Watch our Online Travel Show about this tour and earn a $100 credit for your next booking with Holiday Vacations.
Tuscany & the Italian Riviera
Culture & History
Cinque Terre Rail Adventure
Tuscany Countryside & Wine Tasting
Volterra
Regional Cuisine
Discover Tuscany’s charming, picturesque countryside while staying in an upscale hotel for four nights and visiting breathtaking locations each day. Become immersed in history dating back to the 5th century with stops in the medieval hill towns of Volterra, Cortona, and San Gimignano. In Florence, visit the Duomo and the Galleria dell’Accademia, home to Michelangelo’s David, then tour Pisa and wander through the Field of Miracles to see its famous Leaning Tower. Spend two nights in the heart of the Italian Riviera, on the stunning Ligurian Coast, and explore the pastel-colored fishing communities of Cinque Terre. Enjoy a pleasant boat ride to quaint Portofino, the Pearl of the Italian Riviera, before our journey concludes in Milan.
Trip overview may vary by departure.
Highlights
Florence
Known as the birthplace of the Renaissance, this city was the world capital of art in the 15th century! On our walking tour, we admire one of the most famous sculptures in the world, Michelangelo’s David, and observe the architectural beauty of the Duomo. See how it dominates Florence’s skyline and view Giorgio Vasari’s fresco painting, Last Judgment, beneath the dome. We also spend time shopping at the famous Ponte Vecchio Bridge, a medieval arched bridge constructed of stone that was astonishingly spared during World War II.
Cinque Terre
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. During leisure time, you may enjoy walking along clear-water beaches or sipping a local dry white specialty wine from a patio overlooking the sea.
Portofino
Take a relaxing boat ride to the Pearl of The Italian Riviera. Located on its own peninsula, this popular resort town boasts bright vegetation, pastel-colored houses, high-end boutiques, and a small harbor. Time at leisure can be spent seeing the yellow-bricked Church of San Giorgio, the castle and hanging gardens at Castello Brown, the lighthouse beside the Gulf of Tigullio, and the 14th-century Gothic Oratory of Santa Maria Assunta.
Leaning Tower of Pisa & Field of Miracles
Known as the Piazza dei Miracoli in Italian, this iconic site is a stunning blend of history and architectural beauty with timeless white marble buildings, such as the Piazza del Duomo. At the heart of the square stands the worldfamous Leaning Tower of Pisa, one of Italy’s most significant landmarks that has captured attention around the globe for centuries due to its gravity-defying tilt.
- Day 1: Fly to EuropeOur adventure begins with a relaxing overnight flight to Italy.
- Day 2: Tuscan CountrysideUpon arriving in Rome, our Italian guide greets us and we begin the scenic journey through Tuscany’s famous landscapes. 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: Dinner
- Day 3: 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 4: FlorenceOur day begins with a tour of Florence, the 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 taking time to visit Ponte Vecchio’s unique hanging houses and shops or enjoy a fresh gelato. Later, 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 a fantastic selection of wine samplings.
Meals Included: Breakfast, Dinner
- Day 5: 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 displays relics from the Etruscan, Roman, and Egyptian civilizations. The afternoon is yours to enjoy the Renaissance churches, olive groves, and terraces that surround us in this picture-perfect town. Following an included dinner, we head back to our hotel in Chianti.
Meals Included: Breakfast, Dinner
- Day 6: Pisa & Ligurian CoastSay arrivederci to Tuscany as we travel north to Pisa, known for its timeless architecture as well as historic churches and 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 take some time at leisure before our journey continues to Santa Margherita Ligure on the Ligurian Coast, our home for the next two nights.
Meals Included: Breakfast, Dinner
- Day 7: 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 on to Vernazza, and end in Monterosso al Mare, with a lovely beach and beautiful lemon trees. Enjoy superb 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 8: 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 to 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 9: Fly HomeWe return home today with fond memories of our Italian adventure.
Meals Included: Breakfast
What's Included
All Accommodations
- 4 nights at Park Hotel Chianti in Tuscany
- 2 nights Best Western Hotel Regina Elena on the Ligurian Coast
- 1 night at Palace Hotel Legnano near the Milan airport
Attractions & Highlights
- Tuscan countryside
- Volterra guided walking tour feat. Alabaster carving demonstration
- San Gimignano guided walking tour
- Florence guided city tour feat. The Duomo (Santa Maria del Fiore), Galleria dell’Accademia & Michelangelo’s David
- Cortona guided walking tour
- Field of Miracles feat. Leaning Tower of Pisa
- Cinque Terre
- Boat ride to Portofino
- Ligurian Coast
- Time at leisure in all cities
13 Excellent Meals
- Daily European breakfast
- Welcome Dinner in Chianti
- Dinner & wine tasting at Castello di Verrazzano
- Dinner on the Ligurian Coast
- Farewell Dinner in Milan
Learn more about what's included with the Holiday Advantage.
Birmingham - Birmingham-Shuttlesworth International Airport