Traveling to Cuba
 

Considering going on vacation to Cuba in May 2018 and just researching some options after Trump reversed the Obama era policy of person to person. What are the alternatives now? I really want to try to avoid booking 2 separate flight itinerary i.e. LAX-MEX, MEX-HAV because if I miss the connection I would be screwed.

How difficult is it to get permission to visit as a tourist now? What are the strategies?

Leisure tourism has not been permitted at all, even under Obama's relaxation. The so-called people-to-people tours are still permitted and are likely going to be in the future. It means going with an organized group whose itinerary focuses on cultural activities.

Thanks, I have no interest in traveling with an organized group... I don't like that kind of travel :) I guess I just have the one remaining option then ;)

As long as you realize that travel via a third country still doesn't make leisure tourism legal for U.S. citizens ...

No one knows what the changes will be under the new guidelines, which have yet to be published, other than P2P for individuals is supposed to go away.
The "support for Cuban people" category should still be available. Currently it is defined pretty vaguely, and many who spend money with Cubans for housing and transportation and tours in Cuba might qualify, but this may also be more tightly defined in the new guidelines.

"Support for the Cuban People," as presently defined, is:

I don't think it's quite as "vague" as you make it out to be. Most visitors would have a hard time arguing that they are complying. Maybe (1) (iii) is the key, but the intent is likely more than going and saying "Buenos días" to people you meet on the street. ;)

OFAC says:
"Individuals ..... that promote independent activity intended to strengthen civil society in Cuba"

As mentioned above, those visitors "who spend money with Cubans for housing and transportation and tours in Cuba" are promoting independent activity (those businesses) which, since they are independent entrepreneurs and not the usual government paid jobs, strengthen civil society in Cuba.

And that's probably the loophole.

Little Marco's very own recommended one, apparently.

Yes, it's like SJO guy said, yo can as in (going with an organized group whose itinerary focuses on cultural activities). With Obama was a little easier, but now, it's moore complicated with Trump's policy. Good luck

There is nothing more complicated with Trump's policy. Check "Support for the Cuban people" instead of "P2P" and go on about your individual/independent visit. No need for a group tour.
Support includes staying in a Cuban home (casa particular), eating at paladars (privately owned restaurants), using Cuban guides and taxi drivers to get around, anything that puts money in the pockets of Cubans in business for themselves, not working for the state . Your schedule has to be "full time" (an undefined term), but it always had to be under Obama's rules as well.
There are a couple of expensive hotels that are now on the off limits list, and many that aren't, but if you are going to support Cuban people, as well as add depth and cultural richness to your trip, you'd stay at a casa particular (B&B) owned by Cuban entrepreneurs anyway.
Not even many of the businesses on the "official" US government off-limits list are actually off limits. For example, if you do not buy your rum directly from one of the off-limits rum makers, but through a third party such as a shop, there is phrasing in the "new" regs that allows for purchase of even these products. And only a couple of brands are on the list, not all of them.
No one, neither CBP or OFAC, is checking when you re-enter the US, and no one has been audited by OFAC.

Rather sad that the mere perception of changes seems to be discouraging US passport holders from traveling to Cuba. The very Cuban entrepreneurs who Trump stated he wants to encourage are those currently reporting significant loss of tourist income.

I can say that ever since relations with the United States have improved, everything has become quite comfortable!

Thinking of travelling with my wife and 16 year old son independently. Can someone recommend the best guide for Havana. We usually travel to luxury hotels and I am aware this will be quite different. Still would love a guide who knows best places to go? Thanks FTers

Here's a list.
(IMO there is no "best"; they are all competent enough to be making a living. One gets trendy and then gets overburdened by newbie posters who don't do a lot of reading on forums, and begins to farm out the tours to his/her friends.
Would you know anyway if someone told you a building was constructed in 1852 or 1824?)
There are some of the same on this list plus more on TA and CruiseCritic forums on Cuba.
Do your OWN homework with the help of a good guide BOOK or two, then tell the private guide what YOU prefer to experience in Havana.

specialized and general tours:
photo guide, Havana, Ivanna Sarzik at [email protected]or 53 58080824.
walking tour guide: Analay Fernandez (walking tour): [email protected]; +53 5 538972
art tour Havana Sussette Martinez <[email protected]
music and more Radis..... [email protected]

other guides with vehicles:
Humberto Mesa (driver): [email protected]; +53 5 2944372
Jorge: [email protected]
Boris: [email protected]
Geikis: [email protected]
Ronel: [email protected]
Danay: [email protected]
Darien: [email protected]
Jose: [email protected]
Pototo: [email protected]
Claudia: [email protected]
Natalie: [email protected]
Jorge Milanes: [email protected] (011-53) 52419134
Jorge Gonzalaz Estrada on Facebook
Nosotros Cubaneamos (Juan Carlos)
Alejandro Rodruguez Bidondo ([email protected])
Darien Paetz . https://www.facebook.com/darien.p.rodriguez (Joel, driver)
Santiago <[email protected] (+53)76424580(Casa) +53 53833855 (Móvil)
Nosotros Cubaneamos

Kempinski in Havana, but I am sure even there you'll find a friend or 2, called the La Cucaracha!