Cuba Itinerary: 4 Days in Cuba

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I saw a Jet Blue flight deal drop for $244 RT NYC-HAV and hopped on it without hesitating. I then dropped the link in a group chat and got one bite. That one bite turned into three additional invites, minus two, and plus another at the last minute. Did you catch that math? My solo trip to Havana quickly turned into a group trip right before my eyes. I won’t make you wait for my thoughts on that. It was a dope ass trip. Here’s my “Cuba itinerary” and how I spent 4 days in Cuba.

Day 1 – Havana

In addition to my normal travel groups, I tend to join subgroups when heading somewhere new. Naturally I opted in for a Cuba group and immediately picked up on dozens upon dozens of gems on how to navigate the country. Two of the biggest lessons learned? 1. Never check a bag. 2. Always pack snacks.

Checking a bag was the first slip up that not just my friends made, but all those people waiting around indefinitely for their bag to coast along the conveyer belt. I’ve heard horror stories of people waiting two hours on checked baggage and while I was waiting on my friends flight to land, I saw many of the same people aimlessly wandering and waiting. Did it take two hours? Hell no. But it might as well have. My friends probably waited between 20-30 minutes for their bag…as I stood there will my rolling bag that I carried on.

Also, while I had snacks on deck, my friends did not. At night I would curl up with a bag of sour cream & onion chips while they curled up with an appetite. In the mornings when we didn’t have time for breakfast I’d munch on my beloved Trader Joe’s pop tarts while they took naps to avoid the fact that they were starving lol. I said beforehand “no greedies” so hopefully people start to listen to me. Moral of the story: DON’T THINK YOU’RE GOING TO FIND SNACKS IN CUBA. Ain’t no Bodega’s. At least not what you know Bodega’s to be.

Getting from the airport in Havana

I can’t wait to tell you what happened while exchanging money at the airport, but I’ll save that juicy story for my Guide to Cuba. I thought it was a one off incident, only to end up meeting someone days later and find out it happened to them as well. But I digress. The currency exchanges are on both sides of the exits to the airport. You’re welcome. I myself transferred my USD’s to Euros in America, then Euros to CUC’s in Cuba. Some people just deal with the 10% penalty to exchange USD’s in Cuba and honestly, it may come out to about the same after you lose money converting the first time.

Our lovely airbnb host arranged a taxi to pick us up, so not only did we avoid finagling a ride to Calle F and avoid getting hustled (one of many times), we could just hop right in a car and head to our destination. The hosts arranged a trip back to the airport as well but we were so used to taxis at this point we were going to walk to a corner and grab one ourselves.

Where to Stay in Havana

Our airbnb was perfect for the four of us. We’d originally found a penthouse that we were going to book for snapchat videos alone. Unfortunately it wasn’t financially feasible for some of the group so we opted for a second casa. Then when two of the squad dropped out, we settled on a third place in Vedado. Now I’m not one for dropping airbnb listings but not only will I include our three in the guide (signup form above), I’ll include a number of other recommendations from people that have been. If money was no object I swear we would have been penthouse living.

We stayed in Vedado because it came highly recommended for nightlife and it was all around walkable. We walked to or from the clubs every night and the malecon and Hotel Nacional (for a reference point) was always a short walk away. After finally visiting Habana Viejo (Old Havana) on my last day I’m glad we didn’t even consider staying there. Apart from it being uber touristy, it reminded me so much of Western Europe that I knew it’d be super expensive not only for the airbnb, but for food and fun as well.

Why Airbnb?

You know I love living like the locals do. Unfortunately I was probably living better than many locals, and that’s not always a good feeling to have. It did feel nice being the only tourists in our building, as far as I know, and having to walk through

an actual residential neighborhood to get to the main street and walk around. This home also made for the perfect mini-photo shoot. HELLO! And shoutout to DJ Lex and Andi on the DSLR’s.

Our first stop after posing it up was to go and grab food. Along the way we met Jorge who told us about the cheap eats (5 CUC’s per meal & 3-4 CUC drinks) at a spot he worked at on the corner. We vowed to return one day soon but as we saw how expensive everything else along our walk was, we quickly turned around to pay Jorge a visit.

I’ve seen humans actually pack seasonings in little baggies because food in Cuba is often considered bland, or as DJ Lex (not her real name or title) said:

“I’ve never had food that just tasted like…food.” Because I cook for myself 90% of the time and try not to add salt or other bad seasonings, Cuban food was actually okay to me. Not muy delicioso by any means, but, okay. So our pollo con arroz y papas fritas (plantains to Jorge) was just fine. My mojito? Even more delicious. So much so that after our late lunch/early dinner we found a happy hour spot and had several more. HELLO 1CUC HAPPY HOUR! Don’t worry, I’ll drop the name of the joint in the guide.

One thing I will say is that no matter how much I drank, I never even got tipsy. My friends say they woke up feeling like they had been drinking but were never actually drunk. The only common denominator was Havana Club, the national rum. Not even shots would give me a buzz but I promise that says nothing about me and everything about the rum!

We Be Clubbin’

Later that night we headed to Las Vegas and let me tell you now it is a gay club. Gentlemen, don’t write this down and think you’re going to go find your wife at Las Vegas. Doors don’t open until about 10pm and the line will be down the block. Keep in mind that Cuban club culture is not that of the United States, especially gay clubs. It’s mostly people standing around drinking and/or watching videos on a big screen, waiting for a drag show to start later in the night. Beware of the prostitutes and sugar babies. If at some point during you’re conversation full of broken Spanish, homebody gives you a price…run.

Day 2 – Cuba Excursions

Horseback Riding Vinales

I was set on taking at least one day trip while in Cuba. While I was hoping for two, one worked itself into our itinerary just perfectly. On day two we would awake at 6am to prepare for our journey to Viñales to hang with the Horseback Riding Viñales team. IT. WAS. EPIC. If you’re headed to Cuba soon then don’t wait until the end of this. Head here and email Yubier asap.

I was floored when I found out how affordable this tour was. 5 CUC’s per person,  per hour, for 5 hours? Count me in. Yubier even went the extra mile to accommodate our group and arrange transportation for us. Not having to find someone to pick us up in Vedado and drive 2.5 hours to Viñales took a weight off our our shoulders. I won’t lie, I was just afraid of being hustled by taxi drivers all over the world. Plus when I inquired about arranging a taxi I was quoted a far higher than what Yubier quoted.

After our long ride where everyone slept on and off, we arrived in the quaint town of Viñales. Gorgeous isn’t the word. The small, colorful homes and street markets made me feel as though I should have booked a stay there for at least a couple nights. Pulling up to the small house that served as a starting point, I wasn’t sure what to expect. Shortly after, our guide, Edel, showed up and we set off to the path behind the house to meet our horses. As I had a crazy amount of mojitos during this trip, it was only right that my horse was in fact named Mojito.

The last time I was actually on a horse was a few years ago when I visited Costa Rica. It was memorable to say the least. That was a large group and when one horse took off, all the others tried to as well. I’m convinced mine tried to buck me off and that was my main fear on this day, falling off of Mojito. So I pretty much let him do his own thing an only shooed him to go faster when we were falling behind. He listened to direction and was actually the perfect horse for this journey. I’m sure my friends would say the same about Cuba Libre, Coco Loco, and Piña Colada.

We rode through the Valley for hours and only stopped to get a tour of a tobacco field (and to buy some naturally processed cigars) and visit a cave. I don’t know why I completely forgot about the cave experience but it was a cool side note to the journey. We were armed with flashlights after paying the 2 CUC’s to enter the cave and follow a guide throughout. There was even a chance to swim in a “pool” inside but two other women opted for that experience. Not I, said the cat. I need to see what’s in the water. Hell, I need to see what’s around me.

Our last stop was lunch with the most perfect view of the mountains and valley we had been riding through all day. At one point I took a picture of my friend and looked down at the photo in shock. I’m not exaggerating when I say I can’t believe we were in a place so beautiful…also easting some of the best food we’d had so far during the trip. Shoutout to Edel for recommending I try the honey mojito when I complained of all the sugar bartenders had been giving me.

The long ride back to our starting point was bittersweet. We had the 2.5 ride to take back but I definitely wanted to explore Viñales more. I just didn’t want to pay more money to do so. I say all of this to say, you can’t visit Cuba without taking linking up with the good folks over at Riding Viñales. You also need to make sure you set aside extra time to check out the town. Tell them I sent ya.

If you’re feigning for more details about my Cuban Adventures you’ll be happy to know I’ve created an extensive guide to Cuba.

Day 3 – San Jose Market & Santa Maria Del Mar

Day three in Cuba was pretty dope without effort. DJ Lex had told us about a market where we could buy souvenirs and pretty soon we discovered it was the San Jose Market in Habana Viejo. That was destination #1 before heading to Santa Maria del Mar. We snatched up a cab near our airbnb and basically hired him to take us to the market and the beach all in one. He ended up walking around with us throughout the market to help translate and negotiate (i.e. Lex’s security guard/butler), took us to a popular spot for lunch, and then took us to the beach. I have to admit, it was nice to have his assistance and again…NOT GET HUSTLED BY A TAXI DRIVER. #ImTiredOfEverybodyBeingOnTheComeUp

San Jose Market

This was a market inside of a huge building along the water in Habana Viejo. I don’t do too much souvenir shopping and rarely buy anything for myself, so I think I spent about 18 CUC’s in total (and that was a splurge) by buying things like wooden shot glasses (is it a shot glass if it isn’t glass though?), a coffee mug, a refrigerator magnet, a bracelet and hat, and some wooden cigar holders. Hey, some people are getting more than one gift for once.

I will say pretty much everyone is selling the same thing. You’ll find at least five different vendors with the same exact item so make sure you shop around. You’ll want to kick someone in the throat after hopping on that 10 CUC backpack only to find out that a vendor two aisles over would’ve given it to you for 8. That may not seem like a big deal but I refuse to believe that the CUC is 1:1 with the Euro. So 2 CUC’s go a long friggin’ way, okay? I did a little negotiating but sometimes I just gave up my coins immediately. It’s not always worth it.

TIP: I remember heading to Thailand and trying to figure out how much things should cost since I knew I was going to get hustled (clearly my favorite word of this series).  My friend said either way you’ll get got (read: hustled) but just try to negotiate any price you’re given. Whether it’s cabs, street food, goods…see if they will sell it for less. If it’s not a necessity then simply walk away if they don’t budge. If you really want it, just spend the money if they don’t work with you. It doesn’t hurt to try though.


Look, I don’t know the name of the lunch spot the cab driver took us to, but I do know they have a huge photo of Beyonce out front. That’s their claim to fame. I do wonder if King Bey had hot sauce in her bag, swag, on that particular day. For the prices they wanted (min. 16 CUC for basic meals) it was not what I would expect. But maybe we were just irritated at the fact that we were set at the back of the place behind a shack. After ordering our food to go, because we simply weren’t impressed, we were even more irritated when they combined our sides (rice and beans) and the portions for four people normally fed two at any other restaurant. They were really doing the most by doing the least. I bet people rave about this place and I’m sure I could easily find the name, but I simply just won’t recommend it and all will be right in my world.

Playa del Este

Playa del Este was probably a 20-30 minute ride from Habana Viejo. Varying times are due to the car you’re in. This car? Slow as hell. Everybody passed us on the highway but hey, we made it. I found that the most popular part of this beach was Santa Maria del Mar, so that’s where we went. However, don’t be confused. They’re all one beach. I chowed down on my food while laying out and tanning while my friends sipped their favorite pina coladas of the trip. What made these so special? You could actually taste alcohol for once! You can’t tell me they weren’t guzzling juice those first two days. But that’s none of my business.

We ended up randomly kayaking for a bit because we saw rentals upon entering the beach. 2 CUC’s per person, per hour seemed like a steal and I may never come across those prices again. If I didn’t have a non-kayaking, non-swimming human in my kayak with me I probably would’ve been further out in the ocean. I’m positive she’s the reason both kayaks flipped when a rogue wave hit us too. Just a mess. An all around mess. But it was so much fun!

I definitely recommend this beach even though it’s the only one I visited during my time in Cuba. It’s way too close to the city to not visit so if you have a few hours to be a lazy hot mess in the sun, go for it.

Day 4 – Cuban Adventures (Havana Tours)

My last full day in Cuba was spent with Cuban Adventures and was one of my busiest yet. It was packed with all of the things I like to do closer to when I arrive in a city, but better late than never, right? I opted to do three tours in one day and I have absolutely no regrets. If you can, spread yours out over the course of your trip just to give yourself something to look forward to.

Afro Cuban Religion Tour

This is the first tour of it’s kind that I’ve taken and I’m so glad I jumped on the opportunity. I came to Cuba wanting to learn about the history of Afro Cubans in some way and the Afro Cuban Religion Tour helped me out with that. The history of the religion and the fact that it is practiced by many more than just Afro Cubans is so very interesting. While the religion has changed to suit its practitioners over the years, the basics are still the same.

I don’t want to give up the whole tour but my favorite part had to have been learning about the many African deities worshipped then and now. You’re favorite reference may be Oshun, who’s been channeled by King Beyonce as of late. I’m also glad that Yanet recommended I get a photo with the artist Salvador before the tour even began. He was the artist behind pretty much the entire neighborhood (sculptures and all), Callejon de Hamel. I’ll cherish that day and beautiful neighborhood forever.

Old Havana Walking Tour

Rolando was my guide for the Old Havana Walking Tour and I was surprised to find out he was only a couple months in on the job. He seemed like a pro being able to answer any question thrown at him, and boy did the tourists have a lot. He walked us around Habana Viejo and pointed out certain buildings and areas that were important. We also walked through several squares and learned the history of them.

As this was my second tour of the day and I’d skipped breakfast, it’s safe to assume I was starving. Imagine my excitement when I found out lunch and a drink would be provided. I finally got the chance to have fish for the first (and unfortunately last) time in Cuba. It was so good and this restaurant is truly a hidden gem. I washed it all down with a mojito viejo if you were wondering.

Classic Car Tour

This was the trip that my friends were most excited to tag along on. It was perfect as I had already been on two tours earlier in the day and just wanted to relax. Riding around through the city in an old school convertible on the Classic Car Tour seemed like the perfect way to relax.

I must admit that I didn’t know this tour was such a staple on everyones Cuba to do list but now I know. Not only did we get to see all the popular areas and sights of Havana, but my amazing guide, Yanet, was extremely knowledgeable of everything surrounding us, as usual. She could tell us about architecture, the government, and the overall area we happened to be driving through at the time. No matter who your guide is I’m sure you’ll be amazed, but I just can’t give Yanet enough praise. We ended this tour at Hotel Nacional with a drink on the house.

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