40 years building an unrivaled team of local guides and genuine connections.
Reason #03We seek out genuine experiences, from family-run restaurants and biodynamic farms, to wineries and historic hotels, so you can enjoy every moment.
ActivitiesLeisurely hiking for 3-5 hours per day on gently rolling terrain. Cultural touring with stops at historic sites and wineries.
LodgingIdeally located hotels and villas providing all the comforts of a 4 or 5 star equivalent accommodation. Some lodging equipped with spas and swimming pools.
ClimateTuscany is likely to be warm, with lots of sunshine, and temperatures in 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.
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.
What is the best time to hike Cinque Terre?The best months to hike Cinque Terre are May, early June and September as the daytime temperatures are mild, the weather mostly sunny, and the colors of spring and fall are at their peak. April and October can also be stunning, but there is more chance of rain. July and 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.
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!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.
At MT Sobek, sustainability isn’t just a principle; it’s woven into the very fabric of how we operate. We don’t simply observe the world’s unique cultures and fragile ecosystems—we take an active role in their preservation. Supporting organizations dedicated to environmental conservation and community well-being is part of our DNA. Over the years, we have contributed over half a million dollars to conservation efforts and volunteered hundreds of hours to initiatives like Yosemite Facelift. Our programs work to ensure that the wild and beautiful places we visit will continue to thrive, with a special emphasis on sustainable practices and positive social impact. From funding reforestation projects to supporting local artisans, our commitment to sustainability goes hand-in-hand with unforgettable adventure.
About MT Sobek

This is where adventure travel began! Since our first Everest Base Camp trek in 1969, we’ve been connecting adventurers to the world through genuine, active and immersive experiences. We can’t think of anything more fulfilling than being outside and going deep into nature, exploring hidden places and getting to know local people. It’s what we love to do, so let us share it with you.
To feed your spirit of adventure, Mountain Travel Sobek offers a wide range of unique and perfectly paced itineraries led by incredible local guides. We keep groups small, usually fewer than 10 people, and seek out great food and characterful accommodations everywhere we go. Beyond the seamless logistics and careful attention to detail, our aim is to create a space for truly special moments in unforgettable places.
We are the Adventure Company—come explore with us.
About MT Sobek

This is where adventure travel began! Since our first Everest Base Camp trek in 1969, we’ve been connecting adventurers to the world through genuine, active and immersive experiences. We can’t think of anything more fulfilling than being outside and going deep into nature, exploring hidden places and getting to know local people. It’s what we love to do, so let us share it with you.
To feed your spirit of adventure, Mountain Travel Sobek offers a wide range of unique and perfectly paced itineraries led by incredible local guides. We keep groups small, usually fewer than 10 people, and seek out great food and characterful accommodations everywhere we go. Beyond the seamless logistics and careful attention to detail, our aim is to create a space for truly special moments in unforgettable places.
We are the Adventure Company—come explore with us.