if baby wants to crawl/walk at that time I'm sorry, but flying is an absolute nightmare. it's boring for her, a whingeing baby is annoying for others and could be pretty embarrassing for you - I just hate the looks from others.
I know, I've flown with my older 4 children at various ages, many times for 2 1/2 flights - I just don't do it anymore. plus safety rules make it impossible to take extra (emergency) milk cartons for bottle feeding or baby food in cabin bag, it's so stressful I had a panic attack the last time. oh and babies and toddlers might scream for the entire time of descending due to painful ear popping... (though if you feed them through it the swallowing action can reduce discomfort/pain)
perhaps I gave up because I traveled on my own while DH at work, it was just too much...
I understand your reasons and of course don't want to scare you away, you might have a lovely and easy time, but I had to warn you! sorry!
I found it easier to fly once they are a year old and older and can be distracted easier with books, colouring, and you can do without special milks and bottles (if bf of course that's no probs anyway)
(btw we have 6 kids and I can cope with a lot of things - flying with a baby who can't sit still, but wants to crawl/walk between the aisles constantly or else it's war and you are stuck there for hours in a cross fire of laser looks - no thank you)
bless you, to be honest if you are breast feeding it does make things easier both from the feeding and the calming point of view, so maybe you should just ignore me and go for it!
but I won't
what made me utterly panic was that mine were just bottle fed by then and I was worried what if they are sick up the feed or I knock over a bottle or whatever, I just can't produce another one... or what if the flight is delayed? or what if there are problems on the arrival side? and I'm mid air or mid traffic and they will starving/screaming and I just can't do anything about it!
so I prepared extra sterilized bottles with 200ml cooled boiled water and pre-measured milk powder and also prepared carton feeds. they wanted me to sip water from the bottles, but I decanted some water into the lid instead to avoid contaminating the water and was made to do this with all 5 bottles. it was humiliating and extremely stressful, but I totally lost my rag when they asked me to open and taste the cartons of milk I had ( just in case) - I told them that I can't! if I did they need to be be used within 2 hours, or kept in the fridge - I can't do either so I might as well just throw them away, but I need them for emergencies unopened and/or also for flight home!
I had a massive panic attack and was crying like a baby ...it was just horrible. Unless I had to fly for wedding or funeral I'd give it a miss until they are 1 year or more
but if the feeding bit is not such an issue, as you are still breast feeding and it's the 2 of you anyway to distract him and share the "aisles" walks it won't be so bad hopefully.
oh yes, you might want to take painkillers for the flight, you can buy 5ml sachets of it from Tesco, Boots or chemist, again just in case of teething pain, fever or earache.
We flew to the Balearics and Dominican Republic with DS2 when he was 6 and 12 months old respectively and it was absolutely fine. He was FF, but there were no restrictions on taking liquids on board then.
We are flying to Mexico (11 hours) with 4 DC in December and my youngest 2 are 8 (he has Downs Syndrome, so not the average 8 year old) and 17 months. I am not really worried about it tbh, although I expect it to be less relaxing than an 11 hour flight sans children. I am still breastfeeding 17 month old DD, although I am not entirely sure how helpful that will really be due to the fact she is so easily distracted and doesn't really breastfeed very much when out now.
As for where to go, we opted for Mexico this time as we wanted guaranteed warm weather and if we did get rain wanted 'carribean rain' (mainly short heavy downpours that dry up very quickly) and the beach for the DC, but lots to do outside of the resort too and the chance to walk into the local villages/towns etc. We've been before and loved it, it's a lot more developed than most of the Carribean. It's also not quite so hot in the winter months as most of the Carribean, but still mid to late twenties. Not sure if that helps?!