I tried to respond to Bizzwire by E-mail, but it bounced back, so I’m posting my advice here.
I’m happy to help you out with what little knowledge I have. I spent two wonderful weeks in Florence (with a brief overnight trip to Venice). Be warned that what follows is highly subjective, opinionated, and based on my limited experience.
Florence is full of bookstores, comic book shops, art supply stores, museums, etc. It’s really a place for a scholar or artist or historian. A lot of people, especially younger people, speak English and they will happily switch to English if they see you are not good at speaking Italian. Interestingly, unlike a lot of other places in the world, they won’t assume you want to speak English from the way you look. They’ll try Italian first, which I found to be very polite and charming.
Outside the Palazzo Pitti, during the day, and in other places in the city, there is a row of artists selling their drawings and paintings. These are originals and unique—they are not licensed to sell prints or posters—and very well priced. There are similar artists selling very nice original work on the streets of Venice. These paintings are well done and insanely inexpensive—it’s almost a crime not to purchase at least one.
Hours: A lot of businesses, museums, and other establishments close around 1 or 2 o’clock in the afternoon and reopen again in the evening, around 5. Keep an eye out for posted hours.
Electronics: Finding places to recharge your electronics can be challenging. Even in your hotel room, the number of outlets will be spare. Be sure you have a handful of good electric plug adapters. The two-prong European adapters do work, but it’s a tight fit. The three-prong Italian adapters are better. The best thing would be to buy a power strip in Italy and have adapters for each device. That way you can recharge everything overnight. I tried to bring my own power strip and it shorted out when I plugged it into the adapter.
Water: Tap water is theoretically available but it can be hard to get snack bars and restaurants to give you free water. If you’re doing Florence right, you’ll be walking a lot and you’ll need plenty of fluids, so I would recommend keeping two or three bottles with you and filling them up in your hotel room. It would suck to pay 3-6 euros every time you needed a drink.
If you do ask for water in a restaurant, you will likely be asked “gas or no gas?” meaning fizzy bottled water or ordinary bottled water. Once I insisted on “tap water” at a restaurant in Venice and the waitress ignored me for the rest of the meal. I suspect that you wouldn’t get such a strong reaction in Florence. Florence is full of foreign students and scholars and has a tradition of hosting expatriate English people, so they are perhaps more accustomed to tourists who are a little more frugal.
Restaurants: A lot of restaurants have a “table charge,” so it’s cheaper to take away. Quite often the restaurants that advertise “no table charge” are more expensive and of lower quality, catering to tourists. (More on eating below.)
Travel and transportation: We booked the round-trip flight and hotel for two weeks through Expedia, and it came to just under $3,000.
If you’re going in the off-season, you can get pretty good deals, and in both hotels we stayed in (Florence and Venice), as soon as we checked in, they said “We’re upgrading you to a better room” just for being there.
My recommendation: Try not to change flights in Italy. Rome’s Fiumicino Airport (Leonardo Da Vinci) is a disaster. Better to get a flight straight into Florence from Paris, London, or Amsterdam, if you can swing it. Air France, Alitalia, and British Airways were good experiences. KLM was not.
Florence Airport is as small as a midwestern bus station and customs is easy. Just walk into the terminal, look to the right for your baggage, turn left towards customs and walk to the side of the divider that says “nothing to declare” and you’re in.
Inside the airport there is a cafe and there are some places to recharge electronics. There is a tourist information booth that will help you with maps and how to take the bus into the central city. Just walk across the street and take the municipal bus to Santa Maria Novella train station and you can walk to anywhere in the central part of the city. My recommendation is to get a hotel in that area so that you can just walk around and avoid taking taxis or buses unless you really have to.
Purchase bus tickets at places called (if I recall correctly), “Tabbacheria” (or something that is similar to “tobacconists.”). There’s one right in S.M.N. railway station in the same hall where you buy train tickets. Purchase intercity train tickets from the self-serve Trenitalia kiosks (the high-speed intercity rail is called Frecciargento.). The prices change hourly, I think.
Wherever you go, you can get a decent tourist map of the central city. It’s deceptive, in that the map makes the central city looks larger than it is. Nothing on the map is very far away by foot, if you’re on holiday and you have time. We packed so that we could comfortably walk from the station to your hotel with our luggage. The stone-paved streets and sidewalks can be rough on wheels, so make sure you have good ones on your bags.
Lodging: We stayed at the Hotel Orto de’ Medici. It’s in a very decent location, about a mile or two walk from the railway station (Santa Maria Novella) and 10-20 minutes walk from the main sights in the central city. It’s a decent hotel, not luxurious, but it’s comfortable and many parts of it have been recently renovated. There’s an excellent free continental breakfast buffet every morning (this is key to our travel plan) — toast, jam, butter, hard-boiled eggs, bread rolls, cookies/biscuits, cheese, cold cereal, milk, freshly squeezed orange juice, prosciutto, salami, mozzarella bocconcici, mixed cut fruit, bananas, oranges, tomatoes, fresh bread, a juice machine, an espresso/capuccino machine, bagged teas, etc. (You can also have a Heineken or make yourself a bloody mary for breakfast.) There’s no room service or bar, so you’re on your own after breakfast. There is a mini bar/fridge in the room with beverages and some snacks but you know how that is. This hotel is literally around the corner from the Galleria dell’Accademia, where Michelangelo’s David is.
In Venice, we stayed at the Hotel Locanda Fiorita in the Campiello Nuovo o dei Morti, just around the corner from the Campo San Stefano. It is easily reached by the Actv Vaporetto Water Bus Route 1, Sant’Angelo stop (there is a big ticket (bigletteria) booth right outside the railway station). From Campo San Stefano, it’s an easy walk to the Piazza San Marco or the Rialto Bridge or the Gallerie dell’Accademia. I never figured out how to buy the water bus tickets in advance when you’re not at the railway station, but I’m sure if you ask around, you can find out. If you don’t have a ticket, as soon as you board, tell the attendant, and he will sell you a ticket.
Museums:
If you are serious about museums, then I would recommend getting a membership in the Amici degli Uffizi. For 100 euros (if I recall correctly), you can get a family membership for the calendar year (expires Dec. 31 and renewable online). That will get you two membership cards and free entry to a good number of the museums in town. I believe the only place to get it is at the Uffizi itself (and online), but I might be wrong.
There is also the Firenze Card, which covers a slightly different but overlapping set of museums, but it’s only good for three days and costs 72 euros per person. The Friends of the Uffizi is a much better deal. If you opt for the Firenze Card, you can get it at one of a handful of municipal information centers—One I recall is across three street from the S.M.N. train station (adjacent to Santa Maria Novella church), and another is a door or two down from the Palazzo Riccardi Medici, and another is inside the Palazzo Vecchio, which is the municipal headquarters.
Book shops:
There are a lot of book shops in Florence, but, of course, most of them are geared towards books in Italian. A very good place for English-language books is the Paperback Exchange Anglo-American Bookshop on Via della Oche, a tiny alleyway around the corner from the Duomo.
Pens and paper:
Florence is a fantastic place to shop for writing implements and materials. I didn’t have the budget for it, but if I could have, I would have taken a couple hundred euros just to buy pens and notebooks.
Food:
My strategy towards food was to not spend a lot, but concentrate on simple, good food, preferably that geared toward local tastes. Also, while eating is a huge part of my interest in exploring a place, I didn’t want to spend a lot of time on it, cutting into time for seeing things. This was my strategy.
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Free hotel breakfast—eat plenty so that you don’t have to worry about a big lunch.
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Lunch—grab a slice of pizza or a sandwich from grocery store delis or snack bars. These places are unbelievably good. I can recommend the the pizza at the Eataly grocery store near the Duomo and the prosciutto panino at Pizzeria Franco, a tiny hole-in-the-wall snack bar on the Via de Guicciardini on the route from the Ponte Vecchio to the Palazzo Pitti. And the Sandwichic Merceria sandwich shop on the Via San Gallo 3/R, just a block or two from the Hotel Orto de’ Medici.
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Fruits—It’s hard to get fruits and vegetables into your diet when sightseeing. We would stop at the Sapori & Dintorni Conad supermarket to get some fresh fruit and take it back to the hotel to eat at night or early in the morning. If there’s a mini fridge in your hotel, you can probably make some room in it for fresh food. The prepared foods at the deli counter at Sapori & Dintorni are also very good.
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We ate most evenings at the Mercato Centrale. The food court upstairs is open from about noon to midnight and there is a stall for everything, and it’s all locally sourced—cheese, desserts, ice cream, pizza, pasta, lampredotto, salads (this is the one place I’d go for a salad), burgers and steaks, seafood, everything you can think of. Each night you can have something different, well-made with fresh, local ingredients. There is also a lot of sampling that goes on when it gets crowded at night. Unlike at a lot of places, seating here is free. Just get your food and sit anywhere there’s a free chair. There’s also a loft with a pizzeria upstairs, but I didn’t get a chance to go up there.
Waiters will come around to take your drink orders or you can get beverages yourself from the bar. I found that especially at the specialty kiosks where they prepared your food right in front of you, they loved it if you took interest, asked them about their food and asked advice about other things to do in town. The local people are for the most part very friendly and warm and if they are preparing food for you, they take pride in it and love to interact.
Downstairs is the regular market and it’s closed by noon. It’s worth seeing though—the fresh food and flowers and produce, all amazing. It’s not very much use to a tourist because you don’t likely have the time or the facilities to take fresh food to cook. There are one or two restaurant booths downstairs, and they are very crowded at lunch time.
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I would definitely try the local specialties, such as lampredotto or tripa (beef tripe) sandwiches, chianina beef hamburgers or meatballs (polpetto) or steak, baked beans with fried sausage (fagiolo all’uccelletto con salsicce fritte), the Tuscan bread soup (ribollita toscana—it’s hardly soup, the bread soaks up the broth). Prosciutto ham and fresh mozzarella cheese are cheap and plentiful and delicious.
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The street-side roasted chestnuts are very good.
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This might not be a problem like you, but I’m not a huge fan of caffè espresso, and it’s hard to get any coffee drink in Florence that doesn’t come out of an espresso machine. They’ll offer you a caffè Americano, which is espresso diluted with hot water. Yuck. There are a very small number of places that prominently advertise “filter coffee,” and that’s where they have real coffee, and it’s good too.
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Okay, once or twice I went to McDonald’s to grab a coffee. Sometimes convenience wins the day—as well as the sight of a real coffee pot. Also, McDonald’s in Florence sells fried polenta triangles, which are … not very good, but at least they were new to me.
Avoid:
— Full-service sit-down restaurants. These are most likely to be geared towards tourists, overpriced, and mediocre. Anything that has a lot of “salads” on the menu is suspect. This is where you will have to pay 6 euros for water. If you do eat at a restaurant, you’ll notice the menu is likely divided into Primi (pasta) and Secondi (meat). The larger the menu, the more suspect its quality. If there is outdoor sidewalk seating or a large tent on a plaza, it’s also likely to be more expensive and lower quality.
But I found in general that at casual places where you order at the counter, the food is excellent, relatively inexpensive, fast, and just wonderful—specify “table” or “takeaway” because there might be a table charge.
— Anything recommended by The Guardian or expatriates or non-locals (especially if they’re British 
). Our worst food experiences resulted from this.
— The “Aperitivo” specials at the bars during the evening happy hours, where if you buy a drink, you can eat all you want from the buffet. The food here is usually not that good and very heavy.
And in general “chicchetti” which are the Venezian version of tapas.