Two-Week Italy Food and Culture Tour: Architecture, Wine, and Culinary Delights

Day 1: Arrival and Roman Exploration

Rome, Italy on May 5, 2025

9:00am

Breakfast at Tazza d'Oro

Start the morning with top-notch Italian coffee at Tazza d'Oro near the Pantheon, perfect for the husband’s coffee passion.
EUR5, 0h30m

10:00am

Pantheon and Piazza Navona Tour

Explore the Pantheon’s magnificent ancient architecture and stroll to Piazza Navona to admire Baroque fountains and lively street art.
EUR0, 2h

12:30pm

Lunch at Roscioli

Enjoy Roman specialties such as carbonara and burrata in a historic deli and restaurant known for its exceptional Italian wines and cheeses.
EUR50, 1h30m

2:30pm

Colosseum and Roman Forum Visit

Discover ancient Roman engineering and ruins, soaking in stunning architectural history that is a cornerstone of Rome.
EUR16, 3h

6:00pm

Chocolate Tasting at Venchi

Indulge in artisanal chocolates and gelato at Venchi, a luxurious spot perfect for the wife’s chocolate interests.
EUR15, 1h

7:30pm

Dinner at Trattoria da Enzo

Experience authentic Roman dishes in a cozy, traditional trattoria that emphasizes local ingredients and handcrafted pasta.
EUR45, 1h30m
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Day 2: Historic Rome and Artistic Immersion

Rome, Italy on May 6, 2025

8:30am

Espresso at Sant'Eustachio Il Caffè

Visit this famous coffee shop known for its secret blend and old-school espresso machine to delight the husband's palate.
EUR5, 0h30m

9:30am

Vatican Museums and Sistine Chapel Tour

Admire priceless Renaissance masterpieces and Michelangelo’s ceiling fresco, a must for art and architecture lovers.
EUR30, 3h

1:00pm

Lunch at Pizzarium

Taste gourmet Roman-style pizza by the slice, famed for its creative toppings and light crust.
EUR20, 1h

2:30pm

Chocolate Painting Lesson

The wife can enjoy a unique painting lesson using edible chocolate, blending creativity with her love for chocolate, offered nearby in central Rome.
EUR70, 2h

5:00pm

Walk the Spanish Steps and Via Condotti

Stroll through elegant streets with classic architecture and high-end boutiques, perfect for relaxed sightseeing.
EUR0, 1h

7:00pm

Dinner at Osteria del Pegno

Enjoy a refined meal featuring seasonal Tuscan ingredients in a charming, intimate atmosphere.
EUR50, 1h30m
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Day 3: Leisure and Departure to Florence

Rome to Florence, Italy on May 7, 2025

7:30am

Breakfast at Ciampini

Enjoy a rich Italian cappuccino and freshly baked pastries ideal for an early start before travel.
EUR10, 0h30m

9:00am

Train to Florence

Take a fast train (about 1.5 hours) to Florence, setting the stage for Renaissance architecture and culinary delights.
EUR50, 1h30m

11:00am

Florence Duomo and Baptistery Visit

Marvel at the stunning Renaissance dome designed by Brunelleschi and intricate baptistery mosaics in the city's heart.
EUR20, 2h

1:30pm

Lunch at Trattoria Mario

Relish traditional Tuscan fare at this lively eatery known for its authentic grilled meats and local wines.
EUR40, 1h30m

3:00pm

Coffee and Chocolate Pairing at La Cité

Explore a pairing session where the husband can taste premium coffees while the wife enjoys exceptional artisan chocolates.
EUR30, 1h

5:00pm

Uffizi Gallery Tour

Experience the world’s finest collection of Renaissance art, including works by Botticelli and Leonardo da Vinci.
EUR20, 2h

7:30pm

Dinner at Il Latini

Savor hearty Tuscan specialties in a bustling, traditional setting that celebrates local recipes.
EUR50, 1h30m
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Day 4: Florence and Painting Lesson

Florence, Italy on May 8, 2025

8:30am

Breakfast and Coffee at Ditta Artigianale

The husband enjoys expertly brewed specialty coffee while the wife indulges in sweets from the patisserie.
EUR15, 0h45m

9:30am

Painting Lesson for Wife

A private painting lesson focused on Renaissance-inspired art in a local studio, offering skill development with expert guidance.
EUR100, 3h

1:00pm

Lunch at La Ménagère

A trendy eatery combining floral, culinary, and artistic ambiance, serving fresh and inventive Tuscan dishes.
EUR40, 1h30m

2:30pm

Ponte Vecchio and Artisan Shops

Wander the famous medieval bridge and browse exquisite jewelry and artisanal shops in Florence’s historic center.
EUR0, 1h30m

4:00pm

Boboli Gardens

Relax in vast Renaissance gardens with sculptures and beautiful views of Florence’s skyline.
EUR10, 2h

7:00pm

Dinner at Enoteca Pitti Gola e Cantina

Enjoy a fine dining experience paired with a vast selection of Tuscan wines in proximity to the Pitti Palace.
EUR70, 2h
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Day 5: Horseback Riding and Tuscan Countryside

Florence to Montepulciano, Italy on May 9, 2025

7:30am

Breakfast at Café Rivoire

Taste classic Italian espresso and pastries with views of the Piazza della Signoria.
EUR15, 0h45m

9:00am

Departure to Montepulciano

Travel by car or train for about 2 hours to reach the beautiful hill town known for its wine and charming medieval architecture.
EUR40, 2h

11:30am

Lunch at Osteria Acquacheta

Enjoy robust Tuscan cuisine with local meats and cheeses in this beloved Montepulciano spot.
EUR45, 1h30m

2:00pm

Afternoon Horseback Riding in the Tuscan Hills

Explore scenic trails around Montepulciano on horseback, ideal for immersing in the pastoral beauty of Tuscany.
EUR70, 2h

5:00pm

Visit Montepulciano Historic Center

Stroll narrow medieval streets to admire Renaissance palaces and panoramic views.
EUR0, 1h

7:00pm

Dinner at La Grotta

Dine inside ancient grottos with hearty Tuscan specialties and an excellent wine list.
EUR50, 1h30m
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Day 6: Montepulciano Wine Tour

Montepulciano, Italy on May 10, 2025

8:30am

Breakfast at Bar Il Palazzone

Start with a refreshing espresso for the husband and pastries for the wife at this popular local café.
EUR10, 0h30m

9:30am

Guided Wine Tour of Montepulciano Vineyards

Spend the day touring renowned vineyards and cellars sampling Vino Nobile di Montepulciano and learning about the winemaking process.
EUR100, 5h

3:00pm

Lunch at La Bottega del Nobile

Light lunch featuring antipasti paired with wines directly from Montepulciano cellars.
EUR40, 1h30m

5:00pm

Relax and Walk Montepulciano Walls

Take in sunset views from the town’s ancient walls overlooking the picturesque valley below.
EUR0, 1h

7:00pm

Dinner at Etrusco Ristorante

Experience fine dining with modern Tuscan flavors and fresh local ingredients in a sophisticated setting.
EUR65, 2h
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Day 7: Medieval Siena Charm

Montepulciano to Siena, Italy on May 11, 2025

7:30am

Breakfast at Caffè Poliziano

Enjoy a rich Italian espresso and fresh baked goods in town before departure.
EUR10, 0h30m

9:00am

Travel to Siena

Take a 1.5-hour drive to the medieval city of Siena famed for its Gothic architecture and rich history.
EUR40, 1h30m

11:00am

Siena Cathedral and Piazza del Campo Tour

Explore the ornate Siena Cathedral and the lively Piazza del Campo, where the famous Palio horse race takes place.
EUR15, 2h

1:30pm

Lunch at Antica Trattoria Papei

Savor traditional Sienese dishes including pici pasta and wild boar sauce in a warm local atmosphere.
EUR40, 1h30m

3:00pm

Chocolate and Coffee Discovery Walk

Follow a guided food walk tasting regional chocolates and stopping by specialty coffee shops adored by locals.
EUR35, 2h

6:00pm

Relax at Hotel before Dinner

Rest in your accommodations to prepare for an elegant night out in Siena’s historic center.
EUR0, 1h

7:30pm

Dinner at La Taverna di San Giuseppe

Enjoy a blend of rustic Tuscan dishes and fine wines in a famous cellar restaurant known for historic ambiance.
EUR60, 2h
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Day 8: Siena Art and Leisure

Siena, Italy on May 12, 2025

8:00am

Breakfast at Nannini Pasticceria

Start with specialty coffee options for the husband and exquisite pastries for the wife at this popular Siena bakery.
EUR12, 0h45m

9:00am

Painting Lesson in Siena

The wife enjoys a morning painting class focusing on local historical architecture inspired by Siena’s stunning artistic heritage.
EUR90, 3h

12:30pm

Lunch at Osteria Le Logge

Delight in refined Sienese cuisine with locally sourced ingredients and excellent wine pairings.
EUR50, 1h30m

2:00pm

Visit Museo Civico and Torre del Mangia

Explore medieval and Renaissance art, then climb the Torre del Mangia for panoramic views of Siena and the Tuscan countryside.
EUR15, 2h

5:00pm

Coffee Stop at Caffè della Posta

Enjoy a late afternoon espresso at a historic café, ideal for the husband’s coffee interest.
EUR5, 0h30m

7:30pm

Dinner at Ristorante Guido

Experience elegant Tuscan dining with traditional recipes and a cozy ambiance close to the cathedral.
EUR60, 2h
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Day 9: Travel to Venice and Explore

Siena to Venice, Italy on May 13, 2025

7:00am

Early Breakfast at Hotel

Light breakfast available before departure for Venice.
EUR0, 0h30m

8:00am

Train to Venice

Travel by train for approximately 3.5 hours from Siena to Venice, enjoying changing landscapes.
EUR60, 3h30m

12:00pm

Lunch at Trattoria al Gazzettino

Traditional Venetian seafood dishes in a relaxed and inviting atmosphere near the canals.
EUR45, 1h30m

2:00pm

St. Mark’s Basilica and Piazza San Marco

Visit the stunning Byzantine architecture of St. Mark’s Basilica and enjoy the lively atmosphere of the piazza.
EUR5, 2h

4:30pm

Chocolate Tasting at VizioVirtù

Taste artisanal Venetian chocolates in a stylish shop specializing in small-batch sweets perfect for the wife.
EUR15, 1h

6:30pm

Coffee Break at Torrefazione Cannaregio

Husband enjoys premium Venetian coffee roasts at this cozy and authentic café.
EUR5, 0h30m

7:30pm

Dinner at Osteria alle Testiere

Sample exquisite Venetian seafood dishes crafted from fresh local catch in an intimate setting.
EUR70, 2h
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Day 10: Venetian Art and Canals

Venice, Italy on May 14, 2025

8:30am

Breakfast at Pasticceria Tonolo

Begin with Venetian pastries and rich coffee in a favorite local bakery.
EUR12, 0h45m

9:30am

Painting Class for Wife

Private art class focused on Venetian landscapes and architecture using watercolors, guided by a local artist.
EUR100, 3h

1:00pm

Lunch at All’Arco

Informal lunch with delicious cicchetti (Venetian tapas) paired with local wines.
EUR30, 1h

2:30pm

Gondola Ride and Grand Canal Tour

Experience Venice’s charm from the water on a classic gondola trip highlighting the city’s stunning architecture.
EUR80, 1h

4:00pm

Explore Doge’s Palace

Tour this magnificent Gothic palace with lavish halls and historical artifacts of Venetian power.
EUR25, 2h

7:00pm

Dinner at Antiche Carampane

Enjoy fresh seafood with authentic Venetian recipes in a beloved hidden gem restaurant.
EUR70, 2h
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Day 11: Leisure and Farewell Venice

Venice, Italy on May 15, 2025

8:30am

Coffee and Pastries at Café Florian

Savor historic coffee and pastries in one of the world’s oldest cafés while enjoying the vibrant atmosphere.
EUR20, 1h

9:30am

Leisure Day Shopping and Sightseeing

Spend your final day exploring artisan shops for chocolates, ceramics, and coffee blends, or revisit favorite spots at a relaxed pace.
EUR0, 4h

2:00pm

Lunch at Ristorante Quadri

An upscale lunch overlooking Piazza San Marco with an exquisite menu combining Venetian tradition and innovation.
EUR75, 1h30m

4:00pm

Relaxation at Hotel or Spa

Enjoy some downtime preparing for departure with optional spa services available at your hotel.
EUR50, 2h

7:30pm

Farewell Dinner at Michelin-starred Venissa

Celebrate your enchanting Italian tour with creative Venetian cuisine and exceptional wine pairings in a secluded island vineyard restaurant.
EUR120, 2h
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