Rob O'Neal Key West Photography : Keys Stock Photography | Legal, Fascinating and Fun Travel to Cuba

Cuba Photo Safari 2018


Ever since travel restrictions were eased in 2014, more and more Americans are interested in visiting Cuba. Without a doubt, anyone can go buy a ticket, find a private house online, change money and try to find as many cool things, reliable drivers and great food as possible in seven days. My trips include all of the above and much more. I will arrange flights, meals, rooms and all of the required paperwork involved in legal Cuba travel. And while it’s impossible to “blend in,” you are more than just another tourist when you’re with my Cuban friends and me.


At the moment, direct flights from Key West to Havana have been suspended thanks to new legislation, however, I am fully-licensed and life goes on. For seven days and nights, I invite you and your small group to spend as much or as little ‘down time’ as you like. There will be several opportunities to venture out on your own to explore and after much time and effort, I now have several preloaded cell phones that work in Cuba so we can easily stay in touch. This is literally a game-changer. As much as most people love the idea of being away from their phone, being connected in a foreign country makes things much more efficient.


In order to travel legally to Cuba, we are required to follow an itinerary that encourages a “People to People” experience. This is not a museum tour, nor a 'big-bus' full of zombie tourists. This is a one-of-a-kind experience where you'll meet the people I've called 'amigo' for more than 20 years. In addition to that, we will be engaging lots of wonderful people and making new friends along the way.

Cuba is a beautiful country, but everyone agrees, my friends make the difference and it’s my pleasure to include and hire them for my tours. From tour guides, to artists, dentists, photographers, fishermen and writers, you will walk away from this trip with new friends for life.

Per U.S. law, my trips are centered on digital photography. From beginners to expert level, all are welcome. If you don’t know how to shoot or manipulate a camera, I will share many tips and insights. If you are an expert shooter, I will show you things that have taken me decades to find. Additionally, I have lots of camera gear I’m happy to loan. Over the week, we will cover lots of interesting ground and in the evenings, if you’d like, we can review your images.


Unlike 20 years ago, Cuba is not a really cheap place to visit. Sure, if you want to sleep in a side bedroom of someone’s house in some far-flung neighborhood, eat at gas stations and street kiosks and use the bus system, you can do Cuba on the cheap. However, for a reasonable price, you can stay in private, comfortable, perfectly-located homes, eat amazing food and have a chauffeured vehicle every day. Our driver, Roberto, is at our disposal for the whole week so there’s no searching or waiting for taxis. This is a major perk as taxi fares add up quickly and finding available cabs, at times, can be a drag. Another perk with a private driver is that you don't have to haul everything (backpacks, camera bags, daily purchases) in and out of different cabs all day long.


A typical itinerary is listed below, however, customized trips are welcome.


Arrive in Havana, change money, load up our awaiting vehicle and head right into the boonies. Havana can wait.


Our first two nights are spent in the gorgeous and historically-rich region of the Bay of Pigs, more specifically, Playa Larga. Depending on the time of year, we can see thousands of flamingos plying the flats of the Zapata Swamp, visit crocodile farms, explore natural sink holes offering amazing snorkeling opportunities and plenty of fascinating reminders of the Bay of Pigs invasion that helped shape both Cuban and American history. Google it.

Over the past several years, I've made a handful of new friends in and around Playa Larga and every one of my clients have thoroughly enjoyed this leg of the trip.


After two nights on the southern shores of Cuba, we head for my personal favorite location. Since 1999, I have visited all 15 provinces and the village of Vinales remains at the top of my list. It’s a magical place. Activities available are horseback riding, organic farm and botanical garden visits, cave tours, zip line canopy tours and an incredible visit to one of the country’s top tobacco farms where my friend, Osvaldo, will dazzle you with his knowledge of the art of cigar making, from seed to stogie. Whether you smoke cigars or not, it’s a fascinating experience.  


After two nights in the mountains of Western Cuba, we will head back to Havana to a very nice, private home, which is exclusively for our group.  I have several highly-secure apartments, all with stunning ocean views, full kitchen and multiple bathrooms.


While in the capital city, we can visit 'Hemingway haunts' as well as Hemingway’s home, Finca Vigia, which features his boat, the “Pilar,” along with countless other original artifacts. We will also have an English-speaking tour guide for a day in Old Havana, plus visits to the historic Hotel Nacional de Cuba, Morro castle, an optional evening at the Tropicana nightclub and much, much more.

I always encourage my clients to do some Googling to find other points of particular interest. Even though I’ve been to Cuba nearly 50 times, I'm still discovering new things. If you’re interested, there are art museums and galleries, gorgeous architecture and centuries-old churches that are open to the public, and with our small group size it’s much easier to move around than the dreaded bus tours filled with expressionless tourists. If you wanna see something in particular, just let me know.


If there is one thing that has certainly changed in the past 20 years, it’s the food. In 2008, the Cuban government began issuing a lot more licenses for private citizens to open restaurants and the resulting competition has led to some truly amazing fare.


So while the food is no longer a concern, any visitor to Cuba must realize that it really is a third-world country and things tend to happen (or not) from time to time. A random blackout, or an attraction is closed for no reason. Thankfully, it has been my experience, year after year, that when one door closes, at least one more opens.


As for luggage, we are able to bring the same amount of luggage on the charter plane as you can on a regular airline. Each person can bring one suitcase and a personal item. There is a $25 charge for the suitcase on the American side. Cuba does not charge us on the way back.


Everyone asks me how much spending money to bring.. I have always suggested bringing enough for $100 per day. However, with so much included in my program, all that remains to pay for is your lunches, a few dinners, and perhaps the, ahem, “occasional beer.”  Both lunch and dinner will range from $10-$20.


As for shopping, there really isn’t a whole lot to buy. There are a few clothing stores here and there, but Cuba isn’t really a shopping destination. We will, however, visit an artisan market where reasonably-priced Cuban art and trinkets are plentiful and I've seen some art lovers happily drop some serious dinero.

The U.S. government continues to move the proverbial goal post when it comes to Cuban-made products. According to the U.S. Customs and Border Patrol's website, which was updated on May 22, 2018, you can now bring back an unlimited amount of Cuban rum and cigars. I will provide the link at the bottom of the page.

As for art, the last I had heard, you may bring back a total of $400 worth of Cuban art. At times, they'll hit you at the Havana airport for $3 apiece for artwork, sometimes they don't. This is classic Cuba.

There are a lot of options out there for Cuba travel from spending $6,000 to be led around by your nose with a boring, stuffy group tour, to 'going-it alone.' And while I certainly understand the value, both literally and figuratively of doing the latter, I will say this, if you would like to get some serious bang for your buck, I can show you a hell of a lot in seven days and most importantly, you will be welcomed by some of the nicest people you'll ever meet, and that's a fact.

Feel free to contact me with any questions.


Thanks for your time,


Rob O.




Per person cost of $1795 for this trip includes:


Airport transfers in Cuba.

All personal transportation for seven days.

Private, clean and secure accommodations for seven nights.

Daily breakfast (all-organic eggs, meat, bread, fruit, juice, coffee).

Lunch at Hector Luis Prieto’s rural tobacco farm.

Lunch at two other fabulous restaurants. 

3 huge, traditional dinners (including a Cuban pig roast).

Preloaded Cuban cell phone usage with ability to call the U.S. if necessary.

Wifi card.

Guided tour of Havana by English-speaking guide.



Not included is:

Roundtrip airfare from Miami to Havana: (Rougly $275-$325)

OFAC Cuban travel visa: ($200)

Nominal tips for driver, butlers and maids 

Four dinners/four lunches





Link to U.S. Customs and Border Patrol re: cigars and rum