Talk to the front desk the day before your transfer and they will arrange and pay for the whole thing. If you leave at 6 am, you will avoid the traffic in Montego Bay and get there in just over 2 hours. Have done it 3 times now!
We just came home from a split stay between CSA and CSS. We left CSA at 6am on a Tuesday morning and were at CSS well before 9am. Believe it or not, when we arranged this we asked for a "Wally transfer" and they knew exactly what we were talking about!
We were at C.S.A and transferred to C.N.
Went to the front desk and checked out asking for the transfer to C.N. which they had on file.
Called ahead to see if we could get an early check in and took the van which was a 4 minute ride. We were in our room within one hour.
Couples will take care of it all, but if you want to hire a private driver (like if you're going between Negril and Ocho Rios), you certainly can.
We did a split between CTI and CSS. Our thoughts were to checkout around 11:00, (or a bit earlier), after breakfast, then head to CSS. What they like to do though is put you on one of the buses heading back to the airport.
However, we ended up doing the horseback riding that day, since we had to cancel earlier in the week when I was too sick. So we checked out, went on the 11:00 ride, then returned and showered at the spa. We then ended up catching the 2:00 horseback riding bus over to CSS after dropping off the afternoon riders. it all worked out just fine.
So if you're staying in the same area (CTI-CSS, or CN-CSA), then it's can be very flexible. Just tell them when you want to go. Just remember if you leave really early your room may not be ready yet at the second Couples.
We're interested in doing a split stay as well, next year between CSS and CTI. But I'm having a hard time because flights our of Vancouver are only once a week and I'm not sure what day it will be next year. But I really do want to take advantage of the specials that are going on right now.