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Ultimate 14-Day Italy Adventure: Rome, Sicily, Alberobello, Naples, Tuscany, Positano

Ultimate 14-Day Italy Adventure: Rome, Sicily, Alberobello, Naples, Tuscany, Positano Itinerary

Last updated: 2024 Jun 14

Iconic Rome: The Colosseum to Vatican City

Morning
Start your Italian adventure with a visit to the iconic Colosseum. Afterward, take a leisurely stroll through the ancient ruins of the Roman Forum and Palatine Hill.
Afternoon
Enjoy a traditional Roman lunch at Da Enzo Al 29 near Campo de' Fiori. Then, explore the grandeur of the Pantheon and the stunning Trevi Fountain.
Evening
Conclude your day with a visit to the beautiful Piazza Navona. For dinner, savor the local cuisine at Roscioli.
Bedtime
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Colosseum

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Roman Forum

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Vatican Wonders: Museums and Basilica

Morning
Spend the morning exploring the world-renowned Vatican Museums, including the Sistine Chapel. Don't miss the opportunity to visit the St. Peter's Basilica.
Afternoon
For a delightful lunch, head to Pizzarium near the Vatican. Afterward, relax in the peaceful St. Peter's Square.
Evening
Enjoy a leisurely evening in the charming neighborhood of Trastevere. Dine at the authentic Trattoria Da Cesare al Casaletto.
Bedtime
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Visit Vatican Museums (Musei Vaticani) in Rome, Italy
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Vatican Museums

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Sistine Chapel

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Rome's Hidden Gems: Catacombs and Appian Way

Morning
Explore the fascinating Catacombs of Rome and the ancient Appian Way.
Afternoon
Have a traditional Roman lunch at Ristorante Aroma. Spend the afternoon discovering the artistic treasures of the Borghese Gallery.
Evening
Enjoy a relaxing evening at the beautiful Spanish Steps. For dinner, indulge in a culinary experience at Il Pagliaccio.
Bedtime
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Catacombs of Rome

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Appian Way

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Welcome to Sicily: Palermo and Street Food

Morning
Arrive in the vibrant city of Palermo, Sicily. Start your day with a visit to the Norman Palace and Palatine Chapel.
Afternoon
Delight your taste buds with a street food tour in Palermo, sampling local specialties.
Evening
Enjoy a traditional Sicilian dinner at a local trattoria.
Bedtime
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Ancient Wonders: Agrigento and the Valley of the Temples

Morning
Explore the impressive Valley of the Temples in Agrigento, a UNESCO World Heritage Site.
Afternoon
Enjoy a leisurely Sicilian lunch in the area. Visit the archaeological museum to learn more about the history of the region.
Evening
Relax and enjoy the sunset at the Valley of the Temples.
Bedtime
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Trulli Magic in Alberobello

Morning
Discover the unique trulli houses of Alberobello, a UNESCO World Heritage Site.
Afternoon
Enjoy a traditional Apulian lunch in a local trattoria. Visit the Trullo Sovrano, a two-story trullo house.
Evening
Stroll through the charming streets of Alberobello and savor a romantic dinner in a trullo restaurant.
Bedtime
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Naples: Pizza and Pompeii

Morning
Arrive in Naples and start your day with a visit to the archaeological site of Pompeii.
Afternoon
Enjoy a classic Neapolitan pizza for lunch. Explore the historic center of Naples, a UNESCO World Heritage Site.
Evening
Sample the local street food for dinner and take in the vibrant atmosphere of the city.
Bedtime
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Enchanting Tuscany: Florence and Chianti

Morning
Travel to Florence and visit the world-famous Uffizi Gallery.
Afternoon
Enjoy a Tuscan lunch in the heart of Florence. Visit the Duomo and climb the Brunelleschi's Dome for panoramic views of the city.
Evening
Stroll across the Ponte Vecchio and have a delightful dinner in a traditional osteria.
Bedtime
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Brunelleschi's Dome

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Charming Siena and San Gimignano

Morning
Explore the medieval streets of Siena and visit the Siena Cathedral.
Afternoon
Enjoy a leisurely lunch in Siena. Continue to the hilltop town of San Gimignano and sample the famous Vernaccia di San Gimignano.
Evening
Watch the sunset over the Tuscan hills and savor a gourmet dinner in San Gimignano.
Bedtime
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Wine and Relaxation in the Chianti Region

Morning
Take a scenic drive through the Chianti countryside and visit a local winery for a wine tasting.
Afternoon
Enjoy a traditional Tuscan lunch at the winery. Relax and take in the beauty of the vineyards.
Evening
Return to Florence and have a farewell dinner at a Michelin-starred restaurant.
Bedtime
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Amalfi Coast Paradise: Positano and Ravello

Morning
Arrive in the picturesque town of Positano and spend the morning relaxing on the beach.
Afternoon
Enjoy a seafood lunch with a view of the sea. Take a boat trip along the coast to the charming town of Amalfi.
Evening
Explore the gardens of Villa Cimbrone in Ravello and have a romantic dinner overlooking the Mediterranean.
Bedtime
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Island Escape: Capri and Anacapri

Morning
Take a ferry to the island of Capri and visit the Blue Grotto.
Afternoon
Enjoy a leisurely lunch in Capri. Take the chairlift to Monte Solaro in Anacapri for panoramic views.
Evening
Explore the chic boutiques of Capri and have a farewell dinner on the island.
Bedtime
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Blue Grotto

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Relaxation in Positano: Beaches and Views

Morning
Spend your last day in Italy relaxing on the beaches of Positano.
Afternoon
Enjoy a leisurely seafood lunch. Take a walk through the town and savor the stunning views of the Amalfi Coast.
Evening
Watch the sunset with a glass of local limoncello. Have a farewell dinner at a cliffside restaurant.
Bedtime
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Departure Day: Positano to Rome

Morning
Depart from Positano and travel back to Rome for your return flight.
Afternoon
Depending on your flight time, you may have some free time in Rome for last-minute shopping or sightseeing.
Evening
Conclude your 14-day Italy adventure with a final dinner in Rome at a restaurant of your choice.
Bedtime
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