• 15 Days
  • From $12,099
  • Airfare Included

Grand Adventure: Rome, Venice, Tuscany & the Italian Riviera

Tour Style:
Land
Activity Level:
Very Active
Highest Elevation:
1,742 feet at Volterra

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 and Roman Forum, 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.

  • Day 1: Italy Bound
    Our adventure begins with an overnight flight across the Atlantic Ocean.
  • Day 2: Padua
    Upon 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: Venice
    This 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: Tuscany
    Today, 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: Florence
    We’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: Siena
    Our 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 Rome
    Today’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 Chapel
    We’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 Countryside
    We 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 Gimignano
    Today, 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: Cortona
    We 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 Coast
    Say 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 Terre
    Today, 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 Riviera
    Enjoy 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 Home
    We return home today with treasured memories of our Italian Grand Adventure.

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.