You are about to go to Tuscany and are going to stay in a non-self-catered accommodation, like a hotel, b&b, and the likes. Therefore you will be eating out most of the time, and very probably it will be in Tuscan restaurants.
The problem is that you have some kind of food allergy or intolerance, such as to lactose or gluten, by far the most common, which may hinder your chances of eating a satisfactory meal that does not include wheat or milk products.
However fear not, as in the great majority of Tuscan restaurants you will find satisfactory alternatives for your meals. Some restaurants are becoming more and more aware that they need to keep a small stack of gluten-free products (as pasta, bread, flour) for celiacs, while many others are very willing to accommodate your necessities.
You will find that Tuscan cheese is mainly from sheep milk (pecorino cheese) which, unlike cow milk, lactose intolerant people tend to tolerate. Cow milk is used in pasta sauces (small to none in quantity), bechamel (white sauce for lasagnas and similar), and of course in sweets, cakes and pastry preparations, ice creams, and chocolate products. Second courses are usually gluten and lactose free, with some exceptions like the Milanese veal cutlet, the ossobuco (not always), and saltimbocca to name the most popular. Side dishes are a quite safe alternative, being mainly vegetable based mostly seasoned with olive oil, vinegar and herbs. There is no creamy sauce in salads in Italy, especially in Tuscany, nor bread crumbs (whoever invented the Caesar salad must have visited another country!). In addition all side dishes are never brought on the same serving plate as the second course, so if you make a mistake and are suspicious you can still eat your entry and send back the side dish.
As far as sweets you do not have to forgo them entirely. Ice cream shops will serve delicious sorbettos (egg white, water, sugar and fruit), and pastry shops have spumoni, made with egg white and sugar, or the famous amarettos, with almond, egg white and sugar.
“Ok, but how do I make sure I make myself understood?”
The solution is pretty straight forward, and entails simply asking the restaurant what food alternatives they have, telling them about your food intolerance. They know exactly what to do and will help you if you make them aware. They feel and are responsible for your health after you made it clear to them. Ultimately, their goal is to make you happy and be happy, therefore if they can keep the customer they will show you all the alternatives, otherwise they will politely tell you that they cannot satisfy you. So do not be afraid, ask. Most places in Tuscany speak English nowadays, especially in Florence, Siena and other tourist cities.
However, here is the basic Italian sentences you will need if no English is spoken.
“I am lactose intolerant“: Sono intollerante ai latticini [latti-ch-ini] (both genders) / Sono allergica ai latticini (female), Sono allergico ai latticini (male)
Latticini stands for milk and all derivatives.
“I am wheat intolerant“: Sono celiaca [chehleeaka] (female), Sono celiaco (male)
At the ice cream shop: “Can you rinse the ice cream scoop in clear water please? I am lactose intolerant“: Può lavare il cucchiaio [kookkeeaheeoh] in acqua corrente per favore, sono intollerante ai latticini.
“No milk, no wheat products please“: Non posso mangiare né latticini né derivati del grano.
The best thing to practice the pronunciation is listening to it. Google translate does a great job at pronouncing few words at a pinch for you. Here the link.
If you find it hard to learn and remember the words, just write the sentences above on cards and bring them along when you go out to eat in a Tuscan restaurant.
And do not be afraid of speaking Italian. You will make the day of almost any Italian that hears you just trying to speak his language!
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