The Peloponnese in Late June/Early July - Pre-book Hotels or Play it By Ear

I would pre book as those locations are popular with tourists. You certainly can find affordable lodging when booking ahead. We went to the same places in late September and the hotels were full.

I would pre-book. Those places, as Suki says, are very popular and crowded. They sell out.

You are travelling in Greek school holidays (plus most of Southern Europe is also on holiday), so book now. Places will be busy.

By all means pre-book. Finding a last minute room big enough for 4 or, worse yet, two rooms, will consume much precious time and you could wind up sleeping in your car. Hydra will not give you even that option (no cars)!

Your wife is so wrong -- in the season you're coming, on-the-spot booking will be MORE expensive than advance arrangements ... these days, savvy travellers seek out the good values far ahead of time, and fill all the rooms ... what's left will either be tacky, inconvenient AND expensive, or just inconvenient and Really Expensive. Also, there are not as many accommodations with 2 BR, or 2 joined rooms, and in Greece there certainly are VERY few that sleep 4 in ONE room -- so you may have to try for 2 adjacent rooms ... your boys are old enough not to be scaredy-cat if mommy doesn't tuck them in, so next-door is good. But don't waste a minute -- I've been reserving since early December for our early June visit, and was very relieved to be able to book my excellent-value places in Athens, Nafplio, Naxos and Santorini. They now are fully booked for our dates.

Thank you all for your advice. We have started booking ahead yesterday for all our stays and we just about have a place for each location. Again, thank you for taking the time to read my post and providing your valuable input. May your travels always exceed your expectations and may pleasantness follow you wherever you may go.