14 days in Italy
14 Days in Italy: Rome + Florence + Venice + Cinque Terre + Dolomites Itinerary (2026)
Two weeks fits 5 essential Italy stops. Here’s the optimized circuit — Rome (3) → Florence (3) → Cinque Terre (2) → Venice (3) → Dolomites (3).
Days 1-3: Rome
Morning
Day 1: Colosseum + Roman Forum + Palatine Hill. Day 2: Vatican Museums + St. Peter’s. Day 3: Trevi Fountain + Spanish Steps + Pantheon.
Afternoon
Day-specific: walk Trastevere, eat carbonara at Roscioli, climb Aventine Hill’s keyhole view.
Evening
Roman trattoria dinner + gelato at Giolitti.
Day 4: Rome → Florence via Italo train
Morning
1h 30m train to Florence (book ahead, 30-50 EUR).
Afternoon
Walk Ponte Vecchio + Piazza della Signoria + Duomo exterior.
Evening
Dinner at Trattoria Mario or ‘Ino Sandwich.
Days 5-6: Florence
Morning
Uffizi Gallery (pre-book) + Accademia (David). Day-trip to San Gimignano or Siena.
Afternoon
Cooking class or wine tour. Climb Duomo dome (463 stairs, pre-book).
Evening
Florence dinner — Trattoria Sostanza for bistecca alla fiorentina.
Day 7: Florence → Cinque Terre
Morning
2-hour train to La Spezia, then Cinque Terre train.
Afternoon
Settle into Vernazza or Monterosso. Beach time or hiking between villages.
Evening
Seaside seafood dinner.
Day 8: Cinque Terre village-to-village hike
Morning
Hike Vernazza-Monterosso (1h 30m, moderate).
Afternoon
Train between villages — Manarola + Riomaggiore + Corniglia.
Evening
Dinner at Belforte (cliff-top in Vernazza).
Day 9: Cinque Terre → Venice
Morning
5-hour train via Milan to Venice. Or via Florence.
Afternoon
Arrive Venice + Vaporetto to hotel. Walk to Piazza San Marco.
Evening
Dinner at a Cannaregio bacaro — cicchetti + spritz.
Days 10-11: Venice
Morning
Doge’s Palace + St. Mark’s Basilica (pre-book). Murano + Burano islands.
Afternoon
Wander Cannaregio + Dorsoduro neighborhoods. Peggy Guggenheim Collection.
Evening
Venetian dinner — Osteria alle Testiere or Trattoria al Gatto Nero on Burano.
Day 12: Venice → Dolomites (Cortina d’Ampezzo)
Morning
3-hour drive or bus to Cortina (or 2-hour train to Calalzo + bus).
Afternoon
Check into Cortina hotel. Walk through town + first impressions.
Evening
Alpine dinner — pizzoccheri + speck + canederli.
Day 13: Tre Cime di Lavaredo OR Lago di Braies
Morning
Drive to Tre Cime + hike the 9.5km loop (4-5 hours).
Afternoon
OR Lago di Braies rowboat + Seceda cable car for the iconic ridge.
Evening
Cortina dinner + grappa at Bar Centrale.
Day 14: Dolomites → departure
Morning
Lago di Sorapis hike (3-hour loop) if previous day was Tre Cime.
Afternoon
Drive to Venice or Innsbruck for departure.
Evening
Final pre-flight dinner.