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Cuba from Canada then on to Central America

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We're planning on travelling to Cuba in mid-Feb and going on a 15 day G-Adventure tour. Cuba Colonial.
We'll be flying out of Vancouver, BC and once we are finished the two week tour, we'd like to fly to Costa Rica or Nicaragua for a week or so, and end up in Belize for a couple more weeks.
Looking into airfares that may work, we can fly Westjet from Vancouver to Varadaro, and then fly back from Cancun to Vancouver, which could work as it's fairly easy to get to Cancun from Belize (done it a few times now). The Westjet option is a bit pricy though.

Alternatively, we could fly with a number of airlines from Vancouver to Cancun, and then catch a flight to Havana. It would make our return flight more flexible if we didn't have to book Westjet both ways too. We could then fly back from Belize City via United or Delta, I think. The flight to Cancun is very reasonable, and the flight back from Belize City to Vancouver also not too bad. However, I'm not sure how much extra the Cancun/Havana portion will then be?
(Oh, the charters Sunwing and Air Transact are out, as we can't book just one way - must be round trip)

We've never been to Cuba, so I have a few questions:
1) Anybody ever done the 15 day G Adventures tour?
2) The GA tour departs from Havana, and we would land in Varadaro. How easy, and what is the cost, and how long would it take to hire a cab/driver/shuttle from Varadaro to Havana. If we caught that Westjet flight, I believe we get in about 6 or 7 pm.
3) If we flew to Cancun, then we would be able to fly to Havana. Which airline is the best/most reliable etc
4) Which airlines fly from Havana to Costa Rica? To Nicaragua?
Thansk very much for any and all advice!

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