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Italy Night Travel Itinerary: Milan, Venice, Florence & Rome from Arrival to Departure

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Day 1: Rome Arrival & Milan Night Transfer

Rome arrival, Milan, Italy on May 22, 2025

5:00pm

Arrive in Rome

Land at Rome Fiumicino Airport and transfer to a lounge or nearby café to refresh before overnight travel.
EUR0, 1h

6:00pm

Dinner near Airport or Lounge

Have a light dinner or snack nearby to regain energy for the night trip.
EUR20, 1h

8:00pm

Night train or late direct train to Milan

Board a late evening high-speed train (approx. 3h) to Milan to arrive late and check in at the hotel.
EUR40, 3h

11:00pm

Check into Hotel in Milan

Check in and rest, ready for the busy day ahead.
EUR0, overnight
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Day 2: Milan Day Tour

Milan, Italy on May 23, 2025

7:30am

Breakfast at Panificio Pattini

Start your Milan day with fresh pastries and espresso at this renowned bakery.
EUR7, 30m

8:30am

Duomo di Milano and Rooftop

Visit Milan’s iconic Cathedral and climb onto the rooftop for panoramic city views; opens from 9am.
EUR15, 2h

11:00am

Galleria Vittorio Emanuele II

Explore Europe’s oldest shopping arcade with luxury shops and beautiful architecture.
Free, 1h

12:00pm

Lunch at Luini Panzerotti

Enjoy famous Milanese stuffed panzerotti, a quick and traditional local bite.
EUR10, 1h

1:30pm

Sforza Castle & Parco Sempione

Visit the historic castle with museums and relax in the adjacent park.
EUR10, 2h

3:45pm

Santa Maria delle Grazie (The Last Supper)

Pre-book to see Leonardo da Vinci's masterpiece painting; visit times starting afternoon.
EUR15, 1h

5:30pm

Aperitivo in Navigli District

Experience Milan’s famous pre-dinner social tradition with drinks and snacks alongside canals.
EUR20, 1.5h

8:00pm

Dinner at Ratanà

Enjoy contemporary Milanese cuisine in a stylish setting.
EUR40, 1.5h

10:30pm

Night Train to Venice

Board a night train or late train (~2.5h) to Venice, arriving late for check-in.
EUR50, 2.5h

1:00am

Check-in Hotel Venice

Check into your Venice accommodation and rest.
EUR0, overnight
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Day 3: Venice Day Exploration

Venice, Italy on May 24, 2025

8:00am

Breakfast at Pasticceria Tonolo

Delight in fresh pastries and coffee to start your day in Venice.
EUR8, 30m

9:00am

St. Mark's Basilica and Square

Visit the stunning basilica and enjoy the lively atmosphere of the piazza, open 9:30am-5pm.
Free (museum €3), 1.5h

11:00am

Doge’s Palace Tour

Explore the historic Doge's Palace and cross the Bridge of Sighs; open 9am-7pm.
EUR25, 1.5h

1:00pm

Lunch at Osteria alle Testiere

Savour authentic Venetian seafood at this intimate and acclaimed spot (reservation recommended).
EUR50, 1.5h

2:45pm

Gondola Ride

Experience Venice from its scenic canals on a 30-minute gondola ride.
EUR80, 30m

3:30pm

Rialto Bridge and Market

Wander through the iconic Rialto Bridge area and local markets.
Free, 1h

4:45pm

Visit Accademia Gallery or Dorsoduro

Choose to admire Renaissance art at Gallerie dell’Accademia or explore quieter Dorsoduro district.
EUR15, 1.5h

6:30pm

Dinner at Trattoria al Gatto Nero

Enjoy traditional Venetian dishes in Burano, a short waterbus ride or dine back in Venice town center.
EUR40, 1.5h

9:00pm

Night Train to Florence

Catch a late train (about 2h) to Florence and check into hotel late night.
EUR40, 2h

11:00pm

Check into Hotel Florence

Rest and prepare for your Florence day.
EUR0, overnight
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Day 4: Florence Art & Culture

Florence, Italy on May 25, 2025

7:30am

Breakfast at Caffè Gilli

Start your day with an elegant Florentine breakfast near Piazza della Repubblica.
EUR10, 45m

8:30am

Uffizi Gallery

Discover Renaissance masterpieces by Botticelli and Michelangelo; open 8:15am-6:50pm.
EUR20, 3h

11:45am

Florence Cathedral (Duomo) Complex

Visit the Duomo, Baptistery, and climb the dome for city views, open 8:30am-7pm.
EUR18, 2h

2:00pm

Lunch at Trattoria Mario

Taste authentic Tuscan cuisine in a beloved casual trattoria near Mercato Centrale.
EUR25, 1h

3:30pm

Accademia Gallery

Visit Michelangelo’s David and Renaissance art; open 8:15am-6:50pm.
EUR16, 1.5h

5:15pm

Ponte Vecchio and Oltrarno

Stroll the historic bridge and browse artisan shops across the Arno river.
Free, 1h

6:30pm

Piazzale Michelangelo at sunset

Enjoy spectacular panoramic views over Florence’s skyline especially at sunset.
Free (Transport ~EUR10), 1h

8:00pm

Dinner at La Giostra

Savour refined Tuscan dishes with a romantic ambiance.
EUR40, 1.5h

10:00pm

Night Train to Rome

Take a late high-speed train (about 1.5h) back to Rome and check in.
EUR45, 1.5h

11:30pm

Check into Hotel Rome

Rest up for your full final days in Rome.
EUR0, overnight
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Day 5: Rome Explore Day 1

Rome, Italy on May 26, 2025

7:30am

Breakfast at Pasticceria Regoli

Delight in fresh baked goods and espresso to start your Rome morning.
EUR5, 30m

8:30am

Colosseum and Roman Forum Tour

Explore the Colosseum and Roman Forum on a guided tour; open until 7:15pm.
EUR18, 2h

11:00am

Piazza Venezia and Capitoline Hill

Take in panoramic views and historic landmarks nearby.
Free, 1h

12:15pm

Lunch at Roscioli

Experience Roman delicacies in a top-rated deli and restaurant.
EUR30, 1.5h

2:00pm

Pantheon and Piazza Navona

Admire the Pantheon and lively piazza with baroque fountains.
Free, 1.5h

4:00pm

Trevi Fountain and Spanish Steps

Visit iconic Roman landmarks, toss a coin and climb the steps.
Free, 1h

5:30pm

Coffee and Gelato at Sant’Eustachio Il Caffè

Recharge with premium coffee and gelato near the Pantheon.
EUR7, 45m

7:00pm

Dinner at Trattoria da Enzo al 29

Enjoy authentic Roman dishes in friendly Trastevere.
EUR35, 1.5h

9:00pm

Evening stroll along the Tiber River

Relax with a peaceful riverside walk as your day winds down.
Free, 1h
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Day 6: Rome Explore Day 2

Rome, Italy on May 27, 2025

7:30am

Breakfast at Bar Fondi

Start your final full day in Rome with fresh pastries and espresso.
EUR6, 30m

8:30am

Vatican Museums & Sistine Chapel

Visit the Vatican Museums early to avoid crowds, open from 9am to 6pm.
EUR30, 3h

11:45am

St. Peter’s Basilica and Dome Climb

Tour the basilica and opt to climb the dome for stunning city views; open 7am-7pm.
Free (dome climb EUR10), 1.5h

1:30pm

Lunch at Da Marcello al Corso

Savour Roman flavors in a cozy spot close to the historic center.
EUR25, 1h

2:45pm

Villa Borghese and Galleria Borghese

Explore the beautiful gardens and impressive art collection; reservation needed, open until 7pm.
EUR20, 3h

6:00pm

Shopping and Strolling Around Via del Corso

Enjoy last-minute shopping and people-watching on this popular street.
Free, 1.5h

8:00pm

Farewell Dinner at Il Gabriello

Dine on refined Italian dishes and toast your memorable trip in style.
EUR45, 2h
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Day 7: Departure Day

Rome, Italy on May 28, 2025

6:00am

Early Breakfast at Hotel

Enjoy a relaxed early breakfast before airport transfer.
Included, 30m

7:00am

Transfer to Airport

Head to Rome Fiumicino Airport for your departure flight.
EUR50, 1h
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