Italy: Tuscany and Umbria Vineyard Walks
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From AUD $4999 Was AUD $6249
Small Group
Average
Rating
(3 reviews)
Italy: Tuscany and Umbria Vineyard Walks
Use code BONUS10 to get an extra 10% off all tours — for a limited time only. T&Cs apply
8 days
Small Group
Moderate
Average
English
Experience Overview
Spend time in the Tuscan countryside in landscapes dotted with farmhouses and castles all while experiencing Italy in perfect harmony with the land.
Includes
Activities
- Your Welcome Moment: Meet Your CEO and Group Your Foodie Moment: Molino di Grace Visit & Lunch, Panzano Your Foodie Moment: Wine Pairing Dinner Your Foodie Moment: Pecorino Cheese Tasting Your OMG Day: Rome Walking Tour or Fully Guided Vespa Tour, Rome
- Welcome lunch
- Guided walking tour of San Gimignano
- Guided walking tour of Montepulciano
- Guided walking tour of Siena
- Guided walking tour of Città della Pieve
- Cooking class in Umbria
- Walk Strove to Colle Val d'Elsa
- Walk Monteriggioni to Siena
- Walk Montefioralle to Panzano
- Walk Volpaia to Lamole
- Walk the Gladiator Trail
- Visits to towns in the Italian countryside like Montefioralle, Greve in Chianti, and Panzano
- Free time in Rome
- Farewell dinner
- All transport between destinations and to/from included activities
- All tips for meals and activities, except for CEO and porterage
Accommodation
- Hotels (7nts).
- 7 breakfasts, 4 lunches, 4 dinners
Transport
- Private vehicle, walking.
Group Leader
- CEO (Chief Experience Officer) throughout.
Highlights
- Hike from the tiny village of Abbadia a Isola along the ancient Via Fancigena
- Sip wine on a vineyard terrace in Tuscany during a lunch-time wine tasting
- Walk through medieval towns like Greve in Chianti
- Montefioralle and Panzano
- Sample local cuisines directly from the source within the many vineyards dotting the hills of Tuscany’s Chianti Region
Trip Details
8 days
Private vehicle, walking.
English
Florence, Italy
Rome, Italy
Moderate
Luxury, Budget
Average
Itinerary
Day 1: Tuscany: San Gimignano, and Walk Strove to Colle Val d'Elsa
After an informative morning welcome briefing with your CEO you will travel to San Gimignano for a visit before today's trek. Discover one of the most well preserved Italian medieval sites by marvelling at both the Gothic and Romanesque architecture of the historical centre, and by sampling some of the regional delights at lunch in town. Your trek begins after lunch, heading to the final destination of Colle Val d'Elsa.
Meals included: Dinner
Exclusive inclusions: Activity - Your opportunity to meet your CEO and fellow travellers, and learn more about your tour. Don't forget to see the notice in the lobby (or ask reception) for the official time and place to meet up with the group.Transport - Settle in and scan the scenery from the convenience of a private vehicle.Activity - Today enjoy the walled town of San Gimignano on a guided visit. Feel yourself be lured by the palpable sense of history and medieval streetscapes in this enchanting rural setting.Transport - Settle in and scan the scenery from the convenience of a private vehicle.Activity - Begin in the medieval village of Abbadia a Isola and follow the historic Via Francigena. Walk through peaceful countryside, past vineyards and olive groves, and take in the beauty of rural Tuscany on your way to Colle Val d'Elsa. Length - 3h Duration - 8km Elevation - 300 metersAccommodation - Hotel Palazzo Pacini
Day 2: Tuscany: Walk Monteriggioni to Siena
After the hike, explore Monteriggioni's charming streets and well-preserved medieval walls. Then, relax and enjoy a well-earned lunch with local flavors before heading back to Colle di Val d'Elsa, where you will have some free time to explore this historic town at your own pace.
Meals included: Breakfast,Lunch
Exclusive inclusions: Transport - Settle in and scan the scenery from the convenience of a private vehicle.Activity - Begin at the Chiocciola and Villa Castles and make your way through the dense bush, heading toward the enchanting Monteriggioni. Walk on dirt paths, gravel roads, and narrow trails. Elevation: 150mTransport - Settle in and scan the scenery from the convenience of a private vehicle.Free_time - There is plenty to see and do; now is your chance to explore however you wish. Head out to explore more of the local hiking trails or enjoy the unique architecture.Accommodation - Hotel Palazzo Pacini
Day 3: Tuscany: Exploring the Chianti Region
After a decadent and leisurely lunch, continue on to Greve in Chianti, considered the "gateway" to the Chianti region. Greve in Chianti is formed around a beautiful triangular piazza, at the centre of which is a statue of the explorer Giovanni da Verrazzano, one of the town's most illustrious sons, who went down in history for discovering the bay of New York. End the day relaxing with a cold drink at your Tuscan Villa perched above the vineyards.
Meals included: Breakfast,Lunch,Dinner
Exclusive inclusions: Transport - Settle in and scan the scenery from the convenience of a private vehicle.Activity - Montefioralle is one of the gems of the Chianti region and sits atop a high plain. The houses in the small town surround the historic castle. In some places the town is still protected by the original defense walls. Spend some time walking around and stretching those legs after breakfast.Activity - Start in the rolling hills of the Chianti region and continue along a dusty, dirt road winding through vineyard rows and enjoy this storybook setting all the way to the hamlet of Panzano. Distance: 6km Duration: 2.5 hours Elevation: 150-200mActivity - Enjoy a guided tour of the Molino di Grace vineyard and cellar with an included private farmhouse lunch.Activity - Known as the gate to the Chianti region, Greve in Chianti is a town dating back to the Middle Ages.Transport - Settle in and scan the scenery from the convenience of a private vehicle.Accommodation - Borgo Casa al Vento
Day 4: Tuscany: Volpaia to Lamole
After lunch, sample four varieties from the local Tuscan estates, continuing to learn not only about the process of wine making in Tuscany, but about the people who make their life here in Chianti. Tonight enjoy a special wine pairing dinner.
Meals included: Breakfast,Lunch,Dinner
Exclusive inclusions: Transport - Settle in and scan the scenery from the convenience of a private vehicle.Activity - Set out on a short walking tour of Siena with your CEO to gain a sense of Italy's loveliest medieval city.Free_time - Enjoy free time to explore more of Siena.Transport - Settle in and scan the scenery from the convenience of a private vehicle.Activity - Relax and enjoy an apertivo along with views of the Italian countryside on a panoramic terrace before a wine and dinner experience. Sit down together and pair 4 wines with 4 local dishes and sip an apertivo and fully immerse yourself in the Chianti region.Accommodation - Borgo Casa al Vento
Day 5: Tuscany: Visit Montepulciano and Walk the Gladiator Trail
Your morning walk concludes just in time to sample another Tuscan favourite, pecorino cheese. A tasting of locally produced pecorino and ricotta cheeses is served with a glass of Montepulciano wine. After indulging in a glass of Montepulciano wine, it's only fitting to visit the town itself. A local guide welcomes you to this ancient hilltop town and provides an in depth walking tour of the old centre. Here we leave Tuscany and head into Umbria to Città della Pieve.
Meals included: Breakfast
Exclusive inclusions: Transport - Settle in and scan the scenery from the convenience of a private vehicle.Activity - Begin in the historic center of Pienza before hiking to the Romanesque parish church of Corsignano and ending up at an old film location for "The Gladiator" before returning to Pienza. Elevation gain: 225m Distance: 6km Duration: 2 hoursActivity - Taste a variety of pecorino cheeses in Pienza. The cheeses will be accompied by fruit compotes and samples of ricotta cheese. Wine and water will be provided. Learn about each of the cheeses and the production process as you sample.Activity - Enjoy a visit to Montepuliciano with a local guide. Nestled between the Val D'Orcia and Val di Chiana this quintessential Tuscan medieval village is a must-see. Think glowing green landscape, hills unraveling for miles, and castle ramparts to explore.Transport - Settle in and scan the scenery from the convenience of a private vehicle.Accommodation - Hotel Vannucci
Day 6: Umbria: Cooking with a Local Chef
After you devour the fruits of your cooking labor, alongside a few glasses of delicious wine, the afternoon is yours to spend at leisure. A local guide will lead a walking tour of Città della Pieve, our home while in Umbria, known as the birthplace of renaissance painter Pietro Vannucci.
Meals included: Breakfast,Lunch
Exclusive inclusions: Activity - See Città della Pieve on a walking tour led by a local guide. The city is considered a historic medieval centre and was built of bricks in different shades of dark pink. A distinguishing marker from other Umbrian towns which are mainly made of stone. The best feature of this town are its many winding, maze-like alleys which acted as a defensive system, making the town impenetrable to enemies. The narrow streets also helped shield the town from the heat of the summer sun and the winter winds.Activity - Take part in a cooking class surrounding by breathtaking views of the Italian countryside. Learn from a professional chef and cook handmade pasta using traditional Umbrian recipes and pair your creations with local wines.Accommodation - Hotel Vannucci
Day 7: Rome: Your OMG Day
Take a short orientation walk of Rome after arriving to the hotel. If you are up for more walking, join your local Roman guide and walk the historical centre, visiting Piazza Barberini and Piazza di Spagna. Drop a coin into the Trevi Fountain and sip a cappuccino in Piazza Navona. If you are ready for less walking, more adrenaline, hop on the back of a Vespa with a professional driver and whiz through Rome from Trastevere to the Colosseum and lots more.
Meals included: Breakfast,Dinner
Exclusive inclusions: Transport - Settle in and scan the scenery from the convenience of a private vehicle.Activity - Enjoy a brief walk with your CEO. They will give you some tips on finding things like supermarkets, main squares, and ATMs. For more specific or in-depth information, an official guided tour is recommended.Activity - Option 1: There are many ways to see Rome, but sometimes the best way is on foot. Discover the Eternal City on walks through the squares that have marked history. Start from Piazza Barberini, become enchanted by the charm of the Spanish Steps, and get ready to turn your luck with a coin toss into the Trevi Fountain. This leisurely walk continues towards the Pantheon and Sant'Ivo della Sapienza, ending in Piazza Navona. Option 2: When in Rome... live "la dolce vita". To see the Eternal City like the locals, hop onto a Vespa! Cruise around the city and visit Rome's must-see landmarks with a local guide. Your professional driver will show you the majesty of ancient monuments such as the Colosseum, Keyhole, Trastevere District, or even the view of the Roman Forum from the top of the Capitol hill.Free_time - Take advantage of free time in Rome and opt for a CEO-led orientation walk of the city or simply keep exploring on your own before your final group dinner tonight.Accommodation - Mama Shelter Roma
Day 8: Rome
Meals included: Breakfast
Exclusive inclusions: Activity - Not ready to leave? Your CEO can help with any onward travel arrangements you require.
- Flights to and from origin and destinations
- Airport transfers (unless otherwise stated)
- Anything else not explicitly listed in tour inclusions
- Recommended gratuities/tipping
- Optional activities/tours
- Personal expenses
- Travel insurance
- Visas, meals and beverages not stated in the list of inclusions.
When meals are not included, your tour leader (where available) will be happy to help with restaurant recommendations, bookings, and directions. Please let us know if you have any dietary needs or preferences. We will do our best to accommodate these, though we cannot guarantee that every request can be met.
You are responsible for your personal belongings throughout the tour. You will need to carry your own bags between the vehicle and your hotel room. Drivers will assist with loading and unloading luggage from the vehicle.
Travellers requiring wheelchair access should contact our sales and service team, who can make enquiries on your behalf.
This tour requires an average level of fitness. Activities are paced gently and include leisure time. You may be expected to join guided walks of up to one hour, navigate short stairways and mild inclines, and manage your own luggage. You should also be able to board and exit all transport without assistance.
Travellers are expected to be self-sufficient and capable of handling all aspects of their journey. Please discuss your circumstances and support needs with your booking agent to confirm this trip is suitable.
If you are unsure, we recommend consulting your doctor before booking or travelling.
If a planned site visit is unavailable due to changes in operating hours or holiday closures, the itinerary may be altered, or a comparable activity will be substituted where possible and subject to availability.
Visa conditions can change. Once you receive your travel documents, check with the relevant embassy, consulate, or immigration office of your destination for the latest information.
- It is your responsibility to ensure you have the correct and valid travel documents and to comply with all entry requirements.
- Non-Australian citizens must also confirm visa and identification requirements with the appropriate consulate or visa agency.
- Certain occupations (for example, journalists, government officials, or those working in charities) may face additional restrictions when applying for visas, which could affect the type of application required.
From
AUD $6249
Duration: 8 days
Trip Type: Small Group
Activity Level: Average
Spend time in the Tuscan countryside in landscapes dotted with farmhouses and castles all while experiencing Italy in perfect harmony with the land.
Price based on per person in Double Room for departure 20 Apr 2026
Customer Reviews
06/21/2024
Tuscany/Umbria were dazzling in their beauty. Our guide Vincenzo was exceptional in this knowledge, passion and thoughtfulness. Fond memories and friendships were made. Such a gift! I'll be back!
06/04/2024
My family (ages 21 -62) enjoyed the tour immensely. Much can be attributed to the leader, the location and itinerary (walking tour of Tuscany/Umbria) and the members of our group. We liked the mix of rural and city life. The cheese and wine tours and ...
Tour Operator
G Adventures, founded in 1990 by Bruce Poon Tip, is a global adventure travel company specializing in small-group tours that emphasize authentic, sustainable, and culturally immersive experiences. Originally launched as GAP Adventures (“Great Adventure People”), the company pioneered the concept of community-driven travel by offering affordable trips that connect travelers with local communities while minimizing environmental impact. Today, G Adventures operates in more than 100 countries, offering a wide range of itineraries across themes such as active adventures, wildlife, wellness, family, and National Geographic–partnered tours, while maintaining a strong commitment to responsible tourism and social enterprise through its Planeterra Foundation.
In Business Since 1990
06/21/2024
Tuscany/Umbria were dazzling in their beauty. Our guide Vincenzo was exceptional in this knowledge, passion and thoughtfulness. Fond memories and friendships were made. Such a gift! I'll be back!
06/04/2024
My family (ages 21 -62) enjoyed the tour immensely. Much can be attributed to the leader, the location and itinerary (walking tour of Tuscany/Umbria) and the members of our group. We liked the mix of rural and city life. The cheese and wine tours and ...
05/29/2024
I will be talking about this trip for years to anyone who will listen. Could not be happier!!
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