The Jacobs Take Cuba!

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,



  1. David Nesbitt on 02/05/2019 at 5:26 PM

    Hey Olivia, Looks like you had a wonderful time. We enjoy reading about your adventures. Sandy & Dave

    • Olivia Jacobs on 02/05/2019 at 7:14 PM

      Thanks Dave! I’m glad you do because sometimes I wonder if I should be writing about them. 😀

  2. Rich Hanke on 02/05/2019 at 5:35 PM

    Thanks for sharing your adventures in Cuba.
    A Great family, having an amazing time.

    • Olivia Jacobs on 02/05/2019 at 7:13 PM

      Thanks Rich! I’m glad you enjoyed it 🙂

  3. JC Mooney on 02/05/2019 at 5:37 PM

    Thanx a bunch for sharing your journey. You are living life large!

  4. Ricardo Romero on 02/05/2019 at 5:44 PM

    Hey! We were there with you! Amazing recap of your (and our) trip! What a wonderful family you have. We were privileged to meet you all! Hope to see you again someday at your studio!
    —Rick and Kathy Romero

    • Olivia Jacobs on 02/05/2019 at 7:12 PM

      It was a pleasure meeting you as well! I’m glad you enjoyed the write up. I wasn’t sure if everyone would feel the same way as I did in some of the places.

  5. Marilyn on 02/05/2019 at 6:12 PM

    Wonderful story and striking images! Made me want to go back to Cuba sooner rather than later…

    • Olivia Jacobs on 02/05/2019 at 7:11 PM

      Thanks Marilyn! I had fun with my camera. Just need to upgrade my lens next for even better pics! 😀

  6. Kirby Montgomery on 02/05/2019 at 6:34 PM

    Great story of your Trip Olivia! My wife Marcie and I met your dad a couple of years ago on a Park west VIP cruise! Of course being a Harley Owner we had to get a few of his pieces! We were just on an 11 Day Park West VIP cruise in January, led by Park West’s Jason Betteridge. One of the featured artists along with us was Patrick Guyton! He did this awesome piece of Castello di Amoroso in Napa that we were blessed to acquire. I understand your Dad will be at a Park west event at the Castle in April to play in a band along with Patrick, Jason, and Gary Puckett! We expect to be there an hope you will be too!

    • Olivia Jacobs on 02/05/2019 at 7:10 PM

      Thanks Kirby!!

      Is that the castle in Napa? If so, yes he will be there!

      • Kirby Montgomery on 02/05/2019 at 10:26 PM

        Yes, the castle is in NAPA!!! Marcie and hope to see you there!!!

  7. Deb Weeks on 02/05/2019 at 6:57 PM

    Great Blog, almost felt like I was with you on this adventure. Happy you had such a good time.

    • Olivia Jacobs on 02/05/2019 at 7:09 PM

      Aww miss you Deb!

  8. Regis Spaniel on 02/05/2019 at 7:38 PM

    I really enjoyed reading your blog! It looks like you all had a great time. Your whole family seems like wonderful people and I really hope to get to meet all of you one day.

    • Olivia Jacobs on 02/05/2019 at 8:58 PM

      Thanks Regis!

      I love hearing that people are enjoying what I spend time writing. We hope you can make it out to Deadwood some time.

  9. Gail Alba on 02/05/2019 at 8:16 PM

    Hi Olivia; please tell Scott and the rest of your family, Gail Alba and Stu say HI! Thank you so much for sharing your wonderful vacation and photos (love your comments on the photo’s). What a beautiful and talented family. As soon as I get Scott’s art up on my walls (I’ve finally received some of my pieces and still awaiting others) I’ll send photos. I hope to get out to Deadwood to see the Studio / Gallery. This was very timely as I leave for Cuba in 2 days. I’ll be looking to see if I can identify some of the locations you showcased! Again, thank you.

    • Olivia Jacobs on 02/05/2019 at 8:57 PM

      I will tell him! He’s currently in South America on another cruise, but he’ll be back in a couple days.

      Enjoy Cuba since you’re going so soon! Good luck finding the locations I captured!

  10. Terry Bray on 02/05/2019 at 8:44 PM

    Looking forward to a relaxing nite tonight and reading about your Cuba trip. We are going next month for a week cruise on the Sea Dream……Cuba bound. If your ready to go again~ come join us and Geoff and Lori Bodine. 😁

    • Olivia Jacobs on 02/05/2019 at 8:56 PM

      Haha! I’m not sure I’m ready to go back, but have fun! It is quite the experience!

      Enjoy the read later on 🙂

  11. Patty on 02/06/2019 at 1:24 AM

    Cuba is on my bucket list and moving up to the head of the list after reading this blog. Thanks for sharing.

    • Olivia Jacobs on 02/06/2019 at 5:16 PM

      I’m glad that my Blog did that for you! Enjoy it when you go!

  12. Charlotte Kahrs on 02/06/2019 at 4:54 PM

    Olivia thanks for the photos and commentary. When I saw the photo of the door and bared window I thought – painting reference for Scott; then you had that comment about just that. Can hardly wait to see what he paints. Also enjoyed the hint of the ship in the last photos; after your earlier tease about it’s difference from the larger cruise ships. Loved “sharing highlights with you”. Thanks!

    • Olivia Jacobs on 02/06/2019 at 5:58 PM

      Yes! He has so many options you haven’t seen… All on purpose 🙂

      Thank you for reading!

  13. Julie on 02/06/2019 at 6:37 PM

    Olivia, sounds like quite the experience! Humbling I’m sure, and getting back onto U.S. soul, a blessing.
    Day 9 sounds like one you could have missed, but all other days full of surprises. Pink classic cars…wow beautiful. The Versace mansion would be something to see. You all looked so happy! Glad Scott’s art auction was successful. Can’t wait to see his new paintings! Welcome home! xoxo Julie

    • Olivia Jacobs on 02/06/2019 at 8:48 PM

      Hey girl!

      Thank you for reading and remembering so much of it! Your reading retention must be high haha. It was very humbling to be there. It was depressing and made me want to go back on the stop which then made me feel even worse for not experiencing their world. They have no choice but to live in those conditions and we’re so blessed to be able to “vacation” in their backyard and travel home to our cushy lives.

  14. Roberta Iacino on 02/08/2019 at 4:07 PM

    Great blog and pictures. Thanks for taking me there via your blog!

    • Olivia Jacobs on 02/08/2019 at 6:56 PM

      You’re welcome Roberta! Thank you for reading 🙂

  15. Tim Rakers on 02/08/2019 at 10:23 PM

    Great story wonderful trip for the family.
    I deal with Ron for our purchase and he mentioned his trip to Cuba and the Villa they rented something I and and the family are looking in to.
    We miss you guys since the HSRs but we got to see Scott last year in Daytona and caught up a bit.
    Wishing you all well and hope to see you soon.

    • Olivia Jacobs on 02/08/2019 at 10:33 PM

      I hope you have fun there as well! It’s a cool place to experience and I’m happy you were able to catch up with Scott in FL!

  16. Jon Lynch on 02/08/2019 at 10:32 PM

    Wow what a great read on a cold Sturgis day, thanks for the story, do they have any American beer at all ? sounds like the food was great also do they have any motorcycles on the roads ? or scooters ? but thanks for sharing…

    • Olivia Jacobs on 02/08/2019 at 10:34 PM

      Right? Weather is a little different here in SD. We don’t drink beer so I have no idea! The food was decent; it wasn’t great and it wasn’t bad. There were scooters and TONS of horse-drawn carriages.

  17. Butch Hudkins on 02/08/2019 at 10:49 PM

    It had to be a most interesting and memorable trip. Enjoyed reading about it and seeing your family and the surrounding photos.
    Hello from an old bike rider in Texas who is still riding vintage bikes.

    • Olivia Jacobs on 02/08/2019 at 11:16 PM

      Thanks Butch! I appreciate you taking the time to comment and I will say hi to the rest of the family for you 🙂

  18. Chip Harding on 02/09/2019 at 5:12 AM

    That was a great read on a cold winter evening. Thanks so much for sharing! Hope to see you all again this summer!

    • Olivia Jacobs on 02/11/2019 at 5:29 PM

      Thank you for reading Chip! Stay warm!

  19. Martin on 02/11/2019 at 2:55 PM

    Cool blog Liv.
    Welcome home.
    Would love to see more car pics. More everything pics haha
    Looks like a fun trip.
    Hope you sold lots of art.
    Thanks for sharing.
    Went to your booth in Scottsdale.
    Said hi to Ron & Tate
    Lousy location for the booth.
    No traffic .😐
    Miss you guys.
    Tequila Tuesday?
    Come over .
    It’s not freezing😐

    • Olivia Jacobs on 02/11/2019 at 5:32 PM

      Hey Martin!

      We have lots more pics in our archives! You’ll have to come visit to see them, muahahaha.

      Tequila Tuesday isn’t the same without you! Xo

  20. Leon Muenks on 02/11/2019 at 10:34 PM

    Great account of your trip, thanks for sharing !!

    • Olivia Jacobs on 02/11/2019 at 11:56 PM

      Thanks for reading, Leon!

  21. Harry Bayne on 02/18/2019 at 4:24 PM

    Sounds like the trip of a lifetime. Patsy and I got to spend time with your Dad in Antarctica. It was great to see him again, but we both wish you had been there. Congratulations on your burgeoning art career by the way. You are doing some really interesting paintings.
    It won’t be long before you start having sell out shows.

    • Olivia Jacobs on 02/18/2019 at 6:57 PM

      It sure was!

      I wish that our time on the ship wasn’t just Sea Days! I was scared to be on a ship during another rough sea! (Barf) I’m glad that you didn’t have that this time.

      Alexa is doing great! Her career is really beginning to kick off!