Ever since travel restrictions were eased in 2014, more and more Americans became interested in visiting Cuba. However, as of June 2019, the U.S. government has begun rolling back Cuba travel. Thankfully, for now, it is still possible.

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 the above and much more. I will help arrange flights, and will provide most meals, rooms and all the required paperwork involved in legal Cuba travel. And while it’s impossible to “blend in,” you are much more than just another tourist when you’re with my Cuban friends and me.

 

For the time being, there are no regularly scheduled flights between Key West and Havana, so we must travel through Miami. Without a doubt, it's not as easy as flying out of Key West, but it is half the price.

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.

 

There are several requirements that make these trips legal. The good news is that the things off limits to Americans are things we wouldn't dream of doing in the first place. To be sure, 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 some 20 years. In addition to that, we will be engaging lots of other wonderful people and making new friends along the way.

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

In years past, my trips were centered around digital photography and I still have some camera gear I'm happy to loan. For beginners, I'm happy to help with camera settings, etc. For experts, I'm fine with sharing locations most tourists rarely see. Nowadays, all you need is an itinerary that includes spending meaningful time with a meaningful amount of everyday, Cuban citizens. If you're looking to sit by the beach all day and sip colorful drinks, this is not allowed by our government. That's mainly because it is technically illegal according to U.S. law, and besides, you can do that in Cancun or Bimini, though I'm not sure why one would. This is a far more adventurous trip and much more memorable than drinking strawberry daiquiris.

 

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 noisy 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 is at the group's disposal from 8a.m. to 6 p.m.  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. Trust me on this one, it makes a huge difference. 

 

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

 

Arrive in Havana, change money, load up our awaiting vehicle and head right out 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 will see countless flamingos and roseate spoonbills plying the flats of the Zapata Swamp, visit crocodile farms, explore natural sink holes offering crystal-clear 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 many new friends in and around Playa Larga and every one of my clients have thoroughly enjoyed this leg of the trip. The first of at least three full-blown dinners, which I include, will be at Paladar Alexi. Typical fare includes octopus, shrimp, marlin, grouper, and crab. If it lives in the water, this guy's family caught it within the past 24 hours. Watching Alexi create our dinner over locally made charcoal, often, right next to the table, is an experience in itself.

 

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 they all have a lot to offer, but 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 safe, secure and sparkling clean apartments. I currently have two, four-bedroom, four bathroom homes, with staff included, as well as a gorgeous, two bedroom, two bathroom apartment on the Malecon with an ocean view. These are my preferred properties, but there are countless others should you desire a particular area of the city. After a few 'less-than-optimum' experiences, I try to stay away from rentals in Old Havana. It's a cool part of the city, but it's loud, and everyone is stacked on top of each other, so client pickups and drop-offs can be difficult.

 

While in the capital city, we can visit 'Hemingway haunts' as well as Hemingway’s home, Finca Vigia, which features countless original artifacts. We will also have an English-speaking tour guide for several hours one 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 personal interest. Even though I’ve been to Cuba more than 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, or cruise shippers with numbered stickers on their shirts, following some guy with a paddle in his hand. If you would like to see something in particular, just let me know, we can do it, or, I can arrange a private guide. Simply stated, the options are unlimited.

 

If there is one thing that has certainly changed over 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 can bring the same amount as any other airline. I usually use American Airlines. Each person can bring one suitcase and a personal item. There is a $25-$30 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-$25. Most of my clients spend less than $50 per day. 

 

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 can, 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 per person to be led around by your ear with a crowded and stuffy group tour, to 'going-it alone.' And while I certainly understand the value of doing the latter, both literally and figuratively, I will say this, if you would like to get some serious bang for your buck, I can show you a lot more 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.

 

 

 

Tour Includes:

Airport transfers in Cuba.

All personal transportation for seven days from the time we leave in the morning each day, to 6 p.m..

Private, clean and secure accommodations for seven nights.

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

Lunch at Tres J Restaurant in Vinales.

Lunch at two other fabulous restaurants. 

Three traditional Cuban-style dinners including-

....countryside traditional Cuban pig roast in Pinar del Rio.

....Paladar Alexi at the outskirts of the Bay of Pigs.

....Top shelf tapas-style dinner and Happy Hour at my best friend's home in Central Havana.

Preloaded Cuban cell phone usage with ability to call the U.S. if necessary. (One phone per couple)

Wifi card for Internet access.

Guided tour of Havana by English-speaking guide.

$1995 per person

 _________________________________________________________________________________________________________________________________________

 

Not included:

Roundtrip airfare from Miami to Havana (roughly $300)

Cuban travel visa: ($75-$100)

Nominal tips for driver, butlers and maids 

Four dinners/four lunches

Alcoholic beverages:) 

 

 

 

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

 

https://help.cbp.gov/app/answers/detail/a_id/82/noIntercept/1/session/L3RpbWUvMTUyODI5NDU2OC9zaWQvSmIzSEp3T24%3D