14-Day Italian Food & Architecture Journey with Wine and Horseback Riding

Day 1: Arrival & Ancient Rome

Rome, Italy on May 5, 2025

8:00am

Breakfast at Roscioli Caffè

Start your day with traditional Italian pastries and espresso at this iconic Roman café, setting a perfect tone for your culinary adventure.
EUR15, 1h0m

9:30am

Colosseum and Roman Forum Tour

Explore the iconic Colosseum and the adjacent Roman Forum, marveling at ancient architecture and rich history with a guided tour.
EUR18, 3h0m

1:00pm

Lunch at Trattoria Vecchia Roma

Enjoy authentic Roman cuisine such as carbonara in a cozy, traditional trattoria known for its charming atmosphere.
EUR35, 1h30m

3:00pm

Explore Piazza Navona and Pantheon

Stroll through Piazza Navona’s stunning fountains and admire the Pantheon's impressive dome, soaking in Renaissance and Baroque architecture.
Free, 2h0m

6:00pm

Dinner at Armando al Pantheon

Dine near the Pantheon with classic Roman dishes paired with regional wines to end your day beautifully.
EUR50, 2h0m
View Hotel Availability

Day 2: Vatican & Local Flavors

Rome, Italy on May 6, 2025

7:30am

Breakfast at Pasticceria Regoli

Treat yourself to freshly baked maritozzi and espresso at this local favorite bakery before your day starts.
EUR10, 0h45m

8:30am

Vatican Museums and Sistine Chapel

Visit the Vatican Museums early to admire Renaissance masterpieces and Michelangelo’s stunning Sistine Chapel ceiling.
EUR30, 3h30m

12:30pm

Lunch at Osteria delle Commari

Enjoy local Roman dishes made with seasonal ingredients in a cozy osteria near the Vatican.
EUR40, 1h30m

3:00pm

Visit Castel Sant’Angelo and Stroll along the Tiber River

Explore the historic fortress offering panoramic city views and a scenic walk along the riverbanks.
EUR15, 2h0m

7:00pm

Dinner at Roscioli

Indulge in a top-rated wine bar and delicatessen serving refined Italian dishes and an excellent wine selection.
EUR60, 2h0m
View Hotel Availability

Day 3: Trastevere & Leisure

Rome, Italy on May 7, 2025

8:00am

Breakfast at Bar San Calisto

Enjoy a simple yet authentic Roman espresso and pastry experience in the lively Trastevere neighborhood.
EUR8, 0h45m

9:00am

Walk through Trastevere’s streets and visit Santa Maria in Trastevere

Explore the charming cobblestone streets and beautifully adorned basilica known for its mosaics.
Free, 2h0m

12:00pm

Lunch at Da Enzo al 29

Savor traditional Roman plates made with fresh ingredients in a small, popular trattoria in Trastevere.
EUR40, 1h30m

3:00pm

Leisurely afternoon and shopping at Via del Corso

Spend your afternoon discovering shops and enjoying the Roman street atmosphere before your next travel day.
Variable, 3h0m

7:30pm

Dinner at Enoteca Ferrara

Experience an elegant dinner paired with fine Italian wines in a refined setting in Trastevere.
EUR70, 2h0m
View Hotel Availability

Day 4: Renaissance Florence

Florence, Italy on May 8, 2025

8:00am

Breakfast at Caffè Rivoire

Start your day at Piazza della Signoria with excellent coffee and delicious pastries.
EUR12, 1h0m

9:30am

Uffizi Gallery Visit

Discover world-renowned Renaissance masterpieces including Botticelli’s ‘The Birth of Venus’ with advance tickets to avoid queues.
EUR25, 3h0m

1:00pm

Lunch at Trattoria Mario

Enjoy hearty Tuscan specialties in this bustling local spot near the Mercato Centrale.
EUR30, 1h30m

3:00pm

Visit Florence Cathedral and Baptistery

Climb the dome for stunning views and admire the intricate gothic and renaissance facade.
EUR20, 2h0m

7:00pm

Dinner at Osteria Vini e Vecchi Sapori

Dine on traditional Tuscan dishes with a curated wine list in a cozy, intimate atmosphere.
EUR50, 2h0m
View Hotel Availability

Day 5: Florence Art & Markets

Florence, Italy on May 9, 2025

8:00am

Breakfast at Pasticceria Giorgio

Enjoy freshly baked croissants and espresso close to the historic center.
EUR10, 1h0m

9:30am

Accademia Gallery: Michelangelo’s David

See the iconic statue and other remarkable Renaissance artworks early to avoid crowds.
EUR22, 2h0m

12:00pm

Lunch at Mercato Centrale

Explore a vibrant food market offering a wide variety of fresh, artisanal Tuscan foods and wines.
EUR30, 1h30m

2:30pm

Walk across Ponte Vecchio and explore artisan shops

Admire the historic bridge and browse unique jewelry and craft shops along it.
Free, 2h0m

6:00pm

Sunset at Piazzale Michelangelo

Enjoy spectacular panoramic views over Florence as the sun sets over the city.
Free, 1h30m

8:00pm

Dinner at La Giostra

Experience romantic dining with exquisite Tuscan cuisine in an atmospheric setting.
EUR70, 2h0m
View Hotel Availability

Day 6: Horseback Riding & Countryside

Florence, Italy on May 10, 2025

7:30am

Breakfast at Hotel or local café

Enjoy a light breakfast to prepare for active morning horseback riding.
EUR15, 0h45m

9:00am

Horseback Riding Tour in the Tuscan Countryside

Spend a morning riding through scenic landscapes outside Florence with a guide to appreciate Tuscany’s natural beauty and rural tranquility.
EUR90, 3h0m

1:00pm

Lunch at a countryside agriturismo

Enjoy authentic farm-to-table Tuscan meals made with local ingredients in a rustic setting.
EUR40, 1h30m

3:30pm

Relax and stroll in Florence’s Boboli Gardens

Wander through grand Renaissance gardens with sculptures and spectacular views of the city.
EUR10, 2h0m

7:00pm

Dinner at Il Latini

Feast on generous Tuscan portions and enjoy warm service beloved by locals and visitors alike.
EUR50, 2h0m
View Hotel Availability

Day 7: Arrival & Wine Tour

Montepulciano, Italy on May 11, 2025

8:00am

Travel to Montepulciano from Florence

Take a morning train or private transfer to the charming hill town of Montepulciano known for its wine.
EUR40, 2h0m

11:00am

Check into Hotel Palazzo Carletti

Settle into this elegant 15th-century hotel with panoramic views of the Tuscan countryside.
EUR150 per night, 0h30m

12:00pm

Lunch at La Grotta

Dine in a cozy restaurant in the historic center offering local specialties and Vino Nobile di Montepulciano.
EUR40, 1h30m

2:00pm

Wine Tour and Tasting at Avignonesi Estate

Join a renowned guided tour with tastings of premium local wines including the famous Vino Nobile.
EUR70, 3h0m

6:30pm

Evening stroll through Montepulciano’s piazzas

Absorb the medieval charm of town squares and views from tower terraces.
Free, 1h0m

7:30pm

Dinner at Osteria Acquacheta

Enjoy traditional Tuscan meats and comfort food with an excellent wine list in a rustic setting.
EUR50, 2h0m
View Hotel Availability

Day 8: Montepulciano & Wine Cellars

Montepulciano, Italy on May 12, 2025

8:00am

Breakfast at Bar Caffè Poliziano

Start your day with espresso and pastries at a well-loved local café.
EUR10, 0h45m

9:00am

Explore Montepulciano’s medieval streets and Palazzo Comunale

Visit town halls and piazzas featuring Renaissance architecture and panoramic terraces.
EUR10, 2h0m

12:00pm

Lunch at Le Logge del Vignola

Enjoy elegant dining with exquisite local dishes and Vino Nobile di Montepulciano in a refined atmosphere.
EUR55, 1h30m

2:30pm

Guided cellar tour & tasting at Cantina Contucci

Discover historic wine cellars dating back to the 14th century with a guided tasting session.
EUR40, 2h0m

6:30pm

Relax at Piazza Grande

Enjoy evening people-watching in Montepulciano’s main square surrounded by stunning architecture.
Free, 1h0m

7:30pm

Dinner at Ristorante La Bottega del Nobile

Sample refined Tuscan cuisine paired with outstanding Montepulciano wines in an intimate setting.
EUR60, 2h0m
View Hotel Availability

Day 9: Countryside & Leisure

Montepulciano, Italy on May 13, 2025

8:00am

Breakfast at Hotel

Enjoy a leisurely breakfast with local jams and freshly brewed coffee.
Included in hotel, 1h0m

9:30am

Day trip: Horseback Riding through Tuscan Vineyards

Embark on a scenic horseback ride through vineyards and rolling hills around Montepulciano, perfect for nature and wine lovers.
EUR100, 4h0m

2:00pm

Lunch picnic with wine near vineyards

Enjoy a relaxing lunch picnic featuring local cheeses, meats, breads, and bottle of Vino Nobile amid beautiful landscape views.
EUR40, 1h30m

4:00pm

Relax and shop in town

Spend your afternoon enjoying Montepulciano’s artisanal shops, cafes, and historical sites at a relaxed pace.
Free, 3h0m

7:30pm

Dinner at Osteria Lunetta

Close your stay in Montepulciano with refined dishes highlighting local ingredients and wines in a historic building.
EUR50, 2h0m
View Hotel Availability

Day 10: Siena’s Charm

Siena, Italy on May 14, 2025

8:00am

Breakfast at Pasticceria Nannini

Try Siena’s famous cantucci biscuits and cappuccino at this popular café near the city center.
EUR12, 1h0m

9:30am

Arrival and walking tour of Siena’s Historic Center

Discover Piazza del Campo, Siena Cathedral, and medieval streets filled with stunning Gothic architecture.
EUR15, 3h0m

1:00pm

Lunch at Osteria Le Logge

Enjoy refined Tuscan dishes paired with excellent wines in a charming setting near the Piazza del Campo.
EUR50, 1h30m

3:00pm

Visit Museo dell’Opera del Duomo

Explore a museum housing artwork and artifacts from Siena Cathedral's history in elaborately decorated halls.
EUR12, 2h0m

7:00pm

Dinner at La Taverna di San Giuseppe

Relish hearty traditional dishes and an extensive wine list in a cozy medieval cellar ambiance.
EUR60, 2h0m
View Hotel Availability

Day 11: Siena & Surroundings

Siena, Italy on May 15, 2025

8:00am

Breakfast at your hotel or local café

Start your morning with fresh baked goods, espresso, and fruit.
EUR10, 1h0m

9:30am

Day trip to Chianti wine region

Experience a guided wine tour with tastings in famous Chianti vineyards and enjoy a traditional Tuscan lunch.
EUR100, 7h0m

5:00pm

Return to Siena, relax

Take a well-deserved rest after a full day exploring the vineyards and tasting great wines.
Free, 2h0m

7:30pm

Dinner at Antica Trattoria Papei

Dine on classic Sienese dishes with homemade pasta and local ingredients in a warm setting.
EUR45, 2h0m
View Hotel Availability

Day 12: Siena & Departure

Siena, Italy on May 16, 2025

8:00am

Breakfast at Pasticceria Nannini

Enjoy a final sweet breakfast sampling Italian pastries and coffee.
EUR12, 1h0m

9:30am

Visit Basilica di San Domenico

Explore this Gothic basilica with beautiful frescoes and important relics related to Saint Catherine.
Free, 1h30m

11:30am

Last stroll in Siena and shopping

Use your last half-day to buy souvenirs and enjoy the city atmosphere.
Variable, 2h30m

2:00pm

Travel to Venice

Depart for Venice by train or plane, preparing for the next leg of your journey.
EUR60, 3h0m

5:00pm

Check into hotel in Venice

Settle in at a charming hotel near St. Mark’s Square or Grand Canal.
EUR180 per night, 0h30m

7:00pm

Dinner at Osteria alle Testiere

Enjoy fresh seafood and Venetian specialties paired with excellent local wines in an intimate bistro.
EUR70, 2h0m
View Hotel Availability

Day 13: Venice Classics

Venice, Italy on May 17, 2025

8:00am

Breakfast at Pasticceria Tonolo

Start with Venetian pastries and a cappuccino at this popular neighbourhood spot.
EUR10, 1h0m

9:00am

St. Mark’s Basilica and Doge’s Palace Tour

Explore Venetian Gothic architecture and history with skip-the-line tickets to two iconic landmarks.
EUR35, 3h0m

12:30pm

Lunch at Trattoria Al Gazzettino

Relax with hearty Venetian dishes and fresh seafood dishes popular among locals and tourists.
EUR45, 1h30m

2:30pm

Walk along the Grand Canal and visit Rialto Bridge and Market

Enjoy the vibrant atmosphere and stunning architecture along the key waterway and bustling market.
Free, 2h30m

6:30pm

Gondola Ride at Sunset

Experience the magic of Venice from the water with a romantic gondola ride through its canals.
EUR80, 0h45m

8:00pm

Dinner at Ristorante Quadri

Dine on refined Venetian cuisine in a historic setting overlooking St. Mark’s Square for a memorable farewell.
EUR90, 2h0m
View Hotel Availability

Day 14: Venice Departure

Venice, Italy on May 18, 2025

8:00am

Breakfast at hotel

Enjoy your final Italian breakfast with a view of the Venetian canals.
Included, 1h0m

9:30am

Leisurely morning stroll through Dorsoduro neighborhood

Explore lesser-known artistic and charming parts of Venice, perfect for culture lovers before departure.
Free, 2h0m

12:00pm

Lunch at Cantina Do Mori

Savor cicchetti (Venetian tapas) and a glass of local wine in one of Venice's historic bacari.
EUR35, 1h0m

2:00pm

Departure to airport or next destination

Head to Venice Marco Polo Airport or train station for your onward journey.
Variable, Variable
View Hotel Availability