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All the reading I had done on the Schengen rules indicated that they might not check but they might so you definitely want to leave the Schengen countries before the 90 days are up. Gibraltar is owned by the UK which means it is out of Schengen, so on the 90th day I crossed over into Gibraltar - and all they had at the border was someone glancing at your passport as you held it out and walked past. So I circled back and said I needed a stamp because of Schengen, he insisted that no stamp was required for Schengen, so in the end we compromised and he gave me a "souvenir stamp". So who knows what the rules really are, but if anyone wants to search through my passport looking for stamps on the correct dates, I'm covered.
Gibraltar was strange after being in Spain - English pounds, English accents, pubs, fish and chips, everything closes down early where in Spain things are just getting started at 9pm. Cars were bigger, lots of big boats in the harbour, definitely more money. There are natural caves that we could walk through, and miles of man-made caves that were drilled by the English during the Great Seige with Spain in the 1700s. Up on the rock itself (you can walk up, be driven up by a taxi/tour guide, or take the gondola up) there are troups of Barbary Macaques roaming around. They can bite and be aggressive, but mostly they just ignored us and let us take photos.
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