Chicago to Rome & Italy Adventure: October 14 - 26, 2025

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

Morning: Depart from Chicago O'Hare International Airport via American Airlines on your direct or connecting flight to Rome.

Afternoon: Arrive at Rome Fiumicino Airport, take a taxi to your accommodation. Settle in and rest after the flight.

Evening: Enjoy a gentle stroll around Piazza Navona and a casual Italian dinner nearby to soak in your first taste of Rome’s atmosphere.

Day 2: October 15 - Rome Historic Sights

Morning: Visit the iconic Colosseum and explore the Roman Forum on foot, soaking in the grandeur of ancient Rome outdoors.

Afternoon: Walk through the Palatine Hill area, then head to the Capitoline Museums for classic art and archaeological displays.

Evening: Taxi to Trastevere neighborhood for an atmospheric dinner with local Roman cuisine amid cobblestone streets.

Day 3: October 16 - Vatican City & Gardens

Morning: Explore the Vatican Museums including the Sistine Chapel, an outdoor/indoor marvel of art and history.

Afternoon: Walk the Vatican Gardens and visit St. Peter’s Basilica, taking in breathtaking views from the dome.

Evening: Enjoy dinner near Piazza di Spagna and a sunset stroll by the Spanish Steps.

Day 4: October 17 - Rome to Florence by Train

Morning: Take a morning high-speed train from Rome Termini to Florence Santa Maria Novella (approx. 1.5 hrs).

Afternoon: Visit Florence’s Duomo (Cathedral of Santa Maria del Fiore), climb the dome for spectacular outdoor views, then explore nearby Piazza della Signoria.

Evening: Relax with dinner near the Arno River, witnessing the sunset at Ponte Vecchio.

Day 5: October 18 - Florence Museums & Gardens

Morning: Visit the Uffizi Gallery to enjoy Renaissance masterpieces.

Afternoon: Head outdoors to the Boboli Gardens to enjoy beautifully landscaped grounds with panoramic city views.

Evening: Take a taxi to the hillside Michelangelo Square for a sunset panorama and dinner.

Day 6: October 19 - Florence to Cinque Terre (4-night stay)

Morning: Take a train from Florence to the Cinque Terre region (approx. 2.5 - 3 hrs with train changes at La Spezia).

Afternoon: Check into your accommodation in one of the five villages (recommended: Vernazza or Manarola). Begin exploring with a walk along the famous Sentiero Azzurro hiking path.

Evening: Enjoy fresh seafood dinner with views of the Mediterranean Sea.

Day 7: October 20 - Cinque Terre Hiking & Outdoor Exploration

Morning: Hike from Monterosso al Mare to Vernazza, stopping to swim and take in dramatic cliffs and vineyards.

Afternoon: Explore the village of Corniglia and relax outdoors at local terraces.

Evening: Take a taxi or ferry to another village for dinner under the stars.

Day 8: October 21 - Cinque Terre & Beach Time

Morning: Visit Riomaggiore and the scenic harbor, enjoy outdoor kayaking or a boat tour along the coast.

Afternoon: Leisurely beach time at Monterosso, the largest beach in the Cinque Terre.

Evening: Dine at a local trattoria with sunset views overlooking the sea cliffs.

Day 9: October 22 - Day trip to Portovenere and Palmaria Island

Morning: Take a ferry to Portovenere, a charming UNESCO site with historic castles and a picturesque harbor.

Afternoon: Explore Palmaria Island hiking trails and coastal views, great for outdoor lovers.

Evening: Return to Cinque Terre for your final dinner, enjoying fresh Ligurian specialties.

Day 10: October 23 - Cinque Terre to Pisa & Lucca Stopover; Evening Train to Rome

Morning: Take a train to Pisa, visit the Leaning Tower and surrounding Piazza dei Miracoli.

Afternoon: Continue by train (15 mins) to Lucca to cycle or walk atop its historic city walls and explore the medieval town center.

Evening: Return to Pisa and take an evening train to Rome (approx. 3 hrs).

Day 11: October 24 - Rome: Outdoor Exploration & Museums

Morning: Visit Villa Borghese Gardens, rent bikes or paddle on the lake, then explore Borghese Gallery to see Bernini and Caravaggio works.

Afternoon: Stroll the Janiculum Hill for expansive Rome views and walk down to the Trastevere area outdoor markets.

Evening: Farewell dinner near Piazza del Popolo, soaking in the lively Roman atmosphere.

Day 12: October 25 - Last Day in Rome: Outdoor Historic Sites

Morning: Visit the outdoor Baths of Caracalla, a massive ancient complex surrounded by gardens.

Afternoon: Walk along the Appian Way (Via Appia Antica) enjoying one of Rome’s oldest roads and nearby catacombs.

Evening: Relax with a light dinner and pack for departure.

Day 13: October 26 - Departure from Rome to Chicago

Morning: Taxi to Fiumicino Airport for your American Airlines flight back home to Chicago.

Afternoon: In flight.

Evening: Arrive in Chicago, concluding your incredible Italian adventure.

Time and Cost Estimates

• Colosseum & Roman Forum: 3 hours; €18 entry fee
• Vatican Museums & Gardens: 4 hours; €30 entry + garden tour €12
• Train Rome to Florence: 1.5 hours; €35 per person
• Uffizi Gallery: 2-3 hours; €20 entry fee
• Train Florence to Cinque Terre: 3 hours; €30 per person
• Cinque Terre hiking & ferry passes: Multiple days; €16 for hiking card + up to €30 ferry pass
• Boat tour & kayaking in Cinque Terre: 2 hours; approx. €40
• Day trip to Portovenere & Palmaria: Ferry €15
• Pisa Leaning Tower: 1 hour; €20 entry and climb
• Lucca city walls bike rental: 2 hours; €10
• Train Pisa/Florence to Rome: 3 hours; €40 per person
• Borghese Gallery: 2 hours; €20 entry fee
• Taxi rides total estimate: Approx. €100 (airport + local)
• Meals (approximate per day): €40 per person x 13 days = €520
• Total estimated cost: ~€936 per person (excluding airfare)

Tips

• To extend your trip, consider adding 2-3 days in Tuscany countryside (e.g., Siena or Chianti region) for more outdoor vineyard hikes and medieval towns.
• If you want to reduce the duration, shorten the Cinque Terre stay to 2 nights and skip Portovenere for a faster pace prioritizing Rome and Florence.
• Booking train tickets and museum entrances in advance is highly recommended to save time and avoid lines.
• Bring good hiking shoes for the trails in Cinque Terre and comfortable walking shoes for historic sites.