The Jacobs Take Cuba!

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The Jacobs Trip to Cuba

On January 14th, we caught the first flight out of South Dakota to begin our trip to Florida.  The temperature was in the teens at 0330 as we loaded the truck full of suitcases and sleepy-eyed family members.

We arrived at the Ft. Lauderdale Airport that afternoon and took a taxi to Miami to check into our hotel.  I took a much-needed nap and the rest of the family relaxed by the pool.

Later, we got dressed up and hit the streets of the famous South Beach.

Instead of taking the sidewalks, we chose to walk barefoot on the beach.  It had been a while since I felt sand between my toes and heard the sound of waves crashing onshore.

We weren’t in a real hurry since our dinner reservation at Versace’s Mansion was in a few hours.  Scott was very excited for us to dine there.  It had been something he planned weeks before.

We stopped at an outdoor bar to have the first Mojitos of the trip!  We had to get in the Cuban mood, obviously…

olivia jacobs-chrisman and alexa jacobs in miami

After some very expensive, non-South Dakota priced drinks, we made our way towards the infamous home of Gianni Versace.  As we got closer to his house, Scott filled us in on what happened to him and the sick individual that murdered him on his front steps.

Side Note: I didn’t know much about the story until after we got home and stumbled across The Assassination of Gianni Versace: American Crime Story on Netflix. (It’s a good yet disturbing show if you’re into that kind of stuff.)

We walked through a set of extravagant black and gold Versace-esque gates and made our way to the bar to wait for our table.

I had no idea what to expect as we ventured deeper onto his property.  His inner courtyard was even more lavish than the entrance and the interior was even more than the courtyard!

Inside the bar, the ceilings were hand-painted with a gold leaf overlay and massive crown moulding to complete the luxurious look.

Gianni Versace's personal bar in Miami, Florida alexa jacobs, sharon jacobs, scott jacobs, olivia jacobs-chrisman, and jared chrisman in Gianni Versace's home

For dinner, we were seated along Versace’s pool on the patio.  The meal was delicious and the atmosphere would have been nice if it weren’t for constant camera flashes going off around our table.  Looking back, I think it was because the show, The Assassination of Gianni Versace that brought SO many young adults there.  They wanted to get a few selfies for their Instagram.  *Sigh*

scott jacobs, sharon jacobs, alexa jacobs, olivia jacobs-chrisman, jared chrisman at Versace house

Day 2:  Boarding the Azamara Journey

We had the morning to walk the streets, find a local organic restaurant and shop on Lincoln Road.  After, we stuffed our suitcases into two Uber’s and headed to the Port.

Once aboard, we explored the ship that we’d be calling Home for nine days. With only 700 people, it was much smaller than any Royal Caribbean or Celebrity ship I had traveled on.  The overall decor was more elegant and clearly for a more mature clientele.

It took a while to get our suitcases, but when we did, we quickly unpacked before the mandatory Boat Drill and Scott’s Park West introduction.  His intro seemed to be well received by the 100 Park West VIPs.  He talked about how he got started, his achievements, as well as the motorcycle accident that changed his life.

Don’t know about his 2016 motorcycle accident?  Read about it here.

Day 3: Havana, Cuba

The next morning, we got off and grabbed two classic taxis to take a tour of the city.  Alexa, Jared and I hopped in a pink ’52 Chevy with flowers all over it and Sharon and Scott hopped in another ’53 pink convertible.

olivia jacobs-chrisman, alexa jacobs, and jared chrisman in havana cuba in classic car scott jacobs and sharon jacobs in havana cuba

We paid our drivers to take us around the city and show us famous landmarks.  Jared quickly began practicing his Spanish on our driver, Yudel and Jared relayed some history back to us in English.

general maxino gomez statue in havana, cuba Monument of General Máximo Gómez, a war hero from the Dominican Republic who fought for Cuban independence.

Our first stop was Castillo De Los Tres Reyes Del Morro, a popular tourist spot that overlooked the city.  It was originally a fortress that guarded the entrance to the Havana bay in the late 1500s!

scott and sharon jacobs in havana cuba 2019 view of havana cuba

Lunch at the Paladar

You’d never think the place we pulled up to was anything other than a home.  Our drivers told us that it was one of the best Paladres around, so we followed their instructions and walked to the backyard to discover a huge outdoor restaurant.

There were 30-40 tables spread throughout a large thatched hut with a band of teenagers playing Cuban music. Chickens roamed the patio while we ate and startled me a few times when they ran in between my legs!  I think they were doing it on purpose.

chicken at paladar in havana cuba

After lunch and a small photo shoot that Scott and Jared conducted, we drove to Parque Morro-Cabaña.  I heard that going to Cuba and not buying a cigar is like going to the Moon and not taking a rock, so we had to pick a few up for friends.

We arrived at La Triada Shop to purchase cigars and were lucky enough to meet Jose, the Guinness World Record holder in 2011 for the longest cigar.

Jose Castelar Cairo rolling fresh cigars in Havana, Cuba

Jared insisted that we buy the cigars that Jose just made and that he take a picture with the real Jose and the creepy wax Jose (to the right).

Jose’s story here.

jared chrisman with Jose Castelar Cairo, Guinness world record holder olivia jacobs-chrisman and alexa jacobs doing yoga in havana cuba Busting out some poses because that’s what yogis do!

Next Stop – Ernest Hemingway’s Home

In order to get to Hemingway’s home, we had to drive through the real Havana.  It was as if there was an invisible line that separated the Havana for tourists and the Havana for locals.  As we got farther away from the port, trash became more prevalent and the buildings were dilapidated.

ernest hemingway's home in havana, cuba

We pulled onto a long driveway engulfed in trees before hitting a large gate.  We each paid 5 CUC to enter Hemingway’s property and take a tour.

We quickly found out that we weren’t allowed to go inside his house, so we peered through his windows like the curious tourists that we were.

ernest hemingway's typewriter in havana, cuba ernest hemingway's closet in havana, cuba

I could tell Hemingway was an intelligent yet lonely person by the amount of book shelves he had throughout his home.  My favorite was the fairly large bookshelf next to his toilet and the lizard in formaldehyde on the shelf above.

ernest hemingway's pet in havana, cuba

After we had enough peeping, we drove back to the center of town, said goodbye to our drivers and explored the streets.

the jacobs in havana cuba

It was amazing how few stores there were… so after another batch of Mojitos, we boarded the ship to get ready for an evening performance by Lizt Alfonso Dance Cuba.  This was Jared’s highlight of the trip.  He said that he could have watched the whole thing all over again.

Check out this teaser video of them, here.

adorable kids in Havana Cuba

Day 4: Art Auction in Havana

Today was Scott’s big day!  Park West was having the first art auction of the trip and that meant we all had to be on our A Game.  Scott had finished over 30 paintings for this event and we all waited anxiously to see how they were received by the Cuban group.

The auction was a success and as a way to celebrate, we got off the ship and stopped at Dos Hermanos, Hemingway’s frequented watering hole, to enjoy our last Mojito and meal in Havana.

musical performance in havana cuba sharon jacobs and olivia jacobs-chrisman in havana cuba

Once on the ship, we got dressed up for a formal night with clients.  We had already started forming friendships with many of the couples, so it was a nice opportunity to get to know them better.

jared chrisman, olivia jacobs-chrisman, alexa jacobs, sharon jacobs, scott jacobs on Azamara Journey

Day 5:  Sea Day

Drinks, pool, relax, repeat… until midday when we cleaned up to watch the next artist be introduced.

Allison Lefcort is an artist best known for her pop art and Andy Warhol style.  We wanted to show our support during her event because she has been a fan of my dad’s since she was a teenager.  She remembered vividly the first time they met at an Art Expo in the 90s.  She spoke so highly of his skills and personality, it was humbling for even me to hear.

allison lefcort and scott jacobs

Here is Alli painting live for her audience.

artist Allison Lefcort

Day 6:  Cienfuegos, Cuba

We got off the ship in what looked like a deserted town in the Middle East.

For some reason, we kept walking further down the narrow streets until we came upon a quarter mile of street vendors.  We walked the length of the vendors when I found this DJ on his computer.  I wonder how old the computer is… Perhaps it still uses a Floppy Disk!

dj in cienfuegos cuba

Potholes the size of cars marred the roads and sidewalks.  I wanted to start picking up all of the trash and smuggling all the skinny dogs, but I knew that I couldn’t in a place like this.  I was told by a Cuban that the government will seize homes that have been fixed up.  Apparently, they think you must be hiding money if you start to care about your property…  Sad, but true.

cienfuegos cuba olivia jacobs-chrisman, alexa jacobs, sharon jacobs in cienfuegoes

Day 7:  Santiago de Cuba, Cuba

We arrived into Santiago de Cuba in the evening and made plans to find a local jazz club with some Park West friends.

Two classic cars took our group to a cool spot in the center of town where we enjoyed some drinks.  Can you guess what they were?  Mojitos!

jazz club in santiago de cuba

Day 8:  Santiago de Cuba

Now that the sun was up, we made our way on foot to the town square.  Along the way, we witnessed locals in their every day life.  Scott grabbed my camera and began taking all kinds of pictures for painting ideas; the people, the doors, the stray dogs and cats, you name it!

That being said, I’m withholding photos so you’ll be even more impressed when we show you his painting!  You’ll thank me.  😉

man in santiago de cuba touring Santiago de Cuba

As we got closer to the center of town, it got noticeably nicer.

catherdral in santiago de cuba

We stopped at one of the only Cafes I had seen on the trip to enjoy some Cuban coffee.  It was nice to take a moment to soak in our surroundings from the balcony above.

olivia jacobs-chrisman, sharon jacobs, scott jacobs, alexa jacobs, jared chrisman in Santiago de Cuba

We even had a band serenade us from the street below.

IMG_0142 copy

Later, Jared and Scott disappeared into the building to set up different photo shoots for new research.  It was cute how excited and motivating Jared was for my dad.  I think it was partly from the five espresso shots he had, but I know he still loves helping my dad when he’s sober.

IMG_0143 copy alexa jacobs feeding a young puppy water in cuba Alexa giving a very young puppy water since he was all alone!

Day 9:  The Sea Day of all Sea Days

Let’s just say, the ocean was angry and everyone on the ship paid the price…

Day 10:  Nassau, Bahamas

To say that we were happy to be off the ship would be an understatement.  One of the Park West Collectors told us that he was going to kiss the ground when we got to Nassau.

We spent the day at the ever-so-touristy Atlantis, but we didn’t mind feeling like one.  We hadn’t had a day to relax and let our hair down so a day filled with slides and moments to feel like a kid were welcomed by all.

olivia jacobs-chrisman and jared chrisman at atlantis in bahamas

Once our backs were raw from racing each other down the slides and sunburns were becoming apparent, we grabbed a cab to board the ship for our final voyage back to Miami.


This trip wouldn’t have been nearly as memorable without the wonderful people we met on the ship.

The evenings we spent at the Cafe lounge playing cards, late night storytelling at the bar, and the inside jokes we shared about our Butterfly King in the swimming pool will be the moments I remember forever.

allison lefcort, scott jacobs, olivia jacobs-chrisman, jared chrisman playing cards on ship scott jacobs, sharon jacobs, sarah chinchar, doug chinchar playing cards

Thank you for letting my crazy family into your lives and sharing your vacation with us.


Till next time,


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