Enjoy your holiday! I normally take only 1 handbag (the one I have during the flight) and 1 for sightseeing. And then maybe I'd take 1 small nylon Longhcamp which is easy on the luggage because it is foldable. During my last trip, I didn't intend to use my large Le Pliage for sightseeing, it was a what-if bag for carry-on going back. But it turned out to be more convenient to walk around with that bag. Usually, I don't have dressy evenings out during my trip. But in case, I bring a leather wristlet (Massaccesi Flora for now) which I can use if ever.
Thank you, it's lovely, sunny & very relaxing. I guess how many bags depends on what you are doing and how long you are going for but even if it's a couple of days I can't survive with less than 3

Love your metallics! Especially the copper Chanel and the cute little Jaspal box.
I'm usually take quite a few. For 10-14 days I'll take 6-7 because I need day, evening & beach bags as we almost always go somewhere with nice activities and water. I like to look my best on vacay so I need my best bags (which of course change with my mood) LOL! That's why my upcoming trip is hard. I am limiting myself to 2 bags for 3 weeks.
I keep my bags in my carryons. I'd go crazy thinking of them potentially getting stolen in checked luggage.I have to arrive with my bags and my bras LOL! I can buy anything else when I get to my destination if need be.
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Gosh how do you manage to get 6-7 in your hand luggage? I'm the same and like to bring some of my best ones, I carried a Channel flap & used my WOC as a purse in my Neverfull which was my hand luggage but only managed to get one other in my carry on luggage which was why I decided to risk one in my hand luggage. I know it's insured but I don't like doing it and would only put one in. I used to be able to sneak one into DH's hand luggage but he's stArted bringing so much tech it's impossible now.
We are away for 16 days and I wish I'd bought a medium size bag too. The WOC is brilliant for walking along seafront or trips and my Neverfull GM is a must as Beachbag. That still limits me in the evening, we usually dress "up" for dinner so I have the choice of 2 bags which have to co-ordinate with my whole wardrobe for 16 days

