Hello SrPeter:

I had a wonderful time in Cayo Largo and also Havana on one of my trips to Cuba. I flew into Havana and then got a local Aerogaviota flight from Jose Marti (domestic terminal) to Cayo Largo which is about a 45 minute flight. But when leaving Cayo Largo, I flew direct to Varadero and then took a taxi back to Havana several days after that. There are also local domestic flights by Cubana and Aerotaxi.

As to your query, it should be possible for a TA to make all the arrangements before you leave for Cuba, but if you are adventuresome, it can also be done while in Havana. Depends upon your personal schedule. I was 3 nights on Cayo Largo at the Melia Sol Club. In Havana I stay at a private home (Casa Particular). I was in Havana for a few days prior to flying down to CL therefore had the time to make the arrangements. If you want to make a reasonably short connection, it might be better to arrange it in advance. Or spend say 3 days in Havana before you fly to CL, (time then to make local arrangements) then 3 nights at CL, then back to Havana one day before your flight home (assuming 7 day stay).

You can check out my personal website and look at my photos (with explanations and info) of Cuba and also two pages of Cayo Largo and Club Sol.
http://photopilot.tripod.com

Also, here are some other links, some specific to Cayo Largo, and some just listings of other Cuban links. Lots for you to read up on.

Cuban website specific to Cayo Largo. Click on the British flag top left for english pages.
http://www.cayolargodelsur.cu/

also Cayo Largo specific.
http://home.thezone.net/~jmaunder/cayolargo.htm

also Cayo Largo specific.
http://www.cayolargo.net/

Cayo Largo specific discussion forum.
Bilingual (English/French)
http://www.cayolargo.net/forum.htm

Lots of Cuba links for info.
http://www.ibiblio.org/cuba/links.html
also
www.1click2cuba.com

I hope you have a great time in Cuba and have fun at Cayo Largo.

Steve