Great Tuscany & Cinque Terre

9 Days 8 Nights
[wte_itinerary_downloader]

  • First Class Hotels / Agriturismo
  • Rome (FCO)
  • Rome (FCO)
  • Arrival and departure as detailed in the itinerary
  • 17
  • Luxury Minibus
  • 1
  • 1
  • 4/12

Overview

This 9-day handcrafted tour invites you to uncover the true soul of Tuscany — from rolling vineyards and medieval hill towns to family-run kitchens and private tastings. With no more than 20 guests, every experience is personal, meaningful, and beautifully unrushed. Scheduled to depart on a Saturday and return on the following Sunday. Our tour begins in Rome and proceeds throughout the region of Tuscany, there is a visit to Cinque Terre, and the tour ends in the Roman Castles (a summer residence to the Pope). The day trips will have comfortable morning departures from one home-based location in the Chianti region to each of the other cities listed in the itinerary below. During this marvelous tour, you will enjoy ROME, “The eternal city”, FLORENCE, “The birthplace of the Renaissance” as well as many picturesque villages such as SIENA,  MONTALCINO, PIENZA, MONTEPULCIANO, SAN GIMIGNANO, LUCCA,  PISA, ORVIETO, CINQUE TERRE, and the ROMAN CASTLES.  

You will also enjoy hand-selected local restaurants with authentic regional dishes, some of the best wine tastings in the area, experience a fun cooking class, and of course some free time for shopping or enjoying the sights at leisure.  

Expect to be surprised by the many villages and enchanting landscapes of this area, that are always charming in their natural simplicity.

Highlights

  • 9 Day Tour – Rome, Florence, Montalcino, Siena, San Gimignano, Montepulciano, Lucca, Pienza, Orvieto, Cinque Terre and Roman Castles
  • Start in Rome (FCO) – End in Rome (FCO)
  • 17 Meals to include – 8 buffet breakfasts, 2 lunches, 7 dinners, 1 cooking class, 1 winery

Itinerary

  • Day
    01

    Welcome to Rome - Italy

    Upon arrival at Rome’s Fiumicino Leonardo Da Vinci Airport, meet our tour director and tour driver. Airport transfers from the airport will leave at 9:30 am, 12:30 pm, or 3:00 pm to your hotel. In the afternoon meet your travel companions before leaving for a comfortable sightseeing bus tour of Rome’s city center. Sights include views of the Colosseum, Roman Forum, St. Peter’s Square, the Circo Massimo, and Via Veneto. The tour will be followed by a special welcome dinner at one of Rome’s lively restaurants.  

    Hotel: Belstay Roma Aurelia, or similar (1 night)  

  • Day
    02

    Siena - Chianti area

    After breakfast, drive towards Tuscany, passing through the landscapes of gently rolling, vine-clad hills arriving in Siena. In Siena, take a tour with a local guide through the city center to admire the elaborately carved Gothic Cathedral, Town Hall, and the famous Piazza Del Campo, the site of the spectacular Medieval-style horse race. In the afternoon we’ll enjoy a short ride to our hotel in the Chianti area. Tonight, dinner will be served at a local restaurant/hotel.  

    Hotel: Villa San Lucchese Hotel, San Leonino or similar (6 nights)   

  • Day
    03

    Montalcino, Pienza, Montepulciano - Wine tasting

    Drive through beautiful southern Tuscany and enjoy some free time in Montalcino, Pienza, and Montepulciano. These villages are known worldwide for their high-quality red wine production, and the famous cheese “Pecorino di Pienza”. Later, enjoy a wine tasting and dinner at a family run vineyard. In the evening, return to our hotel.  

      

  • Day
    04

    Florence

    Today, go to Florence, the splendid capital of Tuscany and the birthplace of the Renaissance. Follow our local guide to see the marble-clad Cathedral and Baptistery where Ghiberti’s ‘Gates of Paradise’ have been recreated in all their glory. Next, go to the political heart of the city, Signoria Square, which remains an open-air gallery of Renaissance masterpieces to this day. The tour will end by seeing the Santa Croce church where the tombs of Galileo and Michelangelo are kept. In the afternoon there will be free time to enjoy Florence at leisure or learn the secrets of traditional Florentine leatherwork. Dinner will be served at one of Florence’s amazing restaurants.  

  • Day
    05

    San Gimignano - Cooking Class

    Experience a three-hour cooking class with a professional chef and learn how to make some of Tuscany’s traditional dishes. Lunch will consist of delicious food prepared by us during the cooking class. After lunch, drive to the most picturesque of Italy’s perfectly preserved medieval towns, the hilltop of San Gimignano. Visit the city center with some free time to enjoy the town at your own pace and do some shopping. 

  • Day
    06

    Lucca - Pisa

    In the morning, follow our local guide for a light walking tour of Lucca city center. Admire the 14th-century San Martino Cathedral and Piazza dell'Anfiteatro, built on the site of an ancient Roman arena. Then we make our way to Pisa to view the famous “Leaning Tower”. To top off this wonderful experience, we’ll enjoy lunch at an Osteria or dinner at an Agriturismo (farm to table) with Tuscany’s regional specialties.   

  • Day
    07

    Cinque Terre

    Travel to the coastal region of Liguria for a full-day excursion through the colorful villages of Cinque Terre which are built on rugged cliffs overlooking the sea.  See the terraced vineyards sustained by dry walling, an example of innovative engineering to respond to difficult terrain. Weather permitting, travel between the villages by boat to admire Cinque Terre’s sweeping coastal views (if rough seas prevail, a minibus will escort you through some of the villages). Tonight, dinner will be served in the hotel.  

  • Day
    08

    Orvieto - Roman Castles

    Leave the region of Tuscany to reach the gorgeous hilltop town of Orvieto. You’ll have time to enjoy this beautiful city at your own pace. In the afternoon, make our way towards our destination, the hilltops of the Castelli Romani (a group of villages where the Pope spends his summers). Here, enjoy a farewell dinner in the hotel’s restaurant to celebrate the success of your vacation .

    Hotel: Castel Vecchio, Benito al Bosco, or similar (1 night)  

  • Day
    09

    Leaving for Home

    Arrivederci Roma! Our airport transfers arrive to Rome’s Fiumicino Leonardo Da Vinci Int. Airport (FCO) at 7:00 am and 9:30 am.

Map

Experiences

  • Rome: comfortable sightseeing minibus tour of Rome city center
  • Siena: Walking tour *(WLG)
  • Florence: Walking tour *(WLG)
  • Tuscany: Cooking class of typical tuscan menu, lunch included
  • Tuscany: Wine tasting
  • Lucca: Walking tour *(WLG)
  • *(WLG) = With local guide and wireless headsets

Optional Experiences

  • Cinque Terre: boat cruise tickets

FAQs

What type of accommodations are included?

Guests stay in first-class hotels/Agriturismo, featuring:

  • Rome (1 night): Belstay Roma Aurelia or similar
  • Chianti Region (6 nights): Villa San Lucchese Hotel, San Leonino, or similar
  • Roman Castles (1 night): Castel Vecchio, Benito al Bosco, or similar

All hotels are carefully selected for comfort, local charm, and strategic access to regional highlights.

Are airport transfers included?

Yes. Arrival transfers from Rome Fiumicino Airport (FCO) run at 9:30 am, 12:30 pm, and 3:00 pm on Day 1.
Departure transfers to FCO run at 7:00 am and 9:30 am on Day 9.

What cities and regions are visited?

The tour covers iconic Tuscan, Umbrian, and Ligurian destinations, including:

Rome, Siena, Chianti, Montalcino, Pienza, Montepulciano, Florence, San Gimignano, Lucca, Pisa, Cinque Terre, Orvieto, and the Roman Castles (Castelli Romani).

What special experiences are included?

Guests will enjoy:

  • A sightseeing tour of Rome
  • A Tuscan cooking class with lunch
  • A wine tasting at a family-run vineyard
  • A full-day excursion to Cinque Terre
  • Multiple walking tours of historic towns

These curated activities offer authentic cultural immersion.

Is the Cinque Terre boat cruise guaranteed?

The boat cruise is weather permitting.
If sea conditions do not allow navigation, the visit will be conducted via minibus between selected villages.
Tickets for the boat cruise are an optional experience, payable on-site.

How much leisure time is provided?

Guests enjoy free time on several days for shopping, photography, or exploring independently—particularly in Florence, San Gimignano, Orvieto, and various Tuscan hill towns.

Can the itinerary change?

Minor adjustments may occur due to local events, weather conditions, or operational reasons. Any changes will maintain or enhance the overall quality of the experience.

Is this tour suitable for children?

While children are welcome, the itinerary is designed primarily for adults who appreciate history, culture, food, and a relaxed travel pace.