Italy Travel Itinerary: Chicago to Rome via American Airlines (October 14-26, 2025)

Day 1: October 14 - Departure from Chicago & Arrival in Rome

Morning: Depart from Chicago O'Hare International Airport on American Airlines flight to Rome Fiumicino Airport.

Afternoon: Arrive in Rome, transfer to your hotel via taxi or train. Settle in and take a brief stroll around the historic center to get your bearings.

Evening: Enjoy an outdoor dinner near Piazza Navona, soaking in Roman atmosphere.

Day 2: October 15 - Ancient Rome & Outdoor Exploration

Morning: Visit the iconic Colosseum and take a guided walk around the Roman Forum to explore ancient ruins.

Afternoon: Head to Palatine Hill for outdoor panoramic views and history.

Evening: Walk along the Tiber River promenade and enjoy dinner in Trastevere neighborhood.

Day 3: October 16 - Vatican City & Museums

Morning: Tour the Vatican Museums, including the Sistine Chapel.

Afternoon: Visit St. Peter’s Basilica and relax outdoors in the Vatican Gardens.

Evening: Take a taxi to Piazza del Popolo and enjoy the sunset from Pincian Hill.

Day 4: October 17 - Rome to Florence by Train

Morning: Take a high-speed train from Rome to Florence (about 1.5 hours).

Afternoon: Explore Florence’s historic center including the Duomo and Ponte Vecchio.

Evening: Dine outdoors near Piazza della Signoria.

Day 5: October 18 - Florence Museums & Gardens

Morning: Visit the Uffizi Gallery and see Renaissance masterpieces.

Afternoon: Walk through the Boboli Gardens to enjoy open-air sculptures and views.

Evening: Relax with an evening stroll along the Arno River.

Day 6: October 19 - Florence to La Spezia and Cinque Terre Arrival

Morning: Take train from Florence to La Spezia, gateway to Cinque Terre (approx. 2.5 hours).

Afternoon: Check into accommodation in one of the Cinque Terre villages (e.g., Monterosso). Start exploring nearby trails outdoors.

Evening: Dinner overlooking the Ligurian Sea.

Day 7: October 20 - Explore Cinque Terre Outdoors

Morning: Hike the scenic Sentiero Azzurro trail connecting the villages of Monterosso, Vernazza, and Corniglia.

Afternoon: Relax at outdoor beaches in Vernazza and swim in crystal-clear waters.

Evening: Enjoy fresh seafood dinner at a terrace restaurant.

Day 8: October 21 - More Cinque Terre Villages & Outdoor Adventure

Morning: Visit the mountainous villages of Manarola and Riomaggiore by train and footpaths.

Afternoon: Kayak along the coast or rent bikes for an outdoor experience.

Evening: Sunset walk along the Lover’s Lane (Via dell'Amore).

Day 9: October 22 - Relax & Outdoor Leisure in Cinque Terre

Morning: Leisurely morning with optional boat tour to view villages from the sea.

Afternoon: Explore local markets and enjoy outdoor cafés.

Evening: Farewell dinner with Ligurian specialties and sea views.

Day 10: October 23 - Cinque Terre to Pisa & Return to Rome

Morning: Train to Pisa (about 1 hour), visit the Leaning Tower of Pisa and Piazza dei Miracoli.

Afternoon: Explore Pisa’s historic center outdoors and have a light lunch.

Evening: Continue by train to Rome (approx. 3.5 hours), check-in near the city center.

Day 11: October 24 - Final Day in Rome Exploration

Morning: Visit Villa Borghese Gardens for a relaxed outdoor morning and visit Borghese Gallery (optional).

Afternoon: Walk through Campo de’ Fiori and Castel Sant’Angelo's outdoor terraces.

Evening: Farewell dinner in a traditional Roman trattoria near Spanish Steps.

Day 12: October 25 - Departure

Morning: Light breakfast and last walk near your hotel or Trevi Fountain.

Afternoon: Taxi or train transfer to Rome Fiumicino Airport for your American Airlines flight back to Chicago.

Evening: In-flight.

Time and Cost Estimates

• Colosseum & Roman Forum: 3–4 hours, approx. €18 per person
• Vatican Museums & St. Peter’s Basilica: 4–5 hours, approx. €30 per person
• Train Rome to Florence: 1.5 hours, approx. €50 per person
• Uffizi Gallery: 2–3 hours, approx. €25 per person
• Florence to La Spezia train: 2.5 hours, approx. €30 per person
• Cinque Terre National Park Pass (for hiking trails): Per day, approx. €16 per person
• Boat tour in Cinque Terre: 2 hours, approx. €30 per person
• Train La Spezia to Pisa and Pisa to Rome: total approx. 4.5 hours, €45–60 per person combined
• Leaning Tower of Pisa: 1 hour, approx. €20 per person
• Taxi/train transfers in Rome and local areas: Approx. €15–30 per ride depending on distance

Total Estimated Cost: Approximately €350–400 per person (excluding flights and dining)

Tips

If you prefer a longer outdoor trip, consider adding an additional day in Florence or expand your stay in Cinque Terre to 5 nights to fully savor the hiking and sea adventures. For a shorter trip, reduce the stay in Florence to one full day and take a direct train from La Spezia back to Rome without stopping in Pisa, saving travel time.