Bologna is, of course, one thousand times more interesting than Orbetello, especially in autumn, and a better bet for rainy days than coastal towns, especially since so many of its streets are covered. Albergo delle Drapperie is right in the heart of the historic food markets and for every conceivable other kind of shopping too (although having visited the Mercato di Mezzo, I would give it low marks. It's a tourist-gentrification creation that seems kind of silly in the middle of the historic markets. It actually won't take you more than a few minutes to walk though the Mercato di Mezzo unless it it packed with group tours). But the high-end clothes and jewelry shops of via Farini are about a 5 minute walk from Albergo delle Drapperie, and the hotel is also about a 5 minute walk from the more unusual shops of the via Massimo d'Azeglio. And lots of quirky stuff in between. When you are reading reviews for the hotel, see if people say anything about street noise at the crack of dawn (if noise bothers you), because that is when trucks come in to deliver food. But the overall location is great for you and there are many places in the market area where you can eat a small fresh cooked meal rather than a full restaurant meal if you decide to stay in a hotel rather than have a kitchen.
The best of white truffle season in Italy is late November into January, but since Piemonte holds its truffle fair in October, it has become more common to find them in October being served in restaurants and sold in shops. Probably the surest bet for getting a truffle-focused dinner in Bologna is at Da Nello, which is (according to Google) 400 mt from Albergo delle Drapperie.
I think there are a few trains that will get you from Bologna to Arezzo without changing trains in Florence. I really enjoy Arezzo, but as cities go it is actually pretty small, and be aware that the best parts of it sit on a very noticeable slope, so some daily climbing is probably unavoidable. For an extended stay in Arezzo I would want my days there to include an antiques market weekend. I can't remember if Arezzo holds that market once every month or twice every month. The town itself is filled with lovely antique shops which are open during the week, but the huge weekend antiques market, with many visiting vendors, is one of the most interesting of its kind in Italy. Food in Arezzo is nowhere near as interesting as food in Bologna, but the wine is much better.
I was actually thinking of you today as I was walking around my part of Italy, trying to get a few things done, because -- due an extremely minor self-caused injury to my foot -- I found myself constantly reminded of how few places there are to simply sit down it Italy without buying something. Benches are next-to-non-existent, and even department stores and other shops very rarely offer any seating to tired customers. Churches are not always open. Bus stops don't have benches. Italians frown on sitting on the edges of fountains or monuments, or steps of public buildings. And getting things done in Italy often means standing for quite some time waiting for help or to pay for a purchase. At one store I finally spotted a manager's desk with a chair nearer the back room and asked to sit in it ("Certo!"), and at the pharmacy, I simply plopped myself down at the blood pressure machine until it was my turn at the counter. There I bought some relief for my foot, which I took back to the stool and applied right in the store. At the end of my errands I got into a taxi -- not cheap, but I didn't feel like waiting on a train station platform, where there are seldom enough or any places to sit.
That's a really long way of saying that if you will want a way to sit down every few minutes when you go shopping or exploring, you might want to bring something light to carry or easy to roll that is also a seat so you are sure to have a seat whan you want one.
One more thought is that, with so many days before you need to show up for your cruise, have you thought of spending some of the days in one of the quieter and flatter small areas of Rome where you could enjoy an experience similar to what you are looking for in Bologna? Not all of Rome is noisy and filled with mobs of tourists, and there many quiet streets within reach of a lot of variety in shopping, and it is not hard to find cheap but tasty eats in Rome.