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Italy: Tuscany and Umbria Vineyard Walks

8 days, Florence to Rome

8 days

Florence to Rome

From$3999USD
Valid on Apr 20 2026
Trip Code: EIFG

Need a flight? We can help.

Call us to book your flights! We'll find you the best option!

Is this tour for me?

Travel Style: The Geluxe Collection

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

Service Level: Upgraded

Quality accommodations and more inclusions than on other G Adventures tours, like meals, private transport, and activities.

Physical Rating: 3 - Average

Some tours may include light hiking, biking, rafting, or kayaking in addition to walking.

Trip Type: Small Group

Small group experience; Max 16.

Age requirement: 18+

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Before booking, use our handy entry requirements tool so you know which documents you need to enter and travel through the countries on your trip.

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8 days

Florence to Rome

From$3999USD
Valid on Apr 20 2026
Trip Code: EIFG

Need a flight? We can help.

Call us to book your flights! We'll find you the best option!

Chief Experience Officers with a capital E

Call us biased but we've seen 30+ years of proof: our Chief Experience Officers are the best travel guides on the planet. And on Geluxe trips, you'll be led by the most experienced CEOs we have.

Fabi, a Chief Experience Officer on our Geluxe tours in Peru

Fabi

CEO Peru

Yinier, a Chief Experience Officer on our Geluxe tours in Costa Rica

Yinier

CEO Costa Rica

Haidy, a Chief Experience Officer on our Geluxe tours in Egypt

Haidy

CEO Egypt

See how your trip uplifts communities

In a number of impactful ways, your adventure directly benefits the local people and places we visit.

Trees for Days

Help us spread love around the world with Trees for Days. Together with Planeterra, we'll plant one tree in your name for every travel day.

Trees planted for this trip: 8

Ripple Score

Create ripples that change lives. The higher the Ripple Score percentage, the more money stays in the local communities you visit.

Ripple Score for this trip: 100

Map of the route for Italy: Tuscany and Umbria Vineyard Walks

Places visited

Itinerary

Day 1Tuscany: 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.

Exclusive Inclusions:

Your Welcome Moment Welcome Moment - Meet Your CEO and Group

Meals included:

Dinner

Day 2Tuscany: 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.

Meals included:

Breakfast | Lunch

Day 3Tuscany: 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.

Exclusive Inclusions:

Your Foodie Moment Molino di Grace Visit & Lunch

Meals included:

Breakfast | Lunch | Dinner

Day 4Tuscany: 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.

Exclusive Inclusions:

Your Foodie Moment Wine Pairing Dinner

Meals included:

Breakfast | Lunch | Dinner

Day 5Tuscany: 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'.

Exclusive Inclusions:

Your Foodie Moment Pecorino Cheese Tasting

Meals included:

Breakfast

Day 6Umbria: 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!

Meals included:

Breakfast | Lunch

Day 7Rome: 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.

Exclusive Inclusions:

Your OMG Day Rome Walking Tour or Fully Guided Vespa Tour

Meals included:

Breakfast | Dinner

Day 8Rome

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

Meals included:

Breakfast
View full itinerary

Your OMG Stay

Hotel Vannucci

Città della Pieve, Italy

2 nights (Day 5 - 6)

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.

Why we love this stay

  • The romantic story around the history of the hotel is typical Italy.
  • The location of the hotel is in the heart of Citta Della Pieve, a beautiful village not often visited by tourists.
  • The idyllic setting overlooking the Tuscan valley is the perfect place to enjoy the exceptional food served at the hotel.

What's Included

  • Your Welcome Moment: 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

Accommodations

Hotels (7nts).

Meals

7 breakfasts, 4 lunches, 4 dinners
Allow USD170-225 for meals not included.

Transportation

Private vehicle, walking.

Staff & experts

CEO (Chief Experience Officer) throughout.

Available extras (Add these to your tour when you book)

My Own Room - From $1339.00

If you're travelling solo and would prefer to have your own private room throughout your trip, select this option during the online booking process.

Make it a private tour

Book this tour as a private departure, with your own CEO and all the benefits of a G Adventures group tour.

Italy: Tuscany and Umbria Vineyard Walks

| 8 days - Florence to Rome - from $3999 USD