21-Day Ultimate Italy Itinerary: Rome, Florence, Venice, Milan, Lake Como & Amalfi Coast Adventure

Day 1: Arrival and Iconic Rome

Rome, Italy on June 10, 2025

8:00am

Arrive Rome and Hotel Check-in

Arrive at Fiumicino Airport; transfer by Leonardo Express train (€14) to Roma Termini and check into your central Rome hotel near Campo Marzio. Rest and freshen up after the long flight.
EUR14, 1h

12:00pm

Walking Tour of Rome Squares

Explore Piazza Navona, the Pantheon (free entry), and toss a coin in the Trevi Fountain. Soak up the lively Roman atmosphere on foot.
Free, 2h

1:30pm

Lunch at Roscioli

Enjoy classic Roman pasta carbonara at Roscioli, a renowned deli and restaurant near Campo de’ Fiori.
EUR30, 1h

5:30pm

Rooftop Dinner at Aroma

Dine with stunning views of the Colosseum at Aroma, a rooftop restaurant offering refined Italian cuisine. Ideal for a relaxed first evening.
EUR70, 2h
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Day 2: Ancient Rome Exploration

Rome, Italy on June 11, 2025

8:30am

Colosseum, Roman Forum, Palatine Hill Tour

Join a skip-the-line guided tour (~3 hours) to discover Rome’s iconic ancient monuments. Wear sunscreen and comfortable shoes.
EUR50, 3h

12:00pm

Lunch at Trattoria Luzzi

Enjoy classic Roman amatriciana pasta in a lively trattoria close to the Colosseum.
EUR25, 1h

2:00pm

Capitoline Museums Visit

Explore Roman artifacts and see views from the Piazza Venezia area at the Capitoline Museums. Entry €15, about 2 hours.
EUR15, 2h

7:30pm

Dinner in Trastevere at Osteria da Zi Umberto

Experience authentic Roman dishes in the vibrant Trastevere neighbourhood, then stroll along the Tiber River and enjoy gelato at Gelateria del Viale.
EUR30, 2h
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Day 3: Vatican & Roman Delights

Rome, Italy on June 12, 2025

8:30am

Vatican Museums & St. Peter’s Basilica

Enjoy a 4-hour guided tour inside Vatican Museums, the Sistine Chapel, and climb St. Peter’s Basilica dome (€10). Pre-book tickets (~€60).
EUR60, 4h

1:00pm

Lunch at Amalfi Pizzeria

Taste traditional Roman pizza at Amalfi in the Testaccio district, a local favourite.
EUR20, 1h

3:00pm

Campo de’ Fiori Market and Spanish Steps

Visit the lively Campo de’ Fiori outdoor market and then relax at the Spanish Steps area for people-watching.
Free, 2h

7:30pm

Dinner at Giggetto in Jewish Ghetto

Savour artichokes alla giudia and other Jewish Roman specialties in this historic part of Rome. Optional evening walk to lit monuments.
EUR35, 2h
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Day 4: Art and Gardens

Rome, Italy on June 13, 2025

9:00am

Borghese Gallery and Gardens

Visit the Borghese Gallery to view Bernini and Caravaggio masterpieces (book tickets €15 early), then stroll peaceful Villa Borghese Gardens.
EUR15, 2h

12:30pm

Lunch at Pierluigi Seafood

Dine on fresh seafood near Piazza Navona, a Roman institution known for elegant dishes.
EUR40, 1.5h

3:00pm

Aventine Hill Exploration

Visit the famous Keyhole at Piazza dei Cavalieri di Malta and enjoy views from the Orange Garden, an off-the-beaten-track quiet spot.
Free, 2h

7:30pm

Dinner at La Pergola or Felice a Testaccio

Book months in advance for La Pergola, Rome’s top Michelin 3-star restaurant (~€200), or choose traditional Roman dishes at Felice a Testaccio.
EUR100-200, 2h
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Day 5: Rome to Florence

Florence, Italy on June 14, 2025

8:00am

Train to Florence

Board the Frecciarossa to Florence (1.5h). Arrive before 10am, check in close to Duomo, and start your Florence adventure.
EUR30, 1.5h

11:30am

Florence Cathedral & Dome Climb

Visit the stunning Duomo for free, then climb Brunelleschi’s Dome (€30, pre-book) for panoramic city views.
EUR30, 2h

1:30pm

Lunch at All’Antico Vinaio

Grab famous Florentine panini at All’Antico Vinaio, ideal for a quick, delicious lunch.
EUR10, 1h

5:30pm

Ponte Vecchio & Piazzale Michelangelo

Stroll the historic Ponte Vecchio and watch sunset views over Florence from Piazzale Michelangelo.
Free, 2h

8:00pm

Dinner at Trattoria Mario

Taste bistecca alla fiorentina and rustic Tuscan fare in this lively crowd-pleaser spot.
EUR40, 1.5h
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Day 6: Florence Renaissance Art

Florence, Italy on June 15, 2025

9:00am

Uffizi Gallery Tour

Spend 2-3 hours inside the Uffizi admiring Botticelli’s and Michelangelo’s masterpieces. Booking tickets (€20) in advance is essential.
EUR20, 3h

1:00pm

Lunch at Osteria Vini e Vecchi Sapori

Dine at this authentic spot famous for traditional Tuscan dishes and great wine.
EUR30, 1h

3:00pm

Accademia Gallery & Leather Market

See Michelangelo’s David at Accademia (€15), then browse San Lorenzo leather market for souvenirs.
EUR15, 3h

7:00pm

Tuscan Cooking Class or Dinner

Join an evening Tuscan cooking class (~€70) or dine at La Giostra for authentic dishes with truffle specialties.
EUR70, 3h
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Day 7: Tuscany Day Trip

Siena & San Gimignano, Italy on June 16, 2025

7:30am

Guided Day Trip to Siena & San Gimignano

Explore Siena’s medieval Piazza del Campo and San Gimignano’s towers with a small-group tour (~8 hours, €80).
EUR80, 8h

12:00pm

Lunch at Antinori Winery

Enjoy a delicious lunch paired with wine tasting amidst Tuscan hills.
Included, 1h

6:00pm

Return and Relax in Florence

Head back to Florence and unwind with a light dinner or drinks at SE·STO rooftop bar on the Arno.
EUR30, 2h
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Day 8: Florence to Venice

Venice, Italy on June 17, 2025

8:00am

Train to Venice

Take a high-speed train from Florence to Venice (~2 hours) and arrive near noontime.
EUR40, 2h

12:30pm

Hotel Check-in & Water Taxi

Transfer by water taxi (€70 for 4) to your hotel near St. Mark’s Square. Settle in and prepare for sightseeing.
EUR70, 1h

2:00pm

St. Mark’s Square, Basilica & Doge’s Palace

Visit St. Mark’s Basilica (free, €3 for gallery) and Doge’s Palace (€25). Discover Venice’s heart and history.
EUR28, 3h

6:30pm

Gondola Ride

Enjoy a classic 30-minute gondola ride on Venice’s canals (€80), a quintessential experience.
EUR80, 0.5h

8:00pm

Dinner at Osteria alle Testiere

Dine on Michelin-recommended Venetian seafood dishes; booking ahead is essential.
EUR50, 2h
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Day 9: Murano & Burano Islands

Venice, Italy on June 18, 2025

9:00am

Ferry Tour to Murano and Burano

Spend 4 hours visiting Murano’s glass-blowing studios and Burano’s colourful streets (€30 tour).
EUR30, 4h

1:00pm

Lunch at Trattoria al Gatto Nero

Enjoy local seafood specialties on Burano island with waterfront views.
EUR35, 1.5h

3:30pm

Peggy Guggenheim Collection Visit

Admire 20th-century masterpieces in this intimate museum (€15).
EUR15, 2h

7:30pm

Dinner at Antiche Carampane

Savour authentic Venetian dishes away from tourist crowds in Cannaregio.
EUR40, 2h
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Day 10: Venice Markets & Beaches

Venice, Italy on June 19, 2025

9:00am

Rialto Market and Scuola Grande di San Rocco

Browse fresh produce and local goods at Rialto Market, then visit the Tintoretto masterpieces (€10) inside Scuola Grande di San Rocco.
EUR10, 2h

12:30pm

Lunch at Al Covo

Relish seafood dishes made with daily fresh catch at this gem near the market.
EUR40, 1.5h

3:00pm

Relax at Lido Beach or Photography Tour

Take a ferry to Lido beach (€10 round-trip) for sun and sea or join a photography tour capturing Venice’s beauty (€50).
EUR10-50, 3h

7:30pm

Dinner at Quadri & Live Music at Caffè Florian

Enjoy Michelin-star dining in St. Mark’s Square (~€150) followed by live classical music and spritz at historic Caffè Florian.
EUR150, 3h
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Day 11: Venice to Milan

Milan, Italy on June 20, 2025

8:00am

Train Venice to Milan

Travel by high-speed train (2.5h) to Milan. Check-in near Duomo and prepare for fashion and culture exploration.
EUR40, 2.5h

12:00pm

Duomo Visit & Galleria Vittorio Emanuele II

Visit the iconic Milan Duomo including rooftop access (€20) and browse shops in the historic Galleria.
EUR20, 2h

2:30pm

Lunch at Ristorante Francesco

Lunch near the Duomo serving traditional Milanese dishes in a welcoming setting.
EUR30, 1h

4:00pm

Shopping in Brera District

Explore Milan’s artistic district with boutiques, galleries and charming streets.
Free, 2h

7:30pm

Dinner at Nabucco & Optional La Scala Opera

Enjoy Milanese risotto and save optional evening for world-class opera at La Scala (book in advance).
EUR40-200, 2-4h
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Day 12: Leonardo & Milan Sights

Milan, Italy on June 21, 2025

9:00am

Last Supper Tour

See Leonardo da Vinci’s *Last Supper* and visit Santa Maria delle Grazie (€15). Book tickets at least 3 months prior.
EUR15, 30m

10:00am

Sforzesco Castle & Parco Sempione

Tour the historic castle (€10) then relax in the adjacent park with beautiful gardens and a pond.
EUR10, 2h

1:00pm

Lunch on Tram at ATMosfera

Enjoy a unique dining experience on a vintage tram (reservation needed, ~€70).
EUR70, 2h

6:00pm

Aperitivo in Navigli

Try a Negroni at Mag Cafè and experience Milan’s canalside nightlife.
EUR15, 1h

8:00pm

Dinner at Il Luogo di Aimo e Nadia

Michelin-starred dining focusing on innovative Italian cuisine (~€100).
EUR100, 2h
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Day 13: Milan to Lake Como

Lake Como, Italy on June 22, 2025

9:00am

Train to Varenna

Take regional train (~1h) to lakeside Varenna. Settle into your hotel in Varenna or Bellagio.
EUR7, 1h

11:00am

Villa Monastero & Lakeside Walk

Visit the beautiful lakeside Villa Monastero (€10) and enjoy scenic walks along Lake Como.
EUR10, 2h

1:00pm

Ferry to Bellagio and Lunch at La Punta

Short ferry ride (€5) to Bellagio for lunch with lake views at La Punta.
EUR25, 1.5h

7:30pm

Dinner at Ristorante Bilacus

Dine overlooking the lake with traditional Lombardy cuisine in Bellagio.
EUR50, 2h
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Day 14: Lake Como Boat Tour

Lake Como, Italy on June 23, 2025

9:00am

Private Boat Tour of Lake Como

Spend 2–3 hours exploring Lake Como by private boat, including Villa Balbianello (€150 per boat for 4). Swim if weather permits.
EUR150, 3h

1:00pm

Lunch at Locanda La Tirlindana

Enjoy lakeside dining in Como town with fresh, local ingredients.
EUR35, 1.5h

3:00pm

Como Duomo & Lakefront Stroll

Visit the free-entry Como Cathedral and leisurely walk the scenic lakefront promenade.
Free, 2h

7:30pm

Dinner at Al Veluu

Rustic regional dishes await at this charming restaurant in Tremezzo, great for unwinding after your day.
EUR45, 2h
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Day 15: Lake Como Leisure & Milan Return

Lake Como & Milan, Italy on June 24, 2025

9:00am

Morning Leisure or Kayaking

Relax in Varenna/Bellagio or rent a kayak (~€30/hour). Optionally hike to Castello di Vezio (€4) for lake vistas.
EUR30, 2h

12:00pm

Train Back to Milan

Return to Milan (1 hour). Check into hotel and head out to lunch.
EUR7, 1h

1:30pm

Lunch at Spazio Niko Romito

Enjoy contemporary Italian cuisine in Milan’s upscale dining scene.
EUR40, 1.5h

4:00pm

Shopping in Quadrilatero della Moda

Indulge in luxury shopping or window browse the high-end fashion district.
Free, 2h

8:00pm

Dinner at Cracco

Michelin-starred restaurant with innovative Milanese cuisine; perfect for a final city dinner.
EUR120, 2h
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Day 16: Milan to Amalfi Coast

Sorrento, Italy on June 25, 2025

7:00am

High-Speed Train Milan to Naples

Travel south to Naples (~4.5 hours). Arrive by midday and transfer to Sorrento by private car (~1h) or Circumvesuviana train (€4).
EUR74, 5.5h

1:30pm

Hotel Check-in & Lunch at O’Parrucchiano

Settle at your Sorrento hotel and enjoy famous lemon pasta at O’Parrucchiano restaurant.
EUR30, 1.5h

4:00pm

Explore Marina Grande

Walk the charming fishing harbour of Marina Grande, perfect for photos and a coffee break.
Free, 2h

7:30pm

Dinner at La Lanterna

Fresh seafood with local specialties plus sample limoncello at a nearby bar afterward.
EUR45, 2h
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Day 17: Amalfi & Positano Boat Tour

Amalfi Coast, Italy on June 26, 2025

8:30am

Boat Tour Amalfi and Positano

Six-hour small-group boat tour includes swimming and stops in Amalfi and Positano, visiting Sant’Andrea Cathedral (€3).
EUR100, 6h

1:30pm

Lunch at La Tagliata

Family-style hearty Tuscan meals in Positano with soulful views over the coast.
EUR40, 1.5h

5:30pm

Return to Sorrento & Explore

Leisurely explore Sorrento’s Corso Italia shopping street after returning from the coast.
Free, 1.5h

8:00pm

Dinner at Il Buco

Michelin-starred cuisine ideal for a memorable fine dining evening; book in advance.
EUR80, 2h
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Day 18: Capri Island Day Trip

Capri & Sorrento, Italy on June 27, 2025

8:30am

Ferry to Capri and Blue Grotto Tour

30-minute ferry to Capri, then join a 4-hour tour to the Blue Grotto and island highlights including Villa San Michele (€10).
EUR80, 5h

1:30pm

Lunch at Ristorante Il Geranio

Enjoy refined dining overlooking Capri’s Faraglioni rocks near Marina Grande.
EUR40, 1.5h

3:00pm

Relax at Marina Piccola Beach

Unwind by the turquoise waters in this peaceful beach area.
Free, 2h

6:00pm

Return and Dinner at O’Puledrone

Taste freshly caught seafood back in Sorrento and enjoy authentic gelato at Gelateria Primavera.
EUR35, 2h
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Day 19: Pompeii & Relaxation

Pompeii & Sorrento, Italy on June 28, 2025

9:00am

Guided Pompeii Tour

Take a 2-hour guided tour (~€50 with guide) of Pompeii’s ancient ruins accessed via Circumvesuviana train (€3).
EUR53, 3h

12:30pm

Lunch at La Bettola del Gusto

Sample modern Italian dishes in the Pompeii area before returning to Sorrento.
EUR25, 1.5h

3:00pm

Relax at Bagni Regina Giovanna

Enjoy swimming in the natural seaside pool, a tranquil spot near Sorrento.
Free, 2h

7:30pm

Dinner at Terrazza Bosquet

Dine at your hotel’s fine restaurant specialising in lemon-inspired dishes, followed by limoncello tasting.
EUR50, 2h
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Day 20: Hiking & Return to Rome

Positano & Rome, Italy on June 29, 2025

8:00am

Hike the Path of the Gods

Experience a stunning 3–4 hour guided hike (€50) with spectacular Amalfi Coast views or relax at Sorrento beach.
EUR50, 4h

1:30pm

Travel to Rome

Private transfer/train to Naples (~1h) then high-speed train to Rome (~1h). Check into your hotel by mid-afternoon.
EUR60, 3h

7:30pm

Farewell Dinner at Checchino dal 1887

Celebrate your trip with classic Roman dishes in lively Testaccio. Evening walk to lit Colosseum or gelato at Giolitti.
EUR40, 2h
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Day 21: Departure

Rome, Italy on June 30, 2025

7:00am

Transfer to Fiumicino Airport

Take the Leonardo Express train (€14) or taxi to Rome airport for your flight back to Melbourne.
EUR14, 1h

8:00am

Optional Coffee & Shopping

If time allows, enjoy a classic Italian coffee at Sant’Eustachio or purchase souvenirs like pasta and limoncello.
EUR10, 1h
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