We went to Cabo for our first trip 2 years ago for T-day, we are going again this year for T-day. We pretty much hit every club on the main strip and came away with a few impressions. There were 6 of us, ranging from mid-20's to 30 year olds.
- Wabo Cabo: it seemed the drinks were mixed weakly, even those that used the self-named Wabo Cabo tequila. It definately is a good place for "adults", more in the mid-30+ (or 40+?) range than many of the other places
- Giggling Marlin: odd place, they put on shows that involve taking advantage of drunk people's exhibitionist sides, not my favorite spot..boring really, just sitting at a table while drunk people make fools of themselves
- Zoo bar: great for teeny boppers, this is the place the kids on Laguna Beach (on MTV) always go, its packed with the 18-20 year olds who wish they were 21. They play the same top-40 'dance' songs on a loop, stay for more than 2 hours and you get to hear the same songs over and over (just like commercial radio in the states). It was day (night) care with alcohol for teeny boppers on there 'legal' drinking binge from SoCal. Overpriced, diluted and mostly flavorless drinks.
- El Squid Roe: likely the best 'club' in town. Lots of different areas, very mixed crowd of all ages...I saw people ranging from the early 20's to those that must have gotten there with their walkers, but all having a good time. We were sad it was the place we visited last, will be going there again
If you want decent italian food, you can check out Romeo y Julieta's...its on the west end of town after it starts fading out by the marina. This happens to be a short walk from our house in Pedregal that we stay rent.
One of the more challenging things is finding tequila that is unique. We found one place that had a great tequila selection, but most just had the same stuff as you get at any decent liquor store stateside. So if you want to check out some fine tequilas, we had the best luck at Tequilas & Tequilas Boutique Store.
If you are after cigars (not that anyone would bring cuban cigars into the states...) you will have to be careful, a lot of "cuban" cigars just aren't. But there are a couple of great cigar shops that have a wide selection of fine cigars from around the world, though in some cases the prices may not be that much better than stateside.
We also did a booze/sunset cruise on the La Princesa III sailing cat which was fun, and had more drinks than we should have...I'm not sure if we got the drinks free with the cruise, or the cruise free with the drinks...but either way, we got our drink on.
There is also a Costco between the airport on Cabo, they have a pretty decent selection of tequila as well...and a great stop if you are staying in a house, we bought cases of beer, mixers, and groceries for the week there.
Diving wise, we picked one of the shops in the Marina. I don't recall the name of the one we chose, it was one of the smallest shops closest to the main road/dirt parking lot (there are ~3 dive ops in a row). They didn't have their own boat, but instead hired one of the water taxis that ferry people to Lovers Beach/Sunset Beach. The advantage was that it was "private" for our group of 6 and one other diver....and we had 3 divers in our group, and 3 snorklers...overall it was pretty cheap, and allowed the non-divers to just to hang out on the beach or snorkel as they wished.
In Cabo itself, there isn't any real shore dives that I had been able to find. You could shore dive from Lovers Beach, however you'd have to take a water taxi to get there. The better diving is supposed to be in La Paz (such as Club Cantamar), which is ~2 hours out of Cabo and many of them have shuttles that run up for the day. We may do the trip to La Paz this year, its still up for discussion in our group.
I'd also recommend checking Trip Advisor for more restaraunt and club info, or other transportation questions.