Cuba: Exploring Old Havana (with Video)

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Viva la Cuba! Wait, is that even a thing? I don’t know, but I’m making it my signature phrase for this trip. About a month and a half ago, I told you guys that I was going on an influencer retreat to Havana, Cuba with Fit Life Creation. Well, that trip has finally arrived!

I thought it would be fun to do a daily diary of my trip, so I’m posting daily Cuba vlogs on YouTube and blog posts for each day of my getaway to Cuba. Afterwards, I’m going to compile my best tips for planning a trip to Cuba, so stay tuned for that!



I chose Southwest Airlines because they have great ticket prices and they make the Cuban visa process super easy. Southwest has a partnership with Cuba Travel Services. When I booked my ticket, Southwest sent a link to order my Cuban visa and it was being sold at a discounted rate of $50. Once I arrived at my layover city (Fort Lauderdale), I was able to easily pick up my visa right by my gate.

Cuba Day 1: Arriving in Havana, Cuba


I arrived in Cuba late in the evening and the airport was easy to navigate. American credit cards aren’t really accepted anywhere, so I brought cash with me to exchange at the airport. Once I left the airport, I immediately felt like I had stepped straight into a different era. There were classic cars everywhere I looked, and we even got picked up in one. It was sensory overload (in a good way) taking in all these new sights for the first time. Our driver Yoncel helped us with our luggage and drove us to our AirBnB.

Cuba Day 1: Arriving in Havana, Cuba


I am SO glad the retreat accommodations took place at an Airbnb. I immediately felt so welcomed when I arrived here. It was pre-arranged for our Airbnb host to also cook for us, so it was really nice being greeted with a warm meal. Our host Angel takes great pride in his cooking, so the food was muy delicioso. Oh, and if you watch the vlogs, you’ll see just how much of a character Angel is. He has a big personality and kinda reminded me of someone’s funny, happy-go-lucky grandpa.

Cuba Day 1: Arriving in Havana, Cuba


After settling in and eating dinner, we went to bed and woke up the next morning to get our first official day in Cuba going. We decided to spend the day walking around Old Havana—and my senses were totally going haywire. Seeing Cuba during the day was even more wild than seeing it in darkness the night before. Everything felt so vintage. From the perfectly preserved classic cars to the old, colorful architecture—I felt like I was in a completely different period of time.

We got dropped off near the Plaza Vieja. Honestly, just walking around Old Havana is like paradise for a photographer. Every alleyway you turn down, every nook and cranny you see, there’s always something picturesque to take in. We absorbed everything we could on the way to Plaza Vieja and tried to circumvent the hoards of tourists along the way. Even though we went during off peak season in February, it was still fairly crowded—but it could have been a lot worse.

Plaza Vieja was beautiful and colorful, but all the little side streets were really what I loved the most. We kept on trekking until we reached the Plaza de la Catedral, which has been around since the 18th century! It was pretty cool to see buildings that were so old, yet so wonderfully preserved. Of course—that’s the charm of Cuba, isn’t it?

Plaza de la Catedral in Havana, Cuba


Wi-Fi is just not a thing in Cuba. I guess that’s kinda what makes it such a great place to take a real vacation—it literally forces you to unplug. You can find Wi-Fi in some places, but be prepared to pay for it. After we finished exploring the city a bit, we hopped in a bicycle taxi and rode that to Hotel Inglaterra, the only place we knew of with Wi-Fi. You technically can’t access the Wi-Fi unless you’re a hotel guest, but there’s a way around it. You can buy a Wi-Fi access code “under the table” if you know where to look.

We also ate lunch at the hotel’s café, which surprisingly was out of everything I tried to order. They were even out of vegetables! Seriously, how do you run out of veggies though? I wound up ordering a cheese sandwich, because…well…sometimes you just gotta be flexible while traveling. #veganproblems

Cuba Day 1: Arriving in Havana, Cuba


We wanted to do a service project of some kind while we were in Cuba, and ironically we didn’t even have to search for it. It found us. A professor at a private Cuban photography school reached out to us and asked if we’d be open to speaking to the students about our experiences with developing successful careers in photography. I wasn’t sure if I’d have anything interesting to say, but when I got up to speak I realized I had a lot of knowledge in me that I’ve been taking for granted. It also humbled me as I realized just how many opportunities I’ve been given thanks to simply having Internet access – something that is considered a luxury in Cuba. The level of gratitude from both the students and the professors was incredible. They really appreciated learning about all the different ways we’ve used social media to monetize our businesses.


We finished our first day in Cuba by eating a delicious dinner cooked up by Angel and then had our first “Health, Wealth, and Business” workshop. I’ve never been on a retreat before, so this was a first for me and it was actually really laid back and informative. Not stuffy or anything. It was completely chill.

Overall, my first full day in Cuba went really well. I enjoyed spending time strolling through Old Havana and taking in all the architecture and vintage charm of the city. Seeing all those classic cars zipping by on the bumpy roads felt like an unreal experience. And it was nice to come back to such relaxing accommodations and a home-cooked meal. Not a bad way to kick off my Cuba adventure.

Join the Next Retreat: BRAZIL RETREAT September 5-11, 2017
(use discount code “Ashley” with a capital A for 10% off)

Are you thinking of going to Cuba this year? If so, do you think you could survive without Wi-Fi? Let me know in the comments below!


Cuba Day 1: Arriving in Havana, Cuba

One Reply to “Cuba: Exploring Old Havana (with Video)”

  1. I love seeing these videos come to life! That was so funny when the restaurant ran out of vegetables – how does that happen??

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