Back to Top
Mobile Navigation Icon Call Icon
Oct 1 2022

Tuscany and Cinque Terre: Fall 2022


Be among the few Americans to distance yourself from Florence– but only by 20 miles. Few Tuscan tours touch upon this quietly beautiful corner of Tuscany, amidst gentle hills covered by vines and olives. This is a landscape immortalized in many of Leonardo Da Vinci’s works including the Mona Lisa. We’ll settle in for the first few days at a spacious villa hotel, a peaceful respite for those who want to savor life in a town almost untouched by foreigners.

Our pace here will be easy-going, allowing the land to unveil its wonders in a way that we can absorb the magic. Larger towns give a historical overview, while the smaller ones are our window into the local soul. We’ll lunch in farmhouses and castles; walk the streets of Florence and Pisa with a local; and try some of the best Sangiovese wine in these hills. At night we’ll return to satisfying dinners at the villa’s restaurant.

The last part of the week finds us across Italy, in another 4-star hotel by the Mediterranean Sea.  The famous Cinque Terre villages will be the focus of a magnificently full day. Then some fresh pesto pasta and the glamorous Italian Riviera will form the backdrop for a grand final day.


Day 1 – Transfer from Florence to your hotel in the Tuscan countryside
Private coach transfer from Florence to your hotel in Tuscany. Time to settle in and enjoy this spacious villa located strategically between some of Tuscany’s most beautiful cities. Free time to wander the grounds, opt for a spa treatment, or take advantage of the in-depth winery tour and tasting (additional fee).

Lodging for the next 4 nights:  HOTEL VILLA CASAGRANDE ****, less than an hour south of Florence. Welcome drink, D

Day 2 – San Gimignano with gelato tasting (world’s best award winning) and Volterra with saffron lunch
Today will be a full-day excursion to two of Tuscany’s famous hill towns: San Gimignano and Volterra. The iconic towers of San Gimignano can be seen from far away, testimony to the competition among the town’s wealthy families to outdo each other with ever taller towers. The medieval structures of this city have largely remained intact, making it essentially an open-air museum. Before leaving this amazing place you will enjoy an unforgettable ice cream in one of the oldest and most famous gelaterias in Italy. Signor Dondoli produces unique flavors; taste his saffron & pine nuts, a registered trade mark!
Continue on to the alabaster city of Volterra. This former Etruscan settlement is located on a rise with a splendid panoramic view. Lunch today will be at a family-run farmhouse, specialized in saffron production. Tuscan saffron has always been a local delicacy. This region is crossed by the ancient Francigena pilgrim and trade route which introduced saffron from the East hundreds of years ago.

Dinner at the hotel this evening. B, L, D

Day 3 – CHIANTI! Cooking class at a historic Castle followed by lunch
Today features exploration of the Chianti countryside, those rolling hills and vineyards that everyone falls in love with! Activities include a cooking experience at a historic Castle in the middle of the Tuscan vineyards, followed by lunch. On the way back to the hotel, you’ll visit a Tuscan farmhouse to taste local wines and try the foodie staples of Tuscany (pecorino cheese and various salumi — cold cuts). Back to the villa hotel with time to rest before dinner tonight. B, cooking experience and L, D

Day 4 – Excursion to Florence by Train
This is the day of art: you’ll board an early train after breakfast for the 30-minute scenic ride to the regional capital: Florence.  A private guide will spend three fascinating hours strolling through the gorgeous streets and highlighting the history behind Florence’s architectural masterpieces. Every corner of this Renaissance city inspires: Palazzo Vecchio, Ponte Vecchio, Duomo, the Uffizi and Accademia museums, markets, gardens and squares. Entrance fee to see Michelangelo’s Davide and/or to enter one of Italy’s most famous museums (the Uffizi Gallery) can be added upon request. Free time in the afternoon before returning to the hotel by train; dinner in house tonight. B, D

Day 5 – Discover Pisa with its Leaning Tower and the smallest Pasta Factory in Lari before reaching the Mediterranean Coast
Check out after breakfast and board your private coach for a beautiful transfer all the way across Tuscany to the Mediterranean Sea! You’ll stop in Pisa, where the Leaning Tower never disappoints (entrance fee can be added upon request). Get to know more about this important city during your 2-hour guided walk. Then visit Lari, a lesser known Tuscan town located inside castle walls. The Martelli Family has been making pasta there since 1926 and are always happy to show you how. Tour the pasta factory, Europe’s smallest, and pick up a bag or two as a souvenir to bring home with you.

End the afternoon in the seaside town of Sestri Levante, at Hotel Vis-a-Vis. This property is perched on a high promontory above town, providing spectacular views over the two beautiful bays, Baia del Silenzio  (the Bay of Silence) and Baia delle Favole (Bay of Fairy Tales). The bays were named in honor of Hans Christian Andersen, a resident of the town for a short time.  The Vis-a-Vis is a perfect base to explore this region of Italy known as Liguria.

Lodging for the last 3 nights: HOTEL VIS-A-VIS **** , half an hour up the coast from the Cinque Terre. B

Day 6 – The Cinque Terre

The Cinque Terre – literally “Five Lands” — are five fishing villages that dot Italy’s Mediterranean coast, tucked into the habitable terrain between the swaths of lush vertical land and cobalt coves. Each village is unique, and you’ll visit four of them today! Ancient churches, castles and homes are centered on squares that often use the sea as their fourth side. The dramatic topography of the area did not allow for access by cars; even today, these villages are best reached by boat, rail or trail.
Monterosso is the largest and the only one with a sandy beach. Vernazza is considered to be the most photogenic, as its natural pier surrounded by colorful houses is truly charming. Manarola has a small harbor where the Via dell’Amore (“Lover’s Lane“), once started (due to landslides, the walking path is now closed). Riomaggiore is a peaceful place, with its colorful cluster of houses hugging the hills.
The villages lay in what is now a national park, with the water in front of a protected marine area.

You’ll explore this area through a combination of private coach, train and boat excursions today. The day will be full and fun! B

Day 7 – Pesto cooking class with lunch; afternoon discovery of Rapallo, Santa Margherita and Portofino by boat
After a relaxing breakfast, stroll around historic Sestri Levante, ending at a local restaurant where you’ll dive into the most classic Ligurian dish: pasta al pesto Genovese. The fragrant yet simple sauce is a divine combination of basil, pine nuts, olive oil, cheese and garlic. You will make the pesto and enjoy your lunch right in the place where the recipe was born.
The week ends with an afternoon at the glamorous Italian Riviera, for decades the playground of the affluent. Colorful villas and cobalt waters are studded with yachts, and a stroll along its dreamy promenades allows visitors to feel a part of the luxury scene. One of the best ways to see the area is from the sea, so you’ll board a ferry from Rapallo to Portofino and return by boat to Santa Margherita. As you sail along, view the jaw-dropping area and soak up the sunshine and sea breeze. When you dock you can share in the highlife, if only for an hour: smelling fragrant Mediterranean flowers as you sip espressos and Proseccos at charming cafés along the harbor! Back to the hotel for dinner and packing; tomorrow it’s time to go home. B, cooking experience and L

Day 8 – Departure
Private coach transfer from your hotel to Pisa airport. B

Come see the Italy everyone dreams of: Tuscany and Cinque Terre!