Join Shane Hayes, Mr. Tour Guide of Socks in the Frying Pan, on this unforgettable journey through Tuscany. Picture strolling through Florence, gazing up at Michelangelo’s David, or sipping Chianti wine in a centuries-old castle, the perfect pairing to a serene afternoon. Wander through ancient streets in Siena, San Gimignano, and Lucca, where time seems to stand still. The beauty of Tuscany surrounds you—its landscapes, its art, and its rich history—creating the perfect backdrop for an unforgettable escape.
Welcome to the the cradle of the Renaissance and the Italian capital of art! Relax, freshen up and wander the streets of beautiful Florence. Have a Spritz, do some shopping or check out some of Shane’s personal reccomendationsbefore the welcome dinner. Meet your group and your host Shane and enjoy a first taste of authentic Tuscan food. Famous the world over!
Your personal, licensed guide will escort you to the Academy of Fine Arts where your reserved ticket allows you to skip the long lines. You’ll learn the history and significance the David, a monumental and influential sculpture, in the context of Florence and the art world.
Enjoy a guided walking tour through Florence’s historic centre and visit its most important monuments while hearing thestories of famous men of Florence – Galileo, Dante, Leonardo da Vinci and others who left their indelible mark here.
Travel the old Chianti road, winding through the hilly Tuscan countryside amid vineyards and olive groves. You’ll have the opportunity to stop for photographs of this famous and spectacular landscape throughout your trip. You will experience the renowned Chianti wine, we’ll take you to the well regarded winery Castello di Verrazzano where you’ll enjoy a guided visit of the estate and cellars along with a wine tasting and lunch. Afterward, you’ll have time to visit some of the Chianti’s charming and typical stone villages with their characteristic town squares where you’ll have time explore or browse the local shops selling traditional products.
Siena’s architecture reflects its rich history, with Piazza del Campo standing as one of Europe’s greatest medieval squares. This iconic square, home to the renowned Palio horse race, is surrounded by architectural treasures, including the Palazzo del Popolo, Mangia Tower, and Gaia Fountain. A stroll through Siena leads to its striking Romanesque-Gothic cathedral, considered one of Italy’s most beautiful.
Traveling through the picturesque Tuscan countryside—dotted with cypress trees, vineyards, and olive groves—we arrive in San Gimignano. Often called the “Manhattan of Tuscany” for its distinctive medieval towers, this charming town has preserved its feudal character. Explore its winding streets, visit Piazza della Cisterna, and discover the artisan shops that give San Gimignano its unique appeal.
Explore the enchanting walled city of Lucca, Italy, where timeless cobblestone streets, stunning medieval architecture and vibrant local culture await you. Once renowned for its silk production, Lucca was later conquered by Napoleon, who gifted the city to his sister Elisa. She left her mark by designing Piazza Napoleone, a grand square with a distinct French influence.
After exploring Lucca, journey into the Tuscan countryside for a guided tour of vineyards and olive groves. Learn about the art of winemaking and extra virgin olive oil production before enjoying a dinner of traditional Tuscan specialties, perfectly paired with the estate’s own wines.
Discover the breathtaking beauty of Cinque Terre, where five picturesque villages cling to rugged cliffs above the shimmering Mediterranean Sea. Wander trough colourful streets, savor fresh seafood and enjoy panoramic views that will leave you in awe. Our guided tours take you off the beaten path to explore hidden beaches, scenic hiking trails and charming local traditions. Experience the magic of Cinque Terre, a coastal paradise like no other. It’s this isolation that helped to preserve the character & beauty of the area and of each town. Enjoy a day exploring this special coastline, with its kaleidoscope of color: azure sky, verdant hillsides, grey cliffs, turquoise sea & gaily colored houses. Discover each town’s secrets and singularities; then decide which is your personal favorite.
Uncover the awe-inspiring quarries of Carrara, where the world’s finest marble has been sourced for centuries, shaping masterpieces from Michelangelo’s David to contemporary sculptures. Journey into the heart of the Apuan Alps, where dramatic landscapes set the stage for history and artistry to converge. A guided tour offers a rare glimpse into the ancient craft of marble excavation, with the chance to venture deep into the quarries and uncover the secrets behind this legendary stone.
Next, experience the wonder of the Leaning Tower of Pisa, one of the world’s most iconic landmarks where history defies gravity. Explore Piazza dei Miracoli, surrounded by stunning medieval architecture and centuries of heritage. Capture the perfect photo and immerse yourself in the timeless charm of Pisa’s most famous monument.
Say goodbye to Italy, as you check out this morning and prepare for your flight home.
(For all Trans-Atlantic flights, we recommend arriving at the airport 3 hours before departure to ensure a smooth check-in process.)
Map coming soon – stay tuned!
All hotels and accommodations included in your trip are carefully selected to meet a 4-star standard or higher. While we occasionally book 3-star hotels or B&B properties, they must meet our high standards of quality and comfort. To ensure consistency, we strive to have a team member visit each property regularly or conduct a thorough site inspection.
The tour package does not include flights to and from the tour’s starting location, but we are happy to provide you with a flight quote for your trip to Italy, along with travel protection for the duration.
Although booking flights might seem straightforward, hidden fees or service classes without seat assignments, meals, or checked bags can arise. With our experience since 1985, we are familiar with the best routings and have access to great contracts, often offering better prices than those available online.
If you would like to create a custom itinerary before or after the tour to extend your trip, we would be happy to assist with this.
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