Highlights
- Day 1: Italy BoundOur adventure begins with an overnight flight across the Atlantic Ocean.
- Day 2: PaduaUpon arriving in Italy, 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.
- Day 3: VeniceThis morning, we travel to Tronchetto and board a boat for a relaxing cruise to Venice. We then embark on a guided walking tour of the stunning “Floating City” and discover grand examples of Byzantine architecture in St. Mark’s Square, including the Bridge of Sighs and the Doge’s Palace, a former royal residence. Afterwards, take time at leisure to explore on your own, such as visiting St. Mark’s Basilica, before our quintessential gondola ride on Venice’s charming waterways. Tonight, we savor an included dinner and return to Padua.
- 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.
- 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. 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, known as the Gates of Paradise. We then visit the Galleria dell’Accademia to behold Michelangelo’s iconic David and other breathtaking masterpieces. There’s also 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.
- Day 6: SienaOur day begins with a southbound drive through Tuscany, featuring picturesque groves of olive trees and vineyards. We stop in the UNESCO-listed medieval city of Siena, a beautifully preserved hilltop treasure known for its striking Gothic architecture. On a guided walking tour, we explore the heart of the city, admiring iconic sites like the Piazza del Campo and the Siena Cathedral. 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.
- 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. 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.
- Day 8: Vatican City & the Sistine ChapelWe’re immersed in the city’s art, culture, and history during today’s 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. View the impressive relics, including the Altar of the Sacred Heart, the Chair of Saint Peter, and Michelangelo’s Pieta. Tonight, we gather with friends for a special dinner featuring live musical entertainment.
- Day 9: Tuscan CountrysideWe begin our picturesque journey through the famous rolling hills of Tuscany. Our countryside home for the next three nights is nestled within the rolling hills of Chianti, offering breathtaking vistas and a serene atmosphere. This evening, we savor a dinner of authentic Tuscan cuisine, complete with local wine.
- 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.
- Day 11: 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.
- Day 12: 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.
- Day 13: 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.
- Day 14: 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.
- Day 15: Fly HomeWe return home today with treasured memories of our Italian Grand Adventure.
May 8-22, 2027
$12,099
per person
$13,999
per person
Feb 2, 2027
What's Included
All Accommodations
- 2 nights in Padua
- 2 nights in Florence
- 3 nights at Hotel Ponte Sisto in Rome
- 3 nights at Park Hotel Chianti
- 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 guided walking tour feat. The Duomo & Galleria dell’Accademia w/Michelangelo’s David
- Siena guided walking tour
- Rome guided walking tour feat. the Colosseum & 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
- Cortona guided walking tour
- Field of Miracles feat. Leaning Tower of Pisa
- Cinque Terre feat. rail journey
- Boat ride to Portofino
- Ligurian Coast
23 Excellent Meals
- Welcome Dinner in Padua
- Daily European breakfast
- Local wine with every dinner
- Dinner on the Ligurian Coast
- Farewell Dinner near Milan
Learn more about what's included with the Holiday Advantage.
Birmingham - Birmingham-Shuttlesworth International Airport





