Indulge your taste buds on this Tuscan tour, visiting beautiful vineyards and medieval towns like Siena, Volterra, and San Gimignano, where you'll enjoy the flavors of the region with wine tastings and traditional, locally-sourced cuisine. Explore ancient cobblestone streets and monuments, enjoy the old Cypress trees of Bolgheri, and sleep soundly in your cozy farmhouse accommodation. End your trip on the rocky coast of Cinque Terre where you'll enjoy more wine and regional foods, plus one last stop at the Leaning Tower of Pisa.


  • Visit the famous Brunello di Montalcino vineyard, and taste the awarded "noble wine"
  • Discover medieval Tuscan villages like Volterra and San Gimignano
  • Taste Sassicaia wine amongst the Cypress trees of Bolgheri
  • Stroll through breathtaking vineyards in the Chianti Hills and enjoy wine tastings
  • Discover the turquoise waters and famous seaside views in Portovenere and Riomaggiore

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Italy - Stay in the Chianti Hills Colle Val D'Elsa
Day 2 Go Wine Tasting and Visit the Historical City of Siena Colle Val D'Elsa
Day 3 Day Trip to the Town of Volterra and San Gimignano Colle Val D'Elsa
Day 4 Transfer to Cinque Terre - Visit Portovenere and Riomaggiore La Spezia
Day 5 Depart Italy From Pisa  

Detailed Itinerary

Day 1: Arrive in Italy - Stay in the Chianti Hills

Rolling Vineyards of the Chianti Region in Northern Italy
Rolling Vineyards of the Chianti Region in Northern Italy

Welcome to Italy! You'll arrive in the beautiful and historic city of Florence where your driver will transport you from the airport to your accommodation.

For you first night in Tuscany, you'll stay in a cozy accommodation in either Colle Val d' Elsa or San Gimignano, two picturesque villages. This region is popular for agritourism, so you'll sleep well in a charming boutique-style farmhouse surrounded by the stunning and beloved Chianti Hills. 

After settling into your room, enjoy a welcome drink at your accommodation before heading to dinner.

Day 2: Go Wine Tasting and Visit the Historical City of Siena

Val D' Orcia area near Siena
Val D' Orcia area near Siena

After a leisurely breakfast at your accommodation, you'll meet your guide and head towards Val d'orcia, a UNESCO Heritage Site located in the southern part of the Province of Siena.

After about a one-hour drive, you'll reach the renowned vineyard Brunello di Montalcino, which has been awarded the “noble of the wines". Enjoy the beauty of a Tuscan winery by strolling along the vines, visiting the cellars, and indulging in a wine tasting. Afterwards, you'll sit for a light lunch featuring exquisite locally-sourced food and, of course, more wine.

In the afternoon, you'll stop in the beautiful and extremely historic city of Siena. You are free to enjoy the city at your own pace. Stroll trough the cobblestone streets lined with quaint shops and cafes, enjoy the medieval brick architecture, and visit the impressive Duomo di Siena. You can also see Piazza del Campo, where the famous Palio horserace is hosted twice a year.

In the late afternoon return back to your accommodation and relax before dinner.

Day 3: Day Trip to the Town of Volterra and San Gimignano

The Medieval Town of Volterra
The Medieval Town of Volterra

Today's theme is historical medieval towns of the Chianti region. After breakfast, your driver will take you on a very scenic drive, framed by panoramic views of the Tuscan rolling hills.

Your first stop is the town of Volterra, located on the edge of the Chianti Region. You'll enjoy a guided tour of the town, with ample free time to stroll and peruse the charming shops. Then you'll head to San Gimignano where you'll enjoy a traditional lunch in a beautiful restaurant with a panoramic view overlooking the surrounding vineyards. 

After a guided tour of the town, you'll dive into the world of Chianti wine by visiting a wine estate. The owner of the estate will take you through the vineyards and the cellars, followed by a rich tasting of Chianti wine and local foods.

Day 4: Transfer to Cinque Terre - Visit Portovenere and Riomaggiore

The Seaside City of Portovenere
The Seaside City of Portovenere

Today you'll trade the rolling green hills of Tuscany for the colorful, rocky cliffs of Cinque Terre. Known as the "Five Lands", this popular region includes five towns perched high on cliffs overlooking the Ligurian Sea.

You'll start in the village of Portovenere, a picturesque, UNESCO Heritage Site set nearby Cinque Terre. You'll have some time to walk around the town, admiring its charming stone streets and stunning sea views. Here you can break for a snack or a drink.

Afterwards, your driver will take you to the town of Riomaggiore, one of the official villages of Cinque Terre. You'll enjoy a wine tasting and lunch, featuring local white wine, homemade pesto sauce, and traditional charcuterie. 

In the afternoon, you'll transfer to La Spezia, a bustling port city that works as the gateway to Cinque Terre. It's much bigger than the villages you visited earlier, but it still maintains the traditional Ligurian charm with colorful cliffside buildings, a public beach, and beautiful views out into the sea. Enjoy strolling the city, then stop to have dinner in a restaurant overlooking the coast.

Day 5: Depart Italy From Pisa

The Famous Leaning Tower of Pisa
The Famous Leaning Tower of Pisa

After breakfast at your hotel, your driver will transfer you by minivan to the charming village of Bolgheri. World renowned for its local Sassicaia wine, you may recognize this village for its famous roads lined with more than 2,400 Cypress trees.

After strolling amongst its stone streets and red-bricked buildings, you'll enjoy a wine tasting at a popular estate. Learn about the production and tastes of Sassicaia, famous in the Bolgheri region. Then enjoy lunch at a traditional restaurant featuring the specialties of Tuscan cuisine, including truffle, mushrooms, and wild boar.

You'll continue to the bustling city of Pisa. Ask your driver to stop at Miracle Square to marvel at its prized monument, the Leaning Tower of Pisa. This will be one last bit of Italian charm on this trip, as your next stop will be the airport or train station in Pisa. It's time to say goodbye to beautiful Italy!