Pollonia - Gialos
This traditional waterfront Taverna has a very contemporary restaurant feel but without losing any of the joys that Greek waiters can bring to the table. Greek food is sometimes maligned and completely falsely in my opinion - When it's as good, as fresh and as delightfully served as it is at Gialos, you will have the wonderful problem of whether or not it's actually worth finding anywhere else to eat during your stay. I'm not sure how long I could stare out across the most picturesque and typically romantic Greek harbour imaginable. Little bobbing boats of every colour, children playing in the sand, fishermen fixing their nets or casting their rods, it is truly idyllic. The staff are incredibly attentive, from the very hands on and proud owner to the most helpful of wait staff. I cannot recommend Gialos highly enough. The seafood linguine, the seared chicken, the pan fried bream... I could go on. It is great value for money and is one of the few places in the world that if I could click my fingers, I would choose to be. The local wines are exceptional and I Implore you to drink it heartily whilst here. Not only has it improved to world class quality, it is true value for money.
Gialos is almost too good to be true for the simple pleasures....
Mandrakia - Medousa
The very traditional Taverna can be found near the famously unique and picturesque fishing village of Mandrakia, with its little garage-like boatsheds lining the pretty and colourful harbour. This family run eatery overlooks the dark blue Aegean and the day's catch of octopus and squid. You can't get more authentic than this and it is ideal for a long, long olive oily lunch. How they produce the quantities of food they do out of the tiny kitchen is a mystery, although I'm sure the odd temper may flare because of it. Mother's have the right to shout at their son's after all. It's not a place to hurry through. In fact, it's one of those places that you may find yourself happily chatting away to fellow diners for hours at a time in... No doubt extolling the remarkable virtues of this amazing little island. One couple turned up and immediately realised that they had forgotten to bring any money. "No problem." was the response. "You eat. You come back later to pay." Fish rules here but the simply prepared vegetables and salads shouldn't be overlooked. So after a morning at White Rocks Beach, a long languid lunch here before heading off for a beachside nap is highly recommended.
Plaka - Utopia Bar
High up in the town of Plaka sits Utopia Bar and it's a pretty good place to watch the sunset. Plaka is one of those pretty little towns that if you catch it at the wrong, or right moment, will appear as sleepy and as closed as a drugged up clam, but towards sunset, when the town and its afternoon's slumbers have dissipated, islanders and tourists alike awaken to make the pilgrimage up the hill to see to see the sun fall and the hues heighten. It may not be the fanciest bar in the world but it's a pretty good place to be when the day is rolling over and ready to hog all of the blankets. There are enough eateries and options up here to find the right place to suit your mood and it's small enough to make you feel welcome and to fill you with a sense of belonging. There is a also a very good artist/s studio here should you wish to buy paintings or prints of the island.
Pollonia - Enalion
Worth booking in advance during high season if you want a decent table at this very highly rated fish restaurant. I say fish, there other good options too, but should you be in the mood for locally caught prawns or calamari, this should be high on your list of restaurant's to visit. Again, overlooking the harbour, you'd be pretty hard pushed to complain about your life whilst figuring out how many courses you can fit in, and Sigalas wines you can drink, before defying the odds and actually having that moonlit skinny-dip you've been craving.
Whether it's for a picnic or for breakfast, Pollonia isn't short of good bakeries. Flora's on the harbourside between Gialos and Enalion is lovely for a coffee and a really good croissant, and the more traditional 'Κιβωτός των Γεύσεων' is wonderful for more traditional pastry fare etc. Okay, okay, it's called 'Ark of Flavours' but the sign is in Greek so get used to the words.... or just follow your nose.
Please don't forget that you can read more about Milos and some of the places listed by reading OST's Milos blog.