Discovering the Ancient Towns of Tuscany Custom Tour

Independent Tour, Customized to Your Dates

San Gimignano, Lucca, Siena, Greve, Monterosso Al Mare

12 Days / 11 Nights
Tour Language: English

Tour Features

This tour is one of our most requested. It combines the Renaissance towns of Siena and Florence with the country flavors of Tuscany and the opportunity to stroll along the fabulous Cinque Terre. Immerse yourself in a cooking lesson with a real Italian “Mamma” as she teaches you the art of Italian cuisine. Marvel at the city of San Gimingnano silhouetted against the horizon. Wander through the ancient city of Volterra, enjoying the fortress, walls and gates standing mightily over green Tuscan valleys. Travel through the scenic hills of Italy’s Chianti region, discovering the citadels and fortifications of this ancient area. Here wine was once a staple for both rich and poor alike. Mull over the fine wines of Montepulciano and taste the history of ancient Tuscany. Hiking the paths that link the five villages of coastal Liguria is a delight for both mountain and sea lovers. Each village has its unique own personality and each trail has views and scenery that keeps hikers guessing at what is around the next corner.

2021 Tour Price

  • 3 Star Accommodation (Double Occupancy) & economy car with Standard Transmission:€2,585 per person
  • 4 Star Accommodation (Double Occupancy) & intermediate car with standard transmission: €2,799 per person

Current Exchange Rates

Ciao Tours will guarantee the exchange rate at the time of full payment or 45 days prior to departure.


  • 2 Nights Lodging in Central Florence
  • 4 Nights Lodging in an Agritourism near San Gimignano
  • 2 Nights in Central Lucca
  • 3 Nights in Monterosso al Mare, Cinque Terre


  • Customize any option for just $50 (per person, per change)

What's Included

  • 11 Nights Authentic Italian Lodging  including Daily Breakfast
  • 7 Day Car Rental with Standard Transmission
  • 4 Hour Private Walking Tour of Florence
  • 3 Hour Private Walking Tour of Siena
  • Private Wine Tasting, Tour & Lunch at a the Boutique Winery in the Chianti
  • Reservation at the Uffizi Museum
  • 5 Hour Authentic Italian Cooking Lesson with Wine
  • Wine/Olive Oil Tasting and Light Lunch in Siena with Ciao Tours
  • 1st Class Train from Pisa to Monterosso and Return
  • Self-Guided Tours
  • General Driving Instructions Including Maps
  • All Taxes except local city tax
  • Assistance from Ciao Tours’ Italian Representatives

What's Not Included

Air flights, travel insurance, tips, and anything not specifically mentioned in “What’s Included”.

Daily Itinerary

Day 1 - Arrival - Florence

Private transfer to Central Florence hotel and dinner at unique Italian restaurant.

Meal Included: Dinner

Day 2 - Florence
  • Enjoy the Architecture of this Renaissance city on foot
  • 3 Hour Private Walking Tour of Historical Florence
  • Reservations at the Galleria degli Uffizi Museum
  • San Lorenzo market, in piazza San Lorenzo
  • Duomo or Basilica di Santa Maria del Fiore and The Cupola (dome) of the Basilica (cathedral), by Brunelleschi
  • Palazzo Vecchio (Town Hall) and Ponte Vecchio (Old Bridge)
  • Reservations at Galleria dell’Accademia (featuring the infamous Statue of David)

Meal Included: Buffet breakfast

Day 3 - San Gimignano
  • 7 Day Car Rental (Pick up Central Florence and Drop off Pisa Airport)
  • Explore the Chianti Wine Region before proceeding to the agritoursim outside
  • San Gimignano
  • Wine Tasting, Tour & Lunch at the Historical Verrazzano Castle
  • Chianti Classico Region
  • Historical Italian Castles, Renaissance Villas, Romanesque Churches
  • Towns of Chianti: Greve, Panzano, Castellina & Radda

Meal Included: Buffet breakfast

Day 4 - Volterra and San Gimignano
  • 5 Hour Authentic Italian Cooking Lesson Including Wine Tasting
  • Volterra – Palazzo dei Priori, Town Hall, Piazza San Giovanni
  • San Gimignano – Palazzo del Popolo, Torre Grossa, Piazza del Duomo with the Romanesque Collegiata, Basilica of Santa Maria Assunta

Meal Included: Buffet breakfast

Day 5 - Siena
  • Wine & Olive Oil Pairing & Lunch with Ciao Tours
  • 3 Hour Private Walking Tour of Siena
  • Home of the Palio Horse Race
  • Piazza del Campo, Piazza del Duomo and the Basilica
  • Museum of Santa Maria della Scala
  • Palazzo Comunale

Meal Included: Buffet breakfast

Day 6 - Tuscan Countryside
  • Exploring Abbazia di Monte Oliveto Maggiore, Pienza & Montepulciano
  • Monks of Abbazia di Monte Oliveto Maggiore
  • Pienza (Corso Rossellino, Pecorino – sheep cheese, Ancient home of Enea Silvio Piccolomini, Pope Pius II)
  • Montepulciano (Piazza Grande, Renaissance Duomo ,Vino Nobile D.O.C.G. Wine with Sangiovese  and Canaiolo grapes, 14th c Palazzo Comunale in Florentine style)

Meal Included: Buffet breakfast

Day 7 - Lucca
  • Exploring Lucca, Bike Rental
  • City of Bikes – travel 4 kms on top of Ancient Walls surrounding Lucca
  • Cathedral of San Martino
  • Tomb of Ilaria del Carretto
  • Home to the Puccini Opera Festival

Meal Included: Buffet breakfast

Day 8 - Tuscan Mountain Towns
  • Exploring Barga & Garfagnana
  • Garfagnana (“Ponte della Maddalena” or the Devil’s Bridge on the Serchio River because of an ancient tale)
  • Barga (Longobardic Castle, Romanesque Duomo)
  • San Romano (9th centurty B.C., charming village, Fortezza delle Verrucole)

Meal Included: Buffet breakfast

Day 9 - Monterosso
  • Explore Pisa, Return Car Rental and proceed to Cinque Terre
  • Leaning Tower of Pisa- La Torre Pendente and the Battistero
  • Campo dei Miracoli- Square of Miracles
  • Church of Santa Maria della Spina
  • Piazza Cavalieri and Palazzo dei Cavalieri
  • Palazzo dell’Orologio
  • 1st Class Train to Monterosso

Meal Included: Buffet breakfast

Day 10 - Monterosso
  • Explore the 5 Ancient Fishing Villages – Total distance approx. 5 hours
  • Monterosso al Mare, Vernazza, Corniglia, Manarola, Riomaggore
  • Breathtaking vistas of the sea
  • Cliffside walking trails connected by ancient stairs surrounded by olive groves, grapes and flowers connecting the “five lands”
  • Via dell’Amore – Walk of Love

Meal Included: Buffet breakfast

Day 11 - Monterosso
  • Explore the 5 Ancient Fishing Villages – Total distance approx. 5 hours
  • Continue to explore the hiking trails connecting the five towns
  • Suggested Visit to Porto Venere (Venus’ Port) by local bus or take a train to the seaside gem the city of Santa Margherita to the north

Meal Included: Buffet breakfast

Day 12 - ``Galileo Galilei” Airport – Pisa (PSA)

1st Class Italian Train Ticket & conclusion of tour.

Meal Included: Buffet breakfast

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