Adventure Collective
Tuscany Day Tours: Florence to Pisa, Chianti & Siena - Florence

Tuscany Day Tours: Florence to Pisa, Chianti & Siena

Florenceeasy

Difficulty

easy

Duration

8–10 hours

Fitness Level

Basic walking endurance for city tours and winery visits

Overview

Discover Tuscany's top sights in one unforgettable day from Florence. Visit Pisa’s Leaning Tower, savor Chianti wine, and wander Siena’s medieval streets.

Guided Tour
Firenze, Toscana

Tuscany Grand Tour from Florence: Pisa, Chianti and Siena

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Adventure Photos

Tuscany Grand Tour from Florence: Pisa, Chianti and Siena photo 1

About This Adventure

Embark on a captivating journey from Florence, exploring the historic city of Pisa and its iconic Leaning Tower. Delight in a guided wine experience in Chianti, savoring exquisite local flavors. Discover Siena's medieval charm on a guided tour, and capture stunning photos at Monteriggioni Castle, creating unforgettable memories of Tuscany.

Start your day with an early morning departure from Florence at 8:00 AM and enjoy a scenic drive through the picturesque Tuscan countryside. Our first stop is the historic city of Pisa, where you’ll enjoy 1 hour and 15 minutes of free time exploring the Piazza dei Miracoli, Marvel at the grandeur of the Duomo, admiring the intricate designs of the Battistero, and capturing the quintessential photo with the iconic Leaning Tower of Pisa. After exploring Pisa, we'll continue our journey to the heart of the Chianti Classico region. Here, you’ll be welcomed by a sommelier or a local wine producer who will guide you through their beautiful estate. Learn about the fascinating process of wine production, from vine to bottle, and discover the secrets behind Chianti’s renowned wines. Following the tour, indulge in a wine tasting session featuring a selection of the estate’s finest wines, perfectly paired with a delicious lunch of homemade local products. Savor the rich flavors of Tuscany with freshly made pasta, artisanal cheeses, cured meats, and more, all while enjoying the serene vineyard views. Next, we head to the charming city of Siena. Upon arrival, a local guide will lead you on a 1 hour and 15 minute walking tour, revealing the secrets of this medieval gem. Stroll through the stunning Duomo, the majestic Piazza del Campo, and other fascinating landmarks, while learning about the rich history and culture of Siena. Before returning to Florence, we’ll make one last stop for a photo opportunity at the magnificent Monteriggioni Castle, capturing the beauty of this historic fortress. We’ll arrive back in Florence by 6:30 PM, ensuring a safe return after a day filled with unforgettable memories and photos of Tuscany's most iconic destinations.

Adventure Tips

Book in advance

Tours fill quickly, especially in high season, so reserve your spot weeks ahead.

Wear comfortable shoes

Cobblestone streets and castle grounds require sturdy, comfortable footwear.

Bring a camera

Prepare to capture breathtaking views, historic landmarks, and vibrant vino moments.

Stay hydrated

Carry a water bottle to stay refreshed while walking under the Tuscan sun.

Local Insights

Wildlife

  • Common red foxes in countryside
  • Various migratory birds in Chianti vineyards

History

Siena’s Palazzo Pubblico and Piazza del Campo date back to the 13th century and are central to its medieval identity.

Conservation

Chianti’s winemakers increasingly adopt sustainable farming to preserve the region’s natural beauty and soil health.

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Adventure Hotspots in Florence

Frequently Asked Questions

Recommended Gear

Comfortable walking shoes

Essential

Needed for uneven historic streets and light hiking at castle sites.

Sun hat or cap

Essential

Protects from strong sun during outdoor vineyard visits.

summer specific

Light jacket or sweater

Essential

spring specific

Camera or smartphone

Essential

To capture memorable landscapes and architecture.