Here's another take on Cuba. Though the U.S. is still "at war" with Castro, it's a little bit a hassle for Yankees to go and shoot, though it's getting easier.
Scott Kelby of NAPP was there last June and took just his 28-300 due to weight issues. He felt he needed a little wider at times.http://scottkelby.com/2012/im-back-from-2-12-days-in-havana-cuba/
and his video interview:http://www.youtube.com/watch?v=UwgTg-mLHAM
Though i haven't been to Cuba, I've been to Greece, Mallorca and Serbia a few times now. I've taken it all with me and the last trip, I analyzed the previous trips to see what lenses I should use and which should be left behind.
Some of what I've been photographing is very specialized, the Byzantine iconography of my friend/client Miloje Milinkovic from Belgrade. He insists on shooting the interiors with a circular fisheye (8mm) along with the full-frame (15mm) fisheye.
Besides those two lenses, I've also packed a 17-35, 24 PCE, 24-70 or 24-120, 70-200 or 70-300. My 14-24 is simply too big and heavy to pack for street shooting and as it is, I'm already sticking out with the gear I have besides being a Yankee on foreign soil, two strikes against me when I get off the plane!
In many ways, the narrow streets of both Havana and both the ancient villages of Greece, Serbia and Mallorca are similar calling for similar sets of lenses.
I can tell you that the vast majority of images are shot with just two lenses, the 17-35 and the 24-120 with a few fish eye shots of interiors and an occasional long-lens shot, mainly landscape.
Some of the stuff I did with the PCE lens I can now do as well with the 17-35 on the D800 and either crop or by tweaking the geometry in post. There's plenty of pixels to do this as well as I could using the 24 PCE on the D700. However, I do miss the process of setting up the tripod and working with this lens much as I used to work with a view camera.
Now that my friend Miloje has his own fisheye lens, I'll have one less to haul with me on the next trip and simply use his.
The 24-70 even with the D800 and cropping just doesn't have the reach so I've replaced it with the 24-120 f/4. That lens is lighter besides.
Two years ago I went with my 70-200 and TC17. But it's big and heavy & I'm getting old, so it's back to the 70-300 which cropped on the D800 now reaches to 450mm equivalent.
But I may drop the 70-300 next since with the D800 and using the DX crop, the 120mm now becomes a 180mm telephoto with a few more megapixels more than on the D700 and I'm not shooting as long in Europe I'm finding since the air is so nice and thick and doesn't have the grand views like I have here in the Western US.
My pairing of bodies and lenses are thus:
D700 and the 17-35 (less weight and size than the 14-24) and the D800 and the 24-120, usually on 1.2 crop, giving me about a 29-144mm, thus a little reach and a little overlap between the two along with a nice 24MP image.
If I need more reach, I'll run the D800 at 1.5x and then have a 180mm with a 16MP image.
In any case, between the two lenses and pumping up the ISO, I'm quite happy shooting in nearly every situation I've been in so far, even in the darkest monasteries where cameras and flashes are usually frowned upon.
As for a tripod, I do have one with me to to time-lapse and to shoot at the edge of light or light-paint interiors when I'm not shooting people. It's small and light carbon tripod that fits in my check-in bag. I'm using LED flashlights instead of the flash to "light paint" with the camera on a tripod when I can. It's much softer and doesn't call attention to itself on the final prints light blitzing things with flash.
I've considered fixed lenses since they get you speed, but with the high quality and extreme ISOs, they simply don't fit into my style of shooting since much of my street shooting is so fleeting.
Also, I've I found that setting the ISO, shutter and aperture steps to 1/2 instead of 1/3 stops gives me a speed advantage when I've got to change the settings quickly as the light changes. Same thing in shooting Aperture-priority over manual in the street. This gets me my insurance shots better and then if I have time, I then change back to manual to fine-tune everything.
Oh, don't forget to bring lots of big CF cards. Take enough so you don't have to reuse them and some way to back them up easily in the field.
Enjoy your holiday and shoot up a storm!