Highlights
- Discover the medieval Tuscan villages of Volterra and San Gimignano
- Visit the Brunello di Montalcino vineyards and taste the region's best wines
- Explore colorful Riomaggiore and taste Ligurian cuisine in the Cinque Terre
Brief Itinerary
| Day | Highlights | Overnight |
|---|---|---|
| Day 1 | Arrive in Florence, Transfer to Colle di Val D'Elsa | Colle Val D'Elsa |
| Day 2 | Wine Tasting in Montalcino, Visit Siena | Colle Val D'Elsa |
| Day 3 | Day Trip to Volterra & San Gimignano, Chianti Winery Visit & Tasting | Colle Val D'Elsa |
| Day 4 | Transfer to the Cinque Terre, Visit Portovenere & Riomaggiore | La Spezia |
| Day 5 | Sassicaia Tasting in Bolgheri, Transfer to Pisa, Depart |
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Detailed Itinerary
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 homegrown herbs and verdure (vegetables). Savor a glass of the local wine and raise a toast to your Tuscan adventure.
Day 2: 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 for a guided tour of this ancient walled city. 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. Finish your tour with a trip to the medieval Monteriggioni Fortress, and you'll be dropped back at your accommodation in time for aperitivo.
Day 3: 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 4: Transfer to the Cinque Terre, Visit Portovenere & Riomaggiore
Today you'll trade the rolling green hills of Tuscany for the colorful, rocky cliffs of the Cinque Terre. You'll start in Portovenere, a picturesque UNESCO World 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 look across the sea to the nearby Isola Palmaria.
Continue on 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 down to 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). You'll spend the evening and overnight in La Spezia, Liguria's bustling port city, and a perfect spot to wander buzzy streets and enjoy an al fresco aperitivo.
Day 5: Sassicaia Tasting in Bolgheri, Transfer to Pisa, Depart
Enjoy breakfast at your hotel and meet your guide for a one-hour drive south of La Spezia to Bolgheri. Admire the famous Viale dei Cipressi (Cypress Avenue) as you continue toward the town and Castello di Bolgheri (Bolgheri Castle). You'll head to a nearby estate where you'll learn all about—and taste—the town's famous sassicaia wine, considered one of the renowned "Super Tuscans." Pause for lunch and enjoy some of the local specialties, including truffle, mushrooms, and wild boar.
Afterward, your driver will drop you at Pisa's airport or train station (via a quick top to see the Leaning Tower, of course), depending on where you're headed next. Safe travels!
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