Tuscany Itinerary

Montepulciano
Even on a short trip to art- and history-packed Tuscany, take time to enjoy the countryside.
By Rick Steves and Gene Openshaw

So much to see, so little time. How to choose? To help you get started, we've listed our top picks for where to go in Tuscany, and our plan for your best two-week trip.

Depending on the length of your trip, and taking geographic proximity into account, here are our recommended priorities:

  • 3 days: Florence
  • 5 days, add: Siena
  • 8 days, add: Montepulciano, Pienza, and Montalcino
  • 10 days, add: Lucca, Pisa, and Volterra
  • 12 days, add: Elba
  • 14 days, add: San Gimignano and Cortona, slow down

Rick’s Best Two-Week Tuscany Trip (by Car)

Day 1: Arrive in Florence (sleep in Florence)

Day 2:  Florence (sleep in Florence)

Day 3:  Florence (sleep in Florence)

Day 4:  Florence (sleep in Florence)

Day 5:  Bus to Siena (1.5 hours; sleep in Siena)

Day 6:  Siena (sleep in Siena)

Day 7:  Rent car, drive Crete Senesi route to Montepulciano (sleep in Montepulciano)

Day 8:  Follow our guidebook's "Heart of Tuscany Drive," with a stop in Pienza (sleep in Montepulciano)

Day 9:  Follow our guidebook's "Brunello Wine Country Drive" (sleep in Montepulciano)

Day 10:  Head to San Gimignano for a short stop, then Volterra (sleep in Volterra)*

Day 11:  Volterra (sleep in Volterra)

Day 12:  Drive to Lucca, drop off car, enjoy Lucca (sleep in Lucca)

Day 13:  Day-trip to Pisa by bus (sleep in Lucca)

Day 14:  Fly home

*If you'd prefer beach time to more time in well-touristed villages, head to Elba from Montepulciano and spend two nights on the island rather than in Volterra.

With More Time

With another two days or more, you can add Elba without having to skip Volterra and San Gimignano. And drivers visiting the neighboring region of Umbria can easily stop in Cortona en route.

By Public Transportation

Florence, Pisa, Lucca, and Siena are readily linked by public transportation, but the smaller hill towns are more of a challenge. Plan on using a mix of trains and buses, as not all hill towns have rail service. Allow more time in your itinerary — bus service is spotty on weekends. For efficiency, consider taking regional minibus tours to the countryside from Florence or Siena.

Without a car, modify our suggested itinerary like this: On Day 7, bus from Siena to Montalcino (stay there three nights). On Day 8, take the Brunello Wine Bus tour. On Day 9, day-trip by bus to Montepulciano or Pienza. On Day 10, take the early bus from Montalcino to Volterra (transfer in Siena). Spend Day 11 in Volterra; on Day 12, bus to Lucca; and on Day 13, day-trip to Pisa.

Gene Openshaw is the co-author of the Rick Steves Florence & Tuscany guidebook.