Discover some of the most enchanting and historical places of Italy on this Smart Tour, which combines independent & small group touring. Visit Florence, Siena, San Gimignano, and other popular locations throughout Italy.


Discover some of the most enchanting and historical places of Italy on this Smart Tour, which combines independent & small group touring. Visit Florence, Siena, San Gimignano, and other popular locations throughout Italy.

Tour Highlights

  • Daily departures designed for parties from 2-6 passengers - perfect for family and friends traveling! (Can be priced for larger groups as needed)
  • The perfect combination of private & small group touring.
  • Visits to: Florence, Siena, San Gimignano, La Villeggiatura, Montepulciano, Pienza, and Cortona.
  • 24/7 Concierge, as well as 24/7 Celtic Help Line as needed.

Smart Tour Includes

  • Arrival & departure transfer.
  • Four (4) nights in Florence.
  • Two (2) nights in Val d'Orcia (Montepulciano) at an authentic Tuscan estate.
  • Breakfast daily (except day of arrival).
  • Welcome briefing.
  • Traditional Tuscan dinner in the Chianti countryside.
  • Siena & San Gimignano guided visit.
  • Guided visit of the heart of Florence, including Accademia & Michelangelo's David with skip the line reservation.
  • Cooking class in Tuscany with winery visit and farmer's market tour.
  • Full day driver/guide tour of Montepulciano and Pienza with wine tasting & lunch in Montepulciano.
  • Farewell dinner.

Hotel Options

  • Florence: Palazzo Castri or similar
  • Montepulciano (Val d' Orcia): Villa Armenia, Corte dei Papi, Tenuta Svetoni or similar

Additional Notes

City taxes at hotels are not included. Blackouts apply during special events, celebrations, Easter, Carnivals, and Fairs.

Blackouts apply during special events, celebrations, Easter, Carnivals, and Fairs.


Day 01, Friday: Florence

Independent arrival in Florence. In the afternoon, meet your tour guide at your hotel for a welcome briefing. Start your discovery of Florence with an orientation tour in the heart of town, passing along Ponte Vecchio and Piazza della Signoria. Overnight in Florence.

Day 02, Saturday: Magnificent Florence!

Explore Florence, from the unknown to the most picturesque sides of the city. Visit the market of San Lorenzo, where it is possible to see the food arriving from the Tuscan countryside. It’s a chance to taste lots of varieties of local cheeses, fruits, vegetable, and breads. If you're still hungry, there is free time for lunch on your own. In the afternoon, meet your guide in the hotel and get ready to explore the heart of the town. Lorenzo de Medici transformed Florence into the cradle of the Renaissance by attracting the best artists, architects, and writers of the time; Leonardo da Vinci, Michelangelo, and Botticelli, who he commissioned to produce various works of art and architecture. We will visit Piazza della Signoria, walk by the Palazzo Vecchio, the Duomo with Giotto's bell tower (from outside), and Ponte Vecchio. Our walk through Florence will end with a visit to the Accademia to experience the masterpiece of Michelangelo: the statue of David. Overnight in Florence. (B)

Day 03, Sunday: Siena & San Gimignano with Dinner

Today, visit two of the most beautiful towns in Tuscany: Siena and San Gimignano. Starting from Florence, you will arrive in Siena, passing along the beautiful hills of Chianti. In the ancient times, there was only one city in Tuscany that competed against Florence for power, wealth, and artistic beauties: Siena. Once in town, you will enjoy a guided walking tour to discover Piazza del Campo, stage of the famous Palio horse race, as well as explore quieter backstreets. You will learn everything about the 17 medieval city districts that compete against each other in the Palio, called Contrade. Your journey continues to San Gimignano, celebrated for its medieval skyscrapers, high walls, and narrow streets. After some free time in San Gimignano, gaze in awe at a marvelous sunset on the Tuscan hills and then enjoy a typical Tuscan dinner in the cellar of a fascinating noble Villa in the Chianti countryside. During your dinner you will also enjoy a wine tasting, pairing different wines with the various courses of your Tuscan meal. A Tuscan dessert is then served with local sweet wine. Coming back to Florence, you will stop at Piazzale Michelangelo belvedere, for a breathtaking view of Florence, admiring all the lights of the city. Overnight in Florence. (B,D)

Day 04, Monday: "La Villeggiatura” - a relaxing day in the countryside with cooking class

In the middle ages, the Medici family invented the word “villeggiatura” to celebrate the idea that one should take a rest from the crazy life of the city to respite in the rolling pastures and fortress-topped towns of Tuscany. The aristocrats and the rich merchants started to build their “villas” as well as agricultural farmhouses in the countryside around Florence and Siena for the pursuit of villeggiatura. Today, discover this ancient tradition and enjoy the fantastic experience of learning our Chef's secrets on Italian cooking in an intimate and friendly atmosphere immersed in the beauty of the Tuscan countryside. In the morning, take a little walk in the city center and visit Florence Farmers' Market and discover all its beautiful colors and authenticity, getting to know the butchers, bakers, and farmers where Florentines buy their ingredients from. Later, reach a fascinating villa in the Chianti countryside where you will learn about Tuscan food and prepare dishes under the attentive guidance of an expert Chef. The experience includes lunch, plus a wine tasting of three wines and a visit of a boutique winery in Chianti. Return to Florence late afternoon and overnight. (B,L)

Day 05, Tuesday: Montepulciano & Pienza

After breakfast, we make our way to Pienza, where you have free time to have a walk in the city center. Then onto Montepulciano and guided visit of the city. Montepulciano, just eleven kilometres away from Pienza, is a quintessential Tuscan medieval village, boasting a green landscape of rolling hills, castle walls and ramparts, thermal springs, and fine wine. The city, full of elegant renaissance palaces, ancient churches, charming squares, and hidden corners, boasts vast panoramas all over the wonderful Val d'Orcia and Val di Chiana valleys that surround it. The town is also famous world-wide for its Vino Nobile, an Italian product par excellence. Besides the wine and other excellences of this town related to food, such as pici pasta, pork, lentils, and so on, there are many things worth visiting here. You will have the chance to taste all these excellent things during your lunch enjoyed at a local Trattoria, paired with a wine tasting. At the end, continue to Cortona/Montepulciano area where you will arrive late afternoon. Overnight in Montepulciano. (B,L)

Day 06, Wednesday: Relaxing day in the countryside with a farmer's dinner

Our countryside estate is the perfect spot to relax and recover energy. Read a favorite book in the gorgeous garden, walk along the shady roads around the villa, enjoy a horst ride, or visit the town of Cortona (just 10 minutes away). Among the many activities available, we suggest a cooking class with the resident chef. The cuisine of Tuscany stands out for its simplicity and sobriety which combines well with the refinement and attention for high quality local products. Thanks to an experienced chef you will learn all the secrets of the traditional recipes. Tonight, enjoy a full dinner paired with Tuscan wines to say goodbye to Tuscany. Overnight in Montepulciano (B,D)

Day 07, Thursday: Cortona/Montepulciano - Touring ends

Private transfer provided today. Transfer can be arranged (at time of booking) to Florence Airport or Florence Rail station. Touring ends at transfer drop-off. (B)

Please note: documents are not available for Smart Tours until approximately three (3) weeks prior to departure. Documents may be provided electronically.

Rates & Hotels

New Touring Options for you!

To book this package, please contact one of our reservation agents at 1-800-833-4373.

Featured Hotels

Smart Touring - Absolute Tuscany - ST13
Florence Hotel Florence
Montepulciano Countryside Accommodations Tuscany

Tour Details

Your land package begins: / Your land package ends:

(As most International flights are overnight flights - please book air accordingly)

Flight Details

Accommodation Details


Centrally located Florence Hotel

Florence -

This tour uses excellent centrally located hotels in Florence. [more]

Tuscany -



This package is based on a minimum of two (2) persons traveling based on sharing one double room. This tour can be booked online or via our call center. A max of 6 passengers can be booked online. If you have more than 6 passengers, you must contact reservations in our call center.

This tour does not include:

  • Items not noted on the itinerary
  • City Tax to be paid locally


Airfare is additional. Once you select your date, you will be given the opportunity to search our system for the best available airfare from your home city. The dates shown will be the start / end date of your tour. However, you can alter these dates to arrive earlier or extend your stay as needed.

Our system will search for the best possible airfare during your booking process. Note: airfare cannot be booked sooner than eleven (11) months from date of departure.

Departures & Transfers

Tour dates are the date you would arrive in Italy. Please plan your air accordingly, as most flights overseas are overnight flights and you would depart the US one day earlier.