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Not Pre-Booking in Milos

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This summer, a friend and I will be traveling to, among other destinations, three Greek islands: Naxos, Milos, and Santorini. That could change - I do like to be spontaneous.

Question is, considering that MIlos is not heavily populated with either tourists or locals when compared to Naxos and Santorini, and also considering that we don't exactly want to be stuck on a plan of "we absolutely have to get to Milos from Day A to Day B because we've already pre-booked", is it advisable to simply not pre-book in Milos and hope to find a place upon arrival?

We'll (unfortunately) only be in Milos for 2 1/2 days and 3 nights, so won't extensive, week+ long accommodations.

Time period is smack dab in the middle of July.

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