All Trips · Europe
Tuscany: Vineyards, Hilltop Towns & Timeless Italy
Chianti - Siena - Florence
Duration
6 days / 5 nights
Starts
Florence
Ends
Florence
Car
TOYOTA AYGO
Hotels
3 stays
Stay as many nights as you wish
Your package price updates instantly
Flights, hotel & car in one booking
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Overview
Experience the essence of Tuscany—rolling vineyards, Renaissance cities, and postcard-perfect villages. This carefully designed journey combines iconic highlights like Florence and Siena with the scenic countryside of Chianti and Val d’Orcia.
Perfect for
Wine Lovers
Self-Drive
Couples
History Buffs
Food & Wine
Photography
Countryside Escapes
Art & Culture
Your Itinerary Overview
- 1Day 12 nightsFlorence → Chianti Wine RegionAlbergo Del Chianti
Arrive at Florence Airport (FLR) Pick up your rental car Drive into the famous Chianti Experience: Scenic…
- 2Day 2Chianti
Enjoy a full day in the Tuscan countryside Suggestions: Visit boutique wineries Enjoy a long vineyard lunch…
- 3Day 32 nightsChianti → SienaCasa di Osio
Drive to Siena Experience: Explore Piazza del Campo Visit Siena Cathedral Wander through medieval streets…
- 4Day 4Siena – Culture & Slow Travel
Leisure day based in Siena Options: Half-day trip to Monteriggioni or countryside Explore local markets and…
- 5Day 51 nightSiena → FlorenceCapri Moon Guest House
Drive to Florence Experience: Explore Florence’s historic center Visit the Duomo and Piazza della Signoria…
- 6Day 6Departure
Make the most of your final day in Florence Enjoy a relaxed morning, last shopping or café stop Late…
Total: 5 Nights
Your route. Your pace.
Add or remove nights at every destination. Your itinerary and package price update instantly.
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Prices shown for a 7-day rental.
Why You'll Love This Trip
Drive at your own pace through Chianti, Siena, and Florence
Wine tasting at real Chianti wineries in stunning countryside
Stay in historic boutique hotels and converted estates
Explore hilltop villages most tour buses skip
Florence and Siena — two of Italy's greatest cities — in one trip
Long vineyard lunches and local markets on the itinerary
Flexible day-by-day structure — go where the mood takes you
What's Included
5 nights hand-picked accommodation
Airport & inter-city transfers
What's Excluded
International flights
Travel insurance
Personal expenses & tips
From per person$590