Best of Italy Custom Tour

Independent Tour, Customized to Your Dates

Cortona, Chianti Wine Region, Vatican, David, Grand Canal

13 Days / 12 Nights
Tour Language: English

Tour Features

Welcome to a taste of Italy. This trip is meant to whet your appetite – and satisfy your curiosity – for all things Italian! Landing in Venice, you will find yourself taking in the magical city in all its glory. Listen to the bells in San Marco square or watch the daily life of Venetians unfold on the Grand Canal. Travel by train to Florence, the Renaissance city and view the breathtaking artwork of the Uffizi or Michaelangelo’s amazing David. Florence is truly an exquisite walking town. Enjoy the earthy scents of porcini mushrooms and handmade leather while wandering the San Lorenzo market. The Duomo is an architectural masterpiece covered in three tones of marble. Your adventure into the Tuscan countryside begins with tours through Italy’s famous Chianti wine region. The family welcomes you with their warm hospitality when you arrive at the agritourism (family-run renovated farmhouse) where you’ll be staying. Your days will be spent discovering small towns rich in Italian history. A warm meal is on the menu – and you are the chef! Enjoy the robust flavors of Nonna’s recipes. Remember you eat what you cook! Last on our journey is Rome, the Eternal City. Take a journey down the Spanish Steps, marvel at the Trevi fountain and the Pantheon and take in the Piazza Navona. Take a journey back through time as you walk into the Coliseum, and be stunned by the seemingly endless array of priceless and wondrous art housed and protected in the Vatican.

2021 Tour Price

  • 3 Star Accommodation (Double Occupancy) & economy car:€3,699 per person
  • 4 Star Accommodation (Double Occupancy) & intermediate car: €4,119 per person

Current Exchange Rates

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


  • 3 Nights Lodging Central Venice
  • 2 Nights Lodging in Central Florence
  • 4 Nights Lodging at an Agritourism near Cortona
  • 3 Nights Lodging in Central Rome


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

What's Included

  • 12 Nights Lodging in Boutique Hotels & Agritourism
  • Daily Breakfast at all Accommodation
  • 5 Day Car Rental with Standard Transmission
  • Private Walking Tours of Venice, Florence including the Accademia & Rome
  • Wine Tastings
  • Authentic Italian Cooking Lessons
  • Private Transfers
  • 4 Hour Private Tour of the Vatican with Entrance
  • 35 Minute Private Gondola Ride in Venice
  • Self Guided Tours
  • General driving Instructions Including Maps
  • Includes All Taxes except local city taxes
  • Assistance from a Ciao Italian Representative

What's Not Included

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

Daily Itinerary

Day 1 - Arrival - Venice

Arrive at “Marco Polo” Airport– Venezia and transfer to Central Venice Hotel on own.

No Meals Included On Day 1

Day 2 - Venice
  • 3 Hour Private Guided Walking Tour of Venice
  • 35 Min. Private Gondola Ride
  • Piazza San Marco featuring two of the oldest cafes along with the majestic Ducale Palace and the Ponte dei Sospiri- the Bridge of Sighs
  • No cars, but a network of canals and bridges with people moving around by boat, gondola, or on foot
  • Rialto Bridge and market area and the Grand Canal

Meal Included: Buffet breakfast

Day 3 - Venice
  • Explore Venice at Leisure
  • Murano Island famous for hand crafted works of art made from glass
  • Numerous Bridges, squares (in Venice called Campi) and museums

Meal Included: Buffet breakfast

Day 4 - Florence (Firenze)
  • Transfer to Train Station on own, then 1st Class ES train to Florence – 3 hours
  • Transfer to Hotel on Own
  • 4-Hour Private Guided Walking Tour of Florence
  • 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) and the Arno River
  • Galleria dell’Accademia (featuring the infamous Statue of David)
  • San Lorenzo Market
  • Birthplace of the Renaissance or Rinascimento
  • Red roofed Buildings and marble facades

Meal Included: Buffet breakfast

Day 5 - Florence
  • Afternoon Reservations at the Uffizi Museum – no line ups!
  • The Uffizi houses one of the most important and oldest (16th c) art collections in the world, featuring the greatest masterpieces of Italian art and a good collection of paintings by those of foreign schools’ The 16thc Palace by Vasari, and also exhibits ancient Roman and 16thc sculptures.

Meal Included: Buffet breakfast

Day 6 - Chianti Region and Cortona in Tuscany
  • Pick up 5 Day Car Rental with Standard Transmission in downtown Florence and tour Italy’s Chianti region at Leisure
  • Arrive at Agritourism near Cortona
  • Quaint Towns featuring rolling countryside dotted with vineyards and olive groves
  • Chianti Classico Region
  • Historical Italian Castles, Renaissance Villas, Romanesque Churches
  • Enjoy the small towns of Greve, Panzano, Castellina and Radda

Meal Included: Buffet breakfast

Day 7 - Cortona
  • Enjoy the day exploring Cortona
  • Afternoon Cooking Lesson at the Villa – 4:30pm (Wine Included!)
  • Backdrop for the movie “Under the Tuscan Sun”
  • Quaint Historical Center with breathtaking views of the countryside

Meal Included: Buffet breakfast

Day 8 - Montepulciano
  • Wine & Olive Oil tasting & 2-Hour Private Tour in Montepulciano
  • Tour Pienza at Leisure
  • Montepulciano: Piazza Grande, Renaissance Duomo ,Vino Nobile D.O.C.G. Wine with Sangiovese and Canaiolo grapes, 14th c Palazzo Comunale in Florentine style
  • Pienza: Corso Rossellino, Pecorino – sheep cheese, Ancient home of Enea Silvio Piccolomini, Pope Pius II

Meal Included: Buffet breakfast

Day 9 - Assisi & Perugia
  • Explore the Historical Centers of Assisi & Perugia at Leisure
  • Basilica of St. Francis of Assisi (San Francesco)- The patron Saint of animals and ecology
  • Romanesque Cathedral of Saint Rufino home to the Baptismal Font where Francis and his disciples were baptized
  • Basilica di Santa Chiara- houses the Byzantine Crucifix that revealed St. Francis’ life mission
  • Galleria Nazionale dell’Umbria Museum in Perugia
  • Corso Vannucci, a great Italian “people-watching” street
  • Piazza IV Novembre is considered the heart of this sophisticated town dominated by a beautiful fountain- Fontana Maggiore, a 13th century masterpiece

Meal Included: Buffet breakfast

Day 10 - Orvieto & Rome
  • Explore the Historical Center of Orvieto and then proceed to Rome Airport to return rental vehicle
  • Transfer to downtown hotel on own
  • Original Medieval City that developed Guilds and Trades
  • The ancient Etruscan remains of the Temple of Belvedere
  • Clock of Maurizio, the first automation of its kind to regulate working hours
  • Orvieto Underground guided tours

Meal Included: Buffet breakfast

Day 11 - Rome (Roma)
  • 4 Hour Private Guided Walking Tour of Ancient Rome
  • Coliseum and Forum, Piazza Navona, Pantheon
  • See the Tiber river and Castel Sant’Angelo
  • Suggested visit to Villa Borghese Museum and Park

Meal Included: Buffet breakfast

Day 12 - Rome
  • Private Transfer to the Vatican – 7:30am
  • 4-Hour Private Tour of the Vatican – 8am (Including entrance) – no line ups!
  • St. Peter’s Basilica, The Vatican Museum and the Sistine Chapel
  • Large collection of art and treasures collected through it’s 2,000 years of history
  • Large collection of paintings by the best of the Italian masters from the Renaissance

Meal Included: Buffet breakfast

Day 13 - Rome

Private transfer to Rome Airport & conclusion of tour.

Meal Included: Buffet breakfast

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