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Overnight or day trip to Montepulciano?

Hello all—

I am working on the last segments of our upcoming Europe trip (April 26-May3 in Paris with Overnight train on the 3rd, then May 4-15 in Italy (Florence 4 nights, Siena 3 nights, Rome the rest of the nights). My husband just asked if there was anyway to work Montepulciano into our trip for wine tasting, and I can comfortably squeeze it in on May 10th, and still leave us a solid day and a half in Siena. My question is, should I book it as a day trip from Siena and leave for Rome the next day as planned, or book a hotel for the night in Montepulciano, and take the train on the 11th to Rome from there? (I can easily change our RE morning train from Siena to Montepulciano that morning, to catch our Frecciarossa reservation to Rome)

Doing an overnight would mean bringing all of our bags (we will be traveling with 21” cases and backpacks), and would depend on the hotel agreeing to store them until check-in, but being able to enjoy wine tasting throughout the day and evening without traveling back to Siena. Of course, doing a day trip has the opposite benefits — no bags to deal with, but the constrained by train travel back to Siena. And looking for any recommendations for hotel in Montepulciano within the hilltop city, view, historic, charming. Budget negotiable, although for one night probably leaning lower to mid range (180€ or less)

This will be our first Europe trip in decades, and we are in the 55-66 age range for an idea of our basic details. Sadly sedentary due to covid, but currently working on that with exercise to prepare. Overall for the trip I have been trying to factor in some chill days, and limiting reservations to allow for energy fluctuations.

Posted by
3315 posts

Train service between Siena and Montepulciano is sporadic meaning there very well may not be any morning train departures from Siena to Montepulciano. Not only that there are no direct bus routes either.
If you’re willing to rent a car in Siena and drive to Montepulciano for the day you can ride along the picturesque Sienese Crest Road which will show you many different landscapes along the way. No need to get an early start either because this road gets foggy.

Posted by
140 posts

I’ve already found suitable RE train options between the two, for the day/s in question. Granted, things change, strikes, etc., which does add a tick into the day trip column given that we can opt to stay in Siena that day at the last moment if the schedule is disrupted. Which is a strong point in that direction. We definitely will not be renting a car (I hate driving and my husband likes to look at the scenery far too much for me to want us to rent a car 😬)

Posted by
7921 posts

As much as I love overnights at smaller towns (and Montepulciano is charming!), I think this would be easiest to just book a wine-tasting tour that leaves from Siena and goes to Montepulciano and probably another nearby village. Then you can relax and enjoy the day and be taken around by their minivan.