The Great Escape to Tuscany Tour

A 10 day trip to Italy 
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This is a land of gentle rises and fecund meadows, where grapes grow fat in the summer sun and Italian nobles retire to enjoy the countryside. It’s a place of fine art and delectable food, cosmopolitan cities and entrancing towns, timeless history and endless culture. It’s a region of untrammeled natural beauty and unbounded imagination, the home to some of the great minds and great landscapes in the world. This is Tuscany, and there’s nowhere else quite like it.

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General Information

Wine Barrels at Castello Monterinaldi. Photo Credit: Castello Monterinaldi
Sky View of Castello Monterinaldi. Photo Credit: Castello Monterinaldi
Electric Bike Tour. Photo Credit: E-Bikes Florence
Chianti vineyards at sunrise, Tuscany.
Statue of David by Michelangelo.
Inside the Colloseum, Rome.
Detailed Itinerary

Places Visited 

Florence, Lucca, Apuan Alps. Greve, Mutigliano, Bagni di Pisa, Milan

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

 Day 1: Making Your Way from Milan to Tuscany

You land today in the outskirts of marvelous Milan, the largest city in northern Italy and one of the fashion centers of the world, where a private driver will be waiting to escort you to the train station in time to board your first-class passage to Florence. Your first moments on the streets of this singular city will be sure to captivate and inspire, as you follow in the footsteps of some of the greatest artists in the history of the West, names like Leonardo and Brunelleschi, Giotto and Michelangelo. Wind your way along the River Arno and cross at the Ponte Vecchio, one of the city’s oldest bridges and home to a score of excellent jewelers. In the evening, enjoy a typical bistecca alla fiorentina at one of the city’s excellent trattorias.

Day 2: The Magnificent Villas of Tuscany

This morning is left to your own devices. You can enjoy a leisurely breakfast and a cappuccino while you watch the traffic pass in one of Florence’s many piazzas or set out on a shopping expedition for some of the city’s best wares, like fine leather goods and jewelry. After a delicious lunch, you’ll head out to the Tuscan countryside to take in some of the most majestic country villas in Italy. You’ll start by walking along the famed double lane of cypresses that leads to the entrance of the splendid Villa Torrigiani, decorated with classical statues and dramatic balustrades that recall the splendor of Tuscany’s past.

Continue on to Villa Reale, whose renowned garden features the unique and unforgettable Teatro di Verdura – literally, the “Greenery Theatre” but perhaps most eloquently translated as “A Curtain of Green.” This performance space has been designed into the hedges and topiary that fill the gardens. The tour concludes at the most iconic of Lucchese villas, the stunning Villa Mansi, which is now the site of an excellent museum.

Day 3: Hiking the Arresting Alps

Set out for the heart of nature as your guide takes you into the rugged countryside of central Italy and up into the Apuan Alps that dominate the horizon. Much of the marble that makes this region famous throughout the world is still quarried in these mountains, and the scenery remains truly inspiring in its scope and beauty. You’ll get a chance to take in some of Italy’s most beautiful wild flora and fauna before setting out on a leisurely hike through these majestic peaks, making a short ring between Stazzema and the Forte dei Marmi refuge. 

After lunch at a local trattoria, you’ll have the afternoon free to explore the rest of this enchanting region, reveling in the rolling hills and endless expanse of verdant fields that make Tuscany one of the most romantic areas in Europe.

Day 4: A Tour of Chianti, Italy’s Wine Capital

Today, discover the secrets of Italy’s best-known and best-loved wine region as you turn to the famed vineyards and wineries of Chianti. You’ll be taken to the ancient and alluring village of Radda, one of the main towns of the Chianti region, where you’ll be led on an extensive and informative tour of the Castello Monterinaldi, where locals have been making wine for centuries, dating back to the early Roman and Etruscan eras. Not only will this tour delight your taste buds, but you will also have a chance to learn how to make wine by participating in their Winemakers for a Day Tour.

Wander through the superb gardens and the marvelous terraces of the elegant estate before making your way into the center of the former fortifications. Here, you’ll get an in-depth look at the remarkable cellars – including some wines that have been bottled for more than 70 years – and the chance to taste some of the best offerings from Castello Monterinaldi. Enjoy sampling the estate’s wines, oils and vinegars while also indulging in the fine cured meats that come from nearby artisans. The rest of the day is at your leisure.

Day 5: Around Fantastic Florence

Return to the bustle and life of Florence to do a more in-depth exploration of this charming capital of Tuscany. After a morning train ride and a delicious and filling lunch, the afternoon features a tour of this world-famous “City of Flowers.” Wind your way along the River Arno to take in some of the remnants of the city’s Roman and medieval past before turning to the Piazza della Repubblica, the former Forum in days gone by. 

From the piazza, you can explore some of the great monuments of the Renaissance that fill the city. Make you way past the towering dome and the multicolored façade of the famous Santa Maria del Fiore, better known as the Duomo of Florence, whose soaring centerpiece was a marvel in the 15th century and remains a testament to the genius of the age. Walk past the house of Dante, the most famous poet in the Italian language, before taking in the offset tower of the Palazzo Vecchio and the bustling Piazza della Signoria, the political center of the city since the Middle Ages. The tour concludes at the incomparable Basilica of Santa Croce, the largest Franciscan church in the world and the final resting place for some of the luminaries of the Renaissance, from Machiavelli to Michelangelo. 

Day 6: Visiting the Very Best Tuscan Towns

Tour in unexpected fashion today as you cruise through the delightful towns of Lucca and Mutigliano and around the undulating hills of transfixing Tuscany. You’ll enjoy walking around the Piazza Anfiteatro, an exciting hub of Lucca, or simply strolling through the streets of nearby Mutigliano while enjoying the breathtaking weather and stunning scenery of this alluring area before visiting a local farmhouse for an intimate and enchanting wine tasting session, followed by lunch at a highly rated local restaurant.

The afternoon is dedicated to exploring the town of Lucca more fully, a medieval settlement that retains the charm of days gone by and the history of the years that have passed. You’ll certainly want to see the dramatic Piazza Napoleone, Berlinghieri’s triumphant “The Ascension,” a Byzantine mosaic that adorns the Basilica of San Frediano, and the incredible series of sculptures and inlays that fill the façade of San Michele in Foro, featuring interior artwork by Luca della Robbia and Filippino Lippi.

Day 7: A Day of Indulgence in the Heart of Italy

Today is dedicated to complete relaxation and reinvigoration as you make for the immaculate villa-cum-spa of Bagni di Pisa. Nestled serenely in the rolling ridges that ripple on the outskirts of Pisa, this phenomenal facility was built in the 18th century as a home to the Grand Duke of Tuscany and has since been meticulously restored and renovated to return it to the grandeur of its past, including breathtaking frescoes that can be found throughout.

The spa itself is pure bliss, utilizing the healing properties of the waters that flow through Tuscany and harnessing the relaxing power of the best local plants and herbs. You’ll bathe in the pristine waters that run from Mount San Giuliano and enjoy state-of-the-art services that will leave you feeling more invigorated that you have in years.

Day 8: Hitting the Streets of Italy’s Most Fashionable City

Today you leave the calm of Tuscany and turn to the excitement of Milan, northern Italy’s most important financial city and a center of the fashion world, home to such famed designers as Armani, Versace, Prada, and Dolce & Gabbana. This afternoon gives you the chance to experience the haute couture of the city in the way that it deserves, as you’ll make your way down the famous Via Montenapoleone, home to the flagship stores of some of the greatest fashion houses on the planet. Locals also swear by the Corso Buenos Aires, reported to be the longest shopping street in Europe and home to a wide array of boutiques, shops and cafes. In the evening, enjoy some of Milan’s fine cuisine at Savini in the famous Galleria or a freshly made cocktail at Rita after a long day of retail therapy.

Day 9: Saying Arrivederci

Today, a private driver will take you from your Milan hotel to the airport in plenty of time for you to board the flight that will take you back home. Your heart will be filled with memories of that past nine days, your suitcase will be bursting with the mementos from your travels, and your head will be swimming with plans for the next time that you return to inimitable Italy.


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.