Vernazza town on Cinque Terre, Italy

Distinct Trails of Italy Tour: An Active Exploration of Cinque Terre & Tuscany

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited


Places Visited

Volterra, Siena, Colle, San Gimignano...

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Suggested Duration

8 Days

The landscape and history of Italy hint of adventure hidden in the hills of Tuscany and along the trails of Cinque Terre. Your custom tailored tour will introduce you to the everyday beauty of La Dolce Vita on the paths that crisscross the countryside. Uncover seductive wines in secluded vineyards and wander through shaded olive groves to reach pristine views of the Ligurian coast. Explore preserved medieval villages and climb to the top of antique towers as your active tour will embody...

Customizable Itinerary

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Trip Highlights

  • Relish the fresh air and the enchanting landscape during magnificent hikes across the hills of Tuscany and coastal promontories of Cinque Terre
  • Trek the paths of Portofino National Park to discover a lavish array of wild flora, from asparagus to strawberries, growing near the coastal cliffs
  • Indulge in the creamy texture and abundant flavor of gelato on a private gelato tour in the historical town center of Siena
  • Sample Tuscan wines on a private estate outside the city walls of Siena during a walking tour of city center and bordering countryside
  • Enjoy the serene preserved medieval streets of Volterra and San Gimignano
  • Delight in the sea breeze during a private boat ride along the Mediterranean Sea
  • Trek portions of the historical Via Romea, a pilgrimage route that connects France to Rome
  • Enjoy the stunning natural beauty of Tuscany when walking along the banks of the Cecina River
  • Climb to the top of Torre Grossa in San Gimignano for an unadulterated panoramic view of central Tuscany

Detailed Description

Tuscany and Liguria entice visitors from across Italy and around the world with promises of ancient relics, medieval charms, and inspiring nature. Your 8-day tour will combine hiking and culture in a way that is perfect for explorers, adventurers, and history lovers. The journey will begin as your flight lands at Florence International Airport. Your private transfer will escort you to a trailhead to meet your guide. Stretch your legs and enjoy the fresh Tuscan air with an easy introductory walk along the countryside to the medieval hill town of Volterra, which enchants visitors with its ancient foundations and preserved antique district.

The next day, you will traverse the country trails outside of Volterra to visit the farmhouses, olive groves, cypress trees, and oak forests near the hamlet of Ulignano before returning to Volterra to enjoy the town’s traditions. The following day, you have a private transfer to the coastal town of Riomaggiore, one of the five towns of Cinque Terre. Explore the medieval seaside streets before you embark on the trails that connect each town along the shoreline. Board a private boat the next morning to reach the secluded Abbey of San Fruttuoso located inside Portofino National Park.

Wander the trails through the national park to enjoy the glorious views and wild flora before you reach the beautiful Italian Riviera town of Portofino. Continue the next day as you return to Tuscany to visit the town of towers at San Gimignano for a stroll along the medieval streets. Enjoy a panoramic view from Torre Grossa before you take the ancient trail Via Francigena to the town of Colle. The next day, you will venture to Siena for a full day tour of the medieval streets, the lavish Cathedral, the charming churches, and the delectable vineyards found on the outskirts of town.

Explore the Chianti Hills around the ancient pilgrimage route of Via Romea the next day and stop in the villages, hamlets, and towns that rise out of the countryside before you return to Siena. To conclude, your private transfer will meet you at your hotel in Siena ready to take you to Florence International Airport for your flight home. You could also extend your stay and continue your adventure through Italy at a pace that allows you to indulge in the sweet life of Italian culture and tradition.

Starting Price

$2,859 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

Reviews of Zicasso's Referral Service

4.89 stars based on 5240 reviews.

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