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Walking La Dolce Vita

  • Fountain of Neptune, Florence, Italy
  • Montalcino, Italy
  • Montalcino, Tuscany, Italy

WALKING LA DOLCE VITA is our invitation to see Italy by a less trodden path with our local English Speaking Walking Guide, who will escort us throughout the tour offering his expertise and insight into this wonderful region. This once-in-a-lifetime experience will take us from the romance of Florence to the beauty of the Italian Lakes to the medieval towns in Tuscany. Mixed with the well-planned walking tours and the amazing sights there will be ample opportunities to enjoy other Italian icons….no trip would be complete without partaking in fine culinary delights & local wines and taking in the history and arts in a country that is rich in both.

In the medieval town of Siena, we will walk the winding alleys that were once home to some of Italy’s best-known artists and poets -- Dante, Leonardo, Boccaccio and Petrarca. Get to know and taste the local wines in Dievole & San Gimignano, we will savor traditional farmhouse lunches, visit a local trattoria and enjoy an informative cooking class. Walk the World with Goway... One Step at a Time, and encounter a true Italian experience.


Day 1

Arrive in Florence

Upon arrival, you will be met and transferred to your hotel. The rest of the day is at leisure until our welcome dinner.

Our welcome to Italy begins with a walk to a local trattoria for our “Benvenuti” to Italy dinner ….enjoy!

Accommodation: Gallery Art Hotel

Meal Plan Dnner
Duration1 Night
Day 2

Florence – Siena – Panzano

This morning we transfer by coach to the renowned medieval town of Siena, located in the heart of Tuscany. The city is built on three hills and is linked together by winding alleyways and steep steps.

Some of the most important Italian artists and poets walked the Siena streets, for example, Dante, Leonardo, Boccaccio and Petrarca and it is also the home if Monte dei Paschi di Siena – the oldest bank in the world. Upon arrival, we have a guided tour of the city to take in many of these sights and to discover more of the wonderful city. After the tour, there is some free time for lunch (not included) and shopping!

After lunch, we depart by coach for Dievole and a wine tasting. We then continue to the lovely villa property in Panzano, where we will spend the next 3 nights. En route, we will also stop in Monteriggioni, the perfectly round walled town for a quick visit. B

Accommodation Villa San Giovese or similar
Located in the Panzano, in Chianti, in the heart of Tuscany. The Villa is surrounded by vineyards and originally in the 15th century was a winery. Enjoy the views of the rolling hills, vineyards, olive groves, and lines of cypress trees.

Meal Plan Breakfast
Duration3 Nights
Day 3

Panzano & San Gimignano

After breakfast, we depart with our guide for a walk outside the town walls into the countryside, home to an abundance of farming activity. The vineyards surrounding San Gimignano are also well known for their white wine, Vernaccia. The path follows the ridge tops, which will give us panoramic views of this beautifully cultivated region, as well as through the vineyards with row after row of neatly tended grapevines - all punctuated by ancient villas. After a wine tasting/lunch [03 wine+ cheese+ salami+ bruschetta] at a traditional farmhouse, we continue on to one of the most famous of the Tuscan villages, San Gimignano, Italy's best-preserved medieval city, is a fantastic landmark. This is an easy afternoon jaunt, which will have us arriving in the village in time for gelato, an unforgettable experience. After a day of exploring this varied and enthralling land by foot, nothing is better than a simply prepared Tuscan dinner in the hotel restaurant complemented by the esteemed local wines.

Meal Plan Breakfast, Lunch and Dinner
Day 4

Country Walk

Today we will enjoy a classic country walk. Our walk will end in Castellina, where we have a hand’s on cooking class, which is followed by dinner.

Meal Plan Breakfast and Dinner
Day 5

Panzano - Montalcino

After breakfast we depart for Montalcino and the beginning of the next part of our Italian adventure.

We will meet with a guide for an introduction walk through vineyards and olive trees to enter the Sienese Crete area before we arrive in the small region of Pieve a Salti. We get to sample a traditional farmhouse lunch, before continuing our journey on an unpaved road that will take us to the 14th century Abbey of Monte Oliveto Maggiore (entrance free). The Abbey is one of the most impressive religious buildings in Italy. Our final destination, Montalcino is the wine producing area of Brunello (Southern Tuscany) and is known as one of the most famous wine regions in Italy. 

This evening there is a gourmet dinner at Poggio Antico, which will be hosted by one of the most famous Brunello wine producers in the area.

Accommodation Residenza Palazzo Saloni or similar

Meal Plan Breakfast, Lunch and Dinner
Duration2 Nights
Day 6

Sant’ Antimo

This morning we walk with our Guide to Sant’ Antimo, a lovely abbey, which is isolated in the middle of a pastoral landscape and is dotted with grazing flocks of sheep. The Abbey is one of the few places in the world where you can hear the genuine Gregorian chant (no music—only human voice). Sant’Antimo is known as the "the singing stone" because of the travertine marble that makes the
Gregorian chant sound so beautiful. After a picnic lunch, we take a comfortable walk back to the hotel.

Tonight we enjoy a special wine tasting at Castello Romitorio.

Meal Plan Breakfast and Lunch
Day 7

Pienzo – Bagno Vignoni

Today there is an early start as we travel by coach to a nearby trailhead. From here we begin a walk to the village of Pienza with our guide. This idyllic town is known as the place where Pope Pious II (1405-1464) was born. It is said that he wanted to transform Pienza into a beautiful papal residence in Renaissance style. We walk across the quintessential Tuscan landscape of rolling hills, wooded areas and quaint villages and enjoy lunch (not included) in the lovely village.

An afternoon walk takes us to our new home in the village of Bagno Vignoni, a thermal bathing place where the main square is a basin of steaming hot water, alternatively you can choose to travel back via coach. Our dinner tonight is at the hotel restaurant.

Accommodation Hotel Le Terme or similar
Originally a palace dating back to 1400, this family run hotel overlooks the thermal basin. The hotel has 36 rooms and amongst it’s facilities there is a thermal water pool & spa, roman bath and jacuzzi pool.

Meal Plan Breakfast and Dinner
Duration2 Nights
Day 8

Monticchiello & Montepulciano

After breakfast we take a guided walk to the small hill village of Monticchiello, where we stop for lunch [02 course set menu + ¼ wine + water included]. Montichiello is immersed in the Sienese crete, a typical southern Tuscan landscape comprising of clay formations. Here you can

enjoy a gelato or glass of fine wine (not included) while facing one of the most memorable landscapes of your whole trip, before continuing to Montepulciano. Our walk ends in the old town.

Option in Montichiello: a ride is available for those who choose not to walk all the way to Montepulciano.

Meal Plan Breakfast and Lunch
Day 9

Depart Bagno Vignoni

This morning for those not joining us in the Cinque Terre, you will be transferred to the train station for your journey to Florence or south to Rome (train not included)

Meal Plan Breakfast

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