You touch down on the outskirts of the Eternal City, excited to begin your excursion into the history and culture of this incomparable metropolis. The rest of the morning is a leisurely exercise in acclimatization: perhaps take a shower, then grab an espresso at one of Rome’s many excellent cafes before setting off for a guided tour of the best sites of one of the most famous cities on the planet. You begin at the Piazza del Popolo, the city’s northern edge that first greeted newcomers to the city, the bells of the Santa Maria del Popolo ringing brightly through the Roman air. Then make your way to the graceful expanse of the Spanish Steps, the widest staircase on the continent. From here, meander through Rome’s labyrinthine streets and walkways until you reach the spectacular Trevi Fountain, whose peerless opulence and indescribable grandeur will steal your breath from you. Explore some of the masterpieces of classical Rome as you gaze upon the column constructed by Marcus Aurelius that marks the city’s center, and enter the Pantheon, still a feat of engineering more than two millennia after it was completed. The tour ends with a look at Bernini’s Fontana dei Quattro Fiumi in Piazza Navona and a venture into the rambunctious and charming Campo de’Fiori, one of Rome’s best city squares.

Set out for a trip deep into the past, back to the days of Cato and Caesar, of venerable senators, emperors and generals both brilliant and ruthless: the mysteries of ancient Rome never fail to inspire and amaze. Gaze upon the Colosseum and the ruins of ancient Rome from the summit of Colle Oppio before returning to street level and the incomparable Colosseum, arguably Italy’s most recognizable image and a testament to Rome’s former power. Here, you’ll meet an informative and engaging guide who will regale you with stories about this amazing arena. Stop for a minute beneath the Triumphal Arch of Constantine before continuing on to the Palatine Hill, the centermost of the legendary Seven Hills of Rome, where you can gaze upon the Roman Forum down off one slope and the Circus Maximus on the other. End your incredible tour of Rome with a walk down the Via Sacra, the traditional route of triumphant marches and the main street of the ancient city. This is where conquering soldiers were praised after victories and where businessman, gamblers and thieves plied their trades between them.

Outside of Jerusalem and Bethlehem, there are few cities that command the attention of Christendom, quite like Vatican City, where the Bishop of Rome directs the affairs of the Christian Church… and where some of the greatest art in human history can be found. You start your day taking in the exhibits of the Vatican Museum, stretching for more than nine miles and housing tens of thousands of priceless masterpieces. From the renowned Prima Porta Augustus statue to Raphael’s breathtaking fresco The School of Athens, one of a number of frescoes the genius and his studio completed for the Pope. You’ll marvel at the fantastic Gallery of Maps and ogle at the great compositions of Fra Angelico and Titian and Leonardo and Caravaggio before your cultural trek is rewarded in high style at the revered Sistine Chapel, where the pope is chosen beneath the iconic ceiling of Michelangelo. You’ll feel the power of centuries of tradition and the endless brilliance of this true Renaissance man, from the Creation of Adam high above your head to the dominating fresco of the Last Judgment filling the wall behind the altar. More majesty awaits as you leave the Vatican Museums for a tour through St. Peter’s Basilica, one of the most famous churches in the Western world and one of the largest religious buildings on Earth. You find yourself moved by the passionate and the delicate grief of Mary in Michelangelo’s seminal Pietá, before witnessing the opulent splendor of the main nave of St. Peter’s. On the ancient bronze statue of the saint, his right toes are worn down by millions of pilgrims who, over the centuries, have visited the church and traditionally have touched the foot. The day ends in fascinating Saint Peter’s Square, where an expert will show you all of Bernini’s hidden tricks.

You leave the fabled streets of Rome and head to the heart of the Italian countryside, into the scenic hills and gorgeous villas of Tuscany. Your first stop is in the medieval town of Montepulciano, renowned the world over for its Old World charm, its fascinating architecture and its decadent and sumptuous wines. Here you will get the chance to hear Gregorian chants in the church of Sant’Antimo, an experience that is sure to transport you to a place you’ve never known before. Make your way through the picturesque vistas that fill the Val d’Orcia and meander along the winding lanes and alleys and past the ancient structures of Montalcino before finally arriving in Siena, one of Italy’s most beautiful villages and the home of the famous Palio, a twice-annual horse race that features some of the most exciting ninety seconds you’ll ever see. Discover the charm of Siena’s Campo, one of the most beautiful squares in Italy, before enjoying a delicious and traditional Tuscan meal at a neighborhood trattoria.

This morning is dedicated to a languid and leisurely excursion through the streets of Siena, where you’ll learn more about this famous Italian town by a local guide. Discover the stories of the city’s rival contradas and hear about past Palios and horse riding legends. Then, board the train that will take you to the bucolic town of Cortona, where you’ll encounter the lives of true Italians as you spend your evening at a farm, a charming spot for a nature-based vacation nestled deep in the Tuscan hills and deep in Italian culture. You’ll enjoy the one-of-a-kind hospitality of the Russo family and enjoy your immaculate surroundings as you settle down to an evening and night of true Tuscan revelry, a bottle of wine in front of you and your best friends all around you, swapping stories from the past and making new ones for the future.

Relax and enjoy the simple flow of life in this beautiful region of Italy, sampling the fine fare and drink and discovering the hidden gems of an oft-overlooked part of this magical nation. You can stop by Cortona to see the Diocesan Museum’s inspiring collection of works by Fra Angelico or visit one of the two sterling examples of Renaissance architecture in the city: the Santa Maria delle Grazie al Calcinaio is famous for its miraculous Blessed Virgin Mary image, and the Santa Maria Nuova by Giorgio Vasari is an excellent example of the principles of centralized Renaissance design. Epicureans, however, might want to simply stay on the farm and take in the lessons of Roberto Russo, the owner of the estate, who will show you the techniques behind producing organic olive oil and fine Tuscan wine.

You arrive to the bustling capital of Florence, but not before visiting the smaller towns of the surrounding area first: tour the stunning castle at Monteriggioni, fortified by Siena in their Renaissance-era struggles against neighboring Florence, and the charming squares of this fascinating town before turning to the tower-laden streets of San Gimignano. You will find a historic city center that has been inscribed on the UNESCO World Heritage list since 1990. Lunch will be a traditional Tuscan affair in an intimate trattoria in the heart of San Gimignano, where the city’s iconic skyline provides the perfect backdrop for a delicious meal. The afternoon sees you pulling into the Florence train station, the center of the Italian Renaissance and home to some of the greatest artists, thinkers, politicians and poets in Italian history. Check into your centrally located and elegant hotel before hitting the streets of this charming city: walk along the winding banks of the Arno to get a good sense of the Florentine scene, and be sure to stop by the well-known Ponte Vecchio, where some of the best jewelers in the city ply their trade.

Florence has lost little of the luster it gained during the 15th century and the rapid rise of the Medici family, and its vibrant streets and bustling businesses still make it one of the best destinations in Europe. Wander through the stalls that surround the Piazza della Signoria and climb Giotto’s famous bell tower to gain an incomparable look at Santa Maria della Fiore, the famous Duomo of Florence, a marvel of Renaissance engineering and an enduring symbol of the city’s artistic legacy. Discover the incredible works of art on display at Florence’s Accademia, the former school of art that produced a number of geniuses and lesser lights, and that now houses the sublime David of Michelangelo, one of the best-known and greatest sculptures in the history of the West. You might also want to visit some of the city’s fine leather salesman and antique dealers before enjoying more hearty and comforting Florentine food, highlighted by a bold wine from the surrounding hills and fields.

Your last full day in Italy is spent enjoying the immaculate oeuvre at the Uffizi, Florence’s premier art gallery and one of the finest of its kind on Earth. Housing arguably the greatest collection of Renaissance art in the world, this captivating museum is also home to a number of artifacts detailing the history of the ancient Etruscans and the culture and society of ancient Rome. You will find tombstones and jewelry here existing alongside some of the famous art in the world. Two of Botticelli’s finest efforts – Primavera and The Birth of Venus – are on display, as well as Titian’s Venus of Urbino, Caravaggio’s Medusa and The Annunciation by Leonardo da Vinci, one of the finest examples of its type known to man. There’s also an excellent sculpture collection, featuring masterpieces from the ancient world like the Arrotino and Two Wrestlers. Your final evening is spent soaking up the pleasure of this rich and vibrant country, recalling your past week in fond detail while you enjoy one last true great Italian dinner: ossobuco and tiramisu, fine cheese and wine and the trademark Italian charm of the trattoria staff.