Italian Jewels: Rome, Florence, Tuscany & Venice Tour

The main canal in Venice, Italy.
A 10 day trip to Italy 
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The rolling meadows of the Tuscan countryside and the famed Seven Hills of Rome. The soaring dome of the Duomo in Florence and the floating marvel of San Giorgio Maggiore in Venice. With the bucolic countryside and the bustling cityscape, the allures of fine food and the inspiration of fine art, this is the tour that will show you it all, offering an unmatched glimpse into the incomparable jewels of Italy.

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General Information

A Tuscan villa near Pienza, Italy.
Statue of David by Michelangelo.
Detailed Itinerary

Places Visited 

Rome, Vatican City, Pienza, Montalcino, Chianti, Greve, Castellina, Florence, Venice

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Touching Down in the Eternal City

Today you land in regal Rome, the center of the Western world for centuries, and the heart of one of the most important civilizations in history. A private car will take you from the airport to the superlative Majestic Hotel, situated in the heart of bustling Rome on the famed Via Veneto and featuring accommodations that have been earning it praise from movie stars and royalty since the 1920s. Your room features luxurious Egyptian cotton sheets, a stunning marble bathroom and a dazzling view over the Via Veneto or the hotel’s beautiful gardens. The hotel’s restaurants are truly divine: La Ninfa serves up quick bites, delectable cocktails and live music on Thursdays, Fridays and Saturdays, while Filippo La Mantia showcases traditional Sicilian fare with a unique twist for lunch, dinner, and a truly sensational Sunday brunch. 

Spend your afternoon exploring the incredible edifices and moving monuments mere steps from your hotel, like the romantic Spanish Steps and the spectacular Trevi Fountain. Or you can check out the best in Roman fashion and haute couture at the nearby Via Condotti, the home to the world’s most famous fashion houses. It is also where you'll find Caffe Greco, arguably the most famous café in the city, where literary lights like Stendhal, Goethe, Byron and Keats all stopped to enjoy a cup of coffee.

Day 2: The Very Best of the Roman Empire

Tour the crowning monuments to the eternal glory of Rome as you walk through the august grounds of the renowned Roman Forum, the center of Roman life from the times of the kingdom to the heyday of the Empire. It is littered with millennia-old testaments to the city’s greatest victories and most legendary figures. Your small group guided tour will teach you all about the history of ancient Rome, from its legendary founding on Palatine Hill to Caesar’s imperial ambitions to the conquests of Marcus Aurelius and Septimus Severus, all while taking in the remains of the buildings where world history was made. 

You’ll gaze upon the remains of the pagan temples of old, the House of the Vestals, and the Temple of Castor and Pollux. You’ll marvel at the triumphal arches of Septimus Severus and Constantine, proudly proclaiming the greatness of the Roman legions, and you’ll walk inside the iconic Flavian Amphitheatre, the imposing and magnificent structures better known as the Roman Colosseum. Your tour of this architectural wonder will take you inside the famous arches to cast your eye upon the engineering works that were required of this grand stage, the home to gladiatorial games and mock naval battles. 

Day 3: Touring the Seat of Saint Peter

Today, you cross the border between Italy and the world’s smallest sovereign nation as you enter the domain of the Holy See, the center of Catholicism, and one of the most important sites in all of Christendom. Not only is Vatican City an important religious pilgrimage site, attracting millions of visitors a year who yearn to glimpse the Pope, it is also home to one of the greatest art collections in the world. The morning is dedicated to exploring this incredible collection, from Raphael’s masterpiece The School of Athens and Leonardo’s St. Jerome in the Wilderness to modern works from artists like Gauguin, van Gogh, Dali and Rodin. The last gallery is the most spectacular, as you end your small group tour of the museums under the brightly painted ceiling of the Sistine Chapel. Crane your neck to catch a glimpse of Michelangelo’s captivating ceiling capturing scenes from the Book of Genesis, and you’ll be awed by the massive fresco of the Last Judgment that dominates the back wall.

The afternoon can be spent walking through the venerable halls of St. Peter’s Basilica, one of the largest church buildings in the world and perhaps the crowning work of the Italian Renaissance, with works and input from all of the great masters. Ogle at the opulence of Bernini’s baldacchino and marvel at the statues that crown Moderno’s façade before taking in the massive dome that dominates the cityscape, designed by Michelangelo after it had earlier been deemed impossible. There is great artwork in St. Peter’s as well, from the stunning altarpieces to Michelangelo’s incomparable Pieta.

Day 4: The Rolling Hills and Charming Towns of Tuscany

This morning you will leave the busy environs of Rome and turn to the tranquil and picturesque countryside of the Val D’Orcia region of Tuscany for a full-day private tour with your charismatic Italian guide. The region is renowned for its natural splendor and its inestimable impact on Renaissance art and culture. A UNESCO World Heritage Site since 2004, the Val D’Orcia is home to rolling verdant hills broken every so often by the occasional gully. It is the scene of some of the most famous paintings and landscape photographs in Italy, and it is where you’ll find the fascinating town of Pienza, a true landmark in the history of humanism. Here, you can enjoy a truly rustic lunch experience as you sample cheeses at Cugusi Cheese Farm, a two-year award winner for the best Pecorino produced in Italy. Here, you can have a basket of cheese and bread paired with a good bottle of wine, for an amazing picnic in one of the most scenic farms in Siena. 

This evening sees you at the Villa Cicolina, a renovated manor house of an Italian noble family that has since become known for its unbeatable location and its marvelous amenities. A full complimentary Tuscan breakfast will start your day off right, the soothing wood tones and comfortable bed will end it on a high note, and the villa is just minutes from the village of Montepulciano, one of the highlights of Italy’s wine country. Whatever you hope to find in Tuscany, you’ll find the Villa Cicolina simply unsurpassed.

Day 5: Experiencing the Finest of Italy’s Renowned Cuisine

After a leisurely morning spent enjoying a delicious breakfast and a leisurely stroll through the grounds near Villa Cicolina, turn to the nearby town of Montalcino, a settlement that has stood for millennia and best-known for its famed Brunello di Montalcino, one of the most expensive and best-regarded Italian wines. You can explore the fascinating buildings of this ancient city, from the stolid walls and imposing towers of the 13th-century fortress to the graceful curves and gorgeous roof of the Abbey of Sant’Antimo before enjoying a traditional Tuscan meal at Castello Banfi, featuring five fantastic courses perfectly paired with wines from the nearby estate.

After this epicurean delight, you’ll arrive at a local winery to taste the offerings of these lush yet powerful wines, known throughout the world as the very best that Italy has to offer. You can also sample the olive oil pressed from olives grown on the estate, and aged balsamic vinegar that offers a sweet taste with a subtle zing. The evening sees you back at Villa Cicolina.

Day 6: Italy’s Wine Country and the Center of the Renaissance

Set out with your private guide to explore the vineyards and wineries that dot Italy’s wine region, sampling some of the best chiantis in the world and learning all about the long and distinguished history of Italian viticulture. You’ll visit the impressive facilities at the Badia a Passignano winery, where you have a taste of the wines of some of their lesser-known varietals, before turning to the town of Montefioralle, a remarkably preserved Medieval village that was the birthplace of the renowned explorer Amerigo Vespuci.

Then, stop by the quaint town of Greve, whose central piazza is framed by a number of Medieval-era buildings, like the 11th century Chiesa Santa Croce, and whose culinary offerings are truly not to be missed. Stop by the Falorni Butcher shop to check out the varieties of ham hanging from the ceiling, drop in at a local cheese maker to see pecorino aging to perfection, and spend the afternoon at a local winery where you’ll get a fascinating look at how to make wine, vinegar, olive oil and Vino Santo (an Italian dessert wine). 

The day ends on the banks of the River Arno in the heart of the beautiful city of Florence. Your home while in this magnificent metropolis is the four-star Hotel Brunelleschi, located mere steps from the vaunted doors of the Accademia and filled with the luxuries and amenities that you’ve come to expect, a sea of tranquility nestled amongst the bustle of central Florence.

Day 7: Highlights in the Queen City of Tuscany

Discover the many miracles and hidden gems of fantastic Florence as you’re led on a guided tour that will show you all of the high points and let you in on the secrets that only the locals know. You’ll make your way by the prison-turned-art museum at the Bargello and marvel at Brunelleschi’s towering dome and Giotto’s brightly colored bell tower that highlight the unforgettable Santa Maria del Fiore, better known as the Duomo di Firenze. You’ll take in the off-center tower, the fearsome battlements and the replicas of great works of art that fill the courtyard of the Palazzo Vecchio. Walk by the house of Italy’s greatest poet, Dante Alighieri, and cross over the Arno on the Ponte Vecchio, home to some of the best jewelers in the city.

The afternoon is spent perusing the incredible collection at the Accademia of Florence, the city’s main art academy that is now home to one of the best collections of Michelangelo’s sculptures in the world. Feast your eyes on the works of other Renaissance masters, like Giambologna’s original plaster copy of The Taking of the Sabine Women, before entering the main exhibit hall to gaze in awe and reverence at the inspiring and unforgettable David of Michelangelo. This towering statue is breathtaking no matter how many reproductions you might have seen, and it is flanked by Michelangelo’s famous Slaves sculptures meant for the tomb of the pope but went unfinished at the time of the artist’s death. 

Day 8: High Culture and High Fashion

This morning, engage in a little retail therapy as you search out the best shopping in Florence, from high fashion to home wares, from jewelry to gelato. The San Lorenzo Markets offer a bustling and vivid look into the average shopping day for a Florentine, while the Via Tornabouni and the Via Strozzi are the home to the best-known fashion boutiques like Hermes and Prada. Leather goods can be found on the Via dei Calzaioli, and the Ponte Vecchio is perhaps the best place to find excellent jewelry at prices that are more reasonable than you might expect. 

The afternoon is spent with your guide on a small group tour at the unmatched Uffizi Gallery, one of the very best art museums in Europe and the home to perhaps the finest collection of Italian Renaissance art in the world. You’ll get the chance to take in Botticelli’s Primavera and The Birth of Venus, Titian’s Venus of Urbino and Leonardo’s phenomenal Annunciation. The evening is spent in the kitchen, as you learn how to make the classic dishes of Tuscany in a fully-equipped kitchen with the help of a professional chef. You’ll then savor the dinner you created with other like-minded gourmets in a jovial atmosphere, complete with a glass of wine.

Day 9: Exploring Saint Mark’s City

Turn east, to the shores of the Adriatic and the famous waterways of breathtaking Venice, the Queen of the Canals, and one of the most romantic cities on the planet. You’ll be taken by private water taxi to the fabulous Hotel Londra Palace, a gorgeous and elegant hotel that fronts the Venetian lagoon and offers awe-inspiring views of the city’s local landmarks like St. Mark’s Cathedral and the Doge’s Palace. After dropping off your bags in your large and luxuriously appointed room, you’ll be set to stroll this one-of-a-kind city, filled with sights, sounds and experiences that are unlike anywhere else on Earth. 

You’ll never forget the graceful curves and striking colors of St. Mark’s Cathedral dominating Venice’s central piazza, the sound of surf rippling gently through the long lines of gondolas tied to the docks, or the taste of freshly prepared Venetian seafood. The evening concludes with a private gondola ride through the city, getting a truly unique glimpse at this marvelous and mesmerizing metropolis.

Day 10: Visiting Venice’s Famous Lagoon and Romantic Canals

Take another day to explore the culture and traditions of the most serene city of Venice. Stroll through the streets of shops offering everything from leather goods to glassware, check out the wares of the merchants that line the Rialto Bridge, and stop by the famous Harry’s Bar at the Piazza San Marco before crossing the lagoon to visit some of the islands of Venice. 

There are more than one hundred islands that fringe and fill the Venetian lagoon, and your afternoon is dedicated to exploring the best of them. You’ll turn north to visit the glass blowers and master artisans of Murano before taking in the multicolored homes and intricate lacework at Burano. A stop at historic Torcello – the oldest continuously inhabited region in Venice – concludes an unforgettable island-hopping tour, as your final evening in Italy is spent on the Venetian mainland.

Day 11: Ciao, Italia!

This morning, a private driver will escort you from your hotel and take you to the airport in time for you to board the plane that will take you back home. Your heart is sure to be filled with memories of this amazing vacation, your head filled with the stories that you’ve heard and lessons that you’ve learned, and your bags filled with souvenirs from one of the greatest countries on the globe.


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.