Italy Tuscany and Cinque Terre Walking

Spectacular Trails from Chianti to the Italian Riviera & Historic Siena

Immerse yourself in two of Italy's most enchanting regions on this perfectly paced hiking 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 its ancient ramparts and towers. Then journey to Liguria's spectacular coast to hike cliff-side trails 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!

Hike to hilltop towns in the heart of Chianti and follow dramatic coastal trails in the Cinque Terre

Experience the medieval splendor of Siena, San Gimignano, and Monteriggioni -- "Gateway to the Middle Ages"

Sip fine wines, feast on regional culinary delights, and enjoy tranquil stays at charming hotels

Why take this trip with us?

Reason #01

This perfectly paced adventure blends active hiking and cultural immersion, getting you to the heart of Tuscany and the Cinque Terre.

Reason #02

We have been refining our hiking adventures in Italy for over 40 years building an unrivaled team of local guides and genuine connections.

Reason #03

We seek out genuine experiences, from family-run restaurants and biodynamic farms, to wineries and historic hotels, so you can enjoy every moment.

Meet your guides

Silvia Giacon

Silvia is an Italian born and raised in Venice. Now she permanently lives in Tuscany. While she is an architect by training and has a master in history of Architecture, she has over 20 years of professional experience as 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. Languages spoken: Italian, English, French.

Activities

Leisurely hiking for 3-5 hours per day on gently rolling terrain. Cultural touring with stops at historic sites and wineries.

Lodging

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.

Climate

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.

FAQ

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.