We loved our stay at hotel dei Capitani, would highly recommend. Montalcino is famous for truffles, wild boar, wine, and beautiful views, especially from this hotel. It is on top of a mountain and in the country so you can expect to see bugs in your room like spiders, mosquitos, stink bugs, but they are mostly all harmless and more of a nuisance than anything.
When looking for food to eat I recommend “Il Moro SNC di pellegrini Alessandro”, extremely clean kitchen, family run, delicious homemade local food. Don’t trust any of the restaurants hours posted on their websites, the city pretty much closes down once it’s past 8:30 you’ll have a hard time getting food anywhere. Also, the roads are very tight so if you are driving a car I recommend something small. Walking on the walls of the castle was another great highlight of the trip. If you want to visit any wineries make reservations ahead of time. Again, can’t recommend it enough! And thanks to the hotel staff for being so welcoming, hospitable and helpful with recommendations. We loved the whole experience.
