This tour takes you through the gorgeous region of Tuscany, where you'll indulge your tastebuds with locally-sourced cuisine and wine tastings, all while sleeping in a farmhouse surrounded by the scenic Chianti Hills. Visit medieval towns and cities, like Siena, Florence, Volterra, and San Gimignano, tasting wine along the way, including the famous noble wine at Brunello di Montalcino and Sassicaia in Bolgheri. End your trip in beautiful Cinque Terre, where more wine and local food awaits you, plus a private boat tour of all five villages.


  • Stroll through breathtaking vineyards in the Chianti Hills, enjoying local foods and wine tastings
  • Visit the famous Brunello di Montalcino vineyard, and taste the awarded "noble wine"
  • Cruise the scenic coastline of Cinque Terre on a private boat tour
  • Discover medieval Tuscan villages like Volterra and San Gimignano
  • Taste Sassicaia wine amongst the Cypress trees of Bolgheri

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Italy - Stay in the Chianti Hills Colle Val D'Elsa
Day 2 Explore the Historical City of Florence with a Private Tour Colle Val D'Elsa
Day 3 Enjoy Wine Tasting and a Visit to Medieval Siena Colle Val D'Elsa
Day 4 Day Trip to the Town of Volterra and San Gimignano Colle Val D'Elsa
Day 5 Transfer to Cinque Terre via Bolgheri and Pisa La Spezia
Day 6 Visit the Colorful towns of Portovenere and Riomaggiore La Spezia
Day 7 Private Boat Tour in Cinque Terre La Spezia
Day 8 Depart Italy  

Detailed Itinerary

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

Medieval Center of Tuscany's Villages
Medieval Center of Tuscany's Villages

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 agrotourism, 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 a hosted dinner.

Day 2: Explore the Historical City of Florence with a Private Tour

Florence's Skyline by Night
Florence's Skyline by Night

Good morning! After enjoying breakfast at your accommodation, you'll meet your guide for a day trip to the historical city of Florence. Here you can enjoy some of the country's most beautiful architecture, as well as delicious wine and food.

Your guide will host you for a private tour of the city, which you'll learn is the cradle of the Italian Renaissance. During the tour, you'll visit the Uffizi Gallery, with masterpieces by Michelangelo and Donatello, including the famous David statue. You'll also explore Piazza della Signoria, set in front of the 13th-century palace, Palazzo Vecchio.

Carrying on, you'll make a must-see stop at the Il Ponte Vecchio, a medieval stone bridge with an array of charming and colorful shops. Lunch will be in a typical Tuscan tavern, where you can try local dishes, including the famous Fiorentina steak.

In the afternoon, the tour continues with visits to the Basilica of Santa Maria Novella, as well as the famous Cathedral of Santa Maria del Fiore with its Duomo and Giotto's tower. After an exciting day in Florence, your driver will transfer to your hotel in the Chianti area for another hosted dinner.

Day 3: Enjoy Wine Tasting and a Visit to Medieval 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.

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Day 4: 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 5: Transfer to Cinque Terre via Bolgheri and 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. You'll then make your way to one of Italy's most beloved coasts, Cinque Terre.

Your hub will be La Spezia, the bustling port city that works as the gateway to Cinque Terre. Although it's much bigger than the region's famous villages, it still maintains the traditional Ligurian charm with colorful cliffside buildings, a public beach, and beautiful views out into the sea. Settle into you accommodation and enjoy dinner at one of the many cafes lining the hills, perfect for a sunset over the Ligurian Sea.

Day 6: Visit the Colorful towns of Portovenere and Riomaggiore

The Seaside City of Portovenere
The Seaside City of Portovenere

Welcome to beautiful Cinque Terre. Known as the "Five Lands", this popular region includes five colorful villages 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 return to La Spezia. Enjoy strolling the city, then stop to have dinner in a restaurant overlooking the coast, for your final night and sunset in beautiful Italy.

Day 7: Private Boat Tour in Cinque Terre

Manarola, Cinque Terre
Manarola, Cinque Terre

Enjoy breakfast at your accommodation, then prepare for an exciting day on the water. Your driver will transfer you to the Port of La Spezia, where you'll board private boat for a tour of beautiful Cinque Terre.

You'll start by cruising along the scenic coast, admiring the quaint towns, brightly-colored buildings, and dramatic cliffs that make this region so unique. From the boat, you'll see all five of the Cinque Terre villages: Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. Stop in Monterosso al Mare where you'll have free time to enjoy lunch with a view.

As you return to La Spezia in the afternoon, you'll enjoy a wine tasting aboard the boat, where you can learn more about the grapes grown in the region. You'll return back to La Spezia in time to relax at your accommodation before heading out for dinner.

Day 8: Depart Italy

The Skyline of Florence
The Skyline of Florence

After one last breakfast in Italy, it's time to prepare for your departure. Your driver can transfer you to either the train station in La Spezia or the airport in Pisa.