Montepulciano – Medieval Town In The Hills

My gf Cindy invited me to go to Italy for her dear friend’s special birthday, and as alwaysMe and Cindy I’m down to travel, so we booked our flight 3 weeks prior to the celebration. She said that I didn’t have to worry about planning anything which is a relief because I needed a break. All I had to do was book my flight to Rome and take a train to  Chiusi Chianciano Terme Montepulciano. Piece of cake. We got in late so her friends Giorgio & Simon picked us up from the station and drove us straight to the villa. It was dark so I didn’t get a chance to see anything on the way. The next morning when I woke up, the views took my breath away. I didn’t even know I was in Tuscany and I was in for a real surprise.

Montepulciano is a Medieval Town and it’s gotten popular over the years because Twilight “New Moon” was filmed there. Away from all the hustle and bustle and over crowded touristic spots, you can really enjoy this towns’ scenic views.

Travel Cost Breakdown

BCN –> FCO (Flumicino) AlItalia: 5,036 points in the UR Portal ($75.55 USD)
Vueling & Ryanaiar also fly for around $40 USD

Bus from FCO to Termini Train Station.7 €. As you exit the airport follow signs for the bus. Tickets are sold at the machine or there’s a window with a sign showing when the next bus is. The trip is about 50 minutes – 1 hour.
Another option to the Termini Station is the train: 15 € and it takes 32 minutes.

Train to Chiusi Chianciano Terme Montepulciano via 9.95€
If you arrive during the day time there are very few taxis, however there is a bus you can take from this station to the bus station at Montepulciano (about a 50 minute ride). Renting a car is also and option but be aware of the hours. For example, Hertz rental car is open Monday – Saturday, 9:30am – 12:30pm, 3:00pm – 6:30pm and closed on Sundays.



Villa Martiena is a beautiful B&B and Giorgio & Simon are the best hosts ever! The villa can accommodate up to 14 guests and has the most spectacular views of the hills in Montepulciano. Each spacious bedroom has its own bathroom and pleasantly thought out amenities. Every day the room is serviced with fresh towels. The outdoor area is nicely decorated and there are so many places to sit and just chill while enjoying the peace and quiet and listening to the sounds of nature. A short walk down and you can lounge by the infinity pool to watch the sunset. During our stay we were spoiled with delicious foods, made by their personal chef Felice and his wife Maria.



For the first time I actually go to relax on this vacation. It was really nice not having to plan everything since Giorgio & Simon already had a well thought out plan for the group.

  • Abbazia di Sant’Antimo – A beautiful monastery that’s worth checking out.
  • Bar Belvedere in Montalcino for a quick lunch. Don’t forget to grab a gelato!
  • Pienza – a town known for Pecorino Cheese and the Romeo & Juliet classic movie (1968) by Franco Zefferilli filmed at Palazzo Piccolomini.

Giorgio set up a spectacular cheese tasting at the shop. They were very helpful and explained which cheeses could be brought back to the US.
Bottega Del Naturista
Corso il Rossellino, 16
53026 Pienza SI


Wine Tasting

Tenuta di Sesta for wine tasting and a tour. With the family’ expertise in wine making (they have won several awards for best wine!)
53024 Castelnuovo dell’Abate
Montalcino Siena
+39 0577 835612


A 15 minute walk up into town and you can shop and dine with the locals. Don’t forget to visit De’ Ricci Cantine. Its impressive wine cellars in the caves will leave you in awe.
De’ Ricci Cantine
Via Ricci, 11
53045 Montepulciano
+39 0578 757166


Truffle Hunting

I’ve always dreamed of going truffle hunting! And there’s no better place to go truffle hunting than Montepulciano!!! White truffle season is late October through November and black truffles is November through March. With only his zappino (tool) and his experienced and trained dog, Alessandro explained how the process worked and off we went. We got lucky and found 2 fairly decent sized truffles. What an amazing experience it was to have such a lovely guide. You’ll have to wake up early in the morning to do this activity, since that’s when the scent comes up off the ground.

Tartufo Montepulciano
+39 339 7260267
+39 0578 321608


My last day there was the most memorable, celebrating Giorgio’s birthday with the Aloha Spirit and accompanied with amazing friends. If you are thinking of going to Tuscany I highly suggest booking with Giorgio & Simon. I guarantee that they will really take good care of you. Honestly, I can’t wait to go back!



2 Comments on “Montepulciano – Medieval Town In The Hills

  1. Chu Chu, you’re the best! What a wonderful description of a perfect experience. And as beautiful as your pictures are, both you and the villa are even more spectacular in person. I should know….I was there! Bravo, Simon and Giorgio! Xoxoxo,


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