Romantic and active itenary for 10 days


New member
Hi Lourdes, Donna & All,

First time here and was encouraged by your helpful tips on this forum. My husband and I are going to Tuscany in the end of October for 9.5 days (10 nights) and are looking for advice on our itenary. We are 27&31 and love active vacation with a romantic touch and beautiful views + some history & culture. We are arriving to Pisa and planning to take a car. We have reserved 2 days for Florence in the end of our trip and need your advice for the remaining 7.5 days.

We were considering to do day trips from a base (Siena/ Montelpulciano area-?):
Day 1 (half-day only upon arrival): Pisa/Luca or skip and visit Volterra on our way to the base-?
Day 2: Siena + Buenconvento
Day 3: San Gimignano & Monteriggiioni
Day 4: Pienza + other villages in Val d'orcia (castiglione d'orcia/ san quirico d'orcia-?)
Day 5: Bike tour or hike trip (any tips?)
Day 6: Montalcino + Montepulciano + abbazia di san galgano
Day 7: Cortona + Valdichia Outlet Village (or shop in Florence?)
Day 8: Bagni san Filippo + wine tasting in chianti?
Day 9-10: Florence (stay in Florence)

We also love getting of the beaten track, so any tips on other places to see/better planning would be much appreciated! Do you have any good places at a reasonable price in mind for accomodation, like a farmhouse reachable convenient for our itenary? We value view, hospitality and convenience and don't need luxury.

Thank you in advance and can't wait for our Toscana adventure!:):):)

Pro Loco Sovicille

Well-known member
Your itinerary in Tuscany


Great itinerary! You will love Tuscany!
Personally I think it is better to have a base in the countryside around Siena, you'll be closer to everything.
Day 1: Do not skip Pisa or Lucca (both towns are very beautiful!)
Day 2: Probably Siena will need one entire day - it is a wonderful town that offers a lot!
Day 3: Monteriggioni, San Gimignano and, if you have time, here you could add Volterra!
Day 4: "Val d'Orcia" with Montalcino, Bagno Vignoni and Pienza (and you could add a wine-tasting)
Day 5: For your bike tour you could choose the "Val di Merse" - very panoramic, tuscan area with a lot of antique churches (f.ex. the abbey "Abbazia di San Galgano" with sword in the stone) and castels.
Day 6: Chianti (Castellina in Chianti, Radda in Chianti, Gaiole in Chianti - plus wine-tasting)
Day 7: Cortona and Val di Chiana Outlet
Day 8: Choose one of the famous spas in Tuscany (they are in Rapolano Terme, Bagni di Petriolo, Bagni San Filippo ...
Day 9 and 10: Florence

If you need more infos, get in touch:

Have a great holiday!


Well-known member

Sounds like your itinerary is shaping together perfectly.

As for bike tours, have a look at this link for some organized ideas, you might even want to look into getting a Vespa (small motor bike) that would be a fun way to explore the countryside!!

Another idea is looking into a cooking class, that is a fun way to enjoy the culture, the food and the people. Check here for some ideas:

Buon Viaggio,

Donna Denise


New member
Thank you Pro Loco Sovicille and Dona for great tips! I am already in love with Tuscany! Can't wait!

We arrive only at 14.30 on Day 1, so I guess can't make both Pisa and Lucca. What would you recommend?
Is there a way to rent a bike only in Val di Merse without a biking tour? Any bike companies/websites you could advise?

Thank you so much!!!


New member
accomodation tips

Forgot to ask: do you have any farmhouses/ B&Bs in the countryside at a reasonable price you would recommend? Thank you!


Well-known member
Where to go first?


I am saying this just because of the time situation - if you have never seen the leaning tower of Pisa then do that ... however if you have already seen the town then I would head directly to your accommodations. You really won't have enough time to enjoy Lucca (unless you stay the night there)

As per accommodations if you are looking to stay near San Gimignano (or that general area for two nights):

personal favorites: Villa Alba (close to the city can really enjoy S.G.) or Giovanna Vacanze (more in the countryside great views and hospitality)

Have Fun!

Donna Denise

Pro Loco Sovicille

Well-known member
Bike rental in Val di Merse

You could rent your bike in Rosia (little village part of the Val di Merse)
Via Massetana 193
Tel: 0577345407
to give you an idea of the itineraries you could do by bike, visit (section intineraries)