10-Day Italy and Greece Itinerary: Venice, Milan, Rome, and Santorini

Day 1: Explore Milan

Milan, Italy on May 20, 2025

9:00AM

Breakfast at Pavé

Enjoy a classic Italian pastry and coffee at Pavé, a famous Milanese bakery known for its fresh croissants and cappuccinos.
EUR10, 1 hour

10:30AM

Visit Milan Cathedral (Duomo di Milano)

Explore this iconic Gothic cathedral. Don't miss the rooftop terraces offering panoramic views of the city. Open 9:00AM–7:00PM.
EUR15, 2 hours

1:00PM

Lunch at Luini

Taste traditional Panzerotti, a local street food specialty just steps from the Duomo, open from 11:00AM to 8:00PM.
EUR8, 1 hour

2:30PM

Visit Sforza Castle

Explore this historic fortress and museums showcasing Renaissance art and artifacts. Open 9:00AM–5:30PM.
EUR10, 2 hours

6:00PM

Dinner at Ratanà

Dine at Ratanà, known for its modern Milanese cuisine with a cozy ambiance in Porta Nuova.
EUR40, 2 hours
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Day 2: Venice Exploration

Venice, Italy on May 21, 2025

7:30AM

Train from Milan to Venice

Take a morning high-speed train from Milan to Venice (approx. 2.5 hours), arriving before lunchtime.
EUR40, 2.5 hours

11:30AM

Lunch at Osteria alle Testiere

Indulge in fresh seafood Venetian dishes in this intimate, popular restaurant. Open 12:00PM–3:00PM.
EUR35, 1.5 hours

1:30PM

Visit St. Mark’s Basilica

Marvel at the Byzantine mosaics of St. Mark’s Basilica. Open 9:30AM–5:00PM. Entry to basilica is free; museum has a small fee.
EUR5, 1.5 hours

3:30PM

Explore Doge's Palace

Tour the historic palace adjacent to St. Mark’s with rich art and history on display. Open 9:00AM–7:00PM.
EUR25, 2 hours

6:00PM

Gondola Ride

Experience a traditional gondola ride through Venice’s canals, a quintessential Venetian activity.
EUR80, 0.5 hours

7:30PM

Dinner at Antiche Carampane

Enjoy authentic Venetian cuisine in a charming historic setting, open 7:00PM–11:00PM.
EUR50, 2 hours
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Day 3: More Venice + Travel to Rome

Venice to Rome, Italy on May 22, 2025

9:00AM

Breakfast at Pasticceria Tonolo

Start your day with excellent Venetian pastries and coffee at this beloved historic café.
EUR10, 1 hour

10:30AM

Visit Peggy Guggenheim Collection

Discover modern art in this museum housed in her former home. Open 10:00AM–6:00PM.
EUR15, 2 hours

1:00PM

Lunch at Trattoria alla Madonna

Savor traditional Venetian dishes minutes from the Rialto Bridge. Open 12:00PM–3:00PM.
EUR30, 1.5 hours

3:30PM

Train from Venice to Rome

Take an afternoon high-speed train (approx. 3.5 hours) to Rome, arriving early evening.
EUR50, 3.5 hours

7:30PM

Dinner at Trattoria da Enzo al 29

Enjoy classic Roman cuisine in Trastevere, open from 7:00PM to 11:00PM.
EUR35, 2 hours
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Day 4: Rome Ancient Sites

Rome, Italy on May 23, 2025

8:00AM

Breakfast at Roscioli Caffè

Start your day with excellent coffee and pastries near Campo de’ Fiori.
EUR12, 1 hour

9:30AM

Colosseum and Roman Forum

Tour the iconic Colosseum and nearby Roman Forum ruins with a guided ticket. Open 8:30AM–7:00PM.
EUR20, 3 hours

1:00PM

Lunch at La Taverna dei Fori Imperiali

Local eatery serving Roman specialties just steps from the Forum. Open 12:00PM–3:00PM.
EUR30, 1.5 hours

3:00PM

Pantheon and Piazza Navona

Visit the well-preserved Pantheon (open 9:00AM–7:00PM, ticket EUR5) before strolling Piazza Navona’s lively square.
EUR5, 2 hours

6:00PM

Dinner at Osteria dell’Ingegno

Enjoy refined Roman dishes in the heart of the historic center, open 7:00PM–11:00PM.
EUR40, 2 hours
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Day 5: Vatican and Travel to Santorini

Rome to Santorini, Greece on May 24, 2025

7:30AM

Early Breakfast at Pasticceria Regoli

Grab quick Italian pastries before heading out to the Vatican.
EUR8, 0.5 hours

8:30AM

Visit Vatican Museums and Sistine Chapel

Pre-book tickets to avoid lines at the Vatican Museums to see Renaissance art and Michelangelo’s Sistine Chapel. Open 9:00AM–6:00PM.
EUR30, 3 hours

12:00PM

Lunch near Vatican at Ristorante Arlu

Enjoy authentic Roman dishes in a cozy restaurant near the Vatican. Open 12:00PM–3:00PM.
EUR30, 1.5 hours

3:00PM

Fly from Rome to Santorini

Take an afternoon direct flight to Santorini (approx. 2 hours), arriving early evening.
EUR100, 2 hours

6:30PM

Check in & Dinner at Selene Restaurant

Dine with views of the caldera and enjoy fine Greek cuisine at Selene in Pyrgos.
EUR60, 2 hours
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Day 6: Santorini Beaches and Villages

Santorini, Greece on May 25, 2025

8:30AM

Breakfast at Melenio Cafe in Fira

Enjoy fresh Greek pastries and coffee in the island’s main town, open from 8:00AM.
EUR15, 1 hour

9:30AM

Explore Ancient Thera Archaeological Site

Visit the ruins of an ancient city above Kamari beach. Open 8:00AM–8:00PM.
EUR6, 2 hours

12:00PM

Lunch at Kamari Beach Tavern

Relax on the beach and enjoy fresh seafood by the sea. Open 12:00PM–4:00PM.
EUR25, 1.5 hours

2:00PM

Visit Oia Village

Explore this picturesque village famous for whitewashed buildings and stunning caldera views. Best visited mid-afternoon for sunset preparation.
Free, 3 hours

7:30PM

Sunset Dinner at Ambrosia Restaurant, Oia

Dine with a view of the famous Oia sunset, classic Greek cuisine with a fine dining atmosphere.
EUR50, 2 hours
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Day 7: Santorini Volcano and Hot Springs

Santorini, Greece on May 26, 2025

8:00AM

Breakfast at Pelican Kipos

Start the day with a relaxing breakfast in Fira’s lush garden cafe.
EUR15, 1 hour

9:30AM

Boat Tour to Nea Kameni Volcano and Hot Springs

Take a 3-4 hour boat tour hiking the volcano and swimming in hot springs. Tours depart around 10:00AM.
EUR40, 4 hours

2:00PM

Lunch at Metaxi Mas

After your tour, enjoy Cretan-inspired Greek food in a cozy setting. Open 1:00PM–10:00PM.
EUR30, 1.5 hours

4:00PM

Free Afternoon to Relax or Explore More

Optional visit to local wineries or lounging at your hotel.
Varies, Flexible

7:30PM

Dinner at Argo Restaurant, Fira

Dine on Mediterranean dishes with a view of the caldera in Fira town.
EUR45, 2 hours
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Day 8: Santorini to Rome

Santorini to Rome on May 27, 2025

8:00AM

Breakfast at Passaggio Café

Enjoy local Greek breakfast specialties and coffee before departure.
EUR15, 1 hour

10:30AM

Fly from Santorini to Rome

Morning flight back to Rome for final day in Italy.
EUR100, 2 hours

1:00PM

Lunch at Forno Campo de' Fiori

Quick Italian pizza slice or lunch near Campo de' Fiori, open 12:00PM–3:00PM.
EUR12, 1 hour

2:00PM

Visit Trevi Fountain and Spanish Steps

Explore two iconic Roman landmarks. Best viewed in daylight and evening for lights.
Free, 2 hours

5:00PM

Relax at Villa Borghese Gardens

Spend peaceful afternoon in beautiful gardens with a small lake and galleries. Open 9:00AM–7:00PM.
EUR15 for Borghese Gallery if visiting, 2 hours

7:30PM

Farewell Dinner at Enoteca Ferrara

Enjoy exceptional Italian wines and regional dishes in Trastevere to end your trip.
EUR50, 2 hours
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Day 9: Departure

Rome, Italy on May 28, 2025

8:00AM

Breakfast near hotel

Have a leisurely breakfast at a nearby café to fuel up for your travel day.
EUR10, 1 hour

10:00AM

Transfer to Rome Airport

Head to the airport for your departure flight.
Varies, Variable
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