14 Days in Italy: The Classic Two-Week Grand Route

Last reviewed: October 24, 2026 · Prices in Euro (€) are approximate and for orientation only.

Route at a glance

Two weeks lets you experience both the iconic capitals and regional landscapes of Italy, linking Rome, Florence, Venice, Milan, and Naples.

Day-by-day plan

Transport & rail pass notes

Compare point-to-point Trenitalia Frecciarossa & Italo fares against a multi-day pass using our Rail Pass Calculator.

What to book ahead

• High-speed rail legs
• Boutique stays in historic towns

Ways to adapt this route

• Slow the pace by dropping one stop and adding two day trips from your favorite base.