Two-Week Luxury Itinerary Across Italy's Hidden Gems

Day 1: Florence Exploration

Florence, Italy on March 16, 2025

9:00AM

Breakfast at Caffè Gilli

Start your day at this historic café known for its delicious pastries and rich coffee, perfect before a day of exploring.
EUR15, 1 hour

10:30AM

Visit Uffizi Gallery

Explore one of the most admired art museums in the world, home to masterpieces by Botticelli and Michelangelo.
EUR20, 2 hours

1:00PM

Lunch at Trattoria Mario

Savor authentic Tuscan flavors in this lively trattoria famous for its ribollita and pasta dishes.
EUR25, 1.5 hours

3:00PM

Wander Ponte Vecchio

Stroll across this iconic bridge lined with shops selling art and jewelry, capturing the essence of Florence.
FREE, 1 hour

5:00PM

Visit Florence Cathedral

Marvel at the stunning architecture of the Duomo and consider climbing to the top for breathtaking city views.
EUR15, 2 hours

7:30PM

Dinner at La Giostra

Indulge in a gourmet dining experience with a romantic atmosphere, offering both exquisite pasta and wine pairings.
EUR80, 2 hours
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Day 2: More Florence

Florence, Italy on March 17, 2025

8:30AM

Breakfast at Pasticceria Nencioni

Known for their famous Cornetto, enjoy a breakfast pastry along with a rich Italian espresso.
EUR10, 1 hour

10:00AM

Day Trip to Pisa

Visit the iconic Leaning Tower of Pisa and enjoy the scenic surroundings of the Piazza dei Miracoli.
EUR15 (train fare), 4 hours including transit

2:30PM

Lunch near Pisa

Have a quick lunch at a local pizzeria for some classic Italian pizza.
EUR20, 1 hour

4:00PM

Return to Florence and Relax

Enjoy a leisurely afternoon in one of the stunning gardens, such as Giardino di Boboli.
EUR10, 2 hours

7:00PM

Dinner at Osteria All'Antico Vinaio

Known for their famous paninis, grab a quick dinner and experience a local favorite.
EUR15, 1 hour
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Day 3: Siena Day Trip

Siena, Italy on March 18, 2025

8:00AM

Breakfast at Bar Pasticceria Nannini

Enjoy the local pastries and coffee in this beloved bakery, the perfect start for your day in Siena.
EUR10, 1 hour

9:30AM

Explore Piazza del Campo

Discover the famous shell-shaped piazza, home to the historic Palio horse race.
FREE, 1 hour

11:00AM

Visit Siena Cathedral

Admire the stunning Gothic architecture and intricate artworks in this remarkable cathedral.
EUR10, 1.5 hours

1:00PM

Lunch at Osteria Le Logge

Experience exquisite traditional Sienese dishes in this lovely little restaurant nestled by the Piazza.
EUR30, 1.5 hours

3:00PM

Wander the Botanical Gardens

Stroll through these lush gardens filled with native plants, providing a peaceful retreat.
EUR5, 1 hour

6:00PM

Dinner at La Taverna di San Giuseppe

Enjoy hearty Sienese dishes in a cozy atmosphere, offering a true taste of the region.
EUR50, 2 hours
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Day 4: Travel to San Gimignano

San Gimignano, Italy on March 19, 2025

8:00AM

Breakfast at Local Café

Grab a quick breakfast at a local café before heading out to San Gimignano.
EUR10, 1 hour

9:30AM

Travel to San Gimignano

Take a scenic bus ride to the beautiful medieval town of San Gimignano.
EUR5 (bus fare), 1 hour

11:00AM

Explore San Gimignano Towers

Visit the iconic towers that define the city's skyline and offer a fantastic view of the countryside.
EUR10, 2 hours

1:00PM

Lunch at Ristorante Da i Marinaro

Savor wild boar ragu or other local dishes in this charming restaurant.
EUR25, 1.5 hours

3:00PM

Visit Gelateria Dondoli

Try world-famous gelato at this award-winning spot, a delicious treat after lunch.
EUR5, 30 minutes

5:00PM

Wine Tasting at a Local Vineyard

Join a wine-tasting session at a nearby vineyard and indulge in the flavors of regional wines.
EUR30, 2 hours

8:00PM

Dinner at La Mandragola

Enjoy traditional Tuscan cuisine with seasonal ingredients in an elegant setting.
EUR60, 2 hours
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Day 5: Travel to Volterra

Volterra, Italy on March 20, 2025

8:00AM

Breakfast at Bakery

Try a fresh pastry from a local bakery before your trip to Volterra.
EUR8, 1 hour

9:30AM

Travel to Volterra

Take a short bus ride to the enchanting town of Volterra.
EUR5 (bus fare), 1 hour

10:30AM

Visit the Roman Theatre

Explore this ancient theatre dating back to the 1st century BC, offering a glimpse into the past.
EUR12, 1 hour

12:00PM

Lunch at Ristorante La Carabaccia

Taste regional dishes made with local ingredients in a rustic setting.
EUR30, 1.5 hours

2:00PM

Explore the Alabaster Museum

Learn about Volterra's famous alabaster and its significance in the region.
EUR5, 1 hour

4:00PM

Wander through Volterra's Streets

Enjoy the medieval architecture while exploring the charming narrow streets.
FREE, 1 hour

7:00PM

Dinner at Ristorante Vigna di Vetra

Dine at a family-run establishment serving traditional Tuscan meals with an emphasis on local wines.
EUR50, 2 hours
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Day 6: Travel to Cinque Terre

Cinque Terre, Italy on March 21, 2025

8:00AM

Breakfast at Local Café

Enjoy a light breakfast at a local café before heading to Cinque Terre.
EUR10, 1 hour

9:30AM

Travel to Cinque Terre

Take a scenic train ride to the picturesque villages of Cinque Terre.
EUR20 (train fare), 2.5 hours

12:00PM

Lunch at Ristorante da Billy in Manarola

Taste a variety of fresh seafood dishes at this scenic restaurant with a beautiful view.
EUR40, 1.5 hours

2:00PM

Hike Between Villages

Enjoy stunning coastal views while hiking the trails that connect the five villages.
FREE, 3 hours

6:00PM

Dinner at Trattoria Il Porticciolo

Relish delicious pasta with pesto and other Ligurian specialities in a cozy port-side restaurant.
EUR35, 2 hours
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Day 7: Explore More of Cinque Terre

Cinque Terre, Italy on March 22, 2025

9:00AM

Breakfast at Local Bakery

Get fresh focaccia and coffee from a local bakery to start your day.
EUR10, 1 hour

10:30AM

Visit Vernazza

Explore one of Cinque Terre's most beautiful villages with colorful houses and a charming harbor.
FREE, 2 hours

1:00PM

Lunch at Il Pirata delle Cinque Terre

Enjoy local seafood and homemade dishes in a vibrant setting.
EUR30, 1.5 hours

3:00PM

Relax on the Beach in Monterosso

Take some time to unwind at the beach, go for a swim, or just soak up the sun.
FREE, 2 hours

5:30PM

Dinner at Trattoria da Angelo

Savor dishes made with fresh local ingredients in a casual atmosphere.
EUR30, 2 hours
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Day 8: Travel to Bologna

Bologna, Italy on March 23, 2025

8:00AM

Breakfast at Local Café

Enjoy a quick breakfast before departing for Bologna.
EUR10, 1 hour

9:30AM

Travel to Bologna

Take a train from Cinque Terre to Bologna.
EUR20 (train fare), 2.5 hours

12:00PM

Lunch at Trattoria Anna Maria

Sample traditional Bolognese dishes in a comforting atmosphere.
EUR30, 1.5 hours

2:00PM

Visit Two Towers

Explore the iconic Due Torri that define Bologna's skyline, and consider climbing to the top.
EUR5, 1 hour

4:00PM

Stroll through Piazza Maggiore

Enjoy Bologna's vibrant main square teeming with cafes and history.
FREE, 1 hour

6:00PM

Dinner at Ristorante Da Cesari

Experience traditional home-cooked Bolognese meals made from family recipes.
EUR40, 2 hours
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Day 9: Culinary Day in Bologna

Bologna, Italy on March 24, 2025

8:30AM

Breakfast at Pasticceria Imolese

Start your day with a sweet pastry and a robust cup of coffee in this friendly bakery.
EUR10, 1 hour

10:00AM

Cooking Class

Join a local cooking class to learn how to make the perfect Bolognese pasta.
EUR70, 3 hours

1:30PM

Lunch at Atelier del Gusto

Enjoy the pasta you just learned to make during your cooking class, paired with local wine.
EUR40, 2 hours

4:00PM

Visit Archiginnasio

Explore this historic building that houses the oldest university in the world.
EUR5, 1 hour

6:00PM

Dinner at Ristorante Al Cambio

Dine at this Michelin-starred restaurant known for innovative local cuisine.
EUR100, 2 hours
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Day 10: Travel to Venice

Venice, Italy on March 25, 2025

8:00AM

Breakfast at Local Café

Enjoy a classic Venetian breakfast with pastries and coffee.
EUR10, 1 hour

9:30AM

Travel to Venice

Take a train from Bologna to Venice.
EUR20 (train fare), 2 hours

12:00PM

Lunch at Osteria alle Testiere

Treat yourself to fresh seafood and homemade pasta in a charming atmosphere.
EUR60, 2 hours

2:00PM

Explore St. Mark's Square

Wander through the famous square, home to St. Mark's Basilica and the Campanile.
FREE, 1.5 hours

4:00PM

Gondola Ride on the Grand Canal

Experience a romantic gondola ride through the enchanting canals of Venice.
EUR80, 30 minutes

6:00PM

Dinner at Ristorante Antiche Carampane

Indulge in Venetian dishes made with local seafood in a historic restaurant.
EUR70, 2 hours
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Day 11: Discover Venice

Venice, Italy on March 26, 2025

9:00AM

Breakfast at Gran Caffè Quadri

Enjoy a decadent breakfast in this elegant café overlooking St. Mark's Square.
EUR30, 1 hour

10:30AM

Visit Doge's Palace

Explore the iconic palace and learn about the history of Venice's former rulers.
EUR25, 2 hours

1:00PM

Lunch at Trattoria Alla Madonna

Savor traditional Venetian cuisine in a popular trattoria favored by locals.
EUR40, 2 hours

3:30PM

Visit Rialto Bridge

Walk across this beautiful bridge, a key landmark of Venice, offering great views over the Grand Canal.
FREE, 1 hour

6:00PM

Dinner at Osteria da Fiore

Experience fine dining with a menu focused on fresh seafood and innovative dishes.
EUR90, 2 hours
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Day 12: Hidden Gems of Venice

Venice, Italy on March 27, 2025

9:00AM

Breakfast at Hotel

Enjoy a relaxed breakfast at your hotel before a day of exploration.
EUR20, 1 hour

10:30AM

Visit Murano and Burano

Take a boat tour to the colorful islands of Murano and Burano known for glass making and lace.
EUR35 (boat fare), 3 hours

2:00PM

Lunch at Trattoria Ai Pugni

Dine on a selection of fresh seafood and Italian fare in a casual setting.
EUR40, 1.5 hours

4:00PM

Explore Jewish Ghetto

Visit the historic Jewish Ghetto, one of the oldest in the world, and learn about its rich history.
FREE, 2 hours

6:00PM

Dinner at Antiche Carampane

End your evening by savoring more traditional Venetian dishes at this hidden gem restaurant.
EUR70, 2 hours
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Day 13: Relax and Reflect in Venice

Venice, Italy on March 28, 2025

9:00AM

Breakfast at Local Bar

Enjoy a leisurely breakfast at a local bar, indulging in the Venetian way of life.
EUR15, 1 hour

10:30AM

Walking Tour of Hidden Venice

Join a guided tour exploring Venice’s hidden gems and lesser-known secrets.
EUR50, 2.5 hours

1:00PM

Lunch at Osteria Al Bacco

Taste delicious homemade pasta and local dessert specialties in this quaint eatery.
EUR30, 2 hours

3:30PM

Visit Peggy Guggenheim Collection

Explore one of the most important collections of modern art in Europe, located in a spectacular setting.
EUR15, 1.5 hours

6:00PM

Farewell Dinner at Quadri

Conclude your Italian adventure with a memorable dinner overlooking St. Mark’s Square.
EUR100, 2 hours
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Day 14: Departure

Venice, Italy on March 29, 2025

9:00AM

Breakfast at Hotel

Enjoy a final breakfast before packing up for your departure.
EUR20, 1 hour

11:00AM

Check-out and Departure

Wrap up your trip and head to the airport with fond memories of Italy.
EUR0, 1 hour
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