Awesome stuff mate!
My girlfriend and I are doing around the world kiting holiday next year We will be in the carribean from march to may/June. We aim to do most of the islands including cayman is, Jamaica, Dom rep, Barbados etc. Where abouts did you go? Would love to get some more info. Yeww

As we were gone for a month which started with a week in the US and island hopping for 3 weeks in the Carribean, i hired gear. If my sole purpose for going was kiting and i was staying in 1 or 2 places i would def take my gear

Islands we went to Antigua,Jamaica,St Marteen,St Barts and Turks and Caicos.
We got the new Qantas Flights to Dallas. We then flew to NY for a week then from NY to Antigua. I think some islands you can fly from Dallas. Some islands only from Miami.Airlines are 1 checkin bag per person 23kg/50lb (to and from oz you get 2). They are pretty tight with the weight too. An extra bag varied from 30 to 60 dollars. Carry as much as you can onboard and only check 1 bag if getting lots of flights.

In Antigua the main beach they kite at is Jabberwock beach.We stayed near by at blue waters resort which was nice and it was all inclusive. Lots of eating and cocktails. It is also where kitesurfantigua.com is located. It was $50 US and hr to hire everything. Gear is all current models. I used a 2011 Switchy and Custom board. Wind blows cross on from the right. Is great for beginners to expert as there are a couple of small reefs just of the beach which gives you nice smooth water close to the beach. We hired a car one day and drove around the island, was plenty of other places worth kiting around the island.

Jamaica i didnt kite but found where they kite and there were a couple out when we drove past. I think its called bount bay its about 30mins east of montego bay. I think you can hire gear here as well. We hired a car here as well so we could do some sight seeing. Again wind blows cross on from the right.

Was only in St Marteen for a day to catch ferry to St Barts. While waiting there is a bar on the beach at the end of the runway. Great for a drink as planes land are only a few feet away.

St Barts is suppose to ok for kiting as well. I dint see any while i was there. We only stayed here for 3 days as it is pretty expensive.Its not to bad if you stock up your fridge from the supermarket. Everything is in Euros as its a french island. Def worth a visit if possible.

Tuks and Caicos was the most amazing island i have ever been too. The water was incredible. This was the best part of our trip. The water colour was so many diffrent shades of blue. Was windy everyday. The island is made up of mangrove and sands. I went kiting with bigblueunlimited.com. They dont hire out gear on its own. You have to do a downwinder tour which was 250 US and 50 US to hire gear if needed. It went for about 5hrs which isnt to bad i guess. Good for beginners to expert. They take you out in a boat to a small island. There is lots of little bays and coves to explore. At the end they follow you back down wind in the boat to the marina. Its pretty sweet. If you take your own gear it would prob pay to do this the first day so you know where to go on your own the rest of the trip. There is a few spots on the other side of the island which are sweet for kiting as well. We stayed at the Gansevoort. Highly reccomend it. The island is called Providenciales.

Let me know if you have any other queries.
Hope this helps