Here’s the first bit. I’m longwinded, but I’m passionate about Cuba, so this is worse than usual. It rambles. I’ll try to shorten up the rest. Your plans sound good. It is vitally important to go now for the reasons you stated and for reasons you’ll better understand once you go. It’s a special place caught in a very unusual set of decaying circumstances. Castro was right, but he chose the worst possible solution to the problem.
Going legally is best if you can. In my opinion, there’s an awful lot of optimism in the Cuba travel area. Over the past 4 years there’s been a lot of fluctuation in travel restrictions/freedoms. Raina’s uncle is setting up another trip and it’s been on and off for a year now. We were supposed to go in two weeks, but we’re now looking at 9-12 months from now. It changes weekly.
We were lucky enough to coattail on a trip Raina’s uncle was making to teach a martial arts seminar the first time. It was done with necessary Dept of the Treasury permits etc but even at that, we almost couldn’t board the plane. We arrived at the airport in Miami 4-5 hours early for the 9a flight and were only certain we could travel less than 30 minutes before the flight. Legal charter companies are VERY picky about the legal rudiments as the Treasury Dept. will fine them or shut them down for violations. It’s serious business and they can’t afford to screw up.
We traveled during one of the more “open” periods during our relations and the lines were very long at the airport and most travelers brought the maximum amounts of luggage and tons of TVs, air conditioners, you name it. Flatscreen TVs were popular.
Whatever way you decide to go, do everything you can to be sure all paperwork is in order so you don’t wind up spending your vacation in Miami instead. It is equally important to have your Cuba documents in order. They are generally concerned about who enters the country, but with proper paperwork, no trouble.
I’d suggest hiring a Cuba travel consultant on this. Even frequent Cuba travelers do this. There are lots of legal hoops. Ours consultant was a pro and still it was nightmarish, and we nearly didn’t make it due to some of her failings. Once the door shuts on the plane and it starts to back away from the gate, you’re home free.
Entry at Aeropuerto Jose Marti outside Havana was very easy - leaving was the most intimidating aspect (more on that later). The airport experience is much like that of other small Caribbean nations, albeit decrepit. You will have your passport checked and a visa stamped, then you retrieve your bags and meander through the customs line. You are scanned for weapons in a detector and they conduct a rudimentary open bag inspection on every bag. Then you’re IN.
Next you will change your money at the exchange booth, they’re right in front of the doors out of airport. There are two currencies in Cuba. One version for the population and another for tourists. (research this for a less complicated explanation than I would give here - it helps to isolate the citizens from our dollars in an attempt to help them, but fails miserably)
Among the first things you will notice when you walk out of the airport is the smells. Intense smells. The heavy salt air mixes with sweet, acrid smoke from distant trash fires, and gasoline and diesel exhaust that bellows unrestricted from engines limping along. That alone is overwhelming, but couple that with the unimaginable decrepitude of nearly everything you see and a fierce and proud people going about their lives despite this, and… it can be overwhelming. You want to DO something about it.
You can hire a taxi to take you into Havana right from the curb, as with any airport and despite the appearance of the cars and some of the drivers, it is safe. I felt safer traveling nearly anywhere in Havana than in most places in the US. You’ll understand when you’re there.
A number of years ago Raul Castro opened up commerce to allow some private businesses - as you’ve likely heard. Immediately bed and breakfasts popped up, as well as little restaurants and bakeries, all in people’s homes. One of the nicer neighborhoods is called el Vedado and we stayed there. The old Tropicana has been remodeled and is cheap by our standards, and you can stay at 5 star resorts (3 star by our standards) but stay in a neighborhood B&B or in old Havana. Any of that resort crap leaves you completely isolated.
Some of the classic 1950’s mob hotels along the Malecon (the seawall) are getting fixed up and I’d suggest that too. If you have money to spend, the Hotel Nacional de Cuba is legend and it’s where it all happened back in the day. That’s where the US mob planned their take-over, where all the movie stars stayed and so on. It’s by no means a US standard hotel, but classic Havana. It is the pride of Havana and holds a special place in the hearts of Cubans. Beautiful old building. Even if you don’t stay there, go for sundowners - mojitos on the lawn looking out at the Straights of Florida with the strolling band playing requests, a cigar… I want to fucking cry. Perfection. The night we were there, a full moon rose from behind the old fort at the harbor entrance… magical.
Another hotel option, and maybe the best is this: Hotel Inglatera in Old Havana. Actually, if I were you, I’d just stay there. Awesome old hotel and you can walk to almost everything. Right across the square from the hotel is the national art museum, which was good and surprisingly unpopulated. Right next door to it is one of Hemingway’s many watering holes and one of the most famous, La Floridita, home of the daiquiri. Also, you should hire a car for a day and head out to Hemingway’s finca (A MUST SEE - about 1/2 a day) and go to a beach for the rest of the day - the car will wait.
As I said Havana is full of unimaginable decay - I mean to the point that you cannot fathom people living in the structure, and yet… they do. Cubans can lawfully inhabit any structure they care to so long as they file registration papers, and over many decades they improve it.
It took months to fully digest all I saw there. And still there are places where you step back five hundred years. It’s amazing. La Floridita and the Hotel Inglatera and many other places are like this. Bizarre and exciting. Nothing has changed since the late 50’s in some of these places.
There is a sort of bazar or market in an old warehouse on the harbor where you can buy all sorts of stuff. It’s a tourist place, but not like you might think. Buying their crafts really helps the vendors and their families. It’s located in the oldest part of Havana and you really get the feel of 500 years of history. This was the forward operating base from which Spain directed the Conquest of the New World. Pretty amazing.
You should have dinner out where all the mansions are, I’ll dig up some data on that. It’s surreal, especially after seeing how people live throughout Havana…. Stunning mansions from 1900 to the 30’s, in fresh paint, perfectly landscaped, high, wrought iron gates, fences, and walls, Mercedes, BMWs, and a high military/police presence. This is where the ruling elite and their families live - it is a Socialist utopia after all. Hypocrisy at its manicured finest.
There’s a restaurant in one of the old mansions where Castro used to eat from time to time. Excellent food. $10-$15 gets your what would cost $75-$150 in the US.