Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Relaxing Retreat in Tuscany with San Gimignano

Viewed by 78 travelers

Day 1: Historic Exploration

Florence, Italy

9:00AM

Visit the Uffizi Gallery

Immerse yourself in Renaissance art at the Uffizi Gallery, home to masterpieces by artists like Michelangelo and Leonardo da Vinci.
The gallery is located in Piazza della Signoria, easily accessible by foot or public transportation.
EUR 20, 2 hours

1:00PM

Lunch at Trattoria Mario

Enjoy a traditional Florentine meal at Trattoria Mario, known for its authentic Tuscan cuisine.
Trattoria Mario is located near the Mercato Centrale in Florence city center.
EUR 15, 1 hour

3:00PM

Stroll through Piazzale Michelangelo

Relax and take in panoramic views of Florence from Piazzale Michelangelo, a scenic overlook with breathtaking vistas.
Piazzale Michelangelo can be reached by a short walk or taxi ride from the city center.
Free, 1.5 hours

7:00PM

Dinner at La Ménagère

Indulge in a modern dining experience at La Ménagère, a stylish restaurant with a unique ambiance and delectable dishes.
La Ménagère is centrally located in Florence, perfect for a relaxing evening meal.
EUR 30, 2 hours
Find Hotels in Florence

Day 2: Charming Towns

Siena, Italy

9:00AM

Explore Siena Cathedral

Marvel at the stunning Gothic architecture and intricate artwork inside Siena Cathedral, a masterpiece of Italian craftsmanship.
Siena Cathedral is located in the heart of the historic center, a short walk from Piazza del Campo.
EUR 10, 2 hours

1:00PM

Lunch at Osteria Le Logge

Savor Tuscan delicacies at Osteria Le Logge, a cozy restaurant serving fresh, locally sourced ingredients.
Osteria Le Logge is situated near Piazza del Campo, convenient for a lunch break.
EUR 25, 1.5 hours

3:00PM

Walk around Piazza del Campo

Explore the iconic shell-shaped square of Piazza del Campo, known for its medieval architecture and lively atmosphere.
Piazza del Campo is the main square in Siena and a hub for cultural events and gatherings.
Free, 1 hour

7:00PM

Dinner at Enoteca I Terzi

Dine at Enoteca I Terzi for a wine and dine experience, offering a selection of Tuscan wines and gourmet dishes.
Enoteca I Terzi is located in the historic center of Siena, perfect for a relaxing evening meal.
EUR 35, 2 hours
Find Hotels in Siena

Day 3: Wine Tasting Delight

Chianti, Italy

10:00AM

Visit Castello di Verrazzano

Embark on a guided tour and wine tasting at Castello di Verrazzano, a historic winery producing renowned Chianti Classico wines.
Castello di Verrazzano is easily accessible by car from Siena, offering picturesque vineyard views.
EUR 30, 2 hours

1:00PM

Lunch at Ristorante Malborghetto

Enjoy a leisurely lunch at Ristorante Malborghetto, offering a delightful menu of traditional Tuscan dishes paired with local wines.
Ristorante Malborghetto is located in the Chianti region, providing a serene setting for a relaxing meal.
EUR 20, 1.5 hours

4:00PM

Explore Greve in Chianti

Take a stroll through the charming town of Greve in Chianti, known for its picturesque square, local markets, and quaint shops.
Greve in Chianti can be explored on foot, allowing you to immerse yourself in the authentic Tuscan ambiance.
Free, 1.5 hours

7:00PM

Dinner at La Cantinetta di Rignana

Indulge in a gourmet dinner at La Cantinetta di Rignana, a rustic-chic restaurant offering a fine selection of Tuscan dishes.
La Cantinetta di Rignana is nestled in the Chianti countryside, providing a tranquil dining experience.
EUR 40, 2 hours
Find Hotels in Chianti

Day 4: Quaint Beauty of San Gimignano

San Gimignano, Italy

9:00AM

Visit the Towering Skylines

Explore the medieval towers of San Gimignano, a UNESCO World Heritage site known for its well-preserved medieval architecture and captivating views.
Stroll through the historic center of San Gimignano to admire the characteristic towers and picturesque streets.
EUR 5 (for tower entrance), 2 hours

1:00PM

Lunch at Cum Quibus

Enjoy a delightful lunch at Cum Quibus, a cozy restaurant known for its traditional Tuscan cuisine and warm hospitality.
Cum Quibus is located in the heart of San Gimignano, offering a convenient dining spot during your exploration.
EUR 25, 1.5 hours

3:00PM

Gelato Indulgence at Gelateria Dondoli

Satisfy your sweet tooth with a scoop of gelato at Gelateria Dondoli, a renowned gelateria in San Gimignano with a variety of flavors to choose from.
Head to Gelateria Dondoli for a refreshing gelato break and enjoy the vibrant atmosphere of the town.
EUR 3, 30 minutes

7:00PM

Dinner at Ristorante Dorandò

Dine at Ristorante Dorandò for a culinary journey through Tuscan flavors, offering a menu inspired by local traditions and fresh ingredients.
Ristorante Dorandò is a charming restaurant in San Gimignano, perfect for a relaxing dinner after a day of exploration.
EUR 35, 2 hours
Find Hotels in San Gimignano

Day 5: Scenic Splendor

Montepulciano, Italy

10:00AM

Wine Tasting at Ercolenga Winery

Partake in a guided wine tasting session at Ercolenga Winery, a family-owned vineyard in Montepulciano renowned for its Vino Nobile wines.
Ercolenga Winery is located amidst the vineyards of Montepulciano, offering a serene setting for wine enthusiasts.
EUR 25, 2 hours

1:00PM

Lunch at Osteria Acquacheta

Delight in a rustic lunch at Osteria Acquacheta, a traditional trattoria known for its hearty Tuscan dishes and welcoming atmosphere.
Osteria Acquacheta is a popular dining spot in Montepulciano, providing a cozy setting for a leisurely meal.
EUR 20, 1.5 hours

3:00PM

Explore Piazza Grande

Wander around the historic Piazza Grande in Montepulciano, a charming square lined with Renaissance palaces, quaint cafes, and local boutiques.
Enjoy the picturesque surroundings of Piazza Grande, offering a glimpse into the rich history of Montepulciano.
Free, 1 hour

7:00PM

Farewell Dinner at La Grotta

Indulge in a farewell dinner at La Grotta, a refined restaurant known for its elegant ambiance and exquisite Tuscan cuisine, the perfect ending to your relaxing retreat.
La Grotta is a prestigious dining establishment in Montepulciano, ideal for a memorable dining experience.
EUR 50, 2 hours
Find Hotels in Montepulciano
0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version
Itinerary created by AI-assisted, human-reviewed

Plan Your Tuscany (don't forget in san gimignano) Trip

Cost Estimator
Estimate your trip budget
Packing List
Get a custom checklist
Weather Expert
Check weather & best time to go