So basically the US government is ok with you going to Cuba if you meet one of their 12 criteria.
http://www.ecfr.gov/cgi-bin/text-id...98f1cff&mc=true&node=se31.3.515_1560&rgn=div8 So first I advise you to wade through the 29 pages of nonsense you'll find in an easy to use FAQ from the treasury department.
https://www.treasury.gov/resource-center/sanctions/Programs/Documents/cuba_faqs_new.pdf
Done? Ok. Essentially you can go to Cuba as a "tourist" on a people to people trip (Educational Activities §515.565) which consists of 8.5 hours of cultural education/immersion a day. What qualifies as cultural education/immersion? Well that's a great question and there's no definitive list actually. You find out when they choose to audit your trip and tell you what you've done is not legal. Fortunately this doesn't appear to be happening at all really.
My company has decided it is reasonable enough to begin creating trips for our US clients (we've been sending UK clients there for 8 years) which follow the 8.5 hour guideline as we have deemed to be legal. Our trips will be heavy on privately guided tours, you'd have a chauffeur-guide driving you throughout the trip and on call 10 hours a day. We try and use casa particulares, which are locally owned houses which usually have 1-4 extra rooms that they rent out in a B&B type style. Some of them involve sharing living space with a family, others are essentially boutique hotels which use this legal loophole to run a private business which would other be impossible in Cuba. We will not advertise any lengthy leisure time or beach time as that has been deemed illegal by the US government. Essentially the more one on one experiences you have with locals, sharing experiences, etc the better it looks to the government.
You can buy flights directly with 6 different US airlines which operate to a number of Cuban destinations starting in 2017. The airlines will provide you with the Cuban "visa" when you check in at the airport and it is included in the ticket price.
Now, as we build all our trips tailor made, if a client decides they want to go to a beach town, we'll do our best to come up with cultural tours for them to do during their time there. If they choose to skip those tours and sit on the beach, it doesn't bother us at all. Each client has to fill out an affidavit with the treasury department declaring their intent to travel, so at the end of the day you are responsible for following their guidelines, not the company booking the trip. I am sure we will have clients who visit Havana for a few nights and then just chill on a beach for 4 days.
I spent all of October there for work and traveled all throughout the country. Typically tourists will stick to Havana, Vinales (a UNESCO Heritage site for their farming practices), and Trinidad (the best preserved colonial city in Cuba). These have the most options for accommodations but also a huge number of tourists which makes it feel far less than authentic in many ways. Trips that cover the east of the island (Santiago, Camaguey, Baracoa) will give you a lot more off the beaten path experiences where you can see life more or less uninterrupted by western society. There are also a bunch of quite well kept national parks throughout the country which offer great hiking, bird watching, waterfalls, and cave systems.
The biggest obstacle we're going to have with Cuba is setting expectations. Cuba does not have any sort of luxurious hotels or comfort. The closest thing in the country is probably the Saratoga Hotel in Havana and that would qualify as a 3/4 star hotel elsewhere in the world. Service throughout the country at the majority government owned hotels and restaurants is abysmal. Slow, uninterested and uninspired. On the other hand, there are a small number of private restaurants and casa particulares now which are offering great experiences. Havana and Trinidad have some outstanding restaurants and the service at these privately owned places is what you would expect in other parts of the world. Traveling between destinations takes a long time as the roads are full of potholes, farm animals and horse drawn carriages. Local airlines are sometimes on time, but more often than not delayed 6-10 hours or cancelled altogether (we likely won't use them at all).
But if the lack of luxury isn't a problem and you have a bit of patience, Cuba is a great destination. The people are extraordinary; I've never felt safer in another country and strangers are happy to help in whatever way they can. I have heard tour groups complain of being hassled while in Cuba but I never experienced anything like that, which is likely a product of not traveling around in a big tour bus with 50 other people but instead having a local guide who knew where to take us and how to avoid that mess.
Credit cards, atm cards of US banking institutions will not work in Cuba, so there's a good chance you'll need to take all the money you'll need for your trip with you in cash. US dollars get hit with an additional 10% transaction fee in Cuba, so it's best to bring UK pounds or Euros. Wifi access points are few and far between, usually in public parks. You can buy hour scratch cards from hotels or local telephone shops for between $2-3 and then login at those parks. Or you can look for groups of people staring at their phones and then figure out which of them is offering the hacked signal and pay him $1 for an hour. Sketchy, but actually much easier than finding cards and a hot spot.
My mind is shot as I've been putting together our website for launch. If I'm missing anything obvious or if you have any specific questions, just ask.
Liquid, I toured their only 18 hole course while I was there. It's located next to the Dupont's mansion. Amazing views, less than impressive greens.
