Make this trip your own
Create your own free, personalized itinerary in seconds — then sign up to save and edit it.
Create my version

Italy Travel Itinerary - May 2026

Viewed by 319 travelers

Day 1: Arrival & Milan City Intro

Morning: Arrive in Milan via air from YFC. Settle into your accommodation before exploring Milan Cathedral (Duomo di Milano), marveling at the intricate gothic architecture.

Afternoon: Visit Galleria Vittorio Emanuele II for shopping and lunch. Walk to Sforza Castle to enjoy the museums and castle grounds.

Evening: Dine near Brera District, savoring authentic Milanese cuisine like Risotto alla Milanese.

Find Hotels

Day 2: Milan History & Culture

Morning: Tour the Santa Maria delle Grazie and view Leonardo da Vinci’s Last Supper (pre-booked tickets required).

Afternoon: Explore the artistic Pinacoteca di Brera followed by a stroll in Parco Sempione.

Evening: Enjoy aperitivo in the lively Navigli District alongside the canals with local specialties.

Find Hotels

Day 3: Milan to Florence

Morning: Travel by train to Florence (~2 hours). Check in and start with a visit to Piazza del Duomo, admiring the Cathedral, Baptistery, and Giotto’s Campanile.

Afternoon: Explore Uffizi Gallery to immerse yourself in Renaissance masterpieces.

Evening: Dine at a local trattoria, enjoying Tuscan cuisine and Chianti wine.

Find Hotels

Day 4: Florence Art & Hiking

Morning: Visit Accademia Gallery to see Michelangelo’s David. Then embark on a hike up to Michelangelo Square (Piazzale Michelangelo) for breathtaking panoramic views.

Afternoon: Stroll across the historical Ponte Vecchio and explore artisan shops.

Evening: Enjoy dinner in the lively Oltrarno District, known for traditional cuisine and local vibe.

Find Hotels

Day 5: Florence to Venice

Morning: Take the train to Venice (~2 hours). Upon arrival, settle in and start with a walking tour of St. Mark’s Square and St. Mark’s Basilica.

Afternoon: Explore the Doge’s Palace and cross the iconic Bridge of Sighs.

Evening: Gondola ride in the canals followed by dinner featuring Venetian seafood specialties.

Find Hotels

Day 6: Venetian History & Islands

Morning: Visit the Rialto Market and Rialto Bridge.

Afternoon: Take a vaporetto boat to Murano to see glassblowing workshops and Burano to admire colorful houses.

Evening: Return and dine near Campo Santa Margherita, a hub of vibrant nightlife and local eateries.

Find Hotels

Day 7: Venice Hidden Gems & Hiking

Morning: Hike along the lesser-known Zattere Promenade with views of the Giudecca Canal.

Afternoon: Explore the Jewish Ghetto and learn about its rich history.

Evening: Try cicchetti (Venetian tapas) in a traditional bacaro.

Find Hotels

Day 8: Venetian Art & Cuisine

Morning: Visit the Accademia Gallery and Ca’ Rezzonico Museum of 18th-century Venice.

Afternoon: Relax with a walk in Giardini della Biennale.

Evening: Dinner featuring Venetian fritto misto and local wines.

Find Hotels

Day 9: Venice to Cinque Terre

Morning: Train journey to Cinque Terre (~5-6 hours). Check in and take a short hike along the famous trail connecting Monterosso and Vernazza.

Afternoon: Explore the colorful streets of Vernazza.

Evening: Enjoy fresh seafood by the sea with local white wine.

Find Hotels

Day 10: Hiking & Villages

Morning: Hike the Via dell’Amore path from Riomaggiore to Manarola, soaking in stunning coastal views.

Afternoon: Visit Manarola and Corniglia villages, sample local focaccia and pesto.

Evening: Relax in Corniglia with authentic Ligurian cuisine.

Find Hotels

Day 11: Beach & Leisure

Morning: Spend time relaxing on the beach at Monterosso al Mare.

Afternoon: Visit local vineyards for wine tasting tours.

Evening: Dinner overlooking the Mediterranean at a seaside trattoria.

Find Hotels

Day 12: Cinque Terre to Amalfi Coast

Morning: Early train and bus combination to the Amalfi Coast (~6-7 hours). Settle into your accommodation with views of the cliffs and sea.

Afternoon: Explore Positano, walking its steep streets and boutique shops.

Evening: Enjoy seafood pasta paired with local limoncello.

Find Hotels

Day 13: Amalfi & Hiking Path

Morning: Hike the famous Path of the Gods, offering breathtaking coastal panoramic views.

Afternoon: Visit Amalfi Cathedral and explore the town.

Evening: Dine in Amalfi town, savoring Mediterranean flavors.

Find Hotels

Day 14: Capri Day Trip

Morning: Take a ferry to Capri, tour the Blue Grotto and Gardens of Augustus.

Afternoon: Visit Marina Grande and hike to Villa Jovis.

Evening: Return and enjoy a quiet dinner in your Amalfi Coast base.

Find Hotels

Day 15: Amalfi Coast to Rome

Morning: Travel by train/bus to Rome (~3.5-4 hours). Check in and start at the majestic Colosseum and Roman Forum.

Afternoon: Walk through Piazza Venezia and visit Palazzo Venezia.

Evening: Dine in Trastevere, experiencing vibrant nightlife and Roman dishes.

Find Hotels

Day 16: Ancient Rome & Vatican

Morning: Explore Palatine Hill and Capitoline Museums.

Afternoon: Vatican Museums, Sistine Chapel, and St. Peter’s Basilica (advance tickets recommended).

Evening: Dinner near Campo de’ Fiori, sampling Roman specialties like Carbonara.

Find Hotels

Day 17: Rome Historical Walk & Hiking

Morning: Walk the Appian Way (Via Appia Antica) to enjoy a historic hiking experience among ancient ruins and aqueducts.

Afternoon: Visit the Baths of Caracalla and San Clemente Basilica.

Evening: Relax over dinner in the Monti district.

Find Hotels

Day 18: Baroque Rome & Shopping

Morning: Tour Trevi Fountain, Spanish Steps, and Piazza Navona.

Afternoon: Shop along Via del Corso and explore artisanal markets.

Evening: Try Roman Jewish cuisine in the Jewish Ghetto area.

Find Hotels

Day 19: Day Trip to Tivoli

Morning: Visit Villa d’Este for its famous gardens and fountains.

Afternoon: Explore Hadrian’s Villa ruins, a sprawling imperial retreat.

Evening: Return to Rome; dine at a local ristorante.

Find Hotels

Day 20: Rome Leisure & Culinary

Morning: Free time to revisit favorites or explore Trastevere’s cobbled streets and artisan shops.

Afternoon: Take a cooking class focusing on Roman dishes like saltimbocca or supplì.

Evening: Celebrate your last evening with a scenic dinner overlooking the Tiber River.

Find Hotels

Day 21: Travel to Palermo & City Exploration

Morning: Fly/train to Palermo, Sicily (~1.5 hour flight). Settle in and visit the Palermo Cathedral.

Afternoon: Discover the historic Quattro Canti square and nearby Piazza Pretoria.

Evening: Sample Sicilian street food at Mercato di Ballarò.

Find Hotels

Day 22: Palermo Markets & History

Morning: Visit Palazzo dei Normanni and the stunning Cappella Palatina.

Afternoon: Explore Teatro Massimo and walk through Via Vittorio Emanuele.

Evening: Dinner featuring fresh seafood pasta and local wines.

Find Hotels

Day 23: Hiking & Beaches

Morning: Day hike in Monte Pellegrino Nature Reserve, enjoying breathtaking views over Palermo and the sea.

Afternoon: Relax on the nearby Mondello Beach.

Evening: Enjoy Sicilian desserts like cannoli at a traditional café.

Find Hotels

Day 24: Day Trip to Monreale & Cefalù

Morning: Visit Monreale Cathedral with its impressive mosaics.

Afternoon: Continue to coastal town Cefalù for hiking up La Rocca and beach time.

Evening: Return to Palermo for dinner.

Find Hotels

Day 25: Palermo Culture & Farewell

Morning: Wander in Botanical Gardens of Palermo and visit San Giovanni degli Eremiti.

Afternoon: Last-minute shopping and exploration of artisan workshops.

Evening: Farewell dinner featuring Sicilian specialties and local music.

Find Hotels

Time and Cost Estimates

  • Milan Cathedral (Duomo di Milano): 2 hours, €10
  • Last Supper, Santa Maria delle Grazie: 1.5 hours, €15
  • Uffizi Gallery, Florence: 3 hours, €20
  • Accademia Gallery, Florence: 2 hours, €18
  • St. Mark’s Basilica & Doge’s Palace, Venice: 3 hours, €25
  • Venice Gondola Ride: 30 mins, €80 (per gondola)
  • Cinque Terre Hiking Trails: Full day, free (park pass ~€7)
  • Path of the Gods Hike, Amalfi Coast: 4 hours, free
  • Capri Ferry & Blue Grotto Tour: 5 hours, €50
  • Colosseum & Roman Forum: 3 hours, €16
  • Vatican Museums & Sistine Chapel: 4 hours, €30
  • Villa d’Este & Hadrian’s Villa (Tivoli day trip): 6 hours, €25 (transport + entry)
  • Cooking class in Rome: 3 hours, €60
  • Palermo Cathedral & Palazzo dei Normanni: 3 hours, €12
  • Monte Pellegrino hike: 4 hours, free
  • Monreale Cathedral: 2 hours, €5
  • Train and bus intercity travel (estimated total): ~€250
  • Flight YFC to Milan and Palermo to YFC (estimated round trip): ~€600

Total Estimated Cost: Approximately €1,240 (excludes accommodation and meals)

Tips

If you prefer a faster pace or shorter trip, consider reducing days in Venice or Palermo, focusing on main attractions only. Conversely, if you wish to immerse deeper in culture and nature, extend days in Cinque Terre or Amalfi Coast for additional hiking and coastal exploration. Foodies may also add extra days in Rome or Palermo to explore culinary tours and cooking classes in greater detail.

0
Like this trip? Make your own version.
A free, personalized itinerary in seconds — sign up to save and edit it.
Create my version