Quick verdict: Italy needs more planning than appears — Vatican Jubilee 2026 = 35M pilgrims. Book everything 3+ months ahead. Refined across 5 personal Italy trips.
8-step planning checklist
1Pick regions + duration
Classic: Rome + Florence + Venice + Amalfi (10-14 days). Skip Sicily/Sardinia for first trip.
2Book international flights 2-4 months ahead
From US: $800-1500. From UK: EUR 80-300 (lower mid-range). Direct flights to Rome FCO + Milan MXP + Venice.
3Book Vatican + Colosseum 3-4 months ahead
2026 Jubilee Year = 35M pilgrims. Vatican Museums sell out months ahead. Colosseum combined ticket essential.
4Book Italo or Trenitalia trains 60+ days ahead
Online for Sparpreis fares (50-70% off walk-up). Window seats premium. Reservations mandatory on high-speed.
5Reserve premium restaurants 4-8 weeks ahead
La Pergola Rome (book 2 months ahead). Da Enzo al 29 Rome. Bistrot Paul Bert Florence. San Sebastian for foodies.
6Book Tuscan or Amalfi hotels 3-6 months ahead
Premium Amalfi (Le Sirenuse, Hotel Caruso) 6-12 months. Tuscan agriturismi 3-4 months. Mid-range 1-2 months.
7Apply for visa (if needed)
EU passport free. Schengen visa for most Western passports (90 days). EU ETIAS launching 2026 (EUR 7 fee).
8Get travel insurance + Italian SIM
Travel insurance + ATM-friendly bank. TIM or Vodafone Italian SIM ($15-30/week).
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Updated 2026. Some links on Packzup are affiliate links.
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Written by
John Morrison is the founder and lead travel writer at Packzup. Over the past decade he has explored destinations across Africa, the Americas, Asia, Europe, the Middle East, and Oceania — always self-funded, never on a press trip.