8 Days Italy Itinerary: Amalfi Coast, Capri, Rome, Florence, Tuscany, and Milan

Day 1: Arrival & Exploration

Positano, Italy on March 4, 2025

8:00 AM

Neapolitan Breakfast

Start your day with a rich Neapolitan coffee and a warm sfogliatella at Gran Caffè Gambrinus, a historic café with elegant décor.
EUR10, 1 hour

9:30 AM

Spaccanapoli & Underground

Wander through Spaccanapoli, the bustling heart of Naples, and consider visiting the intriguing Naples Underground for some history.
EUR15, 2 hours

12:00 PM

Lunch at Da Adolfo

Enjoy lunch at Da Adolfo, located beachside in Positano, with fresh seafood and stunning views. Accessible by boat.
EUR25, 1.5 hours

2:00 PM

Explore Positano

Stroll through Positano's picturesque streets and visit Fornillo Beach for a quieter beach experience compared to Spiaggia Grande.
FREE, 2 hours

5:30 PM

Sunset at Villa Cimbrone

Drive to Ravello for exceptional sunset views on the Terrazza dell’Infinito at Villa Cimbrone.
EUR10, 1 hour

7:00 PM

Dinner at Rossellinis

Dine at Rossellinis, a Michelin-starred restaurant with fantastic views and delightful Italian cuisine.
EUR100, 2 hours
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Day 2: Capri Adventure

Capri, Italy on March 5, 2025

8:00 AM

Ferry to Capri

Take a scenic ferry ride from Positano to the stunning island of Capri, embracing its natural beauty.
EUR20, 0.5 hours

9:00 AM

Private Boat Tour

Embark on a private boat tour to the iconic Blue Grotto and the beautiful Faraglioni Rocks, capturing breathtaking sea views.
EUR150, 2 hours

12:00 PM

Lunch at Da Paolino

Indulge in a unique lunch under lemon trees at Da Paolino, a beloved spot that offers Mediterranean specialties.
EUR40, 1.5 hours

2:00 PM

Explore Anacapri

Discover the charms of Anacapri, visiting Villa San Michele and the hidden Scala Fenicia stairs.
EUR8, 2 hours

5:00 PM

Sunset at Giardini di Augusto

Enjoy a breathtaking sunset at Giardini di Augusto, a garden with unparalleled views of the Bay of Naples.
EUR5, 1 hour

7:00 PM

Light Dinner in Positano

Head back to Positano for a lighter dinner at your leisure, perhaps enjoying pizza or fresh pasta at a local trattoria.
EUR30, 1.5 hours
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Day 3: Pompeii & Rome

Rome, Italy on March 6, 2025

8:00 AM

Drive to Pompeii

Make your way to Pompeii, where you'll step into ancient history and walk among stunning ruins.
EUR30, 1 hour

9:00 AM

Explore Pompeii

Wander the ruins, visiting key sites like the Forum and Villa of the Mysteries, to truly appreciate this historical site.
EUR18, 2 hours

12:00 PM

Lunch at Caupona

Savor a meal at Caupona, which serves dishes inspired by ancient Roman cuisine, located right in Pompeii.
EUR25, 1 hour

1:30 PM

Train to Rome

Hop on a fast train from Naples to Rome, enjoying the picturesque views along the way.
EUR30, 1.5 hours

3:00 PM

Explore Trastevere

Roam through Trastevere, a charming neighborhood with cobblestone streets, offering a local feel of Rome.
FREE, 2 hours

6:00 PM

Dinner at Taverna Trilussa

Enjoy a classic Roman dinner at Taverna Trilussa, renowned for its delicious carbonara and cacio e pepe.
EUR40, 2 hours

8:30 PM

Drinks at Jerry Thomas Speakeasy

Unwind with creative cocktails at Jerry Thomas Speakeasy, a hidden bar with a unique vibe. Don’t forget to book in advance.
EUR15, 2 hours
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Day 4: Rome Highlights

Rome, Italy on March 7, 2025

7:30 AM

Visit Colosseum & Roman Forum

Begin your day early at the Colosseum and Roman Forum to beat the crowds and immerse yourself in Roman history.
EUR25, 2 hours

10:00 AM

Walk to Trevi Fountain

Take a leisurely stroll to the iconic Trevi Fountain and toss a coin to ensure your return to Rome.
FREE, 1 hour

11:30 AM

Lunch at Roscioli

Savor authentic Roman dishes at Roscioli, a gourmet deli that will leave your taste buds dancing.
EUR35, 1.5 hours

1:00 PM

Visit Pantheon & Piazza Navona

Explore the architectural marvel of the Pantheon and enjoy the lively atmosphere of Piazza Navona.
FREE, 2 hours

3:30 PM

Keyhole of Rome

Discover the Keyhole of Rome for a secret peek at St. Peter’s Basilica through a garden gate, a breathtaking hidden gem.
FREE, 1 hour

5:00 PM

Sunset at Gianicolo Hill

Enjoy a spectacular sunset at Gianicolo Hill, a beautiful viewpoint to appreciate the city skyline.
FREE, 1 hour

6:30 PM

Dinner at Il Margutta RistorArte

Dine at Il Margutta RistorArte for an exquisite vegetarian fine dining experience, surrounded by art.
EUR50, 1.5 hours
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Day 5: Vatican & Florence

Florence, Italy on March 8, 2025

7:00 AM

Visit Vatican Museums

Start your day at the Vatican Museums and Sistine Chapel, marveling at Michelangelo's masterpieces.
EUR30, 2.5 hours

9:30 AM

Tour St. Peter’s Basilica

Proceed to St. Peter’s Basilica, where you can climb the dome for breathtaking views of Vatican City.
EUR10, 1.5 hours

11:30 AM

Lunch at Pizzarium Bonci

Grab a delicious slice of pizza al taglio at Pizzarium Bonci, a local favorite known for exceptional toppings.
EUR15, 1 hour

1:00 PM

Train to Florence

Catch a fast train to Florence and relax as you travel through the Tuscan countryside.
EUR40, 1.5 hours

2:30 PM

Sunset at Piazzale Michelangelo

Reach Piazzale Michelangelo for panoramic views of Florence, perfect for capturing sunset photos.
FREE, 1.5 hours

6:00 PM

Dinner at Osteria Vini e Vecchi Sapori

Enjoy an authentic Tuscan meal at Osteria Vini e Vecchi Sapori, known for its warm atmosphere and traditional dishes.
EUR50, 2 hours
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Day 6: Florence & Tuscany

Florence, Italy on March 9, 2025

8:00 AM

Uffizi Gallery

Visit the renowned Uffizi Gallery early to see masterpieces by Botticelli and Leonardo da Vinci.
EUR25, 2 hours

10:30 AM

Michelangelo's David

See Michelangelo’s David at the Accademia Gallery and marvel at this iconic Renaissance work.
EUR12, 1 hour

12:00 PM

Lunch at Trattoria Mario

Savor classic bistecca alla fiorentina at Trattoria Mario, a local and lively dining spot.
EUR30, 1.5 hours

2:00 PM

Explore Boboli Gardens

Wander through the beautiful Boboli Gardens, showcasing magnificent landscaping and a view of Florence's skyline.
EUR10, 1.5 hours

5:00 PM

Dinner at La Giostra

End your day at La Giostra, where the romantic setting and excellent pasta will create a memorable dining experience.
EUR50, 2 hours
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Day 7: Chianti & San Gimignano

Milan, Italy on March 10, 2025

8:00 AM

Drive through Chianti

Rent a car and drive through the picturesque Chianti wine region, enjoying the scenic vineyards along the way.
EUR40, 2 hours

10:00 AM

Visit Winery

Stop at Antinori nel Chianti Classico Winery for an educational tour and wine tasting in a stunning location.
EUR25, 2 hours

12:30 PM

Lunch at Dario Cecchini

Enjoy lunch at Dario Cecchini’s butcher shop in Panzano, acclaimed for its legendary steaks.
EUR35, 1.5 hours

2:00 PM

Visit San Gimignano

Wander through the medieval streets of San Gimignano, sampling the famous gelato from Gelateria Dondoli.
EUR5, 2 hours

5:00 PM

Drive to Milan

Take a scenic drive to Milan, or opt to return to Florence and travel via train.
EUR50, 3.5 hours

8:00 PM

Dinner at Ratanà

Experience modern Milanese cuisine at Ratanà, well-known for its thoughtful dishes prepared with quality ingredients.
EUR60, 2 hours
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Day 8: Departure & Sightseeing

Milan, Italy on March 11, 2025

8:00 AM

Visit The Last Supper

Start your day with a visit to The Last Supper; ensure to book your tickets well in advance.
EUR15, 1 hour

9:30 AM

Explore Duomo di Milano

Head to the Duomo di Milano, climbing to the rooftop for stunning views of the city.
EUR10, 2 hours

12:00 PM

Lunch at Luini Panzerotti

Indulge in the iconic Milanese street food, panzerotti, at Luini Panzerotti, perfect for a quick bite.
EUR8, 1 hour

1:00 PM

Galleria Vittorio Emanuele II

Stroll through Galleria Vittorio Emanuele II for last-minute shopping and enjoy the elegant atmosphere.
FREE, 1 hour
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