Italy: Tuscany and Umbria Vineyard Walks

G Adventures · 8 days

4.3

3 Reviews

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Duration

8 days

Tour Type

Small Group

Accommodations

Moderate

Physical Rating

Average

Guide Language

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.

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

Duration

8 days

Transportation

Private vehicle, walking.

Tour Type

Small Group

Guide Language

English

Starts

Florence, Italy

Finishes

Rome, Italy

Accommodations

Moderate

Travel Style

Luxury

Physical Rating

Average

Itinerary

Day 1: Tuscany: San Gimignano, and Walk Strove to Colle Val d'Elsa

With golden light stretching across the rolling green hills, the Tuscan countryside is calling. The pace here is slower, coinciding with the wine produced in the region which is meant to be savoured rather than gulped. Your first day sees you begin the trek in the historic village of Abbadia a Isola, following the Via Francigena through the rolling Tuscan countryside. Walk past ancient stone farmhouses, cypress-lined paths, and picturesque landscapes as you make your way toward Colle Val d'Elsa. Welcome to Tuscany, and to Italy we invite you inner serenity in the countryside.
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.

Day 2: Tuscany: Walk Monteriggioni to Siena

Monteriggioni is your quintessential Tuscan medieval walled village. Follow part of the ancient Francigena way; step back in time as you walk past donkeys in green pastures and lush bushes as the Tuscan countryside unfolds before you.
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.

Day 3: Tuscany: Exploring the Chianti Region

Chianti, recognized for its namesake red wine, lies between Florence and Siena in the very centre of Tuscany. Begin the trek from Montefioralle- a small town forming the perimeter around an historic castle. Start the day with a scenic walk through the rolling Chianti countryside, soaking in the breathtaking views of vineyards and olive groves. After working up an appetite, enjoy a delicious, rustic lunch at a traditional farmhouse, where you'll savour local Tuscan flavours in a relaxed setting.
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.

Day 4: Tuscany: Volpaia to Lamole

Start the day with a scenic transfer to Siena, one of Tuscany's most beautiful medieval cities. Upon arrival, join a local guide for a walking tour through its historic streets, exploring highlights like Piazza del Campo and the stunning Duomo. After the tour, sit down for a delicious lunch at a local restaurant, enjoying authentic Tuscan flavors. Take some free time to soak in the atmosphere or browse local shops before heading back to your hotel. Tonight enjoy a special wine pairing dinner.
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.

Day 5: Tuscany: Visit Montepulciano and Walk the Gladiator Trail

UNESCO World Heritage site Val d'Orcia extends from the provinces of Siena to Grosseto, offering up some of Tuscany's most picturesque vistas. The Pienza loop trail begins in historic Pienza, a Renaissance city commissioned by Pope Pius II. From Pienza, pass the Romanesque parish church of Corsignano as you make your way through the green and gold undulating hillside dotted with cypress trees. After a short time, enter the Strada dei Gladiatori, the exact setting of the panoramic countryside scene from Ridley Scott's film 'Gladiator'.
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.

Day 6: Umbria: Cooking with a Local Chef

Walking the Italian countryside is the ultimate gift to yourself. Taking the time to step away from the hustle of your everyday life to intentionally move at a slower pace. Italy is about living and eating well. Speaking of eating, it's time to spend the morning with a local chef learning to prepare some of Italy's most loved dishes. A tagliatelle with ragù perhaps, or a creamy tiramisú. Buon Appetito!
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.

Day 7: Rome: Your OMG Day

Admittedly, Rome is one of those cities that is pretty OMG worthy on its own. If you have an entire week, its a great city to get lost in, wandering from neighbourhood to neighbourhood. To make the most of your time in Rome, you get to choose between a walking tour or a fully guided Vespa tour. No matter which way you choose to explore Rome, you will experience the very best the city has to offer.
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.

Day 8: Rome

Your adventure has come to an end, and you can depart at any time.

Exclusions

Flights to and from origin and destinations
Airport transfers (arrival and departure)
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.

Important Information

Meals

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.

Luggage

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.

Mobility

Travellers requiring wheelchair access should contact our sales and service team, who can make enquiries on your behalf.

Fitness Level

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.

Sightseeing

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.

Visas

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.

Departure Dates & Surcharges: See checkout for live dates and availability.

AUD $6,249

(Tour only)

Per Person Twin Share

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.

Check Availability Brochure

Price based on per person in Double Room for departure 20 Apr 2026

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Customer Reviews

Overall Rating

Excellent

4.5

Guide

Excellent

4.5

Itinerary

Excellent

4.5

Accommodations

Excellent

4.5

Transportation

Excellent

4.5

Tour Operator

Excellent

4.5

Food

Excellent

4.5

4.0

Sandra B.

Traveled, June 2024

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!

4.5

Suzanne G.

Traveled, May 2024

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

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