I recently returned from a solo trip to Italy. I found myself with some unexpected time off, and my wife could not join me-so I did it solo with her encouragement.
It was my sixteenth Europe trip (not counting business which would add around six more trips), the fourth that included Italy (five if I count a cruise in 2011 that stopped in Venice and Ravenna). Last time my wife and I did an Italy trip on the ground was 2007. This trip was booked very on the fly-booked on Wednesday and flew on Saturday. Turns out this time of year United lets you do that on miles, for a reasonable amount of miles, if you have their Explorer card (at least I think that's why).
The itinerary was: five nights Rome; two nights Orvieto; one night Siena; four nights Florence. Before booking I observed on booking.com that hotels were pretty reasonable. I paid and average of about $82 per night for singles in good quality, clean hotels with good to very good location.
Some general reflections:
-The sights really are stunning (Vatican Museums, Borghese Gallery, ancient sights in Rome, Uffizi). There is a reason why Italy is so highly touristed. When I list them out I realize that Rome in particular is special to me.
-Much as I was thrilled to be back in Italy after so long, I don't think this was the trip I needed. I needed to relax someplace where there is not so much to do. Urban Italy is so intense, and there is so much to see. Goal-oriented tourism-so much seems obligatory when there are so many incredible sights to see, even if you've seen them before. (How can you go to Rome and not see the Vatican Museums? I guess you can, but I cannot imagine it).
-This time of year, around All Saints' Day (Nov 1)-not the best time to go as Italians take vacation around this time, apparently, and it was generally pretty crowded especially in Rome and Siena.
-Italy trains are still excellent value, and a great way to travel between the places on my itinerary. Think I paid $60 for the whole trip train tickets, and it was really easy to buy tickets at kiosks.
-Without my wife to keep me in check, I ran myself ragged walking, especially in Rome and Florence. Urban Italy is just exhausting if you can't help pushing yourself to see that one extra sight or what's around the next corner.
-Yep, there are pickpockets. I lost a pair of sunglasses and a case at the Vatican Museums. Stupid me, was in an outer pocket of my backpack. They don't like to take smaller bags at the baggage check at the Vatican.
-Eateries will accommodate if you don't want to eat the full menu, first, second course. Order an appetizer and salad, for example, and you are fine. This time of year the country is over resourced for restaurant seats. The food was better that I remembered, I often had just a salad and a bruschetta.
-The size of wine pours can be pretty small (100 ml which is what, less that 1/7 a bottle for 5-6 Euros?)