Tuscany: Vineyards, Hilltop Towns & Timeless Italy
Chianti - Siena - Florence
Trip code: 934
6 days / 5 nights Tour starts Florence Tour ends Florence
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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 LoversSelf-DriveCouplesHistory BuffsFood & WinePhotographyCountryside EscapesArt & Culture
Itinerary
What you’ll do each day, with your included hotel — or upgrade any stay.
Day 1
Arrive at Florence Airport (FLR)
Pick up your rental car
Drive into the famous Chianti
Experience:
Scenic drive through vineyards and olive groves
Stop in Greve, Radda, or Castellina
Wine tasting at a local winery
👉 Chianti is one of Tuscany’s most iconic regions for wine, landscapes, and rural charm
Pick up your rental car
Drive into the famous Chianti
Experience:
Scenic drive through vineyards and olive groves
Stop in Greve, Radda, or Castellina
Wine tasting at a local winery
👉 Chianti is one of Tuscany’s most iconic regions for wine, landscapes, and rural charm
Make this trip yours
Stay longer or shorter in Radda In Chianti
Your stay in Radda In Chianti
2 nights6 days total
Your itinerary and price update when you change your stay.
Days 1–3 IncludedPalazzo Leopoldo Dimora Storica & Spa
Radda In Chianti
Recommended nights Fully flexible
Adjust the number of nights at this hotel — your itinerary days and price update automatically.
More Hotel Options
IncludedPalazzo Leopoldo Dimora Storica & Spa
Selected
Castello di Fonterutoli Wine Resort
Albergo Del Chianti
Ultimo Mulino Wellness Country Hotel
Relais Vignale & Spa
Castello di Spaltenna- Small Luxury Hotels of the World
Rental car
Florence 6 days
Toyota Aygo
IncludedMini · Alamo
Manual 4 2 Bags A/C
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
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