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Heraklion
We only stayed in Heraklion one night - this is the largest city and is where the airport is that we flew into. We barely saw any of it because most of our time was spent Westward, however I think it's worth checking out.
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Infinity City Boutique Hotel - lovely rooms, really nice breakfast, friendly staff
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THINK TANK cafe - good coffee, beautiful rooftop seating area with lots of greenery
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Plánē - cute restaurant with outdoor seating, right next to the hotel
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Wine and cheese from small markets
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Walking around the harbor
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Old town had a lot of cute looking restaurants that we would have loved to try!