Italian Wine Journey Through Tuscany & Cinque Terre - 7 Days

Day 1: Arrive in Florence, Transfer to Colle di Val D'Elsa

Benvenuti in Toscana! Arrive in Florence, Tuscany's glittering Renaissance capital, where a driver will be waiting to take you to your accommodation in either Colle di Val d'Elsa or San Gimignano, two picturesque hilltop villages 9 miles (15 km) apart and nestled in the rolling Chianti countryside. The area is popular for agriturismo (agritourism), where boutique centuries-old farmhouse accommodation meets delicious fresh produce, exceptional views, and a warm welcome from your hosts.

Settle into your room, and when you're ready, enjoy a tour of the casale (farmhouse) grounds and soak up the rural setting. Sit under the loggia and relax over aperitivo (small plates of snacks including local ham, cheese, and olives, accompanied by an apéritif) while your hosts prepare dinner. Tuscan food varies depending on the province, and Chianti is known for its excellent meat dishes, homemade pasta, beautiful formaggi (cheeses), and locally grown herbs and verdure (vegetables). Savor a glass of the local wine and raise a toast to your Tuscan adventure. 

Day 2: Private Tour of Florence

 After breakfast, you'll swap your rural idyll for the Renaissance-soaked streets of Florence, famous for its impeccable art, architecture, and magnificent Cattedrale di Santa Maria del Fiore (Il Duomo), whose terracotta dome attracts visitors from all over the world. Your guide will take you on a private tour through the city, starting with the Uffizi Gallery, which houses works by Leonardo da Vinci and Botticelli. You'll also explore Piazza della Signoria, set in front of the 13th-century palace, Palazzo Vecchio.

Continue on to Il Ponte Vecchio, a medieval stone bridge with an array of charming and colorful shops and gorgeous views across the River Arno. The city is brimming with great eateries, and your guide will steer you to where the locals go. Try the city's famous bistecca alla Fiorentina (flame-grilled T-bone steak) and a glass or two of the local wine. While Tuscany is famous for its Chianti, there are many other delicious reds to try, including Vino Nobile di Montepulciano and Brunello di Montalcino. 

After lunch, stop by a local gelateria (the city has some of the region's best gelato with a mix of traditional and innovative flavor combinations) and continue your tour. See the Basilica di Santa Maria Novella and finish in the city's central Plaza di Duomo, where you can admire Filippo Brunelleschi's Renaissance masterpiece and Giotto's bell tower. When you're ready, your driver will whisk you back to the casale, where you can relax and unwind before another home-cooked feast.

Day 3: Wine Tasting in Montalcino, Visit Siena 

Spend today discovering the countryside, medieval towns, and wineries of the renowned Val d'Orcia, a UNESCO Heritage Site notable for its iconic cypress-lined hills and roads, hilltop villages, and exceptional wines. Your destination is one of the renowned Brunello di Montalcino vineyards, one of Italy's most prestigious red wines. Accompanied by your guide, you'll explore the vineyards, visit the cellars, and finish your tour with a tasting of these exceptional wines, accompanied by a delicious light lunch of locally sourced produce.

Afterward, your guide will transfer you to nearby Siena, where you'll tour the medieval city's classic sights. See the magnificent Duomo di Siena, a Romanesque-Gothic cathedral known for its intricate marble floor and works by Bernini, Pisano, and Donatello. Stroll the narrow, cobbled back streets until you reach the vast Piazza del Campo and hear from your guide about the origins of the town square's annual Palio di Siena horserace. You'll finish your tour with a trip to the medieval Monteriggioni Fortress and be dropped back at your accommodation in time for aperitivo.

Day 4: Day Trip to Volterra & San Gimignano, Chianti Winery Visit & Tasting

This morning, you'll embark on a guided tour of Chianti's historic medieval towns. Admire the landscape filled with olive groves and dotted with cypress trees and farms as you approach Volterra, known for its Etruscan origins and Roman ruins. Stroll the town's winding streets and browse the artisanal stores renowned for their Tuscan art and handicrafts. Admire the central Duomo and the Palazzo Pretorio (Tuscany's oldest town hall), whose tower is known affectionately to locals as the Torre del Porcellino (Tower of the Piglet), in tribute to the quirky carving of a wild boar at the top.

Continue your tour with a drive to San Gimignano, a UNESCO World Heritage Site whose entire town is a testimony to enchanting medieval architecture and its many torre (towers) that have survived through the centuries. Explore the beautiful cobbled streets dotted with artisanal boutiques and delicatessens, adorned with the region's famous charcuteries, salamis and cheeses. Once you've worked up an appetite, enjoy lunch in a nearby restaurant with wonderful views over the surrounding vineyards and sip on a glass of the local Vernaccia di San Gimignano white wine. 

Your final stop is a winery in the Chianti Hills, where you'll tour the vineyards and cellars behind the region's eponymous wine. Made from a minimum of 80% sangiovese grapes, Chianti Classico is made from vineyards within a distinct area that stretches between the cities of Florence and Siena. Learn about the centuries-old production process and then sit down to a tasting of various vintages accompanied by a selection of local dishes.

Day 5: Transfer to the Cinque Terre via Bolgheri & Pisa

Wave goodbye to the rolling Chianti countryside this morning and transfer to the charming town of Bolgheri, nestled between the villages of Cecina and San Vincenzo in the Maremma on the Tuscan Coast. As you drive up to the village along the famous Viale dei Cipressi (Cypress Avenue), admire the long straight road bordered by ancient cypresses, which leads to the Castello di Bolgheri (Bolgheri Castle). The town is also famous for its prestigious wines, including the renowned sassicaia, known as one of the "Super Tuscans."

You'll get to taste several vintages of sassicaia with a visit to one of the area's notable wineries, where you'll learn about the production of the wine and tour the cellars. Afterward, lunch at a local restaurant where you'll taste typical local dishes such as pappardelle al cinghiale (pasta with wild boar ragù), truffles, and funghi (mushrooms). After a caffè, continue on to the Cinque Terre, with a stop at Pisa to see the city's iconic Leaning Tower.

Your base for the next two nights is La Spezia, Liguria's bustling port city that acts as the gateway to the famous five villages of Riomaggiore, Manarole, Vernazza, Monterosso, and Corniglia. Settle into your accommodation and head out to sample the region's famous Ligurian cuisine, such as ravioli alla Genovese, focaccia, and pesto, considered to be the best in Italy and native to nearby Genoa.

Day 6: Visit Portovenere & Riomaggiore

Spend today touring the scenery and colorful villages perched high on the cliffs overlooking the Ligurian Sea that make up the Cinque Terre. You'll start in Porto Venere, a picturesque UNESCO Heritage site that's often overlooked in favor of its five more famous sisters but just as beautiful. Your guide and driver for the day will take you to the village's best spots, where you'll have time to sip a refreshing drink at one of the cafés that line the harbor and gaze across the sea to the nearby Isola Palmaria (Palmaria Island).

When you're done exploring, your driver will take you to Riomaggiore, one of the famous five villages and a classic example of the Cinque Terre coastline with bright and pastel-hued, slate-roofed houses that tumble atop the rocky beachfront. Make your way to a local restaurant where you'll enjoy a tasting of dry and aromatic white wines followed by a typical Ligurian lunch featuring homemade pasta and pesto, charcuterie, and a delicious dolce (dessert). In the afternoon, you'll return to La Spezia, where the evening is yours to dine out in style against the backdrop of the Ligurian Coast.

Day 7: Depart La Spezia

Say goodbye, or ciao, to Italy for now. Take advantage of any extra time with one last morning stroll before your driver takes you to either the station in La Spezia or the airport in Pisa. Safe travels!

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