Italy: Florence to Rome, Walking the Vineyards of Tuscany and Umbria

As the sun sets in Florence, the city centre becomes bathed in a golden hue as the lights come on, welcoming locals and travellers alike to head out into the city, to dine together and celebrate life's simplest pleasures. The birthplace of the renaissance, Florence remains a fashion and culture icon in the modern world. With so much art, history, and architecture to take in, there is no time to waste. Welcome to Florence, and to Italy, and we invite you to explore the old and the new, the grand and the simple, all in one of the world's most beautiful countries.
After an informative welcome briefing with your CEO and a delicious dinner in the heart of Florence, stretch your legs on an evening walk to get some photos of that beautiful golden Florence glow. Speaking of simple pleasures- your evening stroll includes a stop for a gelato at a famous gelateria. Try the pistachio flavour or the fiordilatte. Or both. It's your first day in Italy, after all. Time to celebrate.

Welcome Moment - Meet Your CEO and Group: Your opportunity to meet your CEO and fellow travellers, and learn more about your tour. Join the group afterwards for a welcome dinner at local restaurant. Don't forget to see the notice in the lobby (or ask reception) for the official time and place to meet up with the group.

: You will be met at the airport and transferred to the hotel to start your adventure.

Meal plan: DINNER

Standing before the Cattedrale di Santa Maria del Fiore, the Duomo, is one of those moments in life where you feel truly small. To take in the magnitude of what the cathedral represents is to transport yourself back in time to the 13th century. Could the people who began to build this magnificent structure have ever imagined that 800 years later people would still come to marvel at its beauty. This morning join your expert guide for a walking tour and see the Duomo, Signoria Square and then head over to the Ponte Vecchio, you will only just be scratching the surface of what there is to see.
The only way to truly appreciate Florence is by walking the streets and plazas. After your walking tour, end the morning at a local market where you can enjoy Italian specialties. During the afternoon, choose to join you CEO at the Piazzale Michelangelo for a delicious view of the city and a well earned refreshing drink. There is plenty to do in Florence, so ask your CEO and make sure you make the most of your afternoon.

Florence Guided Walking Tour With Local Guide: Enjoy more of Florence with a local guide on a 3-hour walking tour hitting all of the can't-miss highlights. Visit Duomo Square, Signoria Square, and Ponte Vecchio.

Free Time: Spend the afternoon on your own. Opt to join your CEO for a drink at Piazzale Michelangelo or opt to visit some museums like Museo Leonardo Da Vinci.

Meal plan: BREAKFAST

The Tuscan countryside is calling. Over the course of the next 5 days, move through Tuscany and Umbria by walking from village to village. The pace here is intentional-many stops are made along the way to ensure you see and experience the true essence of these beautiful places. Your first day sees you begin the trek in the village of Strove walking the Via Fancigena until you reach the Elsa River. Cross the river on foot, wading ankle deep in the blue water.
Leave Florence and travel southeast, but before you begin to trek, get your body moving by a morning visit to San Gimignano. With the insights of a local guide, 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.

Walk Strove to Colle Val d'Elsa: Begin in the tiny village of Strove and walk along the ancient Via Fancigena to the Elsa River. Walk through the park, over bridges, and bask in the ice-blue colour of the water. Length: 8km (5 miles) Duration: 3 hours Elevation: approximately 100m

: Settle in and scan the scenery from the convenience of a private vehicle.

Meal plan: BREAKFAST, LUNCH

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.
After the hike, explore Monteriggioni’s charming streets and well-preserved medieval walls. Then, relax and enjoy a well-earned lunch with local flavors before heading back to Colle di Val d’Elsa, where you will have some free time to explore this historic town at your own pace.

Hike to Monteriggioni: Begin at the Chiocciola and Villa Castles and make your way through the dense bush, heading toward the enchanting Monteriggioni. Walk on dirt paths, gravel roads, and narrow trails. Elevation: 150m

: Settle in and scan the scenery from the convenience of a private vehicle.

Free Time: There is plenty to see and do; now is your chance to explore however you wish. Head out to explore more of the local hiking trails or enjoy the unique architecture.

Meal plan: 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. 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.
After a decadent and leisurely lunch, continue on to Greve in Chianti, considered the "gateway" to the Chianti region. Greve in Chianti is formed around a beautiful triangular piazza, at the centre of which is a statue of the explorer Giovanni da Verrazzano, one of the town’s most illustrious sons, who went down in history for discovering the bay of New York. End the day relaxing with a cold drink at your Tuscan Villa perched above the vineyards.

Stroll around Montefioralle: Montefioralle is one of the gems of the Chianti region and sits atop a high plain. The houses in the small town surround the historic castle. In some places the town is still protected by the original defense walls. Spend some time walking around and stretching those legs after breakfast.

: Settle in and scan the scenery from the convenience of a private vehicle.

Meal plan: BREAKFAST, LUNCH, DINNER

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.
After lunch, sample four varieties from the local Tuscan estates, continuing to learn not only about the process of wine making in Tuscany, but about the people who make their life here in Chianti. Tonight enjoy a special wine pairing dinner.

Siena Walking Tour: Set out on a short walking tour of Siena with your CEO to gain a sense of Italy's loveliest medieval city.

: Settle in and scan the scenery from the convenience of a private vehicle.

Free Time: Enjoy free time to explore more of Siena.

Meal plan: 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'.
Your morning walk concludes just in time to sample another Tuscan favourite, pecorino cheese. A tasting of locally produced pecorino and ricotta cheeses is served with a glass of Montepulciano wine. After indulging in a glass of Montepulciano wine, it's only fitting to visit the town itself. A local guide welcomes you to this ancient hilltop town and provides an in depth walking tour of the old centre. Here we leave Tuscany and head into Umbria to Città della Pieve.

Walk The Pienza loop: Begin in the historic center of Pienza before hiking to the Romanesque parish church of Corsignano and ending up at an old film location for "The Gladiator" before returning to Pienza. Elevation gain: 225m Distance: 6km Duration: 2 hours

: Settle in and scan the scenery from the convenience of a private vehicle.

Meal plan: 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!
After you devour the fruits of your cooking labor, alongside a few glasses of delicious wine, the afternoon is yours to spend at leisure. A local guide will lead a walking tour of Città della Pieve, our home while in Umbria, known as the birthplace of renaissance painter Pietro Vannucci.

Guided Walking Tour of Città della Pieve: See Città della Pieve on a walking tour led by a local guide. The city is considered a historic medieval centre and was built of bricks in different shades of dark pink. A distinguishing marker from other Umbrian towns which are mainly made of stone. The best feature of this town are its many winding, maze-like alleys which acted as a defensive system, making the town impenetrable to enemies. The narrow streets also helped shield the town from the heat of the summer sun and the winter winds.

Meal plan: BREAKFAST, LUNCH

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.
If you are up for more walking, join your local Roman guide and walk the historical centre, visiting Piazza Barberini and Piazza di Spagna. Drop a coin into the Trevi Fountain and sip a cappuccino in Piazza Navona. If you are ready for less walking, more adrenaline, hop on back of a Vespa with a professional driver and whiz through Rome from Trastevere to the Colosseum and lots more.

Rome Walking Tour or Fully Guided Vespa Tour: Option 1: There are many ways to see Rome, but sometimes the best way is on foot. Discover the Eternal City on walks through the squares that have marked history. Start from Piazza Barberini, become enchanted by the charm of the Spanish Steps, and get ready to turn your luck with a coin toss into the Trevi Fountain. This leisurely walk continues towards the Pantheon and Sant'Ivo della Sapienza, ending in Piazza Navona. Option 2: When in Rome... live "la dolce vita". To see the Eternal City like the locals, hop onto a Vespa! Cruise around the city and visit Rome's must-see landmarks with a local guide. Your professional driver will show you the majesty of ancient monuments such as the Colosseum, Keyhole, Trastevere District, or even the view of the Roman Forum from the top of the Capitol hill.

: Settle in and scan the scenery from the convenience of a private vehicle.

Free Time: Take advantage of free time in Rome and opt for a CEO Orientation walk of the city or simply keep exploring on your own before your final group dinner tonight.

Meal plan: BREAKFAST, DINNER

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

Departure Day: Not ready to leave? Your CEO can help with any onward travel arrangements you require.

Meal plan: BREAKFAST