Ok being the self appointed site SME on La Isla Bonita ( 20+ trips, visits, work etc since 1993 either alone or with the memsahib) if I may..
First letting you unit know where you’re going is sound advice and just plain common sense. Even if the Scheduled Country list is no longer, Cuba since Fidel turned over power to baby brother is in a bit of a flux now. Not saying anything is likely to happen, but nice to let anyone know where you are family, employers etc just in case. I've been down there in a hurricane, the Elian Gonzales thing, the two planes shot down thing, the overreaction to the coup attempt against Gorbie in 1994, and the crackdown after the Papal visit and so far so good.
Ok good, now for some current advice try the forums at Lonely Planet, ignore the left wing dribble and you’ll note they are current and full of good real time info. Debbie’s Caribbean Site is also good especially with reviews on resorts there. I don't go there to get info about the CF....
I’d also suggest splurging $20-30 bucks on a decent guide book. Chris Bakers Cuba Handbook by Moon Travel Books is the best out there and he recently updated it. I still drag my 10 year old copy (covered in notes etc) with me. It’s far superior to either Lonely Planets and/or Rough Guides and I’ve even written contributed to both LP and RG guides in the past. BTW Internet access is both slow and controlled there.
Duffel bag should be ok. Make sure it’s locked, Cuban airport workers are as sticky fingered as their collegues around the world. Aside from that avoid military looking clothes, although khaki cargos are almost the tourist uniform.
Mil ID, naah don’t need it. My first trip down I was still in and discovered on the flight down I had mine and my tags. I tried to hide it and then realised if I was stopped and searched it would look worse if they found it hidden, so put them back around my neck, and the card back in my wallet. No probs. Besides easy to spot fellow militarytypes at the pool bar, it's like pregnant women just knowing.
They may hassle single guys at the airport. Back in the mid later 1990’s single guys with multiple entry/exit stamps were getting hassled. Fidel presumed they were either all sex tourists and/or cigar smugglers. MINIT boys would give you the detailed search and 20 questions until you "suggested" they help themselves to a "present" aftershave, soap, Maxim magazine etc. As a first timer with no stamps and part of a tour group should be no problems. There are other scams like the “your bags are too heavy, pay the $20.00 CUPs fine Senor” when leaving.
Money the US dollar was recently banned again so take Cdn. You’ll exchange it there for CUPs the hard currency tourist pesos all tourists use. MN or Cuban Pesos are relatively useless aside from public buses peso restaurants etc. You can draw cash advances from Banks, Casa de Cambios etc on any Canadian Credit Card except AMEX with your Passport. ATMs are few and far between and usually don’t work. Get a safety deposit box at your hotel and keep everything in it, and make copies of all ID, credit cards and have the 1-800.
If you get sick the International clinics are good, better than here actually, but it's hard currecny, cash up front.
The water is safe in most places aside from waay up in the boonies. The local beer is good and cheap so I agree stay with it.
Mopeds stay away from. Unreliable, uninsured and the roads are full of drunk overweight Canadian and European tourists riding on them. Rent a Cars same thing. Over priced and they gouge you on the insurance. Better to stay with taxis either official or a local who’ll make you a deal. Public transit is also fun. The locals get a kick out of seeing tourist swith a sense of adventure on them and it's a great way to get invited to a local party and se the real Cuba.
Remember the local average wage is $20-30 US a month and they’re on a wartime-rationed economy. Tips go a long way there, both cash and small gifts, soap, dollar store flashlights, razor, bic lighters, t-shirts etc. I always tske old clothes and leave them for friends. Goes back to the old days when locals couldn't shop in the hard currency stores and you saw men wearing parts of their old military and/or school uniforms as work clothes etc in the boonies.
Military installations are all over the place and as noted not always well marked. However I’ve blundered into several over the years, play dumb tourist and unless you’re wearing cadpat jammies and carrying a honking big Nikon with a telephoto lens you should be ok.
The Military actually run some of the hotels and tour companies as a source of hard currency. You can sky dive out of a old Colt Anatov Bi-Plane or take a Hip Helo to an isolated beach etc on tours. Or jump in the back of the soviet version of the old deuce and half for an eco trip into the mountains.
Organised tours are ok. Enjoy the scripted patriotic crap the guides spew out. It’s also ok to head off on your own. Unless you’re a complete idiot you should be ok. I’ve seen only 2 Canadians jailed there in my trips and no I wasn’t one. Ripping off or hurting a tourist is 3-5 years hard time cutting sugar cane. The grey berets (tourist police) are pretty brutal at enforcing the rules on the locals, but usually bend over backwards to help tourist unless you break a major rule (making pornography, drugs)
Cigars, unless you really know what your doing stay away from the black market stuff. Legally as of last time I was there you can bring out 23 cigars without a receipt per person. So if you do buy a box of black market, smoke two. Peso cigars are a good deal. Local stuff not for export and average a couple of cents each sold in the towns. Canada customs allows 50 per person BTW and all Cuban Airport Duty frees have Gov't cigar stores.
Jinteros and Jinteras well I’ll let you figure those out yourself. ;D
PM me with exactly where you’re going/staying if you want and I’ll see if I can dig up some more info.