Cuttlefish are very common in Italian waters, and play an important part in everything from appetizers through elegant entrees. The two most common species are Seppia officinalis and Seppia elegans; when they are freshly caught their skins have beautiful iridescent reflections. If the cuttlefish at your local market look tired, you should buy them frozen -- they bear up to freezing better than most other mollusks and their flavor will be relatively unchanged. The one disadvantage (or advantage, depending upon how you look at it) to buying frozen cuttlefish is that they will have been cleaned, and their ink sacks removed. This means you will not be able to prepare some traditional dishes, for example risotto nero (black risotto) or seppie alla veneziana (cuttlefish Venetian style) with frozen cuttlefish.
Once you have decided to serve cuttlefish, what you prepare will in large part depend upon the size of what you buy. Small cuttlefish will work well in a sauce, for example for pasta, while medium-sized ones will work nicely as an entrée, as will large ones. You should figure between a quarter and a half pound of fish per person (the former in a sauce and the latter as an entree) -- with a large cuttlefish you will be able to serve more than one person. The second observation to make is that small cuttlefish will cook relatively rapidly, whereas larger ones will require more time, and will (if fresh) benefit from a day or two in the refrigerator.
When you arrive home with fresh cuttlefish you will have to clean them, especially larger ones you plan to let rest for a day or two. Make a circular cut around the beak of the cuttlefish and remove it, pulling the entrails with it and taking care not to puncture the ink sack. If the opening is wide enough you may be able to slip the bone out as well; otherwise, make a cut along the animal's back to remove it. Also remove the eyes, which are quite bitter. Rinse the fish well under cold running water, pat it dry, and it is ready to use.
A few words on cooking cuttlefish: Like their cousins, octopus and squid, cuttlefish should be cooked briefly, a few minutes, or for more than an hour -- closer to two, even -- because the arms contain quite a bit of connective tissue that toughens after more than a brief cooking, and must be cooked further to give it the time it needs to break down again.
A final consideration: Though these recipes are for cuttlefish, most will also work with squid, if that is what's available in your market -- just make sure the animals you use are roughly the size of those specified in the recipes.
Cuttlefish, Calamari & Octopus recipes on site.
You will find antipasti and pasta dishes listed below, and since octopus and squid are quite similar to cuttlefish I have included them. You will also find cuttlefish (strictly speaking) main courses, and a link to the Cuttlefish, Octopus, and Squid main courses index.
Polpo Affogato, Italian Drowned Octopus Antipasto: A perennial favorite.
Pickled Octopus, Polpetti nell'Aceto: Another favorite
Fried Calamari, Calamari Fritti A summer favorite.
Calabrian Octopus Salad Recipe, Insalata di Polipi: Quite refeshing, with a zing from herbs.
Alfonso's Risotto alla Marinara, with tiny octopusses.
Artusi's Black Risotto With Florentine-Style Cuttlefish: A classic recipe.
Risotto with Squid and Tomato, Risotto ai Calamari con Pomodori: Simple and easy to do.
Squid Ink, and Risotto al Nero di Seppie, risotto with squid ink.
Risotto with Moscardini (Tiny Octopus) and Scampi
Farro with Cuttlefish Ink, Farro al Nero di Seppia: A tasty variation on Risotto, from the Abruzzo.
Spaghetti con le seppie alla calabrese, Spaghetti with cuttlefish Calabrian style
Spaghetti con ragu di calamari, Spaghetti with a rich calamari sauce.
Spaghetti Col Nero di Seppia, with squid ink, Tasty, and exotic, with an unusual smoky black color.
Maccheroni con le seppie, Macaroni with Cuttlefish: Rich, with a hint of tomato.
Seppie ripiene, Stuffed cuttlefish make a superb second course, and provide a sauce for pasta too.
Seppie alla Veneziana, Cuttlefish Venetian Style (with their ink).
Seppie in inzimino, A zesty Tuscan way of preparing octopus, cuttlefish or squid with spinach & red pepper.
Seppie coi peperoncini: Hot peppers give these cuttlefish a zesty zing.
Seppie Coi Piselli: Cuttlefish and peas work very well, and are one of the most classic Italian fish dishes.
Octopus, Calamari, Seppie: Main Ccurse dishes.