Just got back from a wonderful 2 weeks in Tobago and survived hurricanne Ivan! (now 28 1/2wks pregnant)
my tips
do a late booking- not had any major probs during pregnancy plus use to long haul flights otherwise would not have gone so far.
when booking mention pregnancy to ensure you can fly with that carrier. Both ways with BA we got upgraded to traveller plus (all I asked at check in on the way back for a seat to easily get in & out of).
Found a lot of travel insurance did not cover me at 28wks+, however AA did
Discuss with midwife/Dr re flight/holiday - I was advised to use flight stockings, took 1/2 asprin, drank only water and fruit juice during the flight.
take a bikini - I took a swimming costume and even in the shade the dark material was hot over the bump - plus it made going to the loo a pain, but managed to borrow a bikini in the 2nd wk
Took plenty of DH t-shirts as I found that clothes I fitted into at the start of the hols were too tight towards the end and avoids buying loads of maternity wear (in last 2-3wks waist expanded 3" and weight increased 2.5kg, but AI may have something to do with this!)
Plenty of high factor sun cream plus deet mossie repelant.
Had hotel with own beach - could sunbathe, lie in the shade or go in the sea to cool down and make bump weightless (enjoyed loads of snorkelling which partly filled in the withdraw symptoms from no diving this yr)
Had a good hotel that was AI (I normally avoid AI) which made life easy, and room with air con & king size bed (ooohh the space!).
I would hightly recommend a holiday - it was a chance for both DH & I to enjoy some quality time together before all mayhem breaks lose in December
Please feel free to add you own tips