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8 days in Tuscany & Cinque Terre

Tuscan Adventure

Overview
Tuscany was love at first sight on our first Italian road trip, charming us with its timeless beauty. Losing yourself in the rolling hills, indulging in the rich flavors of Tuscan cuisine, exploring the treasures of Florence, or immersing yourself in the idyllic countryside dotted with ancient castles — Tuscany awakens your senses and leaves you longing for more.
6-10

days

6

regions

36

activities

31

curated stays

Catherine fyno curator photo
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Tuscany expert
Spirited explorer with a deep love for diverse cultures and breathtaking landscapes, no matter if it's a solo adventure or a family road trip. Believes in profound transformation through unique travel experiences.

Tuscany & the wider saved route

Choose your days, then leave room for the journey.

The eight-day starting trip extends into Cinque Terre in Liguria and includes Orvieto in Umbria. Allow eight sightseeing days, followed by a separate departure day toward Florence. The complete starting plan is below. Read the practical day notes before treating a full stop list as a feasible schedule.

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Choose one main outing

A museum booking, a hill town and a countryside transfer each need their own time. The busiest saved days offer alternatives; shorten the stop list when the journey takes the day.

Car, rail & ZTL →

Check the actual overnight locality

Le Ragnaie is near Montalcino and Villa Bordoni is near Greve in Chianti. Return to those places when assessing the full driving day.

Compare bases & stays →

Planning review November 5, 2026. Check Florence’s official ZTL guidance, Cinque Terre trail and rail notices and the particular venue or property for your dates.

Make this trip yours

Choose your dates and stops, then save a personal copy to plan with Fyno.

Your saved plan: 8 sightseeing days + departure

Explore Tuscany

Start with this expert-curated route, then customize the days and stops in your trip. Stays below are suggestions; availability depends on your dates.

Day 1Florence

Plan the day: Choose one major art museum, then the Duomo or a church visit. Five saved admissions in one day need substantial pruning.

If plans change: Move the other museum to the next city day or a longer Florence stay.

Things to do

  1. Accademia Gallery1-2h
  2. Duomo di Firenze2h
  3. Basilica di Santa Croce1h
  4. Uffizi Gallery1-3hOptional add-on
  5. Basilica di Santa Maria Novella1hOptional add-on

Suggested stay

Day 2Florence

Plan the day: Walk the centre and cross the river. Choose Boboli or the San Miniato–Piazzale Michelangelo hillside outing as the longer visit.

If plans change: Shorten the outdoor portion when weather, queues or the uphill return take longer.

Things to do

  1. Piazza Della Signoria1h
  2. Ponte Vecchio1h
  3. The Boboli Gardens2h
  4. Abbazia di San Miniato al Monte2hOptional add-on
  5. Piazzale Michelangelo1hOptional add-on

Suggested stay

Day 3Pisa

Plan the day: This is a transfer from Florence via Pisa or Lucca to Riomaggiore in Liguria. Choose one Tuscan city stop and confirm the final luggage approach.

If plans change: Drop the sunset boat trip unless its meeting time comfortably fits the journey.

Things to do

  1. Lucca1-2hOptional add-on
  2. Square of Miracles1-2h
  3. Riomaggiore2-4h
  4. Sunset Boat Tour3hOptional add-on

Suggested stay

Day 4Cinque Terre

Plan the day: Use a rail-based day for Manarola, Corniglia and Vernazza. Include the station-to-village climb at Corniglia.

If plans change: Choose fewer villages, and replace a closed trail with a train journey.

Things to do

  1. Manarola1-2h
  2. Corniglia1-2h
  3. Vernazza2-3h

Suggested stay

Day 5Cinque Terre

Plan the day: This is a long coast-to-countryside move, ending near San Gimignano. Choose beach time OR Volterra before the final estate arrival.

If plans change: Drop Volterra or the beach and arrange any Guardastelle tasting separately from the transfer.

Things to do

  1. Monterosso al Mare1-2h
  2. Monterosso Beach (Fegina)4hOptional add-on
  3. Volterra2hOptional add-on
  4. San Gimignano2-4h
  5. Guardastelle1-3hOptional add-on

Suggested stay

Day 6Siena

Plan the day: Spend time in Siena, then continue toward the selected stay near Montalcino. Montepulciano and Val d’Orcia are additional choices, not quick extras.

If plans change: Keep Siena and the overnight journey; move the other hill-town visit to another day.

Things to do

  1. Duomo di Siena2h
  2. Siena Historic Center1h
  3. Montepulciano2-4hOptional add-on
  4. Val d’Orcia2hOptional add-on

Suggested stay

Day 7Montepulciano

Plan the day: Choose Pienza and a Val d’Orcia day OR a separate southern outing. Orvieto is in Umbria; Pitigliano and Saturnia add substantial driving before returning to Montalcino.

If plans change: Keep the Pienza day and leave Orvieto, Pitigliano and Saturnia for a longer southern extension.

Things to do

  1. Pienza2h
  2. Orvieto1hOptional add-on
  3. Pitigliano2hOptional add-on
  4. Cascate del Mulino (Saturnia)2hOptional add-on

Suggested stay

Day 8Arezzo

Plan the day: Choose Arezzo or Cortona before the overnight at Villa Bordoni near Greve in Chianti. Brolio is a separate Chianti stop with a seasonal calendar.

If plans change: Drop the castle when its access or the drive does not fit; arrange the final countryside arrival before leaving.

Things to do

  1. Cortona3h
  2. Arezzo2hOptional add-on
  3. Castle of Brolio2hOptional add-on

Suggested stay

Day 9Florence

Plan the day: The final empty Florence row is a departure allowance. The selected previous stay is in Chianti, so include the journey back to Florence.

If plans change: Keep airport or station time free of additional sightseeing; no further overnight is selected.

Things to do

Keep this day flexible for travel and exploring.

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