One countryside base, a car and no rush
Your trip at a glance
Six nights in the Chianti hills between Florence and Siena, with a rental car, long lunches and three days out.
Route and nights in each base
- Chianti6 nights · Nights 1–6Chianti countryside
Day 7 is departure, with no extra hotel night.
- Length
- 7 days / 6 nights
- Transfer days
- None: you stay in one base and unpack once.
- Arrival
- This version assumes arrival at Florence airport and a car collected there.
- Departure
- This version assumes departure from Florence airport.
- Car
- A car is required
- Getting around
- Rental car
- Hotel allowance
- €100–€200 per room, per night (example: two adults sharing one room with a rental car). An editorial allowance for the room only, not the trip cost; the full budget is below.
- Pace
- Relaxed: few moves and open time
- Physical demands
- Walking: mostly short walks (our estimate). Steps and slopes: some steps and slopes. Luggage: no hotel changes with luggage.
Book these first
- First Flights, the rental car and your Chianti property. Good farmhouses book out early for spring and the harvest.
- Then A timed Uffizi or Accademia ticket for Day 5, and any lunch or tasting you want to be sure of.
- Closer to the date Parking plans for Siena and the hill towns, and the rental pick-up and drop-off hours.
Nothing here is booked for you. Book once your dates are fixed, and check each official site for current rules and prices.
Who it suits
Couples, friends and families with a confident driver who want a slow week in the countryside rather than a list of towns.
Not suitable without a car and a driver. If nobody wants to drive, use a Florence or Siena base instead.
- Trip PDF
- The PDF is the original 7-day sample itinerary. It is not an export of a trip you have customized. Free with your email: the download starts straight away and we email you a link to it (5 pages, 14.6 KB).
- Saved trip
- Your own editable copy in Build My Trip. Saving asks only for your email, so we can send you a link back to it; there is no password or account. The sample here stays as it is.
- Excel planner
- A workbook made from your saved trip, not from this sample. Download it from Build My Trip once the trip is saved; anything still missing is marked in the file.
Day by day
These are suggestions, not reservations: nothing here is booked for you. Check opening days and ticket availability for your own dates.
Chianti
Day 1 Arrive and collect the car
Collect your rental car at the airport or in Florence, and drive to your base in the Chianti hills. Allow for the rental desk, the drive and the last stretch of country road, and arrive before dark. Keep the evening open for an easy dinner near your base.
Planning note: Check the car's size and fuel type, the insurance terms and any fee for returning it at a different place. Roads into Florence's historic center and Siena's are restricted to most cars.
Day 2 Chianti villages
Spend the day close to home. Drive a short loop through Chianti villages, stopping for a coffee, a market or a tasting where the road suits you. Lunch is the main event; book ahead if the place is popular.
Optional or alternative
- A wine tasting or a cooking class is optional and usually needs a booking; whoever is driving should not taste.
Planning note: Opening hours at wineries and restaurants vary by day and season; confirm before you drive.
Day 3 Siena
Drive to Siena and park outside the historic center. Walk to the central square and the cathedral, take a long lunch and be back at your base for the evening. Siena's center is closed to most traffic, so plan the parking before you go.
Optional or alternative
- Climbing the tall tower on the main square is optional and a separate ticket.
Planning note: Check parking, restricted-traffic rules and the cathedral's current ticket and opening arrangements.
Day 4 A slow day at base
Keep this day open. Stay near your base: a swim if there is a pool, a walk through the vineyards, a long lunch and an early dinner. This is the buffer for weather and tiredness.
Optional or alternative
- A short hike or a cycling loop is an option if the weather is fair.
Planning note: Treat this as the day you can swap with any other if the weather turns.
Day 5 Florence
Spend the day in Florence without driving into the center. Park at the edge of the city or at a station and go in on foot or by tram or train. Book a timed ticket for the Uffizi or the Accademia, then walk the historic center.
Optional or alternative
- Climbing the Duomo dome is a separate timed ticket.
Planning note: Florence's center is a restricted-traffic zone: do not drive into it, as fines are issued automatically. Ask your property where to park.
Day 6 San Gimignano and the hills
Drive to San Gimignano, the hill town of medieval towers, and walk it early before the day visitors. Lunch in the area, then a slow drive home through the hills. Keep the evening open.
Optional or alternative
- A local wine tasting is optional; the driver should not taste.
Planning note: San Gimignano's historic centre is a camera-controlled restricted-traffic zone (rules in force since 1 May 2026). Sightseeing visitors cannot drive in: park outside the walls (P1 Giubileo or P2 Montemaggio) and walk. Only residents, listed categories and guests of accommodation inside the zone, whose plate the property registers in advance, may enter, and an unauthorised entry is fined automatically.
Departure
Day 7 Return the car and depart
Leave enough time to refuel, return the car and reach the airport or station for your airline's or train operator's recommended check-in window. This version assumes returning the car at the airport and departing from there.
Planning note: Confirm the return location and hours of the rental desk, and the fuel policy.
Transport / practical logistics
Getting between cities and around
This trip needs a car. Chianti is a driving trip. Public transport is sparse, so the whole itinerary assumes a rental car for the full stay. The distances below are editorial estimates, not routes.
This itinerary has no transfer days: you unpack once.
Driving requirements
- Driver: At least one confident driver, comfortable with narrow, winding hill roads, manual or automatic as you book. Italian law requires a driver with a licence from outside the EU or EEA to carry an International Driving Permit or an official Italian translation, and driving without one is fined. Some rental companies, Hertz for example, will rent to licence holders from several countries without a permit, but that does not change what the law requires, so carry one unless you hold a UK licence (the Italian consulate says UK visitors need neither). Your rental company may have its own rules on licence age and a surcharge for young drivers; check them before you book.
- Restricted-traffic zones: Florence's ZTL is active Monday to Friday 07:30–20:00 and Saturday 07:30–16:00, and Siena's is active every day, around the clock; cameras read plates and an unauthorised entry is fined automatically (the national range is €83 to €332 plus procedure costs); the notice can arrive months later through your rental company, often with an administration fee. Siena's zone is camera-controlled day and night, and San Gimignano's centre has been a camera-controlled zone with six gates since 1 May 2026. A tourist driving in is not a category Siena gives permits to. Park outside and walk or take public transport in. If your hotel is inside Florence's ZTL, give the plate to the hotel on arrival.
- Parking and fuel: In Siena the Stadio-Fortezza car park was €2 an hour with a daily maximum of €26. San Gimignano's car parks had daily maximums of €7 (P1) and €15 (P2). Florence has park-and-ride car parks on the tram line, including Villa Costanza, Via Sansovino, Viale Guidoni and a free one at Ponte a Greve. Petrol averaged about €2.04 a litre and diesel €2.27 in Tuscany on 9 October 2026. Fuel up in town rather than waiting for the last village.
- Roads: The last stretch to many farmhouses is unpaved. Check the approach and arrival time with your host, and avoid arriving in the dark.
If nobody drives
Choose Florence or Siena as a base instead and use trains, regional buses and guided tours for the hill towns; Build My Trip can set up the route. A guided wine or countryside tour from a city base is the usual car-free compromise.
Airport transfers are separate
- Arrival: This version assumes arrival at Florence airport and a car collected there. Allow for immigration, baggage and the rental desk before the drive.
- Departure: This version assumes departure from Florence airport. Tram T2 from Peretola Airport to the Alamanni – Stazione S.M.N. stop takes about 20 minutes, and a single ticket is €2.00, valid for 90 minutes. Return the car and allow for check-in and security; confirm the first service if your flight is early. Pisa is the alternative gateway and needs its own transfer. Airport transport is not included in the intercity allowances.
A route with less friction
Book the car and the property well ahead for spring and the harvest. Confirm insurance, fuel policy and any one-way fee. Plan the outings so that you are back at your base before dark; country roads are slower at night.
No intercity train is needed. A guided tasting, cooking class or cycling day is optional and needs its own budget.
What to book, and in what order, is listed under Book these first.
Budget / transparent assumptions
Estimated budget
A budget you can reconcile. Illustrative allowances for two adults sharing one room with a rental car, 6 nights and 7 calendar days. All figures are EUR. These are editorial planning scenarios built from Voyaren's 2026 cost data where it has figures (items marked general allowance are not from Voyaren's cost data), not checked hotel quotes or live ticket prices.
| Category and basis | Lower | Upper |
|---|---|---|
| Accommodation 6 nights × €100–€200 per room (mid tier) | €600 | €1,200 |
| Food 7 days × 2 adults × €60–€100 (casual meals plus one nice dinner) | €840 | €1,400 |
| Rental car 7 days × €45–€65 (economy; an illustrative figure from Voyaren's cost data, not a quote) | €315 | €455 |
| Fuel and tolls About 500 km in total (a general allowance for the distance): fuel at about €2.05–€2.25 a litre, plus tolls | €50 | €106 |
| Parking Siena (up to €26 a day), San Gimignano (€7–€15 a day) and Florence park-and-ride (some free) | €10 | €50 |
| Core sights Uffizi €25 on the day or €29 booked ahead, Accademia €20 plus a €4 booking fee, per adult (both galleries) | €98 | €106 |
| Accommodation taxes 6 nights × 2 adults × €3.50–€8 | €42 | €96 |
| Subtotal | €1,955 | €3,413 |
| Contingency 10% of subtotal | €196 | €341 |
| Total for two travelers | €2,151 | €3,754 |
Per person: €1,075.50–€1,877 for the trip.
Daily equivalent for two travelers: €307.29–€536.29 across 7 days.
What this does and does not cover
The core-sights allowance covers the Uffizi and the Accademia for the Florence day; other towns are walked, not ticketed. Confirm the exact basket and booking fees. Premium guided tours, upgrades and private transfers may exceed these allowances.
Excluded: Flights, insurance, shopping, major alcohol spending, insurance and deposits on the rental car, parking fines, any one-way fee, the Duomo dome climb in Florence and the tower climb in San Gimignano, extra nights and excursions not listed above. Any date-specific access charge should be checked separately. Accommodation taxes are a general allowance, not a statement of municipal rates. Avoid counting taxes twice if included in your hotel quote.
Use the range as a starting point. Replace each allowance with actual quotes before booking. The low scenario requires all categories to land near their lower allowances; popular dates and central hotels can exceed the upper scenario. Arrival and departure each receive a full-day food allowance to leave some flexibility.
This is a fixed illustrative example. The Trip Budget calculator gives its own estimate for the route and choices you enter, so the two will not always match.
These allowances are editorial estimates, not quotes or live prices, built from Voyaren’s researched cost tables (compiled 19 September 2026 from 2025–2026 sources). This itinerary was last reviewed on 9 October 2026.
More about this trip
Why this route works
Tuscany works best slowly. One base for six nights lets you stop moving: wake up in the hills, drive a short way for a long lunch, and be back before dark. Chianti sits between Florence and Siena, so both are a day out, and San Gimignano is within reach. The trade-off is that this trip needs a car and a driver comfortable on narrow country roads.
Where to stay
- Chianti: Chianti countryside. A farmhouse or small hotel in the hills between Florence and Siena. This is Chianti, not Val d'Orcia: Val d'Orcia lies further south, beyond Siena, and is a different base with longer drives. Public transport is sparse, so plan on a car for every outing; check the last stretch of road to your property, which is often unpaved.
Seasonal and traveler variations
This is a driving trip. If nobody wants to drive, treat it as a different trip: base yourself in Florence or Siena and use trains and buses instead, which Build My Trip can set up. Chianti and Val d'Orcia are different parts of Tuscany with different driving distances; this guide covers Chianti only. With a spare afternoon, add breathing room rather than another town.
Dates matter: No departure date is assumed. Spring and the fall harvest are the most pleasant seasons; summer is hot and busy, and winter is quiet, with some farms and restaurants closed. Check current schedules, opening days and restaurant bookings for your dates.
This is the standard 7-day, 6-night example. If your trip is a different length, change the nights in Build My Trip, treat any extra days as a slower pace, and review the day-by-day plan again rather than squeezing these 7 days into fewer.
Summer is hot and the hill towns are busy at midday. In winter some farms, estates and restaurants close and days are short. Spring and the fall harvest are the most pleasant.
- Harvest season (Sep-Oct): Estates and restaurants are busier and more seasonal; book lunches and tastings further ahead.
- Summer: Plan outings for the morning, rest at midday and avoid the hill towns at noon. A pool is worth paying for.
- With children: Short drives, a pool and a farm with space to run suit this trip. Check seatbelt and child-seat rules for the rental.
- Car-free alternative: Use a Florence or Siena base with trains, buses and a guided tour for the hills; it will not feel the same, but it works.
Accessibility and walking, in detail
Voyaren has not verified the accessibility of this itinerary. No itinerary here has been verified as step-free. The notes below show what official sources say about each part of this route; where a part is not listed, no official information was found. Check each leg, each sight and your accommodation before you rely on it.
- Walking effort
- Not yet verified Walking effort is an editorial estimate: no official source gives daily walking distances for this route. Short walks in hill towns and vineyards; the main effort is driving, and no official information was found for Siena, San Gimignano or farmhouse access roads.
- Stairs, slopes and uneven surfaces
- Not yet verified Not yet verified: Siena and San Gimignano. Sources: Regione Toscana tourism (accessibility sheet, not read) (checked 2026-10-10)
- Step-free transport
- Not yet verified No official step-free information was found for the transport on this route.
- Accommodation
- Not yet verified Depends on the property you choose. Italian hotel star ratings do not guarantee a lift or a step-free entrance: ask the property about lifts, steps at the entrance and the route from the nearest stop before you book.
- Attractions
- Not yet verified No official accessibility information was found for the sights on this route.
Sources and review date
- Comune di Firenze and Comune di Siena (restricted-traffic zones); Siena Parcheggi and Comune di San Gimignano (parking tariffs) (checked 2026-10-10)
- Ministero delle Imprese e del Made in Italy (fuel prices, 9 October 2026); ACI (Codice della Strada art. 135, International Driving Permit) (checked 2026-10-10)
- Voyaren cost data (accommodation, attractions, tax, car rental) (data/italy-costs.json, compiled 2026-09-19; the car rental rate is illustrative)
Content last reviewed: 2026-10-09.
Suggested activities are ideas, not reservations, and nothing on this page is booked for you. Times, closures, ticket rules and prices change, and the budget is an illustrative planning allowance rather than a quote, so check current details before you book. This page has no affiliate or booking links; see our affiliate disclosure for how Voyaren is paid elsewhere on the site.