5-Day Luxury Foodie Road Trip in Tuscany

Day 1: Florence Highlights

Florence, Italy

8:00AM

Breakfast at Caffè Gilli

Start your day with a delightful breakfast enjoying the upscale ambiance at Caffè Gilli, renowned for its pastries and rich Italian coffee.
Located in Piazza della Repubblica, it's a short walk from Florence's iconic sights.
EUR20, 1 hour

9:30AM

Uffizi Gallery

Explore the Uffizi Gallery, home to some of the world's most significant masterpieces of the Renaissance.
A 10-minute walk from the café via Via de' Gondi.
EUR20, 2 hours

12:00PM

Lunch at Trattoria Mario

Dig into a traditional Tuscan meal at this popular eatery known for its authentic dishes like Ribollita and Pici.
Just a 5-minute stroll from the Uffizi Gallery.
EUR25, 1 hour

1:30PM

Ponte Vecchio

Stroll across the famous Ponte Vecchio, admiring the art and jewellery shops as you take in the Arno River views.
A short 10-minute walk from Trattoria Mario.
Free, 1 hour

3:00PM

Local Wine Tasting

Join a luxurious private wine tasting experience at a nearby vineyard in Chianti, learning about the renowned Sangiovese grape.
Travel for about 30 minutes by car to Chianti.
EUR100, 2 hours

6:00PM

Dinner at Enoteca Pinchiorri

End your day with a Michelin-starred dining experience in the heart of Florence, featuring an exquisite Italian tasting menu.
Return to Florence, approximately a 30-minute drive.
EUR200, 2 hours
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Day 2: Scenic Siena

Siena, Italy

8:00AM

Breakfast at Pasticceria Nannini

Enjoy a pastry and cappuccino in this upscale pastry shop, famous for its delicious ricciarelli.
A short 5-minute walk from your hotel.
EUR15, 1 hour

9:30AM

Siena Cathedral

Marvel at the stunning Gothic architecture of the Siena Cathedral and its magnificent artworks encapsulated in this historical site.
Walk to the cathedral, just 10 minutes away on foot.
EUR10, 1.5 hours

11:30AM

Piazza del Campo

Stroll around the breathtaking Piazza del Campo, knowing it's one of Europe's finest medieval squares.
A 5-minute stroll from the Cathedral.
Free, 1 hour

12:30PM

Lunch at Osteria di Castelvecchio

Savor classic Sienese dishes like pici cacio e pepe and a glass of Chianti in this charming eatery.
Take a 10-minute walk from Piazza del Campo.
EUR30, 1 hour

2:00PM

Explore Torre del Mangia

Climb the famous Torre del Mangia for impressive panoramic views of Siena and its stunning skyline.
Just a 5-minute walk from the restaurant.
EUR10, 1.5 hours

4:00PM

Visit a Local Winery

Indulge in a luxurious wine tour and tasting at a renowned winery, learning about the production of Brunello di Montalcino.
Drive 30 minutes to Montalcino.
EUR60, 2 hours

7:00PM

Dinner at La Taverna di San Giuseppe

Enjoy an authentic Sienese dining experience featuring local ingredients and superb service in a cozy setting.
Return to Siena, about a 30-minute drive.
EUR70, 2 hours
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Day 3: Charming San Gimignano

San Gimignano, Italy

8:00AM

Breakfast at Gelateria Dondoli

Start your day with a unique breakfast gelato experience at the award-winning Gelateria Dondoli, perfect for a sweet kick-off in the medieval town.
Drive for about 40 minutes from Siena to San Gimignano.
EUR10, 1 hour

9:30AM

San Gimignano Towers

Wander around the historic towers and appreciate the remarkable skyline of this UNESCO World Heritage site.
The towers are within a 5-minute walk from the gelateria.
Free, 1 hour

10:30AM

Visit the Santa Maria Assunta

Explore the art and architecture of the Santa Maria Assunta, featuring beautiful frescoes and stunning stained glass.
Located just a 5-minute walk from the towers.
EUR5, 1 hour

12:00PM

Lunch at La Mandragola

Enjoy exquisite Tuscan cuisine made with local ingredients in a delightful patio setting, featuring fresh pasta and seasonal vegetables.
A brief 10-minute walk from the church.
EUR40, 1 hour

1:30PM

Explore Local Artisan Shops

Stroll through San Gimignano’s charming streets, visiting artisan shops showcasing local crafts and delicacies, ideal for souvenir hunting.
Easily walk from the restaurant around the town center.
Cost varies, 1.5 hours

3:00PM

Wine Tasting at Fattoria dei Barbi

End your afternoon with a wine tasting at a recognized vineyard, sampling the iconic Vernaccia di San Gimignano.
A short 15-minute drive from the town center.
EUR30, 2 hours

6:00PM

Dinner at Il Ristorante delle Torri

Indulge in a luxurious dining experience that offers a picturesque view of the Tuscan landscape while savoring expertly crafted dishes.
Drive back to San Gimignano, about a 20-minute drive.
EUR100, 2 hours
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Day 4: Delightful Montepulciano

Montepulciano, Italy

8:00AM

Breakfast at Caffè Poliziano

Enjoy a refined breakfast in an elegant café, with the option to savor local pastries and fresh espresso.
Drive 1 hour from San Gimignano to Montepulciano.
EUR15, 1 hour

9:30AM

Explore Montepulciano Town

Wander through the medieval charm of Montepulciano, visiting its beautiful piazzas and historic sites.
Starting point is the café, easily walkable.
Free, 1.5 hours

11:00AM

Montepulciano Vineyards Tour

Take a guided vineyard tour and learn about the famous Vino Nobile di Montepulciano.
Travel a short 15 minutes to a local vineyard by car.
EUR50, 2 hours

1:00PM

Lunch at Osteria Acquacheta

Taste the local specialty, pici cacio e pepe, in this renowned trattoria known for its rustic charm and incredible flavors.
Drive back into Montepulciano town, about 15 minutes away.
EUR35, 1.5 hours

2:30PM

Visit the Cathedral of Montepulciano

Explore and appreciate the beautiful cathedral, which showcases stunning artwork and stunning architecture.
A pleasant 5-minute walk from the restaurant.
Free, 1 hour

4:00PM

Olive Oil Tasting Experience

Enjoy a luxurious tasting of exquisite local olive oils, paired with artisan breads and cheeses.
Drive to a local olive oil producer, about a 10-minute drive from the cathedral.
EUR40, 1.5 hours

6:00PM

Dinner at Le Logge del Vignola

Delight in a sumptuous dining experience with modern twists on classic Tuscan dishes in an elegant setting.
Return to the town center, approximately a 10-minute drive.
EUR80, 2 hours
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Day 5: Historic Lucca

Lucca, Italy

8:00AM

Breakfast at Pasticceria Taddeucci

Start your day with authentic local pastries and coffee in this charming bakery, inviting you to Lucca's historic ambiance.
Drive 1 hour from Montepulciano to Lucca.
EUR10, 1 hour

9:30AM

Explore the Lucca City Walls

Take a leisurely walk or a bike ride along the historic Lucca city walls, enjoying stunning views of the city and the countryside.
The walls are just a 10-minute walk from the café.
Free, 1.5 hours

11:00AM

Visit Cathedral of San Martino

Explore the architectural beauty of the Cathedral of San Martino, housing significant art and relics from the past.
A 10-minute walk from the city walls to the cathedral.
Free, 1.5 hours

1:00PM

Lunch at Ristorante Da Pasquale

Indulge in local cuisine with seasonal specialties in this intimate, upscale eatery, known for its warm hospitality.
Just a 5-minute walk from the cathedral.
EUR35, 1.5 hours

2:30PM

Explore Lucca's Historical Sites

Discover the rich history of Lucca by visiting the charming Piazza dell'Anfiteatro and surrounding sites.
A short 15-minute walk from the restaurant.
Free, 1 hour

4:00PM

Gelato at Gelateria Boccadamo

Enjoy local gelato flavors featuring handmade ingredients at Gelateria Boccadamo, a highlight among dessert lovers.
A brief 5-minute walk from Piazza dell'Anfiteatro.
EUR5, 30 minutes

5:00PM

Dinner at Ristorante Giglio

Conclude your Tuscan road trip with a fine dining experience featuring innovative interpretations of tuscan classics in a historic setting.
Drive about 10 minutes back to the city center.
EUR100, 2 hours
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