Whilst I don't know much about Kalamata apart from this is where those big olives come from I'm bumping this up for you in case there is someone who can help with your questions.
Good luck and happy holidays!
Click&Boat but there are also a few other local platforms and probably Airbnb has listed boats too. I would recommend hiring a boat from Pylos or Kalamata. You may also find boats to hire at the harbour in Kalamata.
Re places to visit, Mani is indeed amazing (apparently you will find there the true Spartans...) and then definitely Olympia, Sparta, Mycenae and Epidaurous if you are into ancient Greece...
Car hire - we considered that but we were advised by a Greek friend to avoid it cause a) the roads are not in a good condition and a big part of the are is mountainous b) some of the locals are, hmmm let's put it that way, a tad careless when driving...
For me, sailing around the Peloponnese is the best option if you have time and, most importantly, if you have kids. We did that a couple of years ago and it's an ideal option for a family cause you have a lot of space, privacy and you can set sail anytime you want. It's also much cheaper than it used to be (showing my age here...) Overall it's a great experience for a family cause the kids learn something new (although my son didn't appreciate the fact that he had no access to the internet for a few hours...) We hired a boat via Re places to visit, Mani is indeed amazing (apparently you will find there the true Spartans...) and then definitely Olympia, Sparta, Mycenae and Epidaurous if you are into ancient Greece...
Car hire - we considered that but we were advised by a Greek friend to avoid it cause a) the roads are not in a good condition and a big part of the are is mountainous b) some of the locals are, hmmm let's put it that way, a tad careless when driving...
I think the sailing would be great. Beautiful area. I was there too long ago to give any help. We stayed in Hanioti, which I remember was a pretty place. Probably I wouldnt recognise it nowadays.
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