Help needed for our trip to Tuscany: romantic holiday

Help needed for our trip to Tuscany – romantic holiday

Questions & AnswersCategory: Planning Trip to TuscanyHelp needed for our trip to Tuscany – romantic holiday
Anonymous asked 3 years ago
Print Friendly, PDF & Email

Dear Elena,

I am planning a trip to Tuscany with my boyfriend. This will be our first time to Tuscany.We are planning to go around the 29th of May until the 8th of June. We want to spend 10 to 12 days in Tuscany, but are lost with regards to the itenary. We will most likely fly to and back from the airport of Pisa, unless you think this is really not managable from a route perspective.  Is therefore possible to help us out by making an itinerary  for us and also let us know exactly where we need to stay for how many days and what not to miss in those place. Also suggestions for accomdations are very much welcome. We do have a budget, but would like it to be romantic. Important for us is that we can see the beauty of Tuscany and do no rush too much, we want to feel that we are on holiday. Even though we want to see as much as possible, but we should not feel that we need a vacation from our vacation 🙂  Also we want to make it a romantic holiday. So incredible views, seeing the most beautiful villages etc etc. And we want to rent a vespa for sightseeing (but only for 1 day for example) just to experienc the dolce vita life and also thinking of having a picknick etc.I really hope you can help us out!  Kind regards, J.

1 Answers
elena nacci Staff answered 3 years ago
Print Friendly, PDF & Email

Hi! I’m happy to help:-)
10-12 days is enough to get the most out of Tuscany! Arriving at the airport of Pisa is perfect, and I suppose you are going to move by car, which is actually the best way to explore the best of Tuscany. In this case you can pick the car up directly at the airport. For car rentals you can have a look here.
Considering you’re looking for a romantic holiday, incredible views, and the most beautiful villages of Tuscany, here is my suggested itinerary:-)
For not moving continuously from one place to another and change accommodation continuously, I suggest 2 different hill towns as your base, so to have a more relaxing vacation.
1. For the fist 4 or 5 days I’d suggest staying somewhere near Florence, so to visit Florence, its many attractions, and some of the major sights to visit in Tuscany. Do base in San Gimignano, beautiful hill town famous for its wonderful and scenic medieval towers.

San Gimignano itself has much to offer, here you can read about San Gimignano’s Top Attractions I suggest to visit. From San Gimignano you can then start to make a lot of day trips, of course in case you have your own car:

  • Florence town (1 hour drive) and its main sights, from The Uffizi and the Ponte Vecchio to the church of Santa Maria Novella and Brunelleschi Dome.
  • Siena and its main sights, from Piazza del Campo and the Tore del Mangia to the 
  • Chianti, wonderful countryside area of Tuscany known for its fine wine and lovely hill towns
  • Volterra, beautiful Etruscan town
  • Monteriggioni, medieval town with a perfect circle of walls
  • Pisa and Lucca (the more distant from San Gimignano, though taking around 1 hour and half or less)

Coming to your accommodation in San Gimignano, I recommend the B&B Locanda Viani, right outside the city walls with a stunning view over the towers, or if you prefer to stay right in town, I suggest the lovely and very romantic Hotel Antico Pozzo.
I know the owners of both properties, Roberto for the Locanda, and Emanuele for Antico Pozzo, so you can tell them you are a friend of mine and ask for a discount!

2. For the second part of your stay I suggest staying south of Siena, in the fabulous area known as the Val d’Orcia, that honestly is the part of Tuscany I prefer, the region from where come all those beautiful postcards you see of the scenic Tuscan countryside 🙂 the landscape here is stunning, there’s a lot to see and do, there are enchanting hill towns like Pienza, Montalcino, Bagno Vignoni, Montepulciano, and Montichiello, and this is the land of great wines, great food, thermal springs and much more!
You may stay near in the small village of Bagno Vignoni, that is one of he most romantic places to stay. A very characteristic place with fantastic thermal baths and an amazing square with an ancient Renaissance pool at its center.
I suggest you stay at the charming and very romantic B&B La Locanda del Loggiato that offers great breakfasts and lovely views of the square.
Another great and romantic option is La Casa di Adelina B&B, charming bed and breakfast in the fortified village of Monticchiello, that offers stunning views over Pienza and its enchanting hills. 
From Bagno Vignoni you can go for a lot of day trips to some of the most beautiful hill villages and attractions of southern Tuscany:

  • Pienza and Monticchiello
  • Montalcino and its fortress, impressive town atop a hill, famous for its Brunello wine
  • The Abbey of Sant’Antimo, incredibly suggestive
  • Rocca d’Orcia: climb up the tower to enjoy an endless vista
  • The Crete Senesi: the most peculiar Tuscan landscape
  • Cortona, on the top of a hill overlooking a never ending view
  • The Fortress of Radicofani, again with a stunning panorama 
  • Pitigliano: if you wish in little more than an hour you can reach the amazing Pitigliano, one of the most impressive Etruscan towns, rising right out from the rocks! Next to Pitigliano, also take the chance to visit the small and incredibly characteristic villages of Sorano and Sovana.

The Top Ten Attractions to visit in Val d’ Orcia are all to discover! Follow the link to find info and great photos.

As you can see there are quite a lot of places to see, and of course it will be impossible for you to visit all, just choose what you much like to see.
In case you wish more suggestions just get back to me! 

Have a nice evening!

Your Answer

5 + 16 =