Can anyone sway me:
Fact: I did already book in Montepulciano but logistics concerns have me rethinking it
Booking is cancellable with no penalty at this time. Also a booking appears to be available for a nice view room in Pienza
Traveling with wife and young daughter (3 years old)
3 night stay in Sept., likely arriving early afternoon and leaving around noon the last day. Will have a rental car.
Want to within the city walls so we get that history, ancient feel and architecture with walkable shops and restaurants. That is what will make us enjoy the town so have ruled out the farm or staying outside the walls. Have it narrowed down to these 2 t
Logistical problem: plan on doing some driving each day and on likely 2 days a 6 AM drive to see sunrise from a specific location.
So Pienza or Montepulciano.
IMO
Pienza: Hotel I don't like quite as much not as luxurious but has a cool history, both appear to have great views from the room and common areas, is flatter for walking around which on this vacation which will have plenty of hiking and stair climbing before and after Tuscany is a good thing especially with toddler in-tow. Seems inconvenient to not have car nearby and worry about potentially driving around for an hour looking for a spot. Hotel does offer paid valet parking so can book that and don't mind paying but not sure if I can get the car myself if needed since getting someone to get your car at 6 AM I could see posing a problem.
Drive from here is only 10 minutes for my sunrise.
Location in general a little better being in the middle of Montepulciano and Montalcino vs. on either end, closer to San Quirico.
There is a hotel pool which is a plus but not a requirement.
Shopping seems as good as Montepulciano since we really don't drink wine and we do like cheese?
Food options roughly equal in terms of numbers and variety within walking distances?
The town's alleys and piazza's don't seem to have as much character and history, but without ever being inside either town this is a guess and could be a very bad generalization?
Views are good from both towns?
Also the town is much smaller, so I fear we will cover the entire town too easily and then desire to be leaving the town more often than staying in town for our stay.
Other than not being able to park right at the hotel the in and out of town general driving seem much easier and faster.
Parking or access to my car at all hours is my biggest concern.
Montepulciano
Hotel sounds better and has amazing reviews.
Hotel has parking but is at top of hill which appears to be quite the drive to get in and out many times.
Town overall has more appeal to me but have fears about logistics on getting out easily and quickly often at odd hours have me worried.
Wife may tire of the constant up and down hill walking.
Town looks more ancient, historic? Which I like.
Drive from here is 30 minutes for my sunrise and these will be solo trips so quick trips alone while family waits.
a big difference, when the each way becomes a round trip it is much more time out of the room.
To be honest part of the scary curvy drive within the city up to the hotel has appeal to me but think that appeal will more likely turn to major frustration as I revisit it for the 5 time in 2 days or need to get out fast to catch changing light.
Seems to have more areas to explore so could stay for a few days and not cover every inch which I like
Nicer for walking around at night/more scenic?
Visiting Montepulciano for a half day and not staying it in seems like a better walking plan as you can take the lift to the top and then walk down, never having to walk up. Saving your legs for other days/sites.
I would be close enough that we could come back for an evening easily enough one night without having to spend the night in this town.
Lastly though well in advance and no penalty I really hate cancelling a booked room. I feel bad for the proprietor.