Italy: Florence to Rome, Walking the Vineyards of Tuscany and Umbria

G Adventures · 10 days

3.8

3 Reviews

Duration

10 days

Tour Type

Small Group

Accommodations

Moderate

Physical Rating

Average

Guide Language

English

Experience Overview

It’s never been hard to fall under the spell of Italy’s romantic atmosphere.

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
Complimentary Arrival Transfer
Welcome and Farewell dinner
Guided walking tour of Florence
Lunch at an agriturismo
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
Pecorino Cheese Tasting
Visits to towns in the Italian countryside like Montefioralle, Greve in Chianti, and Montepuliciano
Picnic lunches in vineyards
Free time in Rome
All transport between destinations and to/from included activities
All tips for meals and activities, except for CEO and porterage

Accommodation

Hotels (7nts). Agriturismos (2nts).

9 breakfasts, 5 lunches, 4 dinners

Transport

Private vehicle, walking.

Group Leader

CEO (Chief Experience Officer) and local guides throughout.

Highlights

Visit the historic centre of Pienza a Renaissance city commissioned by Pope Pius II
Explore San Gimignano and Montepulciano
Savour Gelato in Florence on an orientation walk through the city
Tour the cellar and vineyard with a farmhouse lunch overlooking the rows of grapes
Hike from the tiny village of Strove along the ancient Via Fancigena
Walk through medieval towns like Greve Montefioralle and Panzano
Sample local cuisines directly from its sources in the many vineyards dotting the hills of Tuscany’s Chianti Region
Enjoy the sites and sounds of Rome and Umbria.

Italy: Florence to Rome, Walking the Vineyards of Tuscany and Umbria

Trip Details

Duration

10 days

Transportation

Private vehicle, walking.

Guide Language

English

Starts

Florence, Italy

Finishes

Rome, Italy

Accommodations

Moderate

Travel Style

Luxury, Budget

Physical Rating

Average

Itinerary

Day 1: Florence: A Golden Stroll

As the sun sets in Florence, the city centre becomes bathed in a golden hue as the lights come on, welcoming locals and travellers alike to head out into the city, to dine together and celebrate life's simplest pleasures. The birthplace of the renaissance, Florence remains a fashion and culture icon in the modern world. With so much art, history, and architecture to take in, there is no time to waste. Welcome to Florence, and to Italy, and we invite you to explore the old and the new, the grand and the simple, all in one of the world's most beautiful countries.
After an informative welcome briefing with your CEO and a delicious dinner in the heart of Florence, stretch your legs on an evening walk to get some photos of that beautiful golden Florence glow. Speaking of simple pleasures- your evening stroll includes a stop for a gelato at a famous gelateria. Try the pistachio flavour or the fiordilatte. Or both. It's your first day in Italy, after all. Time to celebrate.

Meals included: Dinner

Exclusive inclusions: Transport - You will be met at the airport and transferred to the hotel to start your adventure.Activity - Your opportunity to meet your CEO and fellow travellers, and learn more about your tour. Join the group afterwards for a welcome dinner at local restaurant. 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.Activity - Head out for a walk through the heart of Florence with your CEO as the sunshine fades and the monument lights come on. On the return trip stop to eat gelato.Accommodation - Hotel Club Florence

Day 2: Florence: From the Duomo to the Ponte Vecchio

Standing before the Cattedrale di Santa Maria del Fiore, the Duomo, is one of those moments in life where you feel truly small. To take in the magnitude of what the cathedral represents is to transport yourself back in time to the 13th century. Could the people who began to build this magnificent structure have ever imagined that 800 years later people would still come to marvel at its beauty. This morning join your expert guide for a walking tour and see the Duomo, Signoria Square and then head over to the Ponte Vecchio, you will only just be scratching the surface of what there is to see.
The only way to truly appreciate Florence is by walking the streets and plazas. After your walking tour, end the morning at a local market where you can enjoy Italian specialties. During the afternoon, choose to join you CEO at the Piazzale Michelangelo for a delicious view of the city and a well earned refreshing drink. There is plenty to do in Florence, so ask your CEO and make sure you make the most of your afternoon.

Meals included: Breakfast

Exclusive inclusions: Activity - Enjoy more of Florence with a local guide on a 3-hour walking tour hitting all of the can't-miss highlights. Visit Duomo Square, Signoria Square, and Ponte Vecchio.Free_time - Spend the afternoon on your own. Opt to join your CEO for a drink at Piazzale Michelangelo or opt to visit some museums like Museo Leonardo Da Vinci.Accommodation - Hotel Club Florence

Day 3: Tuscany: San Gimignano and Colle Val d'Elsa

The Tuscan countryside is calling. Over the course of the next 5 days, move through Tuscany and Umbria by walking from village to village. The pace here is intentional-many stops are made along the way to ensure you see and experience the true essence of these beautiful places. Your first day sees you begin the trek in the village of Strove walking the Via Fancigena until you reach the Elsa River. Cross the river on foot, wading ankle deep in the blue water.
Leave Florence and travel southeast, but before you begin to trek, get your body moving by a morning visit to San Gimignano. With the insights of a local guide, 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: Breakfast,Lunch

Exclusive inclusions: 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.Activity - Begin in the tiny village of Strove and walk along the ancient Via Fancigena to the Elsa River. Walk through the park, over bridges, and bask in the ice-blue colour of the water. Length: 8km (5 miles) Duration: 3 hours Elevation: approximately 100mTransport - Settle in and scan the scenery from the convenience of a private vehicle.Transport - Settle in and scan the scenery from the convenience of a private vehicle.Accommodation - Hotel Palazzo Pacini

Day 4: 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.

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 5: 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.

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 6: 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.

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 7: 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.

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 8: 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.

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 9: 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.
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 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 - 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 Orientation walk of the city or simply keep exploring on your own before your final group dinner tonight.Accommodation - Mama Shelter Roma

Day 10: Rome

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

Meals included: Breakfast

Exclusive inclusions: Activity - Not ready to leave? Your CEO can help with any onward travel arrangements you require.

Exclusions

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.

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.

From
AUD $7749

AUD $6,199

(Tour only)

Offer ends 24 Mar, 2026 Per Person Standard

Duration: 10 days

Trip Type: Small Group

Activity Level: Average

It’s never been hard to fall under the spell of Italy’s romantic atmosphere.

Check Availability Brochure

Price based on per person in Double Room for departure 18 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

3.5

Linda

Traveled, August 2024

08/25/2024

Luca our tour guide was a wonderful fun guy who made sure we saw everything on our itinerary and more.

4.0

Donna

Traveled, August 2024

08/23/2024

Amazing quaint family owned accommodation, delicious meals, tranquil views. Comfortable unique rooms, areas to snuggle in and read a book. Phenomenal access to Capri and Sorrento. My only suggestion include transportation Island of Capri and other activities following the end of the path of Gods hike; it was annoying that we were constantly asked to contribute another 10 euro for transportation I otherwise would have brought more cash rather than seeking out ATM's. The initial tour in Naples was in my opinion not well curated, the market was terrible, would have preferred the charming street we discovered on route back to the hotel. Our Pompeii guide Amazing and well worth the stop.

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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