Two-Week September Food and Wine Journey in Northern Italy

Day 1: Arrival and Milan Exploration

Milan, Italy on September 1, 2025

9:00am

Breakfast at Pasticceria Marchesi

Begin your culinary journey with a classic Italian breakfast featuring fresh pastries and rich espresso at one of Milan’s oldest and most prestigious cafes.
EUR20, 1h0m

10:30am

Visit the Duomo di Milano

Explore the iconic Gothic cathedral and its terraces, offering incredible views of Milan’s cityscape, perfect for a cultural start to your trip.
EUR15, 2h0m

1:00pm

Lunch at Trattoria Milanese

Enjoy traditional Milanese dishes like risotto alla Milanese and ossobuco in a cozy, authentic setting.
EUR35, 1h30m

3:00pm

Wine tasting at N'Ombra de Vin

Sample a curated selection of Northern Italian wines paired with local cheeses at this popular wine bar near Brera district.
EUR25, 1h30m

7:00pm

Dinner at Ristorante Cracco

Indulge in innovative haute cuisine by renowned chef Carlo Cracco, blending traditional Italian flavors with modern techniques.
EUR90, 2h0m
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Day 2: Venice Food and Sights

Venice, Italy on September 2, 2025

7:30am

Travel to Venice

Take a morning train from Milan to Venice, arriving in about 2.5 hours to maximize your day.
EUR40, 2h30m

10:30am

Breakfast at Farini

Enjoy fresh Venetian pastries and coffee in this modern bakery near the train station.
EUR15, 1h0m

11:45am

Walking tour of Rialto Market

Discover Venice’s vibrant food market with fresh seafood, produce, and local specialties, an ideal spot to understand Venetian cuisine.
EUR0, 1h0m

1:00pm

Lunch at Osteria alle Testiere

Savor a seafood-centric Venetian lunch with fresh catch and wine pairings in this intimate, highly rated osteria.
EUR60, 1h30m

3:00pm

Visit St. Mark’s Basilica

Admire the stunning mosaics and Byzantine architecture of Venice’s most famous church, open till 5 pm.
EUR3, 1h0m

5:00pm

Wine bar aperitivo at Cantina Do Spade

Enjoy a spritz and cicchetti (Venetian tapas) in a lively local wine bar to experience authentic Venetian evening culture.
EUR20, 1h30m

7:30pm

Dinner at Antiche Carampane

Relish traditional Venetian dishes away from tourist crowds, emphasizing fresh seafood and regional wines.
EUR70, 2h0m
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Day 3: Verona and the Valpolicella Wine Region

Verona, Italy on September 3, 2025

8:00am

Travel from Venice to Verona

Morning train to Verona, a cultural city with Roman history and excellent access to the Valpolicella wine region.
EUR15, 1h15m

9:30am

Breakfast in Piazza Bra

Enjoy coffee and homemade pastries at a cafe overlooking the Arena di Verona.
EUR15, 1h0m

11:00am

Valpolicella Wine Tour

Take a guided afternoon tour of top Valpolicella wineries, tasting Amarone and Ripasso wines paired with local cheeses and salumi.
EUR90, 4h0m

4:00pm

Stroll Verona Old Town

Explore the Juliet’s House, Roman Arena, and charming medieval streets for some cultural immersion.
EUR6, 2h0m

7:00pm

Dinner at Osteria Le Vecete

Taste traditional Veronese cuisine with local wines, known for hearty dishes like pastissada de caval and polenta.
EUR50, 1h30m
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Day 4: Bologna Culinary Day

Bologna, Italy on September 4, 2025

8:00am

Train to Bologna

Morning train from Verona to Bologna, famous for its rich gastronomy and medieval architecture.
EUR20, 1h15m

9:30am

Breakfast at Pasticceria Regina di Quadri

Indulge in rich cappuccinos and freshly baked torta di riso or croissants.
EUR15, 1h0m

10:30am

Visit Mercato di Mezzo

Explore this historic market filled with fresh produce, handmade pasta, cured meats, and cheeses.
EUR0, 1h0m

12:00pm

Cooking class: Tagliatelle and Ragù Bolognese

Participate in an authentic Bolognese cooking class to learn making traditional pasta and ragù first-hand.
EUR80, 3h0m

4:00pm

Visit Torre degli Asinelli

Climb the famous leaning towers for panoramic views of Bologna’s tiled rooftops and piazzas.
EUR5, 1h0m

7:30pm

Dinner at Trattoria da Gianni

Sample classic dishes such as tortellini in brodo and mortadella with a glass of local Pignoletto wine.
EUR45, 1h30m
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Day 5: Florence and Tuscan Wine

Florence, Italy on September 5, 2025

8:00am

Train to Florence

Travel south to Florence, the cradle of Renaissance art and close to Chianti’s famous vineyards.
EUR25, 1h30m

9:30am

Breakfast at Pasticceria Nencioni

Enjoy rich Italian espresso and cantucci biscuits dipped in vin santo.
EUR15, 1h0m

11:00am

Visit Uffizi Gallery

Discover masterpieces of Renaissance art; open from 8:15 am to 6:30 pm.
EUR20, 2h0m

1:30pm

Lunch at Trattoria Mario

Enjoy traditional Tuscan dishes like ribollita soup and Florentine steak in this popular local spot.
EUR40, 1h30m

3:30pm

Chianti Wine Half-Day Tour

Afternoon tour through Chianti’s rolling vineyards to taste Sangiovese wines and sample regional specialties.
EUR85, 4h0m

8:00pm

Dinner at Osteria All’Antico Vinaio

Casual dinner featuring famous Florentine sandwiches with local meats and cheeses paired with Tuscan wines.
EUR25, 1h0m
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Day 6: Florence Museums and Food

Florence, Italy on September 6, 2025

8:30am

Breakfast at Caffè Gilli

Start with elegant pastries and cappuccinos at one of Florence’s historic cafes.
EUR18, 1h0m

9:45am

Visit Accademia Gallery

See Michelangelo’s David and Renaissance art; open 8:15 am to 6:50 pm.
EUR16, 2h0m

12:00pm

Lunch at Il Latini

Feast on traditional Tuscan family recipes in a lively atmosphere known for bistecca alla Fiorentina.
EUR50, 1h30m

2:00pm

Florence Food Walking Tour

Discover Florence’s hidden culinary gems, artisanal shops, and street foods on a guided walking tour.
EUR60, 3h0m

6:00pm

Gelato tasting at Gelateria La Carraia

Sample some of the city’s best gelato just before sunset.
EUR6, 0h30m

7:30pm

Dinner at Enoteca Pinchiorri

Experience a Michelin-starred dinner paired with an extensive wine list representing top Tuscan vintages.
EUR120, 2h0m
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Day 7: Day Trip to Siena and Wine

Siena, Italy on September 7, 2025

8:00am

Travel to Siena

Morning bus or drive to Siena, a medieval city famous for its cuisine and proximity to Chianti and Brunello wine regions.
EUR25, 1h30m

9:30am

Breakfast at Pasticceria Nannini

Start with classic Sienese pastries and coffee at a renowned bakery.
EUR15, 1h0m

10:30am

Walking tour of Siena

Explore Piazza del Campo, Siena Cathedral, and local markets highlighting Tuscan specialties.
EUR10, 2h0m

12:45pm

Lunch and wine tasting at Castello di Ama

Visit this Chianti estate with excellent Brunello tastings and traditional Tuscan lunch options.
EUR80, 3h0m

4:00pm

Return to Florence

Relax on your journey back to Florence for your final evening.
EUR25, 1h30m

7:30pm

Farewell Dinner at La Giostra

Celebrate your trip with a cozy dinner featuring exquisite Tuscan fare and a robust wine list.
EUR70, 2h0m
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Day 8: Departure

Florence, Italy on September 8, 2025

7:00am

Breakfast at hotel

Enjoy a light breakfast preparing for your departure, reflecting on your Italian food and wine adventure.
Included, 0h30m

9:00am

Travel to airport

Transfer to Florence Airport for your onward flight home or next destination.
EUR30, 1h0m
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