Chianti & wine country
Plan winery visits and a regional lunch around your tastes. We will review the route, transportation and reservations so the day fits your pace.
ITALY4REAL • PLANNING ITALY TRIPS SINCE 1995
Tuscany tours through wine country & hill towns
Our Tuscany tours bring together hill towns, regional food, wine country and time to enjoy the countryside. Choose a small group itinerary or let us build your custom Italy trip with accommodations, sightseeing and ground transportation.
Plan your Tuscany & Italy tripCompare tour packagesComplete packages of 7 days or longer • Private & small group options
Italy vacation packages featuring Tuscany
Use these itineraries as a starting point. Compare routes, travel styles and inclusions on each tour page, then tell us what fits your plans.
Your complete vacation, in one plan
Choose a tour below or let us customize a package featuring Tuscany, other Italian destinations or multiple countries across Western Europe. Trips of 7+ days include accommodations, sightseeing and ground transportation.
Request your custom trip.Intimate & Small Group Tours
Guided departures with other travelers. Check each itinerary for its maximum group size, dates and inclusions.
Venice, Florence and Rome | The Big 3 Small Group Tour
Ref I4R-14735
Escorted · Small Group · Max 25
8 days
€3,357–€3,797 per person
Venice, Florence, Rome and Sorrento Small Group Tour
Ref I4R-19560
Escorted · Small Group · Max 25
11 days
€4,643–€5,083 per person
Primo Italiano Luxury Small Group Tour of Italy
Ref I4R-11726
Group tour · Group size on request
13 days
$6,199 USD per person
Venice to Sicily Small Group Tour | The Grand Tour
Ref I4R-19569
Escorted · Small Group · Max 25
15 days
€5,739–€6,179 per person
Private & Custom Packages
Itinerary ideas to personalize around your party, dates and interests. Some activities may be shared, as listed in your proposal.
Back Roads of Northern Italy
Ref I4R-11798
Private Custom
7 days
From €2,371 per person
Odyssey by High-Speed Train
Ref I4R-14316
Private Custom
7 days
From €3,069 per person. (double occupancy) See pricing options
Tuscan Villa Cycling Retreat: Authentic Exploration and Serenity
Ref I4R-15608
Private Custom
7 days
€3,298 See pricing options
Tuscany Tour
Ref I4R-11816
Private Custom
7 days
From €3,971 per person
Wine Food Tour of Tuscany from Rome
Ref I4R-11821
Private Custom
7 days
Price on request
Customized Rome, Florence & Venice
Ref I4R-11887
Private Custom
8 days
Price on request
Florence & Chianti Self-Drive Tour
Ref I4R-19503
Self-drive · Private tour
8 days · 7 nights
€3,395 per person
Florence & Cinque Terre Tour
Ref I4R-19445
Semi-Escorted · Private tour
8 days · 7 nights
€3,600 per person
Rome, Florence & Cinque Terre Italian Tapestry
Ref I4R-14432
Private Custom
8 days
Price on request
Tuscan Elegance: An Immersive Journey
Ref I4R-14345
Private Custom
8 days
Price on request
Tuscany Wine Tour for wine lovers
Ref I4R-11897
Private Custom
8 days
From €3,981 per person Customize this tour
Venice, Florence & Rome by Train
Ref I4R-19443
Semi-Escorted · Private tour
8 days · 7 nights
€3,395 per person
Golfing in Italy Tuscany & Rome’s Ryder Cup Course
Ref I4R-15463
Private Custom
9 days
Price on request
Italian Journey by Train: Discover Italy with Italy4Real
Ref I4R-14269
Private Custom
10 days
From €4,249 per person. See pricing options
Italy on a Budget: Milan, Venice, Florence & More
Ref I4R-16502
Private Custom
10 days
From €2,999 per person.
Italian Odyssey by Train North to South Through Culture, Culinary and Coastlines
Ref I4R-14446
Private Custom
12 days
From €€4,456 per person See pricing options
Rome Tuscany, Amalfi Coast Cinque Terre and Italy’s Boot
Ref I4R-373
Private Custom
15 days
Price on request
Prefer different dates, hotels or a slower pace? Request a custom itinerary.
Where is Tuscany in Italy?
City art and countryside in central Italy
Tuscany lies in central Italy, with a coastline on the west. The map highlights the region in red and marks Florence for orientation.
Put your route in context
Plan time in Florence, the hill towns and wine country, with your bases chosen around the places you want to visit. Rome and Venice are options for a longer route.
Plan your custom trip →Travel distances & times for Tuscany
Tuscany is a region, so Florence is the arrival reference for the long-distance routes below. Siena shows how onward travel within Tuscany changes the plan.
| Route | Road distance | By car | By train | Arrival & connections |
|---|---|---|---|---|
| Rome → Florence, Tuscany | 275 km / 170 miles | 3–4 hours | 1½–1¾ hours | High-speed train to Firenze Santa Maria Novella; countryside transfers are additional. |
| Venice → Florence, Tuscany | 260 km / 160 miles | 3–3½ hours | 2–2¼ hours | High-speed train from Venezia Santa Lucia. |
| Florence → Siena | 75 km / 45 miles | 1¼–1½ hours | 1½–2 hours | Regional train to Siena station, then local transport or a walk uphill to the historic center. |
A Florence train arrival is not an arrival at a countryside hotel. Val d’Orcia, Chianti villages and wineries often need a car and driver, with timing based on your exact base.
Planning estimates, not a timetable. Road distances depend on route and hotel access; driving times allow for normal conditions but exclude sightseeing stops and major delays. Train times are station to station, unless a connection is described, and vary by departure, changes and engineering work. Your Italy4Real Travel Expert will confirm transport and transfers in your vacation proposal.
Tuscany beyond the summer season
Plan around your interests
Consider spring or autumn for a trip built around hill towns, food, wine and walking. Tell us which experiences matter most so we can review dates and seasonal availability.
Request your Tuscany itinerary →Late autumn, winter & holidays
Build a different kind of Tuscany stay around Florence’s art, regional meals and selected countryside visits. We will review shorter days, holiday schedules and which hotels and experiences operate on your dates.
Christmas & off-season Italy ideas →Tuscany experiences to add to your package
Already traveling with Italy4Real? Browse these ideas for cooking classes, cooking classes, winery visits, hill-town walks, e-bike rides and countryside outings. Ask your Travel Expert about adding your favorites to your existing package.
For existing customers. These experiences are ideas for additions to an Italy4Real vacation package. They are not sold individually. Additions depend on your itinerary, supplier availability and booking terms, and could involve an additional charge. Contact your Travel Expert before making plans.
A Discovery of Florence by Foot
Ref I4R-12023
Package addition
Complete packages only
Ask your travel expert
An Evening Electric Bike Ride Through Tuscany
Ref I4R-12123
Package addition
Complete packages only
Ask your travel expert
Day Trip To Pisa Tour From Tuscany: A Journey
Ref I4R-11957
Package addition
Complete packages only
Ask your travel expert
Helicopter Wine Adventure from Rome: Truffle Hunting and Gourmet Lunch Experience
Ref I4R-15743
Package addition
Complete packages only
Ask your travel expert
Tuscany Brunello Wine Tour by Helicopter from Florence
Ref I4R-15314
Package addition
Complete packages only
Ask your travel expert
Tuscany cooking class and Winery Visit
Ref I4R-15501
Package addition
Complete packages only
Ask your travel expert
Tuscany E-Bike Adventure: Montalcino & Brunello Wine 🚴♂️🍇
Ref I4R-15515
Package addition
Complete packages only
Ask your travel expert
🍇 Tuscany Winery Visit with Organic Lunch 🍷
Ref I4R-15488
Package addition
Complete packages only
Ask your travel expert
Have another Tuscany activity in mind? Ask your Travel Expert to review it with you.
What would you like to experience in Tuscany?
Choose the places and interests you care about. We will work them into your itinerary with room for meals, rest and independent exploring.
Siena & San Gimignano
Explore historic streets and town squares with room for guided visits and time on your own. Tell us how much walking and how many stops you prefer.
Val d’Orcia & hill towns
Consider Pienza, Montepulciano or Montalcino as part of your countryside route. We will group your visits sensibly around your hotel and travel days.
Cooking & local food
Add a cooking class, winery lunch or market experience within your package. Share dietary requirements early so we can review suitable options.
Florence & its galleries
Include time for Florence’s art and architecture, with Uffizi or Accademia visits if they fit your interests. Your proposal will identify the sightseeing and admissions included.
Active days & downtime
Ask about guided cycling or e-bike outings, then balance activity with a free afternoon. We will discuss fitness, terrain and the level of support each experience provides.
Specific tickets, guides and entry times depend on availability. Reserved entry does not remove security checks or every queue. Your confirmed itinerary lists the services included.
Plan Tuscany around your pace
How long to stay
For a trip focused on Tuscany, start with a package of 7 days or longer. Divide your time between Florence and a countryside base, or choose a slower route with fewer hotel changes.
Choose the right base
A city hotel and a rural property offer different ways to spend your days. We will compare locations within our inspected accommodation network around your interests and transport needs. We do not arrange vacation rentals.
Where to go next
Add Rome, Venice or the Amalfi Coast to a longer itinerary. For city-specific ideas, visit our Florence page.
Getting around the countryside
Country stays and winery visits need a transport plan. We will discuss private drivers, transfers or a rental car where appropriate. Arrange a driver for days involving wine tastings.
Walking & accessibility
Hill towns often involve slopes, stone paving and steps. Tell us about mobility needs before booking so we can review hotels, walking routes and suitable experiences.
Start planning early. Contact us at least two months before departure. Starting 6–8 months ahead gives us more time to review hotels, guides and popular visits.
Your Tuscany tour questions
Do you offer private Tuscany tours?
Yes. We arrange private guided sightseeing as part of complete Italy vacation packages of 7 days or longer. Your custom trip includes accommodations, sightseeing and ground transportation.
How do small group and custom trips differ?
A small group tour follows a scheduled route with other travelers. A custom trip follows a plan created for your party, with private services, shared activities and free time as agreed. Check each tour page for its group size and inclusions.
Do you offer skip-the-line tickets for Florence museum visits?
We always offer skip-the-line ticketing for museum visits and experiences included in your package, where available. Your chosen itinerary determines which admissions we include, and your proposal lists those details. Skip-the-line tickets bypass the regular ticket-purchase queue, but security checks and some entry waits still apply.
Where will we stay?
Many of our trips use inspected four-star hotels with breakfast, with city or countryside locations selected around your route. Your proposal lists the accommodation and room category. Share your preferences and budget before we prepare your itinerary.
How much does a Tuscany vacation package cost?
Your travel dates, total trip length, hotel category and choice of private services affect the price. Review current package details above or request a quote for your party. Your proposal lists inclusions and exclusions.
What happens after I request a trip?
We discuss your dates, interests, budget and pace, then develop a route and proposal. Read our travel planning FAQ for timelines, payments, insurance and cancellation information.
Let’s put your Tuscany plans together
Tell us your dates, number of travelers, approximate budget and the places you want to visit. We will help shape a complete Italy itinerary around your priorities.
Start planning your tripRead our planning FAQ • Why book with Italy4Real? • Email our team
