Plan the whole trip.
Book it yourself, wherever you like.

A week to settle in, deal with jet lag, and see the city before the long haul to Italy. Suggested split: downtown core (CN Tower, waterfront, St. Lawrence Market) first two days, Distillery District + Kensington Market/Chinatown mid-week, a day trip (Niagara Falls is ~1h30 by car/bus) if the group's up for it, rest day before the overnight-adjacent flight to Rome.

Getting around — TTC day pass or Uber; Toronto is walkable downtown but transit covers the rest.

Direct overnight flight YYZ → FCO on Air Canada, ITA Airways, or Air Transat, ~8h45m. Land Rome Fiumicino late morning Nov 9. Leonardo Express train to Termini (32 min) or a pre-booked private transfer, then check in to Rome stay and take it easy — you just crossed 6 time zones.

Day 9 — Easy day. Trastevere wander, dinner at Da Enzo al 29.

Day 10 — Vatican Museums (book skip-the-line entry ahead — see Explore Rome below) + Sistine Chapel + St. Peter's Basilica. Full day, go early.

Day 11 — Colosseum, Roman Forum, Palatine Hill (combo ticket). Evening at Armando al Pantheon near the Pantheon.

Day 12 — Trevi Fountain, Spanish Steps, Villa Borghese gardens (Galleria Borghese if anyone wants a second, smaller museum — book timed entry in advance, it sells out). Dinner in Testaccio at Flavio al Velavevodetto.

Day 13 — Slow morning, Campo de' Fiori market, Salumeria Roscioli for lunch, pack up.

Fastest realistic option: short domestic flight FCO → Lamezia Terme (SUF), ~1h10m — the closest airport to Amantea. Alternative is the Frecciarossa/Italo high-speed train, ~4h30m–5h, scenic but slower. From SUF: pick up a rental car (recommended — Calabria's coast and hill towns are much easier with your own wheels) for the ~35 min drive to Amantea, or the Lamezia–Amantea airport bus (~43 min, runs a few times daily).

Slow, beach-and-hill-town pace. Amantea's old town and 11th-century Norman-Swabian castle ruins, the long sandy beach right in town, day trips with the rental car: Tropea (~1h drive, one of Italy's best coastal towns), Cosenza's old town (~40 min), the Sila mountains for a change of scenery. Fresh seafood and 'nduja everywhere. This is deliberately the least scheduled leg — it's the unwind half of the trip.

Drive back to Lamezia Terme (SUF), return the rental car, fly SUF → FCO → connect home, or route back through Rome/Toronto depending on fares available closer to the date. Build in a 3-hour buffer before international connections.