As mentioned above, it is currently possible to buy most basic foodstuffs in Cuba, including fresh fruits and vegetables, but the availability is highly localized and sporadic. In Havana, for example, there are several supermarkets which between them have a reasonable supply of commodities such as eggs, cheese, meat and cooking oil that are otherwise exceedingly scarce in Cuba. But west of Havana the pickings get increasingly slim the nearer you get to Cabo San Antonio, and in fact if sailing in this direction you will find the next reasonable source of supplies is Nueva Gerona, on the Isla de la Juventud, which is weeks of cruising time away. What this means is that if you see something you like you should stock up while the going is good.
Some things you will just about not see at all. For example, breakfast cereal, oatmeal, decent tea or instant coffee, pre-packaged frozen goods (Paul loves 'chicken nuggets'; we had to load the freezer with them before leaving the USA), fresh milk (the supermarkets have powdered milk, but it is the full-fat variety which has a distinct flavor; it is worth stocking up on low-fat dried milk in the USA since this tastes more or less like regular milk), butter (canned and packaged margarine is available), and numerous other specialized foods (any kind of sauces, such as spaghetti or taco sauce, barbecue sauce, and so on; parmesan cheese; taco shells; salad dressings; pancake or biscuit mix; etc.). These you will have to carry yourself.
Then there are other things that are either scarce or far more expensive in Cuba than elsewhere. Of the basic commodities, flour, and flour-based products such as spaghetti noodles, are the most significant (you may be baking a fair bit since bread is often almost impossible to buy outside the big cities - see below; you also need to carry yeast). Sugar, believe it or not is rarely seen (it all goes for export). Looking at our list of food to have on board (which, obviously, is quite personal) there are cookies (biscuits) and other snack foods, raisins, honey, macaroni, cocoa and chocolate mix, canned fruits and vegetables (particularly the latter, which are needed to tide you over those periods when no fresh vegetables are available), brown rice, baked beans, canned sardines and tuna, and canned or dried soups.
Bread is supplied to the Cuban people as part of the basic State food ration. All towns of any size have a bakery, with all the bakeries apparently using the same recipe. Each bakery has a list of all the households in town, together with the number of people in each house. Bread is sold to Cubans at a highly subsidized price, on the basis of 400 grams per person per day. There is no mechanism to sell it to foreigners. We tried to buy it many times without success. What normally happened was that we would be told we couldn't have any, and then as we left someone would sidle up to us and either tell us to come back later or to go around the back, when we would be given some. We tried to pay, since we certainly do not need to be subsidized by people who have so much less than we do, but never succeeded. However, we generally found we could press a bar or two of soap on the donors, although even this was difficult (the Cubans are incredibly generous, but reluctant to take anything in return; soap, incidentally, is a much appreciated gift as it is in very short supply).
Where does this leave us? There is clearly no source of supplies that even comes close to a well stocked American supermarket. You should load the boat to the gunwales before setting sail for Cuba. If you start to run low on your favorite foodstuffs or snacks, and you are getting tired of rice, beans and dried peas, Key West is less than a day's sail from a good part of the north shore of Cuba, Isla Mujeres and Cancun are about the same distance from Cabo San Antonio, and the Cayman Islands and Jamaica are readily accessible from the south coast.
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