5 Days Exploring Florence and the Heart of Tuscany

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Spend five unforgettable days in and around Florence, the heart of Tuscany and the cradle of the Renaissance. This itinerary blends the best of Florence’s rich cultural heritage with day trips to some of Italy’s most enchanting destinations. Wander through the cobbled streets of Pisa, San Gimignano, and Siena with a taste of Tuscan cuisine and wine. Take in the dramatic coastline and colorful villages of Cinque Terre, with an optional hike or scenic boat ride. Then, slow down and savor the rolling hills, vineyards, and medieval charm of Val D’Orcia, Montepulciano, and Pienza. Whether you’re an art lover, a foodie, or a landscape seeker, this 5-day journey offers the perfect balance of city elegance and countryside escape. (Partially Guided)

1. 01 Day 1

   Arrival Florence

   Florence

   Upon arriving at Amerigo Vespucci Airport , meet your driver in the arrival hall for a transfer to your hotel in Florence . After checking in (available from 14:00), you’ll have free time to explore your hotel at your leisure. Please note that early check-in is subject to availability upon arrival.

   Florence

2. 02 Day 2

   Pisa, San Gimigniano, and Siena: Trip from Florence with Lunch and Tasting

   Pisa

   After breakfast, walk to the nearby meeting point for your group tour. It’s just a short distance from your hotel. The meeting point is at Piazzale Montelungo Depart Florence Your exciting journey begins along scenic roads of the Chianti countryside, before arriving in Siena. Siena Your professional guide will meet you for a fascinating tour of the most important sites in the heart of the city. Learn all about the city as you walk from Piazza del Campo, to the Gothic Cathedral, and visit its stunning interior decorations. At the end of the tour, there will be time to enjoy a coffee and to do some exploring on your own. Wine estate visit Then you will move onto a rustic wine estate in the foothills of San Gimignano, where you can enjoy a typical Tuscan lunch of three courses, enriched by a high quality tasting of local wines. After lunch, you will discover one of the most famous medieval hilltop villages in Italy, San Gimignano, famous for its ancient skyscrapers! You will have free time to explore the maze of cobbled streets, the small squares, and the many local artisan shops. Pisa Your day continues with a trip to the iconic town of Pisa. Your guide will lead you to the famous Square of Miracles, where you will have time to admire the stunning cathedral, baptistery, monumental cemetery, and – of course – the chance to snap photographs of the celebrated Leaning Tower of Pisa. Return to Florence On your journey back to Florence, you can admire the sky light up as the sun sets over the Tuscan hills and vineyards. Don't miss out on this incredible experience in the heart of Tuscany!

   Pisa

   Day tour Pisa, San Gimigniano, and Siena: Trip from Florence with Lunch and Tasting 11 hours 30 minutes · Meets at Piazzale Montelungo Depart Florence Your exciting journey begins along scenic roads of the Chianti countryside, before arriving in Siena See the tour
3. 03 Day 3

   Cinque Terre: Trip from Florence + Boat Tour + Optional Hiking

   Florence

   After breakfast, walk to the nearby meeting point for your group tour. It’s just a short distance from your hotel. The meeting point is at Piazza della Stazione Next, let a swift train ride whisk you away to Corniglia, where an exciting challenge beckons - a climb of 380 steps from the station to the clifftop village. The reward? Jaw-dropping views of the twinkling sea and undulating hillsides, making every step a triumph! After a leisurely lunch, the adventure escalates with a two-mile hike along ancient mule trails, skirting the edges of gorgeous, steep cliffs. These trails serve as historical lifelines between the hilltop hamlets of the Cinque Terre. For those who prefer a more relaxed journey, opt for the tour sans hike, where the train shuttles you between villages. The expedition continues from Vernazza to Monterosso via a brisk train jaunt. Monterosso, renowned for its impressive beach and artisan shops, is a delight to discover. Finally, weather permitting, thrill-seekers can enjoy an exhilarating boat ride along the coast to Riomaggiore.

   Florence

   Day tour Cinque Terre: Trip from Florence + Boat Tour + Optional Hiking 13 hours · Meets at Piazza della Stazione Next, let a swift train ride whisk you away to Corniglia See the tour
4. 04 Day 4

   Val D'Orcia, Montepulciano & Pienza: Trip from Florence

   Montepulciano

   After breakfast, walk to the nearby meeting point for your group tour. It’s just a short distance from your hotel. The meeting point is at Piazzale Montelungo Bus Terminal Heading to Montalcino, home to the famous Brunello wine, you'll explore the ancient and picturesque cobblestone streets that lead to the highest point of Montalcino. Soak up the breathtaking panorama of soft green hills, oak groves, olive trees, and endless vineyards. Then, in the hilltop town of Pienza, which dominates the Orcia Valley, enjoy some free time to explore the romantic beauty before heading to Montepulciano and its extraordinary Vino Nobile vineyards. Explore the town as you please, then join your group for a second wine tasting. Discover the secrets of the wine and how it has historically been stored within the ancient walls of the winery.

   Montepulciano

   Day tour Val D'Orcia, Montepulciano & Pienza: Trip from Florence 11 hours 30 minutes · Meets at Piazzale Montelungo Bus Terminal Heading to Montalcino, home to the famous Brunello wine, you'll explore the ancient and picturesque cobblestone streets that lead to the highest point of Montalcino See the tour
5. 05 Day 5

   Departure Florence

   Florence

   After breakfast, meet your driver and transfer to the Amerigo Vespucci Airport . We recommend scheduling your hotel pick-up up to 4 hours before your flight departure time. Please note that hotel check-out is at 12:00 noon, and late check-out will be subject to availability. ­

   Florence

What's included