This 9 Nights/10 Days Tour of Tuscany and Cinque Terre begins with your arrival in Chianti to spend 3 nights. This is magical wine regions Chianti where you will get to taste the best wine and explore the amazing towns of San Gimignano, Siena, Arezzo, and Cortona.

Then visit Florence, the cradle of the renaissance, and Pisa. During the tour, you will be served breakfasts in the best hotels but also taken on exclusive wine tasting tours throughout Tuscany and fine dining events.

You will be able to see, taste, and explore every bit of Cinque Terre, but also go beyond and visit Portofino, Rapallo, Tigullio, and San Fruttuoso, all picturesque and iconic coastal places in Liguria.

Tuscany and Cinque Terre Classic Tour | 9 Nights/10 Days

Day 01: Florence Arrival | Welcome to Italy! Upon arrival at Florence airport, please collect your luggage inside the customs area. Just outside this area meet your driver who will transfer you to your Hotel in Chianti. The rest of the day is for you to spend at leisure. Overnight in Chianti.

Day 02: Siena and Chianti Private Guided Tour | Breakfast at the Hotel. Meet your Driver at the Hotel Lobby. Your day tour starts in Siena, Italy’s loveliest medieval city. Meet your guide for a private tour of the old city center; walk along the narrow medieval streets, you will admire the splendid Cathedral, the Libreria Piccolomini, and Piazza del Campo, where the famous Palio horse race is held twice a year, overlooked by the Palazzo del Comune. Continue to a Wine Estate where you will enjoy a Lunch/Food a Wine Tasting. After lunch, your driver will take you on a tour of the Chianti little towns. This is the classic Tuscan countryside – Green hills with miles after miles of vineyards producing some of Italy’s best-marketed wines, olive groves, gently rolling hills, ancient walled villages, and panoramic roads. Visit Castellina, Greve, and Radda in Chianti. The splendid Romanesque churches, farmhouses, villas, and castles dotting the landscape complement the region’s enchanting natural beauty. Late afternoon return to your hotel. Overnight in Chianti.

Day 03: Arezzo and Cortona Private Guided Tour | After breakfast at the hotel, meet your driver and guide in the lobby. This morning travel to Arezzo where you will meet your guideArezzo is an extraordinary and ancient city, that is actually as old as Alexandria of Egypt. It is a small treasure with an ancient soul, where history, culture, and art blend together with the classic Tuscan “live-well” philosophy. Explore the historic center to take in the details – the courtyards, the old buildings, the balustrades in wrought iron, the lamp fixtures…an overall charming atmosphere! The heart of the city is the Piazza Grande, a delightful square outlined with imposing public buildings and loggias. The small Piazza San Francesco is more intimate and charming with its outdoor cafes and lived-in feel. After lunch in a characteristic local restaurant, travel to Cortona. The city started as an Etruscan settlement, and its importance can be seen at the Etruscan Academy Museum housed in the lovely Palazzo CasaliPiazza Della Repubblica is still the seat of civic politics, as it has been since the Roman era. Admire Palazzo Comunale and Palazzo Dei Capitani and along with many other treasures. Late afternoon return to your hotel. Overnight in Chianti.

Day 04: Chianti → San Gimignano Private Guided Tour→ Florence | After breakfast at the hotel, meet your driver in the lobby. On route to your Hotel in Florence stop in San Gimignano to meet your Private Guide. San Gimignano is famous worldwide for its urban architecture dating from the XIII-XIV centuries. You will make your way through its tiny, unique streets where Medieval towers and Romanesque churches seem to emerge out of nowhere. The views and the artworks are a must as they testify to the unique character of this city which is both Sienese and Florentine. Founded at the junction between Via Francigena and ancient commercial routes, San Gimignano held a florid trade of saffron and wine with Italian and European markets. After lunch in a characteristic local restaurant, leave San Gimignano for Florence. Overnight in Florence.

Day 05: Florence Private Guided Tour | Breakfast at the Hotel. Meet your guide at the hotel lobby. This morning you will enjoy a 3 Hours Florence Private Walking Guided Tour. As you walk through the streets and piazzas of Florence, you’ll discuss the ideas of the Renaissance. In between the famous landmarks, you’ll take enchanting backstreets and alleys.  After enjoying a walk through the historical center follow your guide along the windy pathways to a stop in Piazza del Duomo. Continue to the Accademia Gallery, home to Florence’s most treasured work of art – “Michelangelo’s David”. You will explore Piazza Della Signoria and the famous Ponte Vecchio. In the late morning, return to your hotel. Lunch and afternoon at leisure. Overnight in Florence.

Day 06: Florence at leisure | Breakfast at the Hotel. Today spend the day at leisure. Overnight in Florence.

Day 07: Florence  → Pisa Private Guided Tour → Cinque Terre | Breakfast at the Hotel. Meet your driver at the Hotel Lobby to private transfer to your Cinque Terre Hotel. On route visit Pisa, undoubtedly among the richest cities in the world for architecture and history. Once in Pisa,  meet your Private Guide: the tour starts in the incredible Piazza Dei Miracoli: here you can admire the baptistery and the famous Leaning Tower, together with a guided visit to the majestic Cathedral. Lunch/Food & Wine Tour in a Wine Estate before continuing to your hotel. Overnight in Cinque Terre.

Day 08: Cinque Terre Private Guided Tour | Breakfast at the Hotel. Meet your Private Guide at the Hotel Lobby for a Private Tour of The Cinque Terre (5 Lands), featuring some of the Mediterranean’s most picturesque seaside villages. Today you will explore 3 of the 5 Borgos: You Tour starts in the old part of Monterosso, dominated by the walls of the ancient fortress, the remains of Fieschi Castle, and the Aurora Tower. Monterosso has brightly colored houses and narrow alleyways. Continue to Vernazza where you will enjoy the view from the Doria Castle. Lined with cozy cafes, craft shops, and wine bars, the seaside Piazzetta (Piazza Marconi) hides a little jewel of a chapel: the Chapel of Santa MartaAfter lunch in a characteristic local restaurant and a short boat tour ride, you will each Riomaggiore. Most of the village of Riomaggiore is squeezed into a narrow and steep valley, with tall colorful houses on either side of the main road and a small harbor below. Late afternoon return to your Hotel. Overnight in Cinque Terre.

Day 08: Portofino, San Fruttuoso, and Rapallo | After breakfast at the hotel, meet your driver and private guide in the lobby for a Private Tour of Portofino, San Fruttuoso, and Rapallo. The most popular resort towns on the Italian Riviera, little Portofino with just over 500 permanent residents.  Visit the Church of San Giorgio and take a stroll down to the lighthouse. A ferry trip to San Fruttuoso is included in the tour. This small fishing village located in a bay at the foot of Mount Portofino can be reached only by boat or on foot, following the trails in Portofino Park.  After lunch in a characteristic local restaurant, take a short Ferry to Rapallo. The waterfront is an elegant walk in the shade of palm trees; halfway along with boat berth with which the other places on the Gulf are reached. Late afternoon return to your Hotel. Overnight in Cinque Terre.

Day 09: Cinque at Leisure | Breakfast at the Hotel. Cinque Terre at Leisure. Overnight in Cinque Terre.

Day 10: Pisa or Milan Departure | After breakfast at the hotel enjoy a Private Transfer to Pisa or Milan Airport.

  • 3 Nights in Chianti:
  • 3 Nights in Florence:
  • 3 Nights in Cinque Terre:
  • Assistance and Porterage at Airports, Train Stations and Hotels
  • Private Transportation by Mercedes E or V Class with English Speaking Driver
  • Private Guided Tours with Professional Local Guides | Door to Door Service
  • Entrances to Museums, Galleries, Archeological Parks and other Venues
  • Breakfast at Hotels, All Food & Wine Tours/Enogastronomic and Most Lunches.
  • 24/7 Assistance and Support from our Ground Operational Office in Italy

Private Package Tours Rates

  • Gold: in 4* Boutique Hotels: Starting at 1,000 Euro per person/per day
  • Diamond: in 5* Luxury Hotels: Starting at 1,500 Euro per person/per day.

For Private Small Groups of 4, 6 and 8 + price per person will be lower.

For Custom Made Tours we work with any reasonable Budget