Our trip to Cuba may have started out with some headaches, but they quickly dissipated as we found ourselves walking down streets frozen in time. Each moment a scene out of a 1950’s movie, classic American cars driving down the street, 1950’s architecture, and a Betty Boop themed restaurant.
After our breakfast at Betty Boom (yes, I said Betty Boom) we booked a classic car tour around Havana through our Air BNB friend. He called up a friend who owns a pink 1950’s convertible and we headed off on our tour.
We were driven through Parque Almendares and found ourselves mesmerized by curtains of green vines draping over old twisted trees. This park holds Cuba’s oldest tree - a 300-year-old banyan tree.
This park is quite significant for Cubans who believe in Santería (meaning rule of the saints) and rituals often take place here. It is accepted that this is a good place to come to make sacrifices to the Santería spirits. Unfortunately, the park is littered with trash- leftovers from the rituals and sacrifice.
After winding around the park we were headed up a hill when the car sputtered to a stop. Our driver got out of his car and our car started to roll backward, thankfully our trusty travel partner Alex quickly put his foot on the brake.
After our driver fixed some things under the hood we headed to the wooded neighborhood of Vedadado. Vedadado means “forbidden” as it originally was a military area restricted from civilians. It lifted its restriction in 1858 and became a gridded neighborhood that would soon be developed into a mix of middle to upper-class mansions and businesses. Many of the buildings are deteriorating as Cubans do not have the means or supplies necessary for the upkeep of the buildings.
Next, we visited La Plaza de la Revolucion which has a giant steel sculpture of Camilo Cienfuegos and Che Guevaran. Underneath Che Cuevaran you can read “Hasta la Victoria de Siempre” -to victory always. This square is one of the largest in the world, comprising over 11 acres and includes the sculptures, government buildings as well as the Jose Marti memorial.
We soon found ourselves in Old Havana on the iconic El Malecon, a street, and seawall familiar from many movie scenes and quickly became accustomed to the thick sea air that slugged off the harbor. A skittle bag variety of classic cars passed us as we made our way down El Malecon.
La Habana Vieja- “Old Havana” is where the main city center is as well as the capital building, the theatre, and many other famous buildings.
Our guide informed us Cuba still burns crude oil for most of its electricity, but is looking for cleaner energy alternatives. I am eerily suspicious that is a contributing factor to why my once white shorts were a greyish-yellow color when I returned to Mexico.
We asked our driver for suggestions about where we should go next on our Havana adventure. Suggesting Havana Club we excited our pink stallion and thanked our guide for our wonderful tour.
We booked a tour at Havana Club - once the classiest private clubs in Havana and dipped into the bar to have a few mojitos while we waited. Listening to the band warm up we turned to a small corner in the room and watched through a fog of cigar smoke as President Trump delivered new travel policies for Cuba. Minutes later the tv was turned off and all was forgotten as the band played on - “Guantanamera, guajira guantanamera”.
After our tour of the Havana Club, we ventured out to walk around the city some more. Wandering without any destination in mind is my favorite type of travel; allowing moments and experiences to find us.
After wandering the rest of the day we eventually made it home to our casa where we spent the night sipping on some Havana Club rum and playing dominoes. Until tomorrow…
Leigh
June 30, 2026I love the photos and stories! I can’t believe your car just started rolling…good thing there was someone up front! Can’t wait to read part II!
Paroma Chakravarty
June 30, 2026Your photos are beautiful, I loved the Che Guevera (I am a big fan of the movie Motorcycle diaries) one and the lounging street dogs:-)
maegan
June 30, 2026I love these photos! They make me want to visit Cuba even more now. History has stood still in many areas of the country, it seems.
Victori Amore
July 1, 2026Your photos are gorgeous! Really captures the energy of the city. I would love to visit one day. Thank you for the glimpse 🙂
Meghna Malhotra
July 1, 2026So fascinating! Going through your post and photos was like being transported to the early 20th century probably. I love the cars and the rustic feel to the city. Totally ‘frozen in time’! =)
Kate
July 1, 2026Your pictures are so beautiful! It really seems to be in a 1950’s movie, I love so much all those vintage car 🙂 thank you for sharing your experience!
Kavey Favelle
July 1, 2026Your photos really show off the nostalgic look and feel of Havana, somewhere I’d love to visit. Love the draping vines in Parque Almendares!
Hannah
July 1, 2026I love your photos, the vintage vibe gives such an authentic feel to your Cuba photo journal. I’ve never been but it’s definitely on my list, everyone says its almost like traveling back in time. Hopefully I can make it there before the American govt gets too strict on travel again 🙁
Erica Lindeman
July 4, 2026Cool steel structures! Reminds me of the art steel sculptures in Penang, Malaysia, just that theirs is smaller.
The vintage cars and the brick structures really give the place a character.
Becci Abroad
March 3, 2026Great Havana pictures! Looks like you had a great time! I really enjoyed the area of Centro Habana which borders Habana Vieja as Habana Vieja quickly gets too mainstream “looking nice for the sake of the tourist”, by wandering around Centro Habana you get a better feel of how Cubans actually live.
Thanks for sharing your great photos and stories for Havana! Gave me a pleasant flashback 🙂
john ray
April 3, 2026I really liked your article it is inspiring.
Eemma Iseman
May 3, 2026Thanks so much John! Are you considering visiting anytime soon?
Michael Ray
July 21, 2026Thanks for sharing this info. it’s really nice.