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Fascinating life of Ernest Hemingway in Cuba: vintage car tour

SPONSORED – Certain things come to mind when you think of Havana. Rum, cigars, vintage cars and Ernest Hemingway. As complicated as he was fascinating, the American writer left a long-lasting effect on the literary world and here in Havana.  Armed with curiosity, we decided to follow in the footsteps of Ernest Hemingway in Cuba. Of course, the best way to do so was with one of the vintage car tours in Havana. 

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Who was Ernest Hemingway?

Ernest Miller Hemingway was born in suburban Chicago in 1899. That means he was born two centuries ago in a very different world. For some reason, I found that fascinating. Hemingway became a journalist, novelist and short-story writer who was also an adventurer and a hunter. His contemporaries and later generations greatly admired him.

Fascinating life of Ernest Hemingway in Cuba: vintage car tour | kasiawrites
Hemingway’s belongings

He published numerous works, strongly influencing 20th-century fiction and literary styles. Hemingway won the Nobel Prize in Literature in 1954 and a Pulitzer Prize for Fiction in 1953.

I must say that although we were both aware of who Hemingway was, we didn’t know that much about his life. Sure, most people might know something about Ernest Hemingway in Cuba, maybe can name a book or two, but as it is with those that died in the past, they become less known to later generations, and Hemingway is no different. Whether you are a hard-core fan or have no idea who he is, his story is captivating.

Hemingway lived in Cuba for two decades. He was a celebrity of his day and had many famous friends that visited his home, the Finca Vigia. Cuba and Havana, in particular, was a different world in those days. It was a playground for wealthy Americans, mobsters and celebrities. 

He was a complicated man, and I’m not entirely sure I found him a likable one. He drank a lot, hunted, and liked many women, even married four of them. I guess not that much of a difference from men with influence in our current world. We had to find out more about this complicated man.

Hemingway before Cuba

Hemingway was from a generation that lived through both World Wars. He worked as an ambulance driver for Red Cross in Italy during WWI until he was severely injured. During WWII, he worked as a journalist in the trenches and was present during the Allied invasion of Normandy as well as the liberation of Paris. He literally witnessed history in the making.

Fascinating life of Ernest Hemingway in Cuba: vintage car tour | kasiawrites
Hemingway’s boat

In between the two World Wars, Hemingway also worked in Chicago and Toronto before moving to Paris. We were surprised at the Toronto connection especially since the paper he wrote for, the Toronto Star, is still around. 

During the 1930s, he lived in the U.S., went on a Safari in Africa where he got sick and later covered the Spanish Civil War. He wrote and lived in Europe and America, finding inspiration in the world around him. Then, in 1939, he sailed his boat to Cuba.

Ernest Hemingway in Cuba

Today, the arrival of Ernest Hemingway in Cuba seems very unremarkable. Just a man taking his boat to an island, he then made his home.  So many decades and political events later, such an act is almost unthinkable. What a different world he lived in.

Once he arrived, Hemingway lived in room 511 in Hotel Ambos Mundos and drank his way around Havana’s local bars. You can visit La Bodeguita del Medio and the Floridita bars in Havana on your own as you enjoy a famous Hemingway cocktail or a dozen, as he was known to do.

images of the outside of finca vigia
Hemingway’s house in Cuba

These places have become very touristy, which detracts from the Hemingway’s Havana we wanted to experience. On our last trip to Havana nine years ago, the Floridita was an interesting bar with few tourists and many locals. Today, the only locals are the staff.

Walking around Havana is akin to what Hemingway’s experience must have been like. The city, celebrating its 500th birthday, hasn’t changed much from his days. As Havana seems frozen in time, it’s easy to picture Hemingway strolling around, taking in the vibrancy of the city around him. Following his steps is an adventure in itself.

Finca Vigia – Hemingway house in Cuba

A trip to Finca Vigia, the Hemingway house in Cuba, is an opportunity to see where the author lived. During his time, the house was in a remote spot on a hill with unobstructed views of Havana.  Today, it’s a small village with many houses and plenty of tourists.

There are other ways to get here, but arriving in a vintage car seems like a blast from the past. I had no idea what to expect at Finca Vigia, but once we got here, I understood why Hemingway loved this place. The tree-lined road to the house with extensive grounds was a little unexpected. Honestly, I didn’t know too much about Hemingway’s house before we came and I was glad I didn’t.

Fascinating life of Ernest Hemingway in Cuba: vintage car tour | kasiawrites
Ernest Hemingway in Cuba – Finca Vigia

The house itself is a single-story, pale coloured structure with large windows and a winding terrace. Although it was built in 1886, Finca Vigia feels almost modern. It’s simple, elegant and orderly despite the extensive décor of many books, mementos and everyday objects.  You can’t actually walk inside the house, which was a bit disappointing, but you are able to see much of the house through the roped-off doors and windows.

The house, filled with so many of Hemingway’s objects, is like a time capsule. You can see his desk and the spot where he wrote standing up, obsessively tracked his weight on the bathroom walls as well as the many animal heads he collected as trophies from his hunting days.

The tower with a view

Outside the main house is a tower with clear views of Havana. The space on the main level became a place for his numerous cats while the top floor held a writing room. The story goes that Hemingway entertained a young woman there on numerous occasions and nobody was allowed to interrupt their time, not even his wife. These sessions went on for hours, making you wonder what exactly transpired between them. 

Hemingway also used to keep an eye on visitors arriving at Finca Vigia from the tower, deciding whether he wanted to let them in or not. Our private tour guide also told us that he watched Ava Gardner swim naked in the pool from that same spot. I guess it must have been quite a sight.

The pool itself is water-free, but its charm is still there. Nestled between the trees and shrubbery, it must have been quite the place back in those days. Dismayed by Ava’s nakedness, Hemingway’s wife Mary left a bathing suit for her to wear. Ava responded by marching to the house from the pool in all her naked glory. I’m sure Hemingway loved every minute of it.

The boat and the guest house

Pilar, the boat that brought Hemingway to the island, is now on display in what was once a tennis court. Hemingway wanted to use it to ambush German submarines off the coast of Cuba during the war. An ambitious plan, although one that didn’t happen. As far as boats go, this one looks very ordinary, its claim to fame being its famous owner.

The former guest house is now a bit shabby. Hemingway’s wife Martha converted a wooden garage into the guesthouse for visitors, including Hemingway’s sons. Far from housing famous visitors, the building now functions as offices and meeting space for the museum director and staff.

The grounds on the property are extensive. Hemingway often invited the local children to play baseball on the property and hosted cockfights, apparently a popular pastime in Cuba. He was well-known and liked by the locals, and many speak fondly of his legacy.

Hemingway House in Cuba is one of the most popular attractions for visitors. There are busses filled with people arriving throughout the day. The crowds rushed through the site, have a loud guide that shouts information as everyone snaps random shots. We were delighted to have a personalized experience and a dedicated tour guide that answered our questions, provided interesting tidbits and information while we took our time looking around.  It was a pleasant experience.

La Terraza de Cojimar

Our next stop on the trail of Ernest Hemingway in Cuba is a small fishing village of Cojimar. Hemingway was a frequent visitor to the area as he enjoyed fishing and drinking at the local bar La Terraza de Cojimar. What was once a popular hangout for celebrities is now very touristy. We arrived between tour buses, so we managed to enjoy the back room to ourselves, again enjoying our tour’s intimate and personalized nature.

As we sipped on our very strong drinks, Hemingway’s favourites, of course, we admired everything from the views to decorations.  It’s easy to see the appeal of Cojimar and the way Hemingway himself shaped it.

Hemingway’s table, prominently displayed in the corner spot, offers fantastic views of the Cojimar Bay. What is even more fascinating are the numerous photographs of Hemingway on the walls. There are few of him and Fidel Castro, often leading to the speculation that the two were great friends. The reality was that the two men met only once during a fishing tournament and only conversed for a few minutes.

The story goes that after Hemingway’s death, the locals collected metal pieces from chain links, propellers and anchors to cast a bronze bust of the writer in his memory. Today, you can see it standing under arches across the remnant of a small Spanish fort known as the Torreón de Cojímar. The fort, built in 1649 is a UNESCO World Heritage Site and provides a nice addition to the already lovely coastline.

After our fill of drinks, we head over to the El Ajiaco restaurant in Cojimar for an authentic Cuban lunch that was simply a feast for the senses. And what goes with a great lunch? More drinks, of course. Hemingway would be proud.

The life and death of Ernest Hemingway

I must say that I didn’t know much about Ernest Hemingway’s personal life. He had four wives and numerous affairs. Hemingway loved women, and it seems he often transitioned from one marriage onto the next one. He had three sons with two different wives. His youngest son Gregory became Gloria Hemingway later in life and died in a jail cell. His relationships with his family were often tense and tumultuous.

Often described as having an overtly macho personality, he had a penchant for bloodshed, war, guns, booze and hunting. He survived wars, plane crashes and encounters with wildlife. He suffered numerous head and body injuries and disorders not fully understood in his day. He was also a heavy drinker.

He was a successful and influential writer with an impressive career under this belt.  Towards the end of his life, Hemingway’s mental and physical health started to deteriorate. Experts suggest that he suffered from bipolar disorder, which contributed to his demise. Before he died, Ernest received numerous electroconvulsive therapy treatments, which most likely contributed to his depressed state.

Like his father before him, on a sunny morning, Ernest Hemingway put a shotgun to his head and killed himself in his home in Ketchum, Idaho, just days before his 62 birthday.

It seems that many members of the Hemingway family suffered from mental health. Besides Ernest, his father, Dr. Clarence Hemingway, two of his siblings Ursula and Leicester, and granddaughter Margaux Hemingway also took their own lives. The Hemingway story is dark yet fascinating even so many decades later.

Havana vintage car tour with Rolling Havana

When you’re in Havana people offering tours in vintage cars will approach you almost all the time. Some of them are better than others and the value you get varies, including the price. We did our Ernest Hemingway in Cuba tour with Rolling Havana and we loved every part of it.

The tour was an insightful look into the life of what many say is one of America’s greatest writers. Our excursion was personalized and provided us with a more intimate experience. We weren’t part of a large crowd shuffled around in a big bus with a loud tour guide. Instead, our whole experience felt less touristy and more personal.

From dealing with the owner, the drivers, tour guides and everyone who served us at the restaurants, the whole process was seamless.  Rolling Havana is a young company but you wouldn’t know it from the professionalism and customer services we received. The company offers a variety of tours in beautiful vintage cars organized during mornings, afternoons or evenings. There are many different tours to choose from, including the Hemingway one.

As the Internet is very recent in Cuba, the best way to contact Rolling Havana is through the company Instagram for prices and detailed tour information. 

Disclaimer: Our tour with Rolling Havana was complimentary; however, my opinion, views and photos are my own.

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    12 Mar 2019

    I did a walking tour of Parisian bars frequented by Hemmingway once. We concluded it would’ve been easier just to visit the handful he never drank in! This tour looks fascinating, but I can’t help but think he was a bit of an a…hole!

      12 Mar 2019

      You know I never thought about doing that when I was in Paris. It seems that he drank his way through a lot of places, judging by the bar trail left behind. This tour was amazing and you got to see where he lived and his personal possessions. I loved that as much as the history. I do agree with you, he was an a-hole. I wonder if he would have become famous is he lived in a different time, but I guess we’ll never know. I”m glad you enjoyed the read 🙂

    the #1 Itinerary
    12 Mar 2019

    Great post 😁

      12 Mar 2019

      Thank you! I’m glad you enjoyed it 🙂

    12 Mar 2019

    How fun!

      12 Mar 2019

      It really was! I didn’t expect to learn so much and like it even more 🙂

    Frances B
    12 Mar 2019

    Sounds great! Have forwarded to my sister who will be visiting Havana soon.

      12 Mar 2019

      I’m so glad you like it! I hope she gets a chance to do the tour. It was pretty cool!

        Frances B
        14 Mar 2019

        Me too!

    13 Mar 2019

    Loved this post. You pretty much gave me a pretty clear picture of his home and history. I had no idea about most of this. It’s all so interesting. It’s a shame its crowded by so many tourists. I feel like when I do eventually make it to Cuba, it will be super commercialized. So nice that you were there 9 years ago and got to experience it during a different time.

      13 Mar 2019

      Thank you so much Kathy! It was all new to me as well. I’m really glad we went and had a chance to see it in person. There are a lot more tourists than there were 9 years ago, so it was really great for us to do a private tour. Still lots of people around us but at a slower pace and more one-on-one guide. I can totally see why he loved this place so much.

    Tim Bradshaw
    15 Mar 2019

    Thank you Kasia for a great review of Ernest Hemingway’s life, and his time in Cuba; I hope to take a Rolling Havana Hemingway Tour on my next trip to Cuba. I’m looking forward to your future post, and I hope to see you and Alex in my future travels. Tim…

      15 Mar 2019

      I’m so glad you enjoyed it Tim! The tour was really great and it was so neat to actually go to his house which is like frozen in time! Hope to see you again too!

    15 Mar 2019

    Loved this!

      15 Mar 2019

      Thank you! So glad you liked it!

    Dippy Dotty Girl
    15 Mar 2019

    A vintage car tour of Havana, and most importantly, Hemingway’s home there. That must have been a neat trip, Kasia. I find Hemingway most inspiring. Everywhere I travelled, I found that he had been there before me, and left his legacy in each and every place. I am yet to see Cuba though and am so fascinated by photos of it. Yours are alluring!

      16 Mar 2019

      Wow thank you! 🤗 I must say that I didn’t know that much about Hemingway before this but he def left a mark in many places in the world! I hope you make it to Cuba and Havana. The tour was really like walking in his footsteps. It was a great insight into his life there