8D7N Tuscany and Umbria Vineyard Walks (EIFG)

8 Days Italy 2 to Go

With perfectly paced itineraries, one-of-a-kind accommodations, and comfort at their very core, these premium active trips are adventure at its finest.

Spend time in the Tuscan countryside in landscapes dotted with farmhouses and castles all while experiencing Italy in perfect harmony with the land. Hike the same paths spiritual pilgrims once walked long ago, sit down for a picnic lunch in the vineyards of Lamole di Lamole and learn about the food and drink you consume in a storybook setting.

DepartureFlorence
ReturnRome
Min. travellers2
Booking periodNow till October 2026
Travel periodApril till October 2026

Tour Highlights

  • 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 Volpaia to Lamole
  •  Walk the Gladiator Trail
  • Visits to towns in the Italian countryside like Montefioralle, Greve in Chianti, and Panzano

Day-by-day itinerary

Day 1 Tuscany

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. Throughout this picturesque adventure, move through Tuscany and Umbria by walking from village to village. Your first day sees you begin the trek in the village of Strove walking the Via Fancigena until you cross the Elsa River on foot, wading ankle deep in the blue water. Welcome to Tuscany, and to Italy, we invite you to find you inner serenity in the countryside.

lunch

Day 2 Tuscany

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.

breakfast · lunch

Day 3 Tuscany

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. Trek from the wavy hills of the Chianti region, along the dusty dirt road that winds through rows of vineyards and the silvery foliage of olive groves, before reaching the provincial road that leads to the hamlet of Panzano. Your reward for another beautiful walk? Lunch at a local winery with a pairing of local wines of course.

breakfast · lunch · dinner

Day 4 Tuscany

From medieval village to medieval village, through the vineyards of Chianti, your walking today sees you leaving Volpaia walking up towards Monte Querciabella, the highest point of the day. Carry on to Poggio del Quercetino and then downhill to Lamole, famous for its terraced vineyards, where you take a luscious rest in the form of a picnic lunch among the vines.

breakfast · lunch · dinner

Day 5 Tuscany

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’.

breakfast

Day 6 Umbria

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!

breakfast · lunch

Day 7 Rome

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.

breakfast · dinner

Day 8 Rome

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

breakfast

What's included

Included

  • 7 nights accommodation
  • Meals as per itinerary
  • Excursions as per itinerary
  • All transport between destinations and to/from included activities.
  • All tips for meals and activities, except for CEO and porterage.

Not included

  • International air ticket
  • Travel insurance
  • Others not mentioned

Prices & dates

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Your hotels

Hotel Palazzo Pacini

★★★★

Colle Val D'Elsa Gracco del Secco, 14, 53034 Colle Val D'Elsa, Italia

Palazzo Pacini in Colle Val D'Elsa is housed in a historic building, offering a unique atmosphere. The property features a sun terrace and a beautiful garden, complemented by free WiFi throughout. ooms include air-conditioning, private bathrooms, and modern amenities such as tea and coffee makers, minibars, and flat-screen TVs. Family rooms and ground-floor units provide additional comfort.

Hotel Vannucci

★★★★

Città della Pieve Via I. Vanni 1, 06062 Città della Pieve, Italy

Hotel Vannucci is a 30 room hotel located in the heart of the small town, overlooking the valley below. Its known for it beautiful setting, excellent service and spectacular cuisine.

Borgo Casa al Vento

★★★★

Gaiole in Chianti Località Casa al Vento, 53013 Gaiole in Chianti, Italy

Borgo Casa Al Vento is in the Tuscan countryside, 3 km from Gaiole In Chianti. It offers sport activities and a panoramic pool. The farmhouse provides rooms with TV and minibar, and apartments for up to 6 people. There is free parking and free Wi-Fi in all public areas of the Borgo. The restaurant at Borgo Casa Al Vento serves typical Tuscan cuisine and wine produced on the vineyards surrounding the property.

Mama Shelter Roma

★★★★

Rome Via Luigi Rizzo 20, Trionfale, 00136 Rome, Italy

Mama Shelter Roma in Rome offers family rooms with air-conditioning, private bathrooms, and modern amenities. Each room includes a balcony, work desk, and free WiFi, ensuring a pleasant stay. Located 27 km from Fiumicino Airport, the hotel is near attractions such as the Vatican Museums (less than 1 km) and St Peter's Basilica (2 km). An ice-skating rink is also in the surroundings. Highly rated for its breakfast, restaurant, and attentive staff.
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From MYR 15,996 Tap for price options