Pylos is a great town to stay and have dinners in the evening. It's platia is one of the most beautiful platias of Greece. A must to sit under the central platanus with the locals. Around the square and along the harbour, there are some nice, local restaurants. From here, you can also do boattrips with the kids to the island Sphacteria. You don't have a good beach here, so for a swim, you better go to the nearby beaches of Gialova, Voidokilia, Romanos in the north or Methoni in the south. Drive or take a cab. You can also rent motorbikes in town. I stayed for a long time as a student in B&B Maria. She took good care of me. It's a bit up the hill, walking distance from the square, in NNE direction.
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