Tuscany & Umbria Vineyard Walks (May ’25)

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.
Exclusive Inclusions: Your Welcome Moment Welcome Moment - Meet Your CEO and Group.
Meals included: Lunch.

Monteriggioni is your quintessential Tuscan medieval walled village. Follow part of the ancient Francigena way into Siena. Step back in time as you walk past donkeys in green pastures and lush vineyards as the Tuscan countryside unfolds before you. Walk up to the main door of the Hermitage of San Leonardo al Lago and knock-your local host will be waiting. Enter and admire the frescoes painted throughout the church.
Meals included: Breakfast | Lunch.

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.
Exclusive Inclusions: Your Foodie Moment Molino di Grace Visit & Lunch.
Meals included: Breakfast | Lunch | Dinner.

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.
Exclusive Inclusions: Your Foodie Moment Wine Pairing Dinner.
Meals included: Breakfast | Lunch | Dinner.

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.

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.
Your OMG Stay: Hotel Vannucci.

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.

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