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The Chianti Hills famous vineyards

Tuscan Hills and Chianti Wines Premium Adventure

Small Group Departure in Italy - Example 8 Day Tour
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Discover iconic Chianti villages and walk sections of the Tuscan hills as you explore the best of the region on this 8-day premium small group adventure. Your journey begins in the medieval town of San Gimignano, and you will spend the next few days exploring the many wonders of Tuscany, including the iconic cities of Florence, Siena, and the wine region of Chianti. Discover the town's cobblestone streets and admire the medieval architecture. During your tour, you will visit some of the best wineries in the area, where you will have the chance to taste some of the best Chianti wines while taking in the stunning Chianti villages. Throughout your journey, you will stay at Villa Arnilu, a tastefully restored Tuscan farmhouse close to the charming village of San Gimignano, surrounded by vineyards and olive groves.
Walking the Tuscan countryside at sunsetThe Torre del MangiaImpressive Medieval Town of San Gimignano, TuscanyCityscape panorama of Arno river, towers and cathedrals of FlorenceVisit local markets and get a taste of the cultureWalking through small villages in ItalyEnjoying friends in TuscanyDelicious cheeses and wines enjoyed at a vineyardWine cellarThe Chianti Hills famous vineyards
  • Discover the stunning countryside of Tuscany and the Chianti villages.
  • Visit the stunning medieval town of San Gimignano
  • Experience a wine tasting tour in Chianti local wineries
  • Join a guided tour in Siena, a medieval city full of gothic monuments
  • Explore the city of Florence, the birthplace of the Italian Renaissance
  • Admire the rolling hills and vineyards surrounding Certaldo
Places Visited
  • Europe
  • Italy
  • Province of Siena
  • Castellina in Chianti
  • Certaldo
  • European Union
  • Florence
  • Greve
  • Panzano
  • San Gimignano
  • Siena
Activity Level: Easy Active
Moderately active but not overly strenuous. This level includes activities like casual cycling, yoga, or excursions/activities that typically last 3-5 hours total each day.

Full Itinerary

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Day 1: Arrive in San Gimignano

Your tour starts in Villa Arnilu, which is 1 mi (1.5km) from the historic center of San Gimignano. Upon arrival, you will be treated to a complimentary aperitivo. What better way to settle in than a glass of bubbles and tasty nibbles? There will be a welcome briefing in the evening, in which the group guide will provide an overview of the week, including useful tips on the area, and answer any questions.

Day 2: Walk San Donato to San Gimignano

  • Hotel
  • 1 Breakfast, 1 Dinner
Enjoy your first delicious breakfast of the trip, and get ready to explore the area. A 10-minute drive takes you to the quaint village of San Donato, where you will start a gentle four-hour walk along open paths and through farm grounds towards Montauto and to San Gimignano Center. After lunch, there will be free time to wander and soak up the atmosphere of this beautiful town. You may wish to visit Palazzo Comunale, a 13th-century stone palace home to the Pinacoteca (Art Gallery) and 177ft (54m) tall medieval Torre Grossa. In the afternoon, you have a guided visit around the vineyards of the Palagetto estate, followed by wine tasting and appetizers, before a transfer back to Villa Arnilu.

Distance Covered: 9.0 km / 5.6 miles

Day 3: History Walk through Chianti | Panzano to Greve

This morning, drive for approximately one hour down the Chiantigiana, an endlessly scenic route bisecting Chianti vineyards and olive groves. Your destination is the small market town of Panzano, where you will take to dusty tracks for a fascinating history walk through the heart of the Chianti region. Expect a constantly changing landscape: from wooded areas to vineyard hills and fortified villages such as Montefioralle to traditional agriturismo. The walk ends in Greve, a vibrant, authentic town with plenty of restaurants. It's a special end to the day as you visit the birthplace of chianti classico: the Ricasoli estate, which sits within the sprawling grounds of the ancient Brolio Castle. You will learn all about the genesis of this world-renowned wine and, of course, sample the local produce at its true home.

Distance Covered: 9.5 km / 5.9 miles

Day 4: Explore Siena

  • Hotel
  • 1 Breakfast, 1 Dinner
After breakfast, you head to Siena, a medieval city dominated by impressive Gothic monuments. It's divided into 17 contra de (districts), each of which goes head to head in the twice-annual Palio, a thunderous horse race around the central square for which the whole city turns out.

You will join a local guide on a tailor-made tour of the city, stopping at the landmarks plus captivating sites most tourists normally pass by. Exploring a local contrada museum and dipping into botteghe (small, traditional shops) to sample sweet local specialties, get a real taste of the history and traditions of this unique destination. 

If you wish to add an optional visit to the grand medieval duomo (cathedral). Booking in advance is required and available at www.operalaboratori.vivaticket.it/en/tour/complesso-monumentale-del-duomo-di-siena/2589. A recommended time-slot between 2 pm and 3.30 pm.

Distance Covered: 7.0 km / 4.4 miles

Day 5: Volterra and Luca | Free Day

Today is free to tailor however you'd like. You may wish to visit Volterra, an ancient hilltop town with an artistic flair and medieval landmarks. Or you could visit Lucca, the town of 100 churches, home to a Roman theatre-turned-piazza and a grand, multi-arched duomo.

Alternatively, dip into the local cuisine with a private cooking class or enjoy an extra-special olive oil-tasting experience. Your tour leader can guide you through all the options and help you book – all the activities are subject to availability and payable locally.

Day 6: Discover Florence

  • Hotel
  • 1 Breakfast, 1 Dinner
Your destination today is Florence, the birthplace of the Italian Renaissance. Most of the greats from the movement lived here or passed through: Leonardo da Vinci, Michelangelo, Sandro Botticelli, and more. Learn about it by joining one of the free local tours, which typically take in the highlights.

Join one of the morning tours, and you will have time to visit the Uffizi, an art gallery housing works by Renaissance masters, including The Birth of Venus by Botticelli and the gruesome Medusa by Caravaggio. If you wish to visit the Uffizi, it's recommended to pre-book your ticket online to avoid lengthy queues. An ideal slot time would be around 2 pm if you're joining the morning walking tour. Tickets can be purchased at www.uffizi.it/en/tickets.

Distance Covered: 4.0 km / 2.5 miles

Day 7: Certaldo Walk and Wine

  • Hotel
  • 1 Breakfast, 1 Lunch, 1 Dinner
A short transfer takes you to the starting point of the last walking adventure of the week. Today, you can explore the vineyards and hills surrounding Certaldo, a walled medieval town where Giovanni Boccaccio, author of the masterpiece The Decameron, was born in 1313. After walking for approximately 3hr 30min, you will reach the town center for lunch, followed by free time to visit attractions related to both Italian history and literature. Later in the afternoon, visit an eco-friendly wine estate, where you will discover the Tuscan wines will be taken to the next level with a sensory and aroma experience accompanied by mouth-watering traditional appetizers.

Distance Covered: 9.0 km / 5.6 miles

Day 8: San Gimignano | Return Home

  • 1 Breakfast
The tour ends in San Gimignano after one final breakfast. Bid Villa Arnilu a fond farewell. It will feel a little like home by now, and begin your return journey back home.


Villa Arnilu - San Gimignano

Villa Arnilu - San Gimignano
Villa Arnilu - San Gimignano
Outdoor Swimming Pool

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  • 7 Breakfasts, 1 Lunch, 5 Dinners
  • 7 Nights Accommodations
  • 4 Days Locally Hosted Guide Service
  • Accommodations as listed
  • Ground transportation as listed
  • Activities as listed
  • Meals as listed
  • Access to a 24-7 Emergency line while traveling
  • Airport Transfers
  • Private chef at Villa Anilu for 5 Dinners 
  • Gratuities
  • Travel Insurance
  • Personal Expenses
  • Flight costs (please request a quote)
  • Additional excursions during free time
  • Fuel and transportation surcharges (when applicable)
  • Local taxes (approximately €10 - €15 per person)
  • Passport, visa, reciprocity and vaccination fees and charges


When to Go

Good to ideal period to travel, and many people choose to visit at this time.
Chance for unpredictable weather but with fewer visitors.


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The trip was terrific with great planning on your part. Most of the adventures were not mainstream and somewhat off the beaten path which made it especially enjoyable!! We felt taken care of and you all were readily available to respond to questions and issues. I would highly recommend your company and friends have already expressed interest based on our pictures and excitement.
Gale Cantor
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