Travelers seeking an immersive Tuscan experience can’t miss this captivating 4-day tour from Florence. It’s a chance to uncover the region’s iconic sights – from the leaning tower of Pisa to the medieval splendor of Siena and San Gimignano. But the true highlights lie in the region’s renowned wine and cuisine, with tastings and traditional lunches offering a delectable introduction to the flavors of Chianti and beyond. With seamless logistics and the freedom to explore at one’s own pace, this tour promises an unforgettable journey through Tuscany‘s cultural and natural wonders.
Key Points

- This 4-day Tuscany tour from Florence showcases the region’s top historic towns, landscapes, and wine culture.
- The itinerary includes visits to Pisa, Siena, San Gimignano, Florence, Chianti, Val d’Orcia, and Cinque Terre.
- Activities feature guided walking tours, wine tastings, and exploration of UNESCO World Heritage sites.
- Flexible booking options and free cancellation up to 24 hours in advance are available.
- The tour is not suitable for children under 2, pregnant women, or individuals with back problems.
Tour Overview

The 4-Day Tuscany Highlights Tour w/Wine Tasting offers a comprehensive exploration of the renowned region, providing visitors with an immersive experience of its historic towns, picturesque landscapes, and renowned wine culture.
Priced from £399.61 per person, the tour lasts 4 days and is available in multiple languages. Travelers can enjoy free cancellation up to 24 hours in advance and flexible booking options.
The itinerary showcases top destinations like Pisa, Siena, San Gimignano, Florence, Chianti, Val d’Orcia, and the Cinque Terre. Along the way, they’ll savor Tuscan cuisine, partake in wine tastings, and explore captivating historical sites.
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Itinerary Highlights

Day 1 of the tour takes visitors on a captivating journey through some of Tuscany’s most iconic destinations. Guests marvel at the leaning tower of Pisa, explore the charming medieval town of Siena, and discover the stunning hilltop village of San Gimignano. Lunch features a delightful array of traditional Tuscan dishes, while a wine tasting in the Chianti region delights the palate. This multifaceted day showcases the region’s rich history, culinary traditions, and natural beauty.
The tour continues on Day 2 with a guided walking tour of Florence, including must-see landmarks like:
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The Duomo
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Piazza della Signoria
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Ponte Vecchio
Afterward, the group ventures into the scenic Chianti hills for additional wine and olive oil tastings, as well as a visit to the fortified town of Monteriggioni.
Day 1: Pisa, Siena, and San Gimignano

Departing from Florence, the tour makes its way to the historic city of Pisa, where participants marvel at the iconic Leaning Tower, a UNESCO World Heritage Site. Next, they explore the charming medieval town of Siena, admiring its stunning Duomo and the Piazza del Campo. The tour then continues to San Gimignano, known as the "Medieval Manhattan" for its well-preserved towers. Participants enjoy a lunch featuring typical Tuscan dishes before heading to a Chianti winery for a tasting.
| Location | Activity |
| — | — |
| Pisa | Visit Leaning Tower |
| Siena | Tour Duomo, Piazza del Campo |
| San Gimignano | Explore medieval town, lunch |
| Chianti | Wine tasting |
Day 2: Florence and Chianti

From Siena, the tour heads north to the iconic city of Florence, where participants embark on a guided walking tour of the historic center.
They’ll discover the magnificent Piazza del Duomo, home to the iconic cathedral and its towering bell tower.
Next, they’ll stroll through the charming Piazza della Signoria, dominated by the grand Palazzo Vecchio.
The tour culminates at the picturesque Ponte Vecchio, the famous bridge lined with goldsmiths’ shops.
In the afternoon, the group travels to the Chianti region for wine and olive oil tastings, followed by a visit to the medieval town of Monteriggioni.
More Great Tours NearbyDay 3: Val D’orcia and Montepulciano

After exploring the charming towns of Siena and Florence, the tour ventures into the captivating region of Val d’Orcia. This picturesque landscape of rolling hills, medieval villages, and vineyards awaits. The highlights include a visit to the historic town of Montepulciano, known for its renowned Vino Nobile wine. Guests also discover the quaint town of Pienza, famous for its Pecorino cheese. Throughout the day, travelers indulge in additional wine tastings, savoring the robust flavors that make this region so renowned.
| Destination | Highlights |
|————-|————|
| Montepulciano | Vino Nobile wine |
| Pienza | Pecorino cheese |
| Val d’Orcia | Picturesque landscapes |
Ready for another glass? Here are more wine experiences we've reviewed in Florence
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Day 4: Cinque Terre Coastal Towns

The tour now shifts its focus to the stunning Cinque Terre region along the Italian Riviera.
Guests will visit the picturesque coastal towns, each with its own unique charm:
The picturesque coastal towns of the Cinque Terre each offer their own distinct allure and character.
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La Spezia, the largest town in the area, serves as the gateway to the Cinque Terre.
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Manarola, a vibrant fishing village known for its colorful houses and vineyards.
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Vernazza, considered one of the most beautiful towns, with its historic harbor and narrow streets.
Travelers will enjoy the breathtaking scenery, explore the quaint towns, and travel between them by train and bus.
This day offers a perfect end to the Tuscany highlights tour.
Inclusions

The tour package includes a variety of transportation, guided tours, meals, and wine tastings to provide a well-rounded Tuscan experience.
Participants will travel by air-conditioned bus to key destinations like Pisa, Siena, and Val d’Orcia.
Guided tours in Siena, Florence, and Val d’Orcia offer in-depth exploration of these historic cities.
Lunches featuring typical Tuscan dishes and wine tastings at Chianti and Val d’Orcia wineries immerse guests in the region’s renowned culinary and wine culture.
A train and bus journey to the Cinque Terre coastal towns rounds out the comprehensive itinerary.
Important Information

To ensure a smooth and enjoyable tour, participants should meet at the designated meeting point of Villa Costanza in Florence.
Guests are encouraged to bring the following items:
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Comfortable shoes for walking
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A camera to capture the stunning Tuscan scenery
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Ample water to stay hydrated
Please note that this tour isn’t suitable for children under 2 years old, pregnant women, or individuals with back problems.
Hotel pickup and drop-off aren’t included, and tips as well as meals (breakfast and dinner) are the responsibility of the traveler.
Availability may vary, so it’s best to check before booking.
The Sum Up

This Tuscany Highlights Tour offers an immersive experience, showcasing the region’s iconic destinations, rich culture, and stunning landscapes. From the historic cities of Pisa, Siena, and Florence to the picturesque Val d’Orcia and the breathtaking Cinque Terre, this 4-day journey provides travelers with a comprehensive and flexible exploration of Tuscany’s finest. With traditional Tuscan lunches, exquisite wine tastings, and guided tours, it’s an unforgettable way to discover the essence of this captivating Italian region.
You can check availability for your dates here:More Guided Tours in Florence
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