Trip to Aruba: What lens(es) should I buy?

So I'm going on a family trip to Aruba around Christmas, I think it's like five or six days, it'll be a welcome change from the cold and rain we've been having up in New England!

I currently own a 400D, the kit lens, and a Sigma 20mm f/1.8 (bought it for front row concert photography). My father has a 350D and a Sigma 18-200 OS, though I doubt I'll get much time to play with his lens since he'll probably be using it. I will be going home to Long Island next week for Thanksgiving, and I plan on taking a trip into NYC to visit B&H to try out some new lenses. I have a budget of about $1000 ($1500 if I stop buying beer...:p), and I'm not entirely sure what I should seriously be considering. The budget is somewhat flexible, though extravagance is kind of out.

I'm looking to cover anything from vegging out on a beach to 4x4 adventuring, and possibly some nightlife (depends on how much I feel like drinking, if there's lots of drinking the fancy camera is staying home and my old PowerShot S45 is coming out). I have no problems using prime lenses (the 20mm f/1.8 hasn't left my camera since spring), and I would prefer constant aperture for any zooms, though that might be out of my price range. I'm also open to suggestions on useful filters to have.

Also, my dad has a few old FD lenses, I'm curious if it's worth $50 to buy a FD/EOS converter to use them, or just save the money for EOS lenses. I'm not sure of the specs on the lenses, he's going to check for me tonight.

I took a 28-135mm IS with me to Jamaica last October and it served me well. If you are not taking any long distance shots, I would think 24-105 f4L, and/or 24-70 f2.8L for night shots.

Do you happen to have any sample photos from the 28-135mm in Jamaica? Some of the reviews I've read say the lens is a little soft till about f/8, though of course, in bright sunlight that'd be a non-issue.

The other two L lenses look *very* nice as well, though I'm thinking of how much I would use them after my trip. A lot of my photography has been concerts, meaning the 24-70L would be better...but I'm thinking I'd want a bit more reach. Knowing me, I'll be deliberating this for the next week...

Stupid expensive hobbies...I need to graduate and get a job so I can better afford this!

Consider picking up a CPL as well (after you decide on a lens). That'll help darken up the skies and vegetation, and really clear up the water in your shots. CPLs were made for the Caribbean.

woloi wrote in post #4321872
Do you happen to have any sample photos from the 28-135mm in Jamaica? Some of the reviews I've read say the lens is a little soft till about f/8, though of course, in bright sunlight that'd be a non-issue.

The other two L lenses look *very* nice as well, though I'm thinking of how much I would use them after my trip. A lot of my photography has been concerts, meaning the 24-70L would be better...but I'm thinking I'd want a bit more reach. Knowing me, I'll be deliberating this for the next week...

Stupid expensive hobbies...I need to graduate and get a job so I can better afford this!

Yea, it took me a while to decide between 24-105 and 24-70. I was leaning toward the longer reach when I happened upon a great deal on a lens over on FredMiranda.com.

I'll post up some Jamaica pics this evening.

One thing I noticed on Aruba is gorgeous sunsets. For that, an ultra-wide could be useful (I owned a Tokina 12-24 at the time).

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As promised, some Jamaica pics. All were shot with a 10D with a 28-135 IS lens. This was also in my early days of shooting, I think most were done in an auto mode of some sort.

This one is hanging in our bedroom in 16x60 format. The only editing was a bit of cropping. f22...ISO 400...1/2000sec.

Nice photos. Negril?

Pitter wrote in post #4323428
Nice photos. Negril?

Thanks.....and yes.

Nice photos there.

I'd love to get a UWA for the beach sunset/sunrise shots, but I already have a 20mm, and I can't really justify buying something even wider before I get something that's at least quasi-telephoto.

How do the Sigma lenses compare, there's 28-70mm and 24-70mm (both f/2.8 EX lenses). There's also the Sigma 70-200mm f/2.8, which sounds nice, though I'm thinking I'd want some sort of IS with that length.

I would go ultra wide, 10-22, etc.