Gondola Ride
Cinque Terre Rail Adventure
Tuscany Wine Tasting
Leaning Tower of Pisa & Field of Miracles
Vatican Museums
Discover Italy’s most spectacular cities and top attractions on an unforgettable Grand Adventure. Begin with a tour of historic Padua, then experience the romanticism and grand waterways of Venice before immersing yourself in Tuscany’s charming countryside. Admire the birthplace of the Renaissance, Florence, with its famous art treasures such as Michelangelo’s David and explore the iconic buildings in Vatican City, including the Sistine Chapel. Stop in the medieval hill towns of Volterra, Cortona, and San Gimignano to learn about their ancient history. Gaze upon Rome’s archaeological masterpieces like the Colosseum, Roman Forum, and Trevi Fountain, then marvel at Pisa’s world-renowned Leaning Tower. Travel into the heart of the Italian Riviera for picturesque views as you venture through the colorful fishing villages of Cinque Terre and quaint Portofino, the Pearl of the Italian Riviera. Celebrate your travel memories with new friends as the trip concludes in Milan with a wonderful Farewell Dinner.
Trip overview may vary by departure.
Highlights
The Italian Riviera
Cinque Terre, meaning “Five Lands,” is a collection of five coastal villages perched on terraced hillsides high above the Ligurian coast. Together, they make up a UNESCO World Heritage Site that’s famous for its natural and cultural history. Arrive by rail on the Cinque Terre Express to visit the villages of Riomaggiore, Vernazza, and Monterosso al Mare. Discover pastel and brightly painted buildings, picturesque harbors filled with traditional fishing boats, winding cliff pathways, and quaint, cobbled streets. Walk along clear-water beaches, or sip a local dry white specialty wine from a patio overlooking the sea.
Rome
Formerly the heart of one of the most powerful ancient empires, Rome is now the enchanting capital of Italy and renowned for its famous historical sites that draw in tourists from all over. Marvel at the largest amphitheatre ever built and one of the New Seven Wonders of the World, the Colosseum. Learn about its fascinating history and become immersed in the past while setting foot on the grounds that mighty gladiators once walked. We also visit the grand Roman Forum that was previously the governmental, financial, and religious center of the city. Be amazed by the open-air public meetings, criminal trials, and more that took place long ago.
Florence
Known as the “Jewel of the Renaissance,” Florence is especially recognized for its art, history, and architecture. Admire one of the most famous sculptures in the world, Michelangelo’s David, which he finished before the age of 30! Shop at the medieval Ponte Vecchio Bridge, astonishingly spared during World War II, and observe the significant architectural achievements of the Duomo. Its beauty dominates Florence’s skyline and showcases Giorgio Vasari’s Last Judgment painting beneath the dome.
- Day 1: Italy BoundOur adventure begins with an overnight flight across the Atlantic Ocean.
- Day 2: PaduaUpon arriving in Milan, our knowledgeable Italian guide and driver greet us. Enjoy a drive through the scenic countryside in the Lombardy and Veneto regions to Padua, a historic city known for its beauty, world-renowned university, and as the setting for Shakespeare’s The Taming of the Shrew. After checking in to our accommodations for the next two evenings, our day concludes with a fantastic Welcome Dinner.
Meals Included: Dinner
- Day 3: VeniceThis morning, we travel to Tronchetto and board a boat for a relaxing cruise to Venice. Reaching our destination, we embark on a guided walking tour of the stunning “Floating City” and discover grand examples of Byzantine architecture in St. Mark’s Square. This city centerpiece features St. Mark’s Basilica, the Bridge of Sighs, and the Doge’s Palace, a former royal residence. Afterwards, take time at leisure to explore on your own before our quintessential gondola ride on Venice’s charming waterways. Tonight, we savor an included dinner and return to Padua.
Meals Included: Breakfast, Dinner
- Day 4: TuscanyToday, we venture into the Emilia-Romagna region for time at leisure in Ferrara, a UNESCO World Heritage Site filled with elegant 14th- and 15th-century palaces. Next, our travels continue through the Apennine Mountains to the gorgeous Tuscany region. We arrive in the historic city of Florence this evening and settle into our hotel for the next two nights before our dinner featuring regional cuisine.
Meals Included: Breakfast, Dinner
- Day 5: FlorenceWe’re off to discover the birthplace of the Renaissance and home to many of the world’s greatest artistic treasures on a guided walking tour this morning. On a guided walking tour, admire the magnificent Duomo (Cathedral of Santa Maria del Fiore), crowned by the world’s largest brick dome, and marvel at Ghiberti’s bronze Baptistery doors, famously known as the Gates of Paradise. We also visit the Galleria dell’Accademia to behold Michelangelo’s iconic David and other breathtaking masterpieces. There’s also ample time at leisure to visit museums, indulge in a fresh gelato, or browse the shops of Ponte Vecchio, a famous covered bridge housing many local vendors. Our evening concludes with an enchanting walk through the illuminated city center.
Meals Included: Breakfast
- Day 6: San GimignanoOur day begins with a southbound drive through Tuscany, featuring picturesque groves of olive trees and vineyards. We stop in the medieval hilltop town of San Gimignano, also known as the Town of Fine Towers, which is best recognized by its 14 magnificent towers and 13th-century encircling walls. Our guided tour explores its deep history and rich culture from the Middle Ages. Later, we arrive in the eternal city of Rome and check in to our accommodations for the next three nights, then gather for a delicious dinner.
Meals Included: Breakfast, Dinner
- Day 7: Ancient RomeToday’s adventure brings us through the fascinating sights and landmarks of ancient Rome. Discover one of the most celebrated monuments of the Roman Empire and the largest amphitheater in the world: the Colosseum. Revel in the chance to walk in the steps of mighty gladiators as we learn about the many uses of this legendary arena! We also tour the Roman Forum, once the governmental center of the city and now home to several well-preserved pieces of architecture like the Arch of Constantine, and marvel at the magnificent Trevi Fountain. Hear about its fascinating legend, then toss a coin into the fountain to ensure your return to Rome! During leisure time, you may enjoy seeing St. Peter's Square, climbing the Spanish Steps, visiting the Pantheon, or exploring the statues and cafés of Piazza Navona.
Meals Included: Breakfast
- Day 8: Vatican City & the Sistine ChapelThis morning, we’re immersed in the city’s art, culture, and history during a guided tour of the famous Vatican Museums. Browse the galleries to see renowned classical sculptures and Renaissance art, then step into the remarkable Sistine Chapel. The iconic ceiling fresco–painted by Michelangelo–is truly a magnificent sight to behold! Our visit to Vatican City continues with a special tour of St. Peter’s Basilica, one of the most extraordinary churches around the globe and home to the Catholic Church. Marvel at the impressive relics, including the Altar of the Sacred Heart, the Chair of Saint Peter, and Michelangelo’s Pieta. Tonight, we gather with new friends one more time for a special dinner featuring live musical entertainment before beginning the second half of our Grand Adventure tomorrow morning.
Meals Included: Breakfast, Dinner
- Day 9: Tuscan CountrysideAfter breakfast, we meet the expert Italian guide who accompanies us throughout the rest of our tour. We then begin our picturesque journey through the famous rolling hills of Tuscany. Our countryside home for the next four nights is nestled within the rolling hills of Chianti, offering breathtaking vistas and a serene atmosphere. This evening, we get to know fellow travelers over a Welcome Dinner of authentic Tuscan cuisine, complete with local wine.
Meals Included: Breakfast
- Day 10: Volterra & San GimignanoToday, we visit two of Italy’s best-preserved medieval hill towns, both of which are surrounded by fortified walls and overlook hilly farmland. Our first stop is Volterra, a once-important Etruscan city that predates the Roman Empire. Learn about its ancient history during a walking tour with views of the 12th-century Romanesque cathedral, medieval frescoes, and iconic bell tower. We also watch an impressive carving of alabaster, a locally mined soft rock and mineral. Our afternoon is spent at San Gimignano, famous for its medieval towers once used by feuding noble families. During your leisure time, roam the quaint cobblestone streets and squares that make this town so mesmerizing. Later, we indulge in regional cuisine for dinner.
Meals Included: Breakfast, Dinner
- Day 11: FlorenceOur day begins with a tour of Florence, birthplace of the Renaissance. Visit the Galleria dell’Accademia and view incredible works, including Michelangelo’s David, then marvel at the Duomo, the largest brick dome ever constructed. Gaze upon Ghiberti’s bronze doors of the Baptistery, often called the Gates of Paradise, before free time to visit Ponte Vecchio’s unique hanging houses and shops or taste fresh gelato. Tonight, we’re treated to a special evening at Castello di Verrazzano, where we learn the history of celebrated navigator Giovanni da Verrazzano and savor a dinner paired with fantastic wine samplings.
Meals Included: Breakfast, Dinner
- Day 12: CortonaWe travel to the hilltop town of Cortona this morning for a fascinating tour with our Italian guide. Admire the medieval architecture of Piazza Garibaldi, the sights and shops along the Via Nazionale, and the opulence of Palazzo Casali, which you may choose to explore at leisure time to view relics from the Etruscan, Roman, and Egyptian civilizations. The afternoon is yours to enjoy the Renaissance churches, olive groves, and terraces in this picture-perfect town. Following an included dinner, we return to our hotel in the Chianti region.
Meals Included: Breakfast
- Day 13: Pisa & Ligurian CoastSay arrivederci to Tuscany as we travel north to Pisa, known for its timeless architecture, historic churches, and opulent palaces. Our guide introduces us to the area famously called the Field of Miracles, where we see the renowned Leaning Tower of Pisa. Grab a bucket list photo in front of this impressive structure, then spend some time at leisure before our journey continues to Santa Margherita Ligure on the Ligurian Coast.
Meals Included: Breakfast, Dinner
- Day 14: Cinque TerreToday, we visit one of Italy’s most well-loved destinations, an Italian National Park and UNESCO World Heritage Site: Cinque Terre. Climb aboard the Cinque Terre Express for a day of exploring quaint cities on this rocky coastline along the Mediterranean Sea. We start in the village of Riomaggiore, then continue to Vernazza, and end in Monterosso al Mare, featuring a lovely beach and beautiful lemon trees. Enjoy stunning views of pastel-colored buildings in charming fishing villages and distinctive terraced vineyards that produce local wine, such as specialty dry whites. Later, we return to our hotel for an evening at leisure.
Meals Included: Breakfast
- Day 15: Italian RivieraEnjoy a relaxing morning before a ferry ride takes us to Portofino, known as the Pearl of the Italian Riviera. This enchanting fishing village, boasting a picturesque harbor, is frequented by some of Europe’s wealthiest and most discerning pleasure seekers. After free time to explore, we travel towards Milan and check in to our overnight accommodations near the airport. Tonight, we gather for a celebratory Farewell Dinner and toast to our adventures.
Meals Included: Breakfast, Dinner
- Day 16: Fly HomeWe return home today with treasured memories of our Italian Grand Adventure.
Meals Included: Breakfast
What's Included
All Accommodations
- 2 nights at Hotel Europa in Padua
- 2 nights at Hotel Roma in Florence
- 3 nights at Hotel Ponte Sisto in Rome
- 4 nights at Villasanpaolo Resort & Spa in the Chianti region
- 2 nights at Best Western Hotel Regina Elena on the Ligurian Coast
- 1 night at Palace Hotel Legnano near the Milan airport
Attractions & Highlights
- Venice guided walking tour feat. St. Mark’s Square, Doge's Palace, the Bridge of Sighs & gondola ride
- Florence evening illumination walk
- Rome guided walking tour feat. the Colosseum, Trevi Fountain & Roman Forum
- Vatican City guided walking tour feat. St. Peter's Basilica, the Sistine Chapel & the Vatican Museums
- Tuscan countryside
- San Gimignano guided walking tour
- Volterra guided walking tour feat. alabaster carving demonstration
- Florence guided city tour feat. The Duomo & Galleria dell’Accademia w/ Michelangelo’s David
- Cortona guided walking tour
- Field of Miracles feat. Leaning Tower of Pisa
- Cinque Terre feat. rail journey
- Boat ride to Portofino
- Ligurian Coast
- Time at leisure in all cities
Learn more about what's included with the Holiday Advantage.
Birmingham - Birmingham-Shuttlesworth International Airport