Cuba seems to be on everyone’s mind lately, as rules and regulations for the country are constantly changing. If you’re looking for the perfect Cuba itinerary for Havana and Viñales, then you’ve come to the right place!

Unfortunately my time in Cuba was quite limited so I was only able to see and do a fraction of all the things that I would have liked to. With only four days in Cuba, we chose to spend 3 nights in Havana, Cuba’s capital, and 1 night in Viñales. This Cuba itinerary will breakdown the best ways to spend your time on a quick trip to Cuba.

Havana possesses this sort of dilapidated beauty. The buildings have crumbled and the facades have slowly been worn down over time, yet the city has lost none of it’s charm. Despite everything, the warm nights of Havana still have a heartbeat that is so very much alive – alive with potent mojitos and icy daiquiris, alive with brilliant music and rhythmic dancing. A trip to Cuba should be on everyone’s bucket list, so take note of this fun Cuba itinerary!

Cuba Itinerary: Before You Go

Visa for Cuba

The first thing that I will say to any Americans hesitant about visiting due to the “strict visa policies and border regulations is “just go”. You do not need to book an expensive tour or travel with a group! In an act of spontaneity I booked my flight to Cuba only two weeks prior to my trip. Despite the time frame, there were ample accommodations available through AirBnb. Additionally, I was able to purchase my visa at the airport for $75 on the day of the flight. *Note, things are constantly changing with our current political situation, so be sure to stay on top of any new developments.

Cash/Credit Cards

American credit and debit cards are not accepted in Cuba! For this reason it is essential that you bring along any money that you will need for the trip in cash. We found that you get a much better exchange rate if you exchange Euros rather than Dollars, so that is definitely something to consider. For four days in Cuba itinerary we budgeted $100/day each, and spent considerably less than that!


Although wifi is slowly becoming more readily available, it is still not easily accessible. If you only have a few days in Cuba this shouldn’t be too much of an issue. Some hotels do have Wi-Fi available. Otherwise, in order to get online it is necessary to buy a 1 hour wifi card (~2 CUC) and then find a local Wi-Fi park in order to connect. Plan ahead and make sure that you have your destinations and sites fully mapped out before arriving! One offline map that I have found particularly helpful for my travels is!


There are two types of currency in Cuba: the cuban peso (CUP) and the cuban covertible peso (CUC). 1 CUC is essentially equal to 1 USD, however the exchange rate for the CUP is currently 25 CUP per 1 USD. Make sure you note which currency you are paying in, and make sure that you are receiving your change in the correct currency as well.

Cuba Itinerary: Where to Eat & Drink in Havana

I will admit that I was thoroughly unimpressed by the Cuban cuisine. That being said, there are definitely a few spots that we tried during our four days in Cuba that are worthy of this Cuba itinerary!

Bar Monserrate

Live music, reasonably priced cocktails, basic dinner fare. This place is right down the street from la Floradita, but you’ll get a lot more bang for your buck and a less touristy atmosphere.

La Guarida

To be honest, we didn’t actually get a chance to eat at the main restaurant, but it wouldn’t be a Cuba itinerary without Havana’s most famous restaurant. We naïvely tried to make a reservation less than a week beforehand. However, we did snag a spot up on the rooftop bar and had a blast! The views are absolutely incredible, especially at sunset, and the bartenders pour the drinks strong! They also have a smaller food menu available for you to choose from.

La Abadia

Located right on the Malecon, this was hands down one of the best meals that we ate during our time in Cuba! The food was fresh and cooked to perfection, served up at very reasonable prices (~$4/plate with side)! We opted for the butter grilled fish and we were definitely not disappointed.

Cafe Bohemia

Located in the Plaza Vieja, this is a great spot for a sunset cocktail. The drinks were great and the food is rumored to be superb! We had attempted to grab a drink at the more famous Factoria Plaza Vieja next door, but after an unsuccessful attempt at getting a table, we opted for this cozy cafe instead.

Cuba Itinerary: Where to Stay

Definitely opt for staying in one of the many casa particulars during your trip to Cuba. Not only are these accommodations cheap (and there are an abundance of them on AirBnb), but they will also give you a more authentic Cuban experience because you will be actually living with a family.

Cuba Itinerary: Best Things to Do


Due to our limited amount of time in the city, we chose two of the more famous museums in Havana. Museo de la Revolucion and Museo de Bellas Artes Cubano were both entertaining and highly informative, definitely worthy of a stop on this Cuba itinerary.

Explore by Car

What better way to see the city then by riding around in one of the 1950s classic convertibles?! As touristy as it is, this was definitely one of the highlights of our time in Havana.

Wander by Foot

There is so much to see on every corner in Havana. We spent hours simply wandering the city in search of the most beautiful streets. The weather was a humid 90 degrees or so, so the many cafes and bars came in handy when we needed to cool down with a local mojito! Definitely make sure to spend some time on the Malecón taking in the beautiful sea breeze!

Horseback Riding Tour (my favorite experience on this Cuba itinerary)

A former horseback rider myself, I was especially keen to participate in one of these tours! The two of us were able to book a private tour on the day of for 25 CUC (~25USD)/person. This was a five hour tour that took you by horseback through the valley, with stops at a tobacco farm, a coffee farm, and a cave. This is an awesome way to experience some of Cuba’s countryside, a must on any Cuba itinerary.

Beach Trip

I am a bit hesitant to recommend this experience, but I figure that I should mention it to anyone who is interested. For 20CUC/person you can book a round trip collectivo to and from Cayo Jutias from Viñales. We were told beforehand that the ride takes approximately 45 minutes each way, however due to poor roads we spent over 2 hours each way! However, we noticed that a lot of the smaller cars were speeding right by us, so booking a private car may be a smart option if you’re looking for a beach escape. The beach itself was very beautiful, even though we had the unfortunate luck of rain shortly after arriving.

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