How often are you visiting Cuba from the US?

[n0s4atu]

I could have posted this question in my little Cuba thread but thought maybe on it's own it would garner more responses.

So, since things are "iffy" right now in the States for traveling to Cuba, how often are people going?  I've seen that many here have gone multiple times, but is that over a few years?  Getting a Visa once was a breeze, but is anyone making multiple trips per year to "support the Cuban people"?  It's actually a great value to get down there and there's a lot of history to check out in addition to the cigars and rum, but I'm wondering if any red flags start going up if you make more than one trip in a calendar year? My wife is a teacher and would like to revisit Havana once their school year is in session and visit one of the schools, and I definitely wouldn't mind tagging along, but obviously I don't want to be put on some sort of list where every time we fly we are "randomly" selected to have our stuff searched, etc. 

[Corylax18]

Once in 2016, once in 2017, twice this year. At least once next year. If you stayed in a Casa, used a Private driver, or ate at private restaurants you are Supporting the Cuban People. No " " necessary. If you are concerned about OFAC, then make sure to keep every single receipt you get and ask everybody for receipts that dont offer. Easier said than done, I know. Gov. run facilities are really the only ones I know to give receipts regularly. 

There is also the realities of OFAC, who is tasked with enforcing not only the Cuban embargo, but ALL worldwide financial embargoes that the US is participating in. The most recent data (2016) that I can find on OFAC's budget indicated their staffing at about 225 people. I don't know if you've seen the news lately, but with Iran, DPRK, Venezuela, and whoever is next on the list 225 employees is probably about 10% of the staffing they need to actually do their jobs. Busting private citizens for occasional travel to Cuba should and appears to be towards the bottom of their to do list.  

Customs/TSA is another story. I've never had a negative experience coming back directly from Cuba or back through Mexico. Last year, coming through Houston at about 11:30 pm on a Saturday night Customs couldn't even be bother to stand up and take our passport check slips, let alone rifle through our bags. I was literally like a smooth, easy, domestic arrival.  

I know there are a few members here that travel US-Cuba-US nearly monthly and have been doing so for years. I think they technically qualify under "Work Visas" but they can elaborate on how all that works. 

[n0s4atu]

Thanks @Corylax18. Good to know that if the wife wants to go check out a school that at the end of the day it's not that big a deal.  I know I'm already looking forward to going back.

[bmf30180]

I'm heading back in November after my first visit this past June.  I'm also in the initial phase of planning another trip in the Spring.  Just waiting to see how much I can cover (and afford) on my November trip, plus gauging the interest from my friends that may want to see the island.  Personally, I am hopeful that travel to the island will remain relatively easy in the future.  IMHO, the embargo is a joke and does nothing but deprive the Cuban people of the basic necessities.  But, that's another rant...

[Derboesekoenig]

I think you're overthinking this a bit. You won't be raising any flags by even going monthly. 

[JY0]

I my first trip was in May. I’m going again in March. I going for a long weekend with my adult sons. 

[GotaCohiba]

I plan to go  a total of 4 times this year then at least once a year moving forward

 

[n0s4atu]

23 hours ago, Derboesekoenig said:

I think you're overthinking this a bit. You won't be raising any flags by even going monthly. 

Based on the responses here, clearly I was. lol I'm very glad to hear that though.  Sounds like I need to figure out when I can swing it in late fall or early spring.