Two-Week Winter Exploration of Tuscany's Charming Towns and Culinary Delights

Day 1: Florence Arrival

Florence, Italy on January 1, 2025

9:00am

Breakfast at Caffè Gilli

Begin your Tuscan adventure with a traditional Italian breakfast at Caffè Gilli, open from 7:30am, famous for its pastries and coffee.

EUR7, 1h0m

10:30am

Uffizi Gallery Tour

Explore masterpieces of Renaissance art at the Uffizi Gallery, open 8:15am - 6:30pm, to admire works by Botticelli and Leonardo da Vinci.

EUR20, 2h0m

1:00pm

Lunch at Trattoria Mario

Enjoy authentic Tuscan cuisine, such as ribollita or pappardelle, at Trattoria Mario, open 12:00pm - 3:00pm.

EUR25, 1h30m

3:00pm

Walk to Florence Cathedral (Duomo)

Climb the Duomo for panoramic city views or visit from 10:00am - 4:30pm to admire Brunelleschi’s dome and exquisite frescoes.

EUR18, 1h30m

6:00pm

Dinner at La Giostra

Savor Tuscan specialties with a romantic atmosphere; La Giostra opens for dinner at 7:00pm and is renowned for its wild boar dishes.

EUR40, 2h0m

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Day 2: Florence to Siena

Florence to Siena, Italy on January 2, 2025

8:00am

Breakfast at Hotel

Enjoy a hearty breakfast at your hotel before departure, typically served from 7:00am to 9:00am, to fuel up for the day.

Included, 1h0m

9:30am

Travel to San Gimignano

Drive or take a bus for about 1 hour to San Gimignano, enjoying views of the Tuscan countryside en route.

EUR15, 1h0m

10:45am

Explore San Gimignano

Visit this medieval walled town with its famous towers, open generally 9:00am - 6:00pm; don’t miss the Collegiate Church with its frescoes.

EUR7, 2h0m

1:00pm

Lunch at Osteria delle Catene

Taste traditional Tuscan dishes like pici pasta in this cozy tavern, open 12:00pm - 3:00pm.

EUR30, 1h0m

2:30pm

Travel to Siena

Transfer to Siena by car or bus in about 45 minutes, settling into your accommodation.

EUR10, 0h45m

3:30pm

Visit Piazza del Campo

Explore Siena’s famous shell-shaped square, often lively even in January, a perfect spot for afternoon strolls.

Free, 1h0m

5:00pm

Siena Cathedral (Duomo) visit

Open from 10:30am to 5:00pm, the cathedral features stunning Gothic architecture and art by Pisano and Donatello.

EUR15, 1h0m

7:30pm

Dinner at La Taverna di San Giuseppe

Enjoy hearty Tuscan fare including saffron risotto in a typical Siena basement setting, open for dinner from 7:00pm.

EUR35, 2h0m

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Day 3: Siena Countryside

Siena, Italy on January 3, 2025

8:30am

Breakfast at Panificio Il Magnifico

Grab fresh pastries and coffee from this beloved bakery open from 7:30am for a quick bite before touring.

EUR6, 0h30m

9:00am

Day trip to Montepulciano and Pienza

Drive 1 hour to Montepulciano, explore its Renaissance palaces and wineries (open 10:00am-5:00pm), then head 20 minutes to Pienza, a Renaissance gem famous for pecorino cheese.

EUR20, 5h0m

2:00pm

Lunch at Osteria Acquacheta in Montepulciano

Indulge in grilled Florentine steak and rustic dishes, open noon-3:00pm, much appreciated for its authentic flavors.

EUR35, 1h15m

5:00pm

Return to Siena

Back to Siena in the evening, relax and get ready for dinner.

Included, 1h0m

7:30pm

Dinner at Antica Osteria da Divo

Dine in a historic church cellar known for its refined Tuscan dishes and impressive wine list, open for dinner from 7:00pm.

EUR50, 2h0m

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Day 4: Montalcino Wine Day

Siena to Montalcino, Italy on January 4, 2025

8:00am

Breakfast at Hotel

Enjoy a comforting breakfast at your Siena hotel before departing for Montalcino, served from 7:00am.

Included, 1h0m

9:00am

Travel to Montalcino

Drive about 40 minutes to Montalcino, famed for its Brunello wine and beautiful countryside.

EUR10, 0h40m

10:00am

Brunello Wine Tasting at Castello Banfi

Tour the vineyard and cellar, enjoy guided tasting sessions of premier Brunello wines, open 10:00am - 5:00pm.

EUR30, 2h0m

12:30pm

Lunch at Ristorante Il Leccio

Dine with views of vineyards and enjoy traditional Tuscan dishes paired with local wines, open from noon to 2:30pm.

EUR40, 1h30m

2:30pm

Explore Montalcino town center

Visit the fortress and stroll the historic streets; the fortress opens from 9:00am to 6:00pm.

EUR8, 1h30m

5:00pm

Return to Siena

Head back to Siena for the evening, relax or enjoy a casual stroll in town.

Included, 0h40m

7:00pm

Dinner at Osteria Le Logge

Celebrate with refined cuisine highlighting local ingredients in an elegant ambiance, open for dinner from 7:00pm.

EUR60, 2h0m

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Day 5: Travel to Lucca

Siena to Lucca, Italy on January 5, 2025

8:00am

Breakfast at Hotel

Start your day with breakfast before the journey north to Lucca.

Included, 1h0m

9:30am

Travel to Lucca

Drive approximately 2.5 hours to the walled city of Lucca, known for its Renaissance walls and charming streets.

EUR25, 2h30m

12:00pm

Lunch at Trattoria da Leo

Enjoy classic Lucchese dishes such as tordelli pasta or farro soup in a relaxed and welcoming environment, open 12:00pm - 2:30pm.

EUR25, 1h30m

2:00pm

Walk or bike on Lucca's City Walls

Open all day, walking or biking the tree-lined Renaissance walls provides scenic views over Lucca’s red roofs and surrounding countryside.

Free, 2h0m

5:00pm

Visit Lucca Cathedral

Explore the Duomo di San Martino, featuring notable artworks and views from its bell tower, open 9:30am - 5:30pm in winter.

EUR6, 1h0m

7:30pm

Dinner at Ristorante Giglio

Dine on refined traditional Tuscan dishes in Lucca’s historic center, open from 7:00pm.

EUR45, 2h0m

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Day 6: Pisa Day Trip

Lucca to Pisa, Italy on January 6, 2025

8:30am

Breakfast at Hotel

Enjoy breakfast before a brief trip to Pisa, available at most hotels from 7:00am.

Included, 1h0m

9:30am

Travel to Pisa

Take a short 30-40 minute drive or train to Pisa, placing you right for the afternoon of exploration.

EUR10, 0h40m

10:15am

Visit Piazza dei Miracoli and Leaning Tower

Explore Pisa’s iconic square including the Leaning Tower (book tickets in advance for tower climb from 9:00am - 6:00pm), cathedral, baptistery, and cemetery.

EUR25, 2h0m