Best of Italy

Your journey begins in Chicago O’Hare, where you will board your overnight flight to Italy.

Welcome to Rome, a glorious city filled with Classical antiquities, medieval buildings, Renaissance palaces, and baroque churches. Upon arrival in Rome, you will be transferred to your hotel. Tonight, meet your Tour Director for a Welcome Dinner, a fun evening of Italian cuisine and wine.  

Hotel: Radisson Blu GHR (or similar) 

Meal: Dinner with Wine  

The day is devoted to the Eternal City. Join a Local Expert for an in-depth visit to the Vatican Museums, full of priceless art treasures collected by the Popes. Insight has arranged special VIP entry to avoid the crowds and behind-the-scenes access to the Bramante Staircase, a marvel of Renaissance architecture normally off-limits to visitors (subject to availability). Visit the Sistine Chapel where the Popes are elected to admire Michelangelo’s famous ceiling. Continue to St. Peter’s Basilica, to wonder at another of his works, the emotive ‘Pietà,’ and stand beneath the dome completed after his death.  The rest of the day is at leisure.  

Hotel: Radisson Blu GHR (or similar) 

Meal: Breakfast  

With our local expert, we will explore the glorious history of the Roman Empire. See the incredible Circus Maximus then enjoy priority reserved entrance ahead of the crowds, we’ll hear tales of deadly gladiatorial combat inside the mighty Colosseum (subject to availability; if tickets for the Colosseum are not available, the group will visit the Forum instead, and have an in-depth walking experience around the exterior of the Colosseum). Come up close and personal with the beautifully preserved Arch of Constantine then walk in the footsteps of Roman soldiers and gaze over the incredible ruins of the Forum, once the center of political, religious, and social life, while hearing tales of the mighty Roman Empire. Truly an incredible vision as history comes alive!  

Hotel: Radisson Blu GHR (or similar) 

Meal: Breakfast 

Travel north through glorious, peaceful Tuscan landscapes. Meet your Local Expert for a guided visit through the house of the Italian Renaissance diplomat and writer, Niccolo Machiavelli, with a special opening of his private office where he wrote ‘The Prince.’ Visit the Italian garden for views of Florence’s iconic domed cathedral and see the historic cellar which connects to the oldest restaurant in Italy by a secret underground tunnel. Enjoy a wonderful cooking demonstration, with superb food and wine, providing warm and genuine Tuscan hospitality. 

Hotel: NH Firenze (or similar) 

Meals: Breakfast, Dinner with Wine 

Join a local expert for a walking tour of the historic city center. A highlight is the visit to the Academy Gallery to see Michelangelo’s monumental figure of David (subject to availability). Continue to the multi-colored marble Cathedral to see Giotto’s bell tower and ‘Gates of Paradise’ before visiting the Piazza Della Signoria, still the political heart of Florence and explore the area around Santa Croce Basilica, famous for the quality of its luxury goods. After a demonstration of leather work in the very place this craft was first established, visit San Gimignano, considered a medieval Manhattan, due to its towers which dominate the skyline. Soak up the unique atmosphere of this ancient gem which has remained intact since the 14th century and today is listed as a UNESCO World Heritage site. In the evening, don’t miss the chance to sample the fine Florentine cuisine of tasty starters and rich pastas accompanied by Chianti wine. 

Hotel: NH Firenze (or similar) 

Meal: Breakfast 

In the morning, journey to the coastal town of Pisa to see the famous Leaning Tower in the Square of Miracles as well as the baptistery, with its intricately detailed marble facade, and the colonnaded bell tower lurching behind the cathedral. Then relax and enjoy the scenery as you cross the spectacular Apennine Mountains, through the Emilia- Romagna region – one of Europe’s most intensely farmed fertile plains. Continue through the marshes of the Venetian Lagoon before crossing the causeway into the floating city of Venice.   As evening falls, day-trippers desert the city to return to the mainland. Appreciate the peace and tranquility of Venice from your centrally located hotel. This evening, indulge in a delicious dinner at a local restaurant. 

Hotel: NH Venezia Santa Lucia Venice (or similar) 

Meals: Breakfast, Dinner with Wine 

In the morning, join a MAKE TRAVEL MATTER® Experience with a visit to an arts center and admire the age-old skill of glassblowing by skilled artisans. In the afternoon, your private boat takes you past historic churches and 13th century palaces to St. Mark’s Square. The first sight is the pink marble of the Doge’s Palace, connected to the prisons by the Bridge of Sighs. It was from here that Casanova made his daring escape. Turn the corner, and the gilded regalia of St. Mark’s Basilica comes into view. Afterwards, board a traditional gondola for a serenade along the romantic canals. Tonight, sit back and take it all in as private water taxis whisk you to Piazza San Marco where we have seats reserved outside a famous Venetian café, in front of a live orchestra and in view of those illuminated St Mark’s sights. Our private water taxis will also take us the length of the Grand Canal, under the Rialto Bridge and back to our hotel, having seen Venice at its most magical. 

Hotel: NH Venezia Santa Lucia Venice (or similar) 

Meal: Breakfast 

Leave Venice and continue through the Appennines to peaceful Assisi, home of St. Francis, and one of Italy’s most beautiful mountain towns, dotted with medieval churches, colorful frescoes, and shady courtyards.  First, see the famous Church of St. Mary of the Angels and then continue up Mount Subasio to the upper town. Step inside the huge Basilica, built in the 13th Century after St. Francis’ death, where the frescoes by Giotto heralded a new era in Italian art. Arrive at your hotel, located in the heart of the medieval Old Town. Enjoy the tranquility of the historic old town during free time.  

Hotel: Giotto Hotel Assisi (or similar) 

Meals: Breakfast, Dinner with Wine 

With an early start today, you will travel south passing Cassino, the scene of a fierce battle during World War II. Follow the spectacular clifftop road to the picturesque resort of Sorrento, overlooking the Bay of Naples to Mount Vesuvius. En route, join a MAKE TRAVEL MATTER® Experience in Vesuvius National Park and visit Casa Barone (subject to availability). This small family run farm on the slopes of the volcano is one of the world’s only producers of Piennolo tomatoes, an endangered fruit that only thrives in the fertile volcanic soil. Each harvest is sustainably farmed and cared for by the extended Barone family, who all work here. Be sure to savor the unique flavors of this rare tomato during a truly unique Farm to-Table lunch. Then visit Pompeii, once buried in A.D. 79 by the historic eruption of Mount Vesuvius. Walk with your Local Expert through the cobbled streets to see a city frozen in time. 

Hotel: Hotel Isabella (or similar) 

Meals: Breakfast, Lunch with Wine  

Cross the Bay of Naples to reach the beautiful Isle of Capri, a rock rising sheer from the Mediterranean! For 2,000 years, Capri has beckoned visitors from Tiberius Caesar to Gracie Fields. Arriving at the Marina Grande by boat, ascend to Capri town by one of the island’s iconic open-top taxis. A Local Expert joins you for an exploration of the narrow alleyways. Browse in exclusive boutiques and wonder at the views over the Tyrrhenian Sea. Weather permitting, experience the spectacular cliffs and famous turquoise waters of Capri during a relaxing cruise to the most beautiful part of the island, the southern side. Descend to the port by funicular and board your private boat to view the beautiful grottoes and unique coastline. Return to Sorrento, where you are at leisure for the rest of the day the day. 

Hotel: Hotel lsabella, (or similar) 

Meal: Breakfast  

Your tour comes to an end after breakfast. Transfer from the hotel to the Naples airport for your flight home.  

Meal: Breakfast 

NOTE: Hotels and Daily Itinerary are subject to change.