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14-Day Italy and Greece Adventure: September 2025 Itinerary

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Day 1: Explore Rome

Rome, Italy on September 1, 2025

8:00AM

Breakfast at Roscioli

Start your day with a traditional Italian breakfast at Roscioli, known for its fresh pastries and espresso. The ambiance is warm and welcoming.
EUR15, 1 hour

9:00AM

Visit the Colosseum

Explore the ancient Colosseum, a marvel of Roman engineering and history, best experienced early in the day to avoid crowds.
EUR18, 2 hours

11:00AM

Roman Forum Tour

Step into history at the Roman Forum, the heart of ancient Rome, and witness the ruins that once shaped the empire.
EUR12, 2 hours

1:00PM

Lunch at Trattoria Da Enzo

Indulge in classic Roman dishes like Pasta Carbonara or Amatriciana at Trattoria Da Enzo, famed for its cozy atmosphere.
EUR20, 1.5 hours

2:30PM

Vatican Museums

Visit the Vatican Museums, a treasure trove of art and history, culminating in the breathtaking Sistine Chapel.
EUR17, 3 hours

5:30PM

St. Peter's Basilica

Discover the awe-inspiring St. Peter's Basilica, the centerpiece of Vatican City and one of the largest churches globally.
Free, 1 hour

7:00PM

Dinner at Osteria dell'Ingegno

Enjoy an exquisite Italian dinner at Osteria dell'Ingegno, offering a menu filled with local flavors and seasonal ingredients.
EUR30, 2 hours
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Day 2: More of Rome

Rome, Italy on September 2, 2025

8:30AM

Breakfast at Pasticceria Regoli

Enjoy traditional Italian cornetti and cappuccino at Pasticceria Regoli, a pastry shop loved by locals.
EUR10, 1 hour

9:30AM

Tour of the Pantheon

Visit the Pantheon, one of the best-preserved ancient buildings in Rome, known for its impressive dome and oculus.
EUR5, 1 hour

10:30AM

Trevi Fountain

Stop by the stunning Trevi Fountain; don't forget to toss a coin for good luck!
Free, 30 minutes

11:30AM

Borghese Gallery

Explore the Borghese Gallery, home to a fantastic collection of Baroque art including works by Caravaggio and Bernini.
EUR13, 2 hours

1:30PM

Lunch at La Carbonara

Savor traditional Roman dishes at La Carbonara, famous for its namesake dish served with guanciale.
EUR18, 1.5 hours

3:00PM

Explore Trastevere

Wander through the picturesque streets of Trastevere, filled with charming shops, cafes, and local history.
Free, 3 hours

6:00PM

Sunset at Piazza Navona

End your day at Piazza Navona, enjoying the stunning fountains and vibrant atmosphere as the sun sets.
Free, 1 hour

7:30PM

Dinner at Il Margutta

Discover vegetarian Italian cuisine at Il Margutta, known for its creative dishes using local ingredients.
EUR25, 2 hours
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Day 3: Travel to Florence

Florence, Italy on September 3, 2025

7:00AM

Breakfast at Hotel

Enjoy a quick breakfast at your hotel before heading to Florence.
Included in stay, 1 hour

8:00AM

Train to Florence

Take a scenic train ride to Florence, enjoying views of the Tuscan countryside along the way.
EUR30, 1.5 hours

9:30AM

Check-in at Hotel

Arrive in Florence and check in to your hotel, preparing for a day of exploration.
Free, 1 hour

10:30AM

Uffizi Gallery

Visit the Uffizi Gallery, one of the most famous art museums in the world, housing masterpieces like Botticelli's 'Birth of Venus.'
EUR20, 2 hours

12:30PM

Lunch at All' Antico Vinaio

Try the Florentine sandwiches at All' Antico Vinaio, renowned for their generous portions and delicious fillings.
EUR10, 1 hour

1:30PM

Florence Cathedral (Duomo)

Climb to the top of the Florence Cathedral for breathtaking views of the city and an appreciation of its architecture.
EUR18, 2.5 hours

4:00PM

Ponte Vecchio

Stroll across the iconic Ponte Vecchio, lined with shops and a perfect spot for photos.
Free, 1 hour

5:00PM

Boboli Gardens

Relax in the beautiful Boboli Gardens, offering stunning views and a peaceful retreat from the busy city.
EUR10, 1.5 hours

6:30PM

Dinner at Trattoria Mario

Experience authentic Tuscan cuisine at Trattoria Mario, a bustling eatery well-loved by locals.
EUR25, 2 hours
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Day 4: Florence Sightseeing

Florence, Italy on September 4, 2025

8:00AM

Breakfast at Caffè Gilli

Start your day at Caffè Gilli, a historic cafe known for its pastries and divine coffee.
EUR12, 1 hour

9:00AM

Accademia Gallery

See Michelangelo's David at the Accademia Gallery, one of Florence's essential cultural experiences.
EUR12, 1.5 hours

10:30AM

Mercato Centrale

Visit Mercato Centrale for a sample of local delicacies and an immersive culinary experience.
Free, 2 hours

12:30PM

Lunch at La Giostra

Lunch at La Giostra promises a memorable meal featuring traditional Tuscan dishes in a cozy atmosphere.
EUR30, 1.5 hours

2:00PM

San Miniato al Monte

Visit the beautiful San Miniato al Monte for panoramic views of Florence and inspiring architecture.
Free, 1.5 hours

4:00PM

Visit Santa Croce

Explore the stunning Basilica di Santa Croce, the burial place of famous Italians like Michelangelo.
EUR8, 1 hour

5:00PM

Gelato at Gelateria dei Neri

Treat yourself to gelato at Gelateria dei Neri, one of the best spots in Florence.
EUR5, 30 minutes

6:00PM

Dinner at Osteria Vini e Vecchi Sapori

Enjoy an intimate dining experience at Osteria Vini e Vecchi Sapori, known for its seasonal menus and local wines.
EUR30, 2 hours
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Day 5: Scenic Venice

Venice, Italy on September 5, 2025

7:00AM

Breakfast at Hotel

Enjoy a classic Venetian breakfast at your hotel before the big day ahead.
Included in stay, 1 hour

8:00AM

Train to Venice

Travel to Venice and experience the enchanting landscapes along the way.
EUR35, 2.5 hours

10:30AM

Check-in at Hotel

Arrive in Venice and check in at your hotel before venturing out.
Free, 1 hour

11:30AM

St. Mark's Basilica

Marvel at the stunning architecture of St. Mark's Basilica, known for its intricate mosaics.
EUR5, 1 hour

12:30PM

Lunch at Osteria al Portego

Stop by Osteria al Portego for local cicchetti (small plates), perfectly paired with a glass of wine.
EUR20, 1.5 hours

2:00PM

Doge's Palace

Discover the magnificent Doge's Palace, a masterpiece of Gothic architecture filled with history.
EUR20, 2 hours

4:00PM

Rialto Bridge

Stroll across the iconic Rialto Bridge, a perfect place for people-watching and souvenirs.
Free, 1 hour

5:00PM

Gondola Ride

Experience a romantic gondola ride as you glide through Venice's unique canals.
EUR80, 30 minutes

6:00PM

Dinner at Antiche Carampane

Savor dinner at Antiche Carampane, offering fresh seafood and local dishes in a charming setting.
EUR50, 2 hours
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Day 6: More Venice

Venice, Italy on September 6, 2025

8:00AM

Breakfast at Hotel

Start your day with breakfast at your hotel, enjoying local pastries and coffee.
Included in stay, 1 hour

9:00AM

Visit the Peggy Guggenheim Collection

Explore the Peggy Guggenheim Collection, a modern art museum featuring works from renowned artists.
EUR15, 2 hours

11:00AM

Visit the Murano Glass Factory

Watch skilled artisans create exquisite glass pieces at the famous Murano Glass Factory.
Free, 1.5 hours

1:00PM

Lunch at Muro Rialto

Enjoy a leisurely lunch at Muro Rialto, known for its seafood risotto and lively atmosphere.
EUR25, 1.5 hours

2:30PM

Explore Burano Island

Take a boat to Burano Island, famous for its colorful houses and lace-making tradition.
EUR20 (round trip), 3 hours

5:30PM

Return to Venice

After exploring Burano, return to Venice for a relaxed evening.
Included in round-trip ticket, 1 hour

6:30PM

Dinner at Osteria da Fiore

Dine at Osteria da Fiore, known for its sophisticated Venetian dishes and Michelin star.
EUR70, 2 hours
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Day 7: Travel to Milan

Milan, Italy on September 7, 2025

7:00AM

Breakfast at Hotel

Start your day with breakfast at your hotel, featuring classic Italian options.
Included in stay, 1 hour

8:00AM

Train to Milan

Take a comfortable train ride to Milan, the fashion capital of Italy.
EUR25, 2.5 hours

10:30AM

Check-in at Hotel

Arrive in Milan and check in at your hotel before starting your day.
Free, 1 hour

11:30AM

Visit Duomo di Milano

Explore the stunning Duomo di Milano, an iconic cathedral with breathtaking architecture.
EUR15, 2 hours

1:30PM

Lunch at Luini

Try the famous panzerotti at Luini, a local favorite stuffed pastry.
EUR10, 1 hour

2:30PM

Galleria Vittorio Emanuele II

Walk through the stunning Galleria Vittorio Emanuele II, one of the world's oldest shopping malls.
Free, 1 hour

3:30PM

Castello Sforzesco

Visit Castello Sforzesco, a historic castle housing museums and beautiful gardens.
EUR10, 1.5 hours

5:00PM

Relax at Sempione Park

Unwind at Sempione Park, a beautiful green space perfect for a stroll.
Free, 1 hour

6:00PM

Dinner at Ratanà

Savor contemporary Milanese cuisine at Ratanà, celebrated for its modern approach to traditional dishes.
EUR35, 2 hours
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Day 8: Flight to Athens

Athens, Greece on September 8, 2025

7:00AM

Breakfast at Hotel

Enjoy breakfast at your hotel before departing for Athens.
Included in stay, 1 hour

8:00AM

Flight to Athens

Fly from Milan to Athens, enjoying the stunning views from above.
EUR80, 2 hours

10:00AM

Check-in at Hotel

Arrive in Athens and check in at your hotel.
Free, 1 hour

11:00AM

Visit the Acropolis

Explore the Acropolis, the ancient citadel, featuring iconic structures like the Parthenon.
EUR20, 3 hours

2:00PM

Lunch at Ta Karamanlidika Tou Fania

Savor authentic Greek flavors at Ta Karamanlidika Tou Fania, known for its cured meats and cheeses.
EUR15, 1.5 hours

3:30PM

Plaka District

Wander through the historic Plaka district, known for its charming streets and local shops.
Free, 2 hours

5:30PM

Visit the Ancient Agora

Explore the Ancient Agora, a significant site of ancient Athens filled with ruins and history.
EUR10, 1.5 hours

7:00PM

Dinner at Klimataria

Enjoy a traditional Greek dinner at Klimataria, featuring delicious grilled meats and souvlaki.
EUR25, 2 hours
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Day 9: Explore Athens

Athens, Greece on September 9, 2025

8:00AM

Breakfast at Hotel

Grab a quick breakfast at your hotel before your day of exploration.
Included in stay, 1 hour

9:00AM

National Archaeological Museum

Visit the National Archaeological Museum, one of the world's most important ancient art and history museums.
EUR12, 2 hours

11:00AM

Visit Mount Lycabettus

Take a funicular ride to the top of Mount Lycabettus for breathtaking views of the Athens skyline.
EUR7, 2 hours

1:00PM

Lunch at Savvas

Savor authentic Greek sandwiches at Savvas, a favorite among locals for its fast and delicious food.
EUR5, 1 hour

2:00PM

Explore Monastiraki Flea Market

Wander around Monastiraki Flea Market, a vibrant market filled with antiques and souvenirs.
Free, 2 hours

4:00PM

Byzantine Museum

Discover the Byzantine Museum, a treasure trove of Byzantine art and history.
EUR8, 1.5 hours

5:30PM

Relax at a Café in Plaka

Unwind at a café in the Plaka district, enjoying a coffee and a pastry.
EUR6, 1.5 hours

7:00PM

Dinner at Taverna Vasilis

Experience a lively atmosphere at Taverna Vasilis, known for its homemade Greek dishes.
EUR20, 2 hours
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Day 10: Travel to Santorini

Santorini, Greece on September 10, 2025

8:00AM

Breakfast at Hotel

Have breakfast at your hotel before flying to Santorini.
Included in stay, 1 hour

9:00AM

Flight to Santorini

Catch a flight to Santorini, the stunning island known for its white-washed buildings and beautiful sunsets.
EUR75, 1 hour

10:00AM

Check-in at Hotel

Arrive in Santorini and check in at your hotel.
Free, 1 hour

11:00AM

Explore Oia

Wander through Oia, famous for its picturesque streets and stunning sea views.
Free, 2 hours

1:00PM

Lunch at Ammoudi Fish Tavern

Enjoy fresh seafood at Ammoudi Fish Tavern, located right by the water with beautiful views.
EUR30, 1.5 hours

2:30PM

Wine Tasting at a Local Vineyard

Experience local wines with a vineyard tour and tasting to savor Santorini's unique flavors.
EUR25, 2 hours

4:30PM

Relax at the Beach

Spend some leisure time at one of Santorini's famous beaches, known for their unique volcanic sand.
Free, 2 hours

6:30PM

Dinner at Sunset at Ammoudi

Savor dinner with a stunning sunset view at Sunset at Ammoudi, known for its romantic atmosphere.
EUR40, 2 hours
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Day 11: Explore Santorini

Santorini, Greece on September 11, 2025

8:00AM

Breakfast at Hotel

Enjoy breakfast with a view at your hotel before heading out for the day.
Included in stay, 1 hour

9:00AM

Visit Akrotiri Archaeological Site

Explore the ancient ruins of Akrotiri, a Minoan settlement frozen in time after a volcanic eruption.
EUR12, 2 hours

11:00AM

Wine Tasting at Venetsanos Winery

Visit Venetsanos Winery for another wine tasting experience complemented by breathtaking views of the caldera.
EUR25, 2 hours

1:30PM

Lunch at To Pakhari Tavern

Enjoy hearty Greek fare at To Pakhari Tavern, known for its warm service and homestyle meals.
EUR20, 1.5 hours

3:00PM

Hike from Fira to Oia

Embark on the scenic hike from Fira to Oia, offering stunning views of the caldera.
Free, 3 hours

6:00PM

Dinner at 1800 Restaurant

Dine at 1800 Restaurant, an upscale venue offering Mediterranean cuisine with exceptional sunset views.
EUR50, 2 hours
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Day 12: Travel to Mykonos

Mykonos, Greece on September 12, 2025

8:00AM

Breakfast at Hotel

Enjoy breakfast at your hotel before traveling to Mykonos.
Included in stay, 1 hour

9:00AM

Ferry to Mykonos

Take a ferry to the iconic island of Mykonos, known for its beaches and vibrant nightlife.
EUR40, 2 hours

11:00AM

Check-in at Hotel

Arrive in Mykonos and check in at your hotel, getting ready for island activities.
Free, 1 hour

12:00PM

Explore Mykonos Town

Stroll the charming streets of Mykonos Town, filled with whitewashed buildings and vibrant shops.
Free, 2 hours

2:00PM

Lunch at Katerina's

Dine at Katerina's, known for its delicious seafood, offering fresh meals and stunning sea views.
EUR35, 1.5 hours

3:30PM

Visit Little Venice

Relax at Little Venice, a beautiful area famous for its waterfront bars and picturesque views.
Free, 2 hours

5:30PM

Relax at a Beach

Enjoy the stunning beaches of Mykonos; spend the afternoon soaking up the sun.
Free, 3 hours

8:30PM

Dinner at Astra

Experience a lively dinner at Astra, known for its great atmosphere and global cuisine.
EUR45, 2 hours
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Day 13: Mykonos Fun

Mykonos, Greece on September 13, 2025

8:00AM

Breakfast at Hotel

Enjoy a leisurely breakfast at your hotel before exploring more of Mykonos.
Included in stay, 1 hour

9:00AM

Visit Delos Island

Take a day trip to Delos Island, a UNESCO World Heritage Site known for its ancient ruins.
EUR20 (round trip by ferry), 5 hours

2:00PM

Lunch at Mykonos' Beach Clubs

Visit one of the famous beach clubs in Mykonos where you can enjoy beachside dining.
EUR30, 2 hours

4:00PM

Relax at a Beach or Party

Spend your afternoon at a beach or one of the vibrant beach parties Mykonos is known for.
Free, 3 hours

8:00PM

Dinner at Mattarello

Enjoy traditional Italian dishes at Mattarello, perfect for a cozy dinner after a lively day.
EUR35, 2 hours
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Day 14: Travel to Thessaloniki

Thessaloniki, Greece on September 14, 2025

7:00AM

Breakfast at Hotel

Enjoy breakfast one last time at your hotel in Mykonos.
Included in stay, 1 hour

8:00AM

Flight to Thessaloniki

Fly from Mykonos to Thessaloniki, your final destination.
EUR60, 1 hour

9:00AM

Check-in at Hotel

Check-in upon arrival in Thessaloniki.
Free, 1 hour

10:00AM

Visit the White Tower

Explore the historic White Tower, a symbol of the city and a must-see landmark.
EUR8, 1 hour

11:30AM

Lunch at Modestou

Savor Greek dishes and friendly service at Modestou, known for its traditional recipes.
EUR15, 1.5 hours

1:00PM

Explore the Rotunda

Visit the Rotunda, an impressive Roman monument with a stunning interior.
EUR4, 1 hour

2:30PM

Relax at Aristotelous Square

Take a break at Aristotelous Square, the city's central square filled with cafes and shops.
Free, 1.5 hours

4:00PM

Dinner at La Doze Vita

End your trip with dinner at La Doze Vita, offering a cozy atmosphere and delicious Mediterranean dishes.
EUR25, 2 hours
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