Florence & Tuscany in 5 Days: Renaissance, Reds & Rolling Hills Chaos

Published on 16 June 2025 at 21:12

Day 1: Florence – Classic Kickoff

  • Morning: Climb the Duomo (Cathedral of Santa Maria del Fiore) dome for breathtaking city views and a workout you didn’t expect.

  • Afternoon: Explore the Uffizi Gallery — home to Botticelli, Da Vinci, and more masterpieces than you can count.

  • Evening: Stroll along Ponte Vecchio and have dinner featuring Tuscan specialties like ribollita or bistecca alla fiorentina.

Day 2: Florence – Art & Local Life

  • Morning: Visit the Accademia Gallery to see Michelangelo’s David — try not to feel too intimidated by the sheer perfection.

  • Afternoon: Wander the San Lorenzo Market for leather goods, souvenirs, and tasty street snacks.

  • Evening: Grab a gelato from Gelateria La Carraia and enjoy it at a piazza while people-watching.

Day 3: Tuscany Day Trip – Wine & Medieval Towns

  • Morning: Head out for a guided Chianti wine tour — sip Chianti Classico, explore vineyards, and soak up the Tuscan countryside vibes.

  • Afternoon: Visit San Gimignano — climb the towers, sample the famous gelato, and get lost in medieval streets.

  • Late Afternoon: Stop by Siena for a quick visit to the Piazza del Campo and admire the stunning cathedral.

  • Evening: Return to Florence for a relaxing dinner and maybe a local vino.

Day 4: More Tuscany Magic

  • Morning: Drive or join a tour to Monteriggioni, a charming walled village that looks like it popped out of a fairy tale.

  • Afternoon: Explore the scenic Val d’Orcia region — rolling hills, cypress trees, and photo ops at every turn. Maybe visit Pienza for its famous pecorino cheese.

  • Evening: Dinner back in Florence or a countryside trattoria if you’re still out and about.

Day 5: Florence Finale

  • Morning: Visit Boboli Gardens for a leisurely walk and stunning views of the city’s skyline.

  • Afternoon: Spend your last hours shopping or revisiting your favorite café.

  • Evening: Celebrate with a final Tuscan feast — pizza, pasta, or something decadent — and soak in the vibes.


Getting Around:

  • Rent a car or book guided tours for Tuscany day trips.

  • Walk or use buses within Florence.

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