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Italy: Tuscany and Umbria Vineyard Walks

5.0Based on
8 days
8 daysDuration
Small Group TourUsually 8-12 participants
16 peopleMaximum group size
18 - 100 yearsAge range for participants
EnglishGuide language
Moderate
Involves sustained activity requiring a reasonable level of fitness and endurance.
Select Date
Best price guaranteedNo credit card or booking fees.Carbon neutral tours.

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

Itinerary

Unwind in the storybook landscapes of Tuscany and Umbria on this 8-day walking trip, designed for those seeking harmony with nature and a taste of Italy’s authentic flavors. Starting in Florence and ending in Rome, this guided small group tour leads you along ancient pilgrim paths, past farmhouses, castles, and vineyards. Enjoy a picnic lunch amid the vines of Lamole di Lamole and gain insight into the thousand-year-old history of the region’s food and wine. The highlight: a slow-paced exploration that lets you truly savor Tuscany’s unique identity, making it ideal for travelers who value meaningful experiences and local traditions.

day 1Tuscany

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.

Meal
Dinner
Accomodation
Hotel Palazzo Pacini (or similar)
Transport
Private Vehicle Duration : 1.5 hr Distance : 60 km, Private Vehicle Duration : 0.5 hr Distance : 22 km
Included Activities
Meet Your CEO and Group Duration : 1.0 hr, San Gimignano Guided Tour Duration : 1.5 hr, Walk Abbadia a Isola to Colle Val d'Elsa Duration : 3.0 hr Distance : 8 km

day 2Tuscany

day 3Tuscany

day 4Tuscany

day 5Tuscany

day 6Umbria

day 7Rome

day 8Rome

What's Included

Accommodation
Hotels (7nts).
Meals
7 breakfasts, 4 lunches, 4 dinners
Note: Allow USD170-225 for meals not included.
Transport
Private vehicle, walking.All transport between destinations and to/from included activities
Guide
CEO (Chief Experience Officer) throughout.
Included activities
Your Welcome Moment: Meet Your CEO and GroupYour Foodie Moment: Molino di Grace Visit & Lunch, PanzanoYour Foodie Moment: Wine Pairing DinnerYour Foodie Moment: Pecorino Cheese TastingYour OMG Day: Rome Walking Tour or Fully Guided Vespa Tour, RomeWelcome lunchGuided walking tour of San GimignanoGuided walking tour of MontepulcianoGuided walking tour of SienaGuided walking tour of Città della PieveCooking class in UmbriaWalk Strove to Colle Val d'ElsaWalk Monteriggioni to SienaWalk Montefioralle to PanzanoWalk Volpaia to LamoleWalk the Gladiator TrailVisits to towns in the Italian countryside like Montefioralle, Greve in Chianti, and PanzanoFree time in RomeFarewell dinnerAll tips for meals and activities, except for CEO and porterage

Customer Reviews

5.0

based on 8 reviews
8
J
Janice HVerified Traveler
5.0 | Excellent

Excellent

An amazing holiday, an exceptional CEO and a lovely group of people in a truly beautiful part of Italy. I wish I could do it all over again!!

G
Gerardina BVerified Traveler
5.0 | Excellent

Excellent

This was a well balanced tour that tok into account everyone’s interests.

F
Fariha LVerified Traveler
5.0 | Excellent

Excellent

Great guide, great accommodations, there was something for everyone!

L
Lukas CVerified Traveler
5.0 | Excellent

Excellent

This Italian adventure exceeded every expectation! From the art-filled streets of Florence to the sun-soaked vineyards of Tuscany, the charm of Siena and Umbria, and the awe-inspiring sights of Rome, each day was packed with rich culture, stunning landscapes, and delicious food. We tasted incredible wines, sampled fresh cheeses, explored historic towns, and hiked through scenic countryside. Our CEO, Barbara, was phenomenal—bringing the trip to life with her passion, knowledge, and warmth. Giancarlo, our amazing driver, not only made every journey smooth but also made us feel like locals with his expertise and personal connections to Tuscany. The entire adventure felt seamless, joyful, and meaningful. It was more than a trip—it was a once-in-a-lifetime experience shared with an unforgettable group of people.

B
BarbaraVerified Traveler
5.0 | Excellent

Excellent

I really enjoyed the Geluxe tour and most of it fit in that class of travel. I think it could use a little bit of work to deliver the full luxury experience.

Good to Know

Travel Insurance
Visa
Other Practical Information

Do you need help from our trip consultants?

If you have any question about this tour or need help with planning a trip, please do not hesitate to get in touch with us.

Our travel experts are ready to help.
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Rasmus Juul Olsen

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