Comprehensive 3-Week Italy Itinerary: Rome, Milan, Lake Como, Florence & Amalfi Coast

Day 1: Explore Ancient Rome

Rome, Italy on May 26, 2025

8:00am

Breakfast at Roscioli Caffè

Start your day with authentic Italian coffee and freshly baked pastries at this popular Roman café, open from 7am to 11pm.
EUR10, 0h30m

9:00am

Colosseum and Roman Forum Tour

Explore these iconic ancient landmarks with a guided tour to immerse yourself in Rome's imperial history. Open 8:30am to 7pm.
EUR18, 3h0m

12:30pm

Lunch at Trattoria Luzzi

Enjoy traditional Roman dishes like carbonara and cacio e pepe at this cozy trattoria near the Colosseum, open 12pm-3pm.
EUR25, 1h0m

2:00pm

Visit the Pantheon

Marvel at the perfectly preserved ancient Roman temple known for its giant dome and oculus, open 9am to 7pm.
Free, 1h0m

3:30pm

Stroll Piazza Navona

Enjoy the elegant fountains and lively atmosphere of this historic square, ideal for people watching and street performances. Open all day.
Free, 1h0m

7:00pm

Dinner at Ristorante Aroma

Dine with a stunning Colosseum view while savoring gourmet Italian cuisine at this Michelin-starred restaurant, open 7pm-11pm.
EUR70, 2h0m
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Day 2: Vatican & City Walk

Rome, Italy on May 27, 2025

7:30am

Breakfast at Pasticceria Regoli

Grab delightful Italian pastries and espresso at this traditional bakery, open from 7am to 8pm.
EUR8, 0h30m

8:30am

Vatican Museums & Sistine Chapel

Experience the world’s greatest art collections and Michelangelo’s Sistine Chapel ceiling frescoes. Tickets must be booked in advance. Open 9am to 6pm.
EUR30, 3h0m

12:00pm

Lunch at Borgo Pio

Enjoy Roman-style pizza and pasta just a short walk from the Vatican, open 12pm to 3pm.
EUR20, 1h0m

1:30pm

St. Peter’s Basilica

Visit the grand basilica featuring Renaissance architecture and climb to the dome for panoramic city views. Open 7am to 7pm.
Free (Dome climb EUR10), 2h0m

4:00pm

Leisure stroll at St. Peter’s Square

Admire Bernini’s impressive colonnades and people-watch in this historic square outside the basilica. Open all day.
Free, 1h0m

7:30pm

Dinner at Osteria dell’Angelo

Savor authentic Roman dishes in a casual setting, open 7pm to 11pm.
EUR35, 1h30m
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Day 3: Travel to Milan

Milan, Italy on May 28, 2025

7:30am

Breakfast at hotel

Enjoy a light breakfast before boarding your train to Milan during operating hours of 7am-9am.
Included, 0h30m

9:00am

High-speed train from Rome to Milan

Travel comfortably with the high-speed train service, approximately 3 hours to Milan Centrale Station.
EUR60, 3h0m

12:30pm

Check-in and freshen up

Settle into your Milan accommodation and prepare for an afternoon of touring.
Variable, 1h0m

1:30pm

Lunch at Luini

Try Milan’s famous panzerotti (fried stuffed pastries) in this casual eatery, open 10am to 7pm.
EUR10, 1h0m

2:30pm

Visit Milan Cathedral (Duomo)

Explore the stunning Gothic cathedral and rooftop terraces offering city views. Open 9am to 7pm.
EUR15, 2h0m

5:00pm

Walk through Galleria Vittorio Emanuele II

Stroll through this historic shopping gallery with beautiful architecture and shops. Open all day.
Free, 1h0m

7:30pm

Dinner at Ristorante Nabucco

Enjoy classic Milanese dishes like risotto alla Milanese in a charming restaurant, open 7pm to 11pm.
EUR50, 2h0m
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Day 4: Milan Highlights

Milan, Italy on May 29, 2025

8:00am

Breakfast at Pasticceria Marchesi

Begin with exquisite pastries and coffee at this famed bakery, open 7am to 8pm.
EUR12, 0h45m

9:00am

Pinacoteca di Brera

Visit Milan’s premier art gallery showcasing masterpieces from the Renaissance to modern times. Open 9:30am to 6:30pm.
EUR15, 2h0m

11:30am

Sforza Castle and grounds

Explore the historic castle, museums and peaceful park areas, open 7am to 7:30pm.
EUR10, 2h0m

1:30pm

Lunch at Paper Moon

Delight in upscale Italian fare in an elegant setting, open 12pm to 3pm.
EUR40, 1h30m

3:30pm

Santa Maria delle Grazie

View the Church and home to Leonardo da Vinci’s The Last Supper (tickets must be booked in advance). Open 9am to 6:15pm.
EUR15, 1h30m

5:30pm

Aperitivo at Navigli Canal district

Enjoy a traditional pre-dinner drink and snacks along the picturesque Navigli canals. Bars open from 6pm onwards.
EUR15, 2h0m

8:00pm

Dinner at Osteria del Binari

Sample authentic Milanese cuisine in a cozy setting near Navigli, open 7pm to 11pm.
EUR50, 2h0m
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Day 5: Lake Como Day Trip

Lake Como, Italy on May 30, 2025

7:30am

Breakfast at hotel

Have an early breakfast before departing for Lake Como.
Included, 0h30m

8:30am

Train from Milan to Como

Ride regional trains to Como town, about 1 hour from central Milan.
EUR10, 1h0m

9:30am

Funicular to Brunate

Take the funicular railway up to Brunate for breathtaking views of the lake and Alps. Open 7am to midnight.
EUR6, 1h0m

11:00am

Explore Como Old Town

Visit the Duomo, central square, lakeside promenade and local shops.
Free, 2h0m

1:00pm

Lunch at La Vita è Bella

Enjoy fresh Italian seafood and pasta near the lakefront, open 12pm to 3pm.
EUR35, 1h15m

2:30pm

Boat tour on Lake Como

Take a 2-hour guided boat tour visiting Bellagio and quaint lakeside villages.
EUR40, 2h0m

5:00pm

Return to Milan

Train back to Milan to rest before dinner.
EUR10, 1h0m

7:30pm

Dinner at Al Mercato

End the day with contemporary Milanese dishes in a trendy spot, open 7pm to 11pm.
EUR60, 2h0m
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Day 6: Travel to Florence

Florence, Italy on May 31, 2025

7:30am

Breakfast at hotel

Enjoy a final Milanese breakfast before your train departure.
Included, 0h30m

9:00am

Train Milan to Florence

Take a high-speed train to Florence, approximately 2 hours journey.
EUR50, 2h0m

11:30am

Hotel check-in and refresh

Settle into your Florence accommodation.
Variable, 1h0m

12:30pm

Lunch at Trattoria Mario

Taste classic Tuscan specialties like ribollita and Florentine steak, open 12pm to 3pm.
EUR30, 1h0m

2:00pm

Explore Florence Cathedral (Duomo)

Visit the iconic cathedral and climb its terracotta dome for breathtaking views. Open 10am to 5pm.
EUR20, 2h0m

4:30pm

Walk across Ponte Vecchio

Enjoy the views and browse jewelry shops on this historic medieval bridge.
Free, 30m

6:00pm

Dinner at La Giostra

Dine on refined Tuscan dishes in a cozy, romantic setting, open 7pm to 11pm.
EUR60, 2h0m
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Day 7: Florence Art & Garden

Florence, Italy on June 1, 2025

8:00am

Breakfast at Caffè Gilli

Start with a classic Italian breakfast of cappuccino and pastries at this historic café, open 7am to 11pm.
EUR12, 0h45m

9:00am

Uffizi Gallery

Visit one of the world’s most important art museums with Renaissance masterpieces. Open 8:15am to 6:50pm. Book tickets in advance.
EUR20, 3h0m

12:30pm

Lunch at Mercato Centrale

Sample a variety of Tuscan street foods in this vibrant market that closes at 3pm.
EUR15, 1h0m

2:00pm

Boboli Gardens

Relax and admire sculptures and fountains in this historic garden behind Pitti Palace. Open 8:15am to 7:30pm.
EUR10, 2h0m

5:00pm

Piazzale Michelangelo

End your day with panoramic sunset views of Florence from this famous viewpoint.
Free, 1h0m

7:30pm

Dinner at Trattoria Cammillo

Enjoy classic Tuscan dishes made from local ingredients in a lively atmosphere, open 7pm to 11pm.
EUR40, 1h30m
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Day 8: Tuscan Countryside

Chianti, Italy on June 2, 2025

7:30am

Breakfast at hotel

Fuel up for a day of wine and countryside exploration.
Included, 0h30m

8:30am

Drive to Chianti wine region

Travel approx. 1 hour southeast of Florence to the renowned region for vineyards and olive groves.
EUR50 car rental, 1h0m

10:00am

Castello di Verrazzano Wine Tour

Tour this historic winery and enjoy tastings of Chianti Classico wines. Tours start at 10am; book in advance.
EUR35, 2h0m

12:30pm

Lunch at Ristoro di Lamole

Dine with vineyard views while savoring regional specialties, open from 12pm to 3pm.
EUR40, 1h30m

2:30pm

Explore Greve in Chianti

Wander the charming town square filled with artisan shops and traditional markets on some days.
Free, 1h0m

4:00pm

Return to Florence

Drive back to Florence for evening rest.
Included in rental, 1h0m

7:00pm

Dinner at Il Latini

Experience lively atmosphere and Tuscan comfort food in this popular trattoria, open 7pm to midnight.
EUR50, 2h0m
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Day 9: Travel to Venice

Venice, Italy on June 3, 2025

7:30am

Breakfast at hotel

Enjoy a final Tuscan breakfast before heading to Venice.
Included, 0h30m

9:00am

Train Florence to Venice

Travel on high-speed train, approx. 2 hours.
EUR50, 2h0m

11:30am

Check-in and freshen up

Settle into your Venice hotel in central location.
Variable, 1h0m

1:00pm

Lunch at Osteria alle Testiere

Enjoy Venetian seafood specialties in an intimate setting, open 12pm to 3pm.
EUR50, 1h0m

2:30pm

St. Mark’s Basilica & Square

Visit this stunning basilica and soak in the iconic piazza atmosphere. Basilica open 9:30am to 5pm.
Free (museum EUR5), 2h0m

5:00pm

Doge’s Palace

Explore Venetian historic palace and Bridge of Sighs, open 9am to 7pm.
EUR25, 2h0m

7:30pm

Dinner at Antiche Carampane

Savor traditional Venetian cuisine away from tourist crowds, open 7pm to 11pm.
EUR60, 2h0m
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Day 10: Venetian Islands

Venice, Italy on June 4, 2025

8:00am

Breakfast at Pasticceria Tonolo

Start with delicious pastries and coffee at this popular bakery, open 7:30am to 8pm.
EUR10, 0h30m

9:00am

Visit Murano, Burano, and Torcello Islands

Take a vaporetto to these colorful islands famous for glassmaking, lace, and historic sites starting from 9am.
EUR20, 6h0m

3:30pm

Return to Venice and rest

Relax at your hotel or nearby café after the island tour.
Free, 1h0m

7:00pm

Dinner at Al Covo

Enjoy refined Venetian seafood cuisine, open 7pm to 11pm.
EUR70, 2h0m
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Day 11: Travel to Amalfi Coast

Amalfi Coast, Italy on June 5, 2025

7:00am

Breakfast at hotel

Have an early breakfast before traveling south to the Amalfi Coast.
Included, 0h30m

8:00am

Train Venice to Naples

Take the high-speed train to Naples. Duration approx. 5 hours.
EUR70, 5h0m

1:00pm

Lunch in Naples at Pizzeria da Michele

Enjoy legendary Neapolitan pizza at this historic location, open 11am to 11pm.
EUR15, 1h0m

2:30pm

Transfer to Positano

Take a bus or private transfer (~1.5 hours) to Positano, famous for its dramatic cliffside views.
EUR20, 1h30m

4:00pm

Check-in and relax

Check in at your Positano accommodation and unwind by the sea.
Variable, 2h0m

7:00pm

Dinner at La Tagliata

Enjoy hearty local dishes with panoramic views in this family run restaurant, open 7pm to 10:30pm.
EUR55, 2h0m
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Day 12: Amalfi Coast Boat Tour

Positano, Italy on June 6, 2025

8:00am

Breakfast at hotel

Enjoy breakfast with stunning views before your boat tour.
Included, 0h30m

9:00am

Boat tour along Amalfi Coast

Take a 3-hour guided boat tour visiting Amalfi, Ravello, and hidden coves. Tours start at 9am.
EUR50, 3h0m

12:30pm

Lunch in Amalfi at Trattoria Eolo

Savor fresh seafood and pasta overlooking the waterfront, open 12pm to 3pm.
EUR40, 1h0m

2:00pm

Visit Ravello Gardens

Explore Villa Rufolo and Villa Cimbrone’s beautiful gardens and views. Open 9am to 7pm.
EUR10, 2h0m

5:00pm

Return to Positano

Relax back at your hotel or explore Positano's charming streets.
Free, 1h30m

7:30pm

Dinner at Chez Black

Dine at this beachfront restaurant famous for pizza and pasta, open 7pm to 11pm.
EUR50, 2h0m
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Day 13: Pompeii & Naples Day

Pompeii / Naples, Italy on June 7, 2025

7:00am

Breakfast at hotel

Prepare for a full day exploring ruins and the vibrant city.
Included, 0h30m

8:00am

Travel to Pompeii

Take a 1-hour train from Positano (via Naples or Sorrento) to the ruins.
EUR15, 1h0m

9:30am

Pompeii Ruins Tour

Explore this vast UNESCO site of an ancient Roman city. Open 9am to 7:30pm.
EUR18, 3h0m

1:00pm

Lunch in Pompeii at Caupona Pompeii Restaurant

Try Neapolitan specialties in a historic-themed venue, open 12pm to 3pm.
EUR30, 1h0m

2:30pm

Travel to Naples

Short train ride (~30 minutes) to Naples city center.
EUR5, 0h30m

3:00pm

Naples National Archaeological Museum

See Roman artifacts from Pompeii and Herculaneum. Open 9am to 7pm.
EUR15, 2h0m

5:30pm

Evening walk and coffee at Piazza del Plebiscito

Relax in this grand square with historic architecture.
Free, 1h0m

7:00pm

Dinner at Sorbillo

Enjoy authentic Neapolitan pizza at this famed pizzeria open till 11pm.
EUR20, 1h30m

8:30pm

Return to Positano

Travel back to your hotel after a full day.
Included in transport, 2h0m
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Day 14: Departure/Relaxation

Positano, Italy on June 8, 2025

8:00am

Breakfast at hotel

Enjoy your last Italian breakfast with ocean views.
Included, 0h30m

10:00am

Leisure day or travel preparations

Spend your remaining time relaxing or shopping before departure.
Free, Variable
View Hotel Availability