Italy Tuscany & Cinque Terre Walking Tour
Spectacular Trails from Chianti to the Italian Riviera & Historic Siena
- Available: April, May, September, October
- Activity: Level 3
- Accommodations: Comfortable Hotels
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
Itinerary
Arrive in Florence & Journey to Tavarnelle
Day 1
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 Tavarnelle. Enjoy a scenic drive on the Via Cassia, an ancient Roman road, then set off on a hike past olive orchards and vineyards to a 12th-century family estate. 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. 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. Here you'll sample some of the region's most celebrated reds. Rest up tonight in your charming hotel in the historic town of Radda.
Accommodation: Hotel Palazzo Leopoldo
Accommodation: Palazzo San NiccoloActivity: 3-4 hours/5 miles hiking
Transportation: 1-hour private van transfer
Meals: Breakfast, Lunch, Dinner
Vineyard Trails to San Polo in Rosso
Day 3
Begin the day with a short transfer to Galenda, a tiny medieval village just south of Radda in Chianti. From here, you'll follow vineyard trails to the fortified medieval estate of San Polo in Rosso, where lunch awaits. Continue walking via enchanting rural villages to San Giusto in Salcio, a pretty Romanesque church. 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
Accommodation: Palazzo San NiccoloActivity: 3-4 hours/4 miles hiking
Transportation: 20-minute private van transfer
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 the "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
Accommodation: Villa SaboliniActivity: 4 hours/2-3 miles hiking
Transportation: 1-hour private van transfer
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
Accommodation: Villa SaboliniActivity: 4-5 hours/8 miles hiking
Transportation: 30-minute private van transfer
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. Perhaps 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 or Florence
Day 9
Bid farewell to Italy as you transfer to Pisa airport or Florence airport.
Transportation: 1.5-hour (Pisa) or 3-hour (Florence) private van transfer
Meals: Breakfast
Why Travel With Us?
This perfectly paced adventure blends active hiking and cultural immersion, getting you to the heart of Tuscany and the Cinque Terre.
We have been refining our hiking adventures in Italy for over 40 years building an unrivaled team of local guides and genuine connections.
We seek out genuine experiences, from family-run restaurants and biodynamic farms, to wineries and historic hotels, so you can enjoy every moment.
Dates & Prices
Price is per person, double occupancy in USD.
The earlier you book, the more choice of available dates you’ll have and once you book, your price is guaranteed.
2026
- Sep 08 - 16, 2026$7,395 price per person dbl occ
Optional:+$1,200 Single OccupancyWaitlistConfirmed - Oct 06 - 14, 2026$7,095 price per person dbl occ
Optional:+$1,200 Single OccupancyCheck AvailabilityConfirmed
2027
- Apr 13 - 21, 2027$7,295 price per person dbl occ
Optional:+$1,300 Single OccupancyAvailableConfirmed - May 11 - 19, 2027$7,295 price per person dbl occ
Optional:+$1,300 Single OccupancyAvailable - Sep 07 - 15, 2027$7,295 price per person dbl occ
Optional:+$1,300 Single OccupancyAvailable - Sep 21 - 29, 2027$7,295 price per person dbl occ
Optional:+$1,300 Single OccupancyAvailable - Oct 05 - 13, 2027$7,295 price per person dbl occ
Optional:+$1,300 Single OccupancyAvailable
- Go Private
- Go Custom
- Inclusions
Go Private
Go Private with MT Sobek
Gather your favorite travel companions—family, friends, colleagues, or club—and enjoy an exclusive departure that’s easy to book and completely unforgettable.
Private Trip RequestPrivate Trip Requirements
A 25% non-refundable deposit is required to confirm your private departure.
Minimum age for guests on this trip is 16 years old.
Choose Your Own Travel Dates
April, May, September, October
Private Trip Pricing: 2026
10 guests from $7,095 per person double occupancy
7 to 9 guests from $7,595 per person double occupancy
6 guests from $7,795 per person double occupancy
Optional:
$1,200 Single Occupancy
Private Trip Pricing: 2027
10 to 16 guests from $7,295 per person double occupancy
9 guests from $7,395 per person double occupancy
8 guests from $7,595 per person double occupancy
7 guests from $7,695 per person double occupancy
6 guests from $8,195 per person double occupancy
Optional:
$1,300 Single Occupancy
*Seasonal rates may apply.
*Trip pricing on the website is provided as an estimate and is subject to change based on rates at the time of request and seasonality.
Take Over One of These Dates
- May 11 - 19, 2027
- Sep 07 - 15, 2027
- Sep 21 - 29, 2027
Go Custom
Create Your Very Own Adventure
Dreaming of a trip designed just for you?
- Our award-winning travel experts craft custom adventures—perfect for families, couples, and and groups.
- Enjoy insider access, expert guides, and decades of on-the-ground experience. Since 1969.
Custom Trip Details
- This is a sample itinerary. Let us work with you to perfect an adventure tailored specifically to you.
- Deposit: A 25% non-refundable deposit is required once your itinerary is confirmed.
When to Start Planning
Plan ahead for the best experience.
- Early planning secures preferred accommodations, top guides, and the widest range of activities.
- Ideal planning window: 6+ months before travel
- Short-notice trips (under 3 months): Availability may be limited
Travel Dates
April, May, September, October
Let's start designing your adventure!
Inclusions
Price Includes
- 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
Price Does Not Include
- 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
Need help picking your next adventure? Call us to answer your questions.
Your Guides
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.
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.
Daniele C.
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 F.
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!
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/4 miles hiking
Day 4
4 hours/2-3 miles hiking
Day 5
4-5 hours/8 miles hiking
Day 7
5 hours/5-6 miles hiking
Day 8
3-4 hours/3-4 miles hiking
*Mileage and elevation change information is approximate and may vary slightly depending on trail conditions, weather, and route adjustments, and the guide’s discretion.
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.
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.
Hotel 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.
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.
Hotel 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.
Palazzo San Niccolo
Villa Sabolini
Weather
Tuscany 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.
FAQs
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.
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.
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.
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.
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.