Authentic 7-Day Florence and Tuscany Food, Wine & Culture Itinerary

Day 1: Florence City Introduction

Florence, Italy on May 23, 2025

8:30am

Breakfast at Caffè Gilli

Begin your day with classic Italian pastries and coffee at this historic café, beloved by locals and situated in the heart of Florence.
EUR10, 1h

9:45am

Walk through Piazza della Signoria and Palazzo Vecchio

Explore the lively square and admire the impressive Palazzo Vecchio, a symbol of Florence’s political history, before heading inside for a guided tour of the Renaissance interiors.
EUR15, 2h

12:00pm

Lunch at Trattoria Mario

Enjoy authentic Tuscan cuisine at this family-run trattoria renowned for its local specialties like ribollita and bistecca alla Fiorentina, popular among Florentines.
EUR30, 1h30m

2:00pm

Visit the Baptistery of St. John and Duomo Complex

Explore the stunning Duomo, climb Brunelleschi’s Dome for panoramic views, and visit the historic Baptistery, famous for its golden doors.
EUR20, 3h

5:30pm

Relax at Piazza Santo Spirito

Absorb the more local atmosphere of this less touristy piazza, perfect for an aperitivo at one of the artisan bars.
EUR10, 1h

7:30pm

Dinner at Vini e Vecchi Sapori

Dine in an intimate setting offering traditional Tuscan dishes made from locally-sourced ingredients and paired with a carefully curated wine list.
EUR45, 2h
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Day 2: Florence Art and Culinary Delights

Florence, Italy on May 24, 2025

8:00am

Breakfast at La Ménagère

Enjoy a contemporary atmosphere while tasting fresh pastries and specialty coffee in this concept space combining florist and café.
EUR12, 1h

9:30am

Accademia Gallery Visit

See Michelangelo’s David and other Renaissance masterpieces; booking tickets ahead is advised to avoid long queues.
EUR20, 2h

12:00pm

Visit Mercato Centrale and Lunch

Explore Florence’s vibrant market featuring fresh produce and artisan foods; enjoy lunch from one of the many vendors specialising in regional dishes.
EUR20, 1h30m

2:00pm

Cooking Class with Local Chef

Participate in a hands-on cooking class focusing on Tuscan recipes like pappardelle al cinghiale and cantucci biscotti, concluding with a shared meal.
EUR100, 3h

6:00pm

Sunset walk along the Arno River and Ponte Vecchio

Enjoy the romantic views over Florence’s iconic river and historic bridge as evening sets in.
Free, 1h

7:30pm

Dinner at Osteria Santo Spirito

Experience traditional Tuscan home-cooked meals with a welcoming local atmosphere in this well-established osteria.
EUR40, 2h
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Day 3: Chianti Wine Region

Chianti, Tuscany, Italy on May 25, 2025

8:00am

Breakfast in Florence at Ditta Artigianale

Quick yet indulgent breakfast featuring artisanal coffee and pastries before departing to the countryside.
EUR10, 45m

9:00am

Drive to Chianti region

Travel south-east from Florence into the lush Chianti countryside, known for picturesque vineyards and olive groves.
Car rental cost, 1h

10:30am

Visit Castello di Ama winery

Tour the estate’s vineyards, contemporary art installations, and cellar followed by a tasting of renowned Chianti Classico wines.
EUR35, 2h

1:00pm

Lunch at Osteria Le Panzanelle

Enjoy rustic Tuscan dishes in this charming rural osteria surrounded by vineyards.
EUR30, 1h30m

3:00pm

Visit Greve in Chianti

Explore this historic town square with artisan shops, a wine museum, and sampling local delicacies at wine shops.
Free, 2h

5:30pm

Return to Florence

Drive back to Florence, relax before dinner.
Car rental cost, 1h

8:00pm

Dinner at Il Santo Bevitore

Modern Tuscan cuisine with innovative flavour combinations paired with excellent local wines.
EUR50, 2h
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Day 4: Siena’s History and Flavours

Siena, Tuscany, Italy on May 26, 2025

7:30am

Breakfast at local café in Florence - Pasticceria Nencioni

Enjoy classic Italian espresso and morning pastries in a lively neighbourhood pastry shop.
EUR8, 45m

8:30am

Travel to Siena by train

Approximately 1.5 hour scenic train ride through Tuscan hills to Siena.
EUR15 return, 1h30m

10:15am

Visit Siena Cathedral and Piccolomini Library

Explore gothic cathedral famous for intricate marble floors and vibrant frescoes, followed by the historic library.
EUR12, 2h

12:30pm

Lunch at Antica Osteria da Divo

Dine in a unique cave setting offering Tuscan specialties with locally sourced ingredients.
EUR35, 1h30m

2:00pm

Walk around Piazza del Campo and Torre del Mangia

Discover the famous shell-shaped square and climb the tower for panoramic views of Siena.
EUR10, 2h

4:30pm

Visit Enoteca Italiana

Wine tasting experience focusing on Tuscan and Italian wines within a stunning historic fortress.
EUR25, 1h30m

6:30pm

Return to Florence

Train back to your base in Florence.
EUR15, 1h30m

8:30pm

Low-key dinner at Trattoria La Casalinga

Simple, authentic home-style Tuscan cooking popular with locals, perfect after a long day exploring.
EUR25, 1h30m
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Day 5: San Gimignano and Countryside

San Gimignano, Tuscany, Italy on May 27, 2025

7:30am

Early breakfast at your Florence accommodation

Fuel up with a light breakfast featuring fresh fruit and coffee before an early start.
Included in accommodation, 30m

8:00am

Travel to San Gimignano by rental car

Enjoy approximately 1-hour scenic drive south through Tuscan hills and vineyards.
Car rental cost, 1h

9:15am

Explore San Gimignano medieval towers and old town

Stroll the historic town famous for its 14 medieval towers and charming alleys, avoiding peak tourist times.
Free, 2h

11:30am

Wine tasting and lunch at Tenuta Torciano

Visit this family-run winery for a tasting of local Vernaccia and Chianti wines paired with Tuscan antipasti.
EUR40, 2h

2:00pm

Visit the San Gimignano 1300 Museum

Experience a fascinating model of the town in the Middle Ages and local artefacts, providing deeper historical context.
EUR6, 1h

3:30pm

Gelato break at Gelateria Dondoli

Taste award-winning gelato at this world-famous gelateria located in the town square.
EUR5, 30m

4:00pm

Return drive to Florence

Leisurely drive back to Florence for an evening rest.
Car rental cost, 1h

7:30pm

Dinner at La Buchetta Food & Wine

End your day with a refined Tuscan meal focusing on local ingredients and a great wine list in a cosy setting.
EUR50, 2h
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Day 6: Lucca and Pisa Day Trip

Lucca and Pisa, Tuscany, Italy on May 28, 2025

7:00am

Breakfast at Hotel in Florence

Enjoy a hearty breakfast to prepare for a full day of exploration outside Florence.
Included in accommodation, 30m

7:30am

Train to Lucca

Catch an early train for the 1.5-hour scenic journey to Lucca, known for its Renaissance walls.
EUR15 return, 1h30m

9:15am

Cycle Lucca’s historic city walls

Rent a bike and enjoy a pleasant ride atop the fully intact city walls, surrounded by gardens and views.
EUR10 bike rental, 1h

10:30am

Explore Lucca’s historic centre and coffee break

Wander cobbled streets visiting Piazza dell’Anfiteatro and enjoy coffee at a local café.
EUR8, 1h

12:00pm

Train to Pisa

Short 30-minute train ride to Pisa to visit its famed monuments.
EUR7, 30m

12:45pm

Lunch near Piazza dei Miracoli

Relax with Tuscan dishes at Ristorante La Buca, just a short walk from the Leaning Tower.
EUR30, 1h30m

2:15pm

Visit Leaning Tower and Cathedral

Climb the Leaning Tower (booking ahead recommended) and explore the beautiful adjacent cathedral.
EUR25, 2h

4:30pm

Return to Florence

Evening train ride back to Florence to rest.
EUR15, 1h30m

7:30pm

Dinner at Trattoria Sabatino

Unwind with hearty traditional dishes and regional wines in this local favourite spot.
EUR35, 1h30m
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Day 7: Val d'Orcia Wine & Countryside

Val d'Orcia, Tuscany, Italy on May 29, 2025

7:00am

Very early breakfast at Florence accommodation

Light breakfast to prepare for long day trip by car or guided tour to South Tuscany.
Included, 30m

7:30am

Drive to Val d’Orcia

Journey through some of Tuscany’s most breathtaking landscapes, known for rolling hills and prestigious vineyards.
Car rental cost, 2h

9:30am

Visit Poggio Antico winery

Enjoy an exclusive tasting of Brunello di Montalcino and a tour of the vineyards and cellars.
EUR40, 2h

12:00pm

Lunch at Osteria Le Logge in Pienza

Delight in Pienza’s famous pecorino cheeses paired with local wines in this charming osteria.
EUR45, 1h30m

2:00pm

Explore Pienza & surrounding countryside walk

Stroll the Renaissance town streets and take a gentle walk in the surrounding UNESCO-listed landscape.
Free, 2h

4:30pm

Visit a local Olive Oil Farm for tasting

Learn about Tuscan olive oil production and enjoy sampling exceptional oils directly from the source.
EUR20, 1h

6:00pm

Drive back to Florence

Return to Florence after a fulfilling day of culture, cuisine, and stunning vistas.
Car rental cost, 2h

8:30pm

Final celebratory dinner at Enoteca Pinchiorri

Conclude your Tuscan experience with a Michelin-starred meal known for exquisite food paired with an exceptional wine cellar.
EUR150, 3h
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