Cuba, ahhh, step into a time-capsule and be sent back to the 1950’s.  What I loved about my visit to Cuba was simply the simplicity.  Wandering the streets and admiring the architecture, meeting the locals, learning about politics, food, art and more.

For pictures visit my instagram: @tarasails (Cuba Trip Pictures: #TaraSailsCuba)


I encourage everyone to visit Cuba when they can!

Here is some help in getting you to Cuba to see what I saw:

Visiting Cuba: Tara Sails

Tour with a local:

To truly capitalize on your time there I encourage hiring a local guide/translator.  My local guide was Pedro Foster, a Cuban Doctor who also is a tour guide. He’s pretty freakin awesome! “Locally Sourced Cuba Tours” / Pedro Foster at

Tour group:

Travendly (local New Yorkers to travel with)

Intrepid (People to People group trips)


You need a Visa to go to Cuba.  When you get to the airport you will fill out a form.  I picked education as I had an itinerary created that was called “People to People”.  If you hire a local tour guide they can help you with this itinerary and a tour group will do the same. (This is for Americans)


I took a Charter flight out of Miami, however, JetBlue started direct fights to Havana on December 1st – lucky you! (This is for Americans)

Airport Logistics:

  • When you depart to Cuba purchase a visa and pay the Cuban departure tax (totals $110).  Save this information/receipts/visa for when you come back to the states – they’ll ask for it!  Big headache if you lose any of this information.
  • Exchange your money in the Cuban airport for CUC.  The exchange is 1:1 on the USD, however, they charge an additional 10% fee for changing USD (they do not charge this if you are exchanging with EURO).
  • Transportation is easy to your casa – there are tons of Taxi drivers that will take you to where you need to go.  I recommend printing out a google image map of your house or hotel to show the driver (keep in mind there is no cell phone and internet service in Cuba!).  


I stayed in house because I did “people to people” plus it was amazing to be with local Cuban family.  It was a beautiful home in the neighborhood of Vedado, Havana.  Also it was right near the Presidential Hotel so I could sneak over for a drink, music and WIFI. I liked this area because it was quiet, safe and a 2-minute walk from the Malecón seafront promenade and beer garden.  It also is near a 24 hour gas station, which helps when you have a late night chocolate ice cream craving 🙂

I visited The Hotel Nacional de Cuba which is considered a symbol of history, culture, and Cuban identity.  I also visited the Hotel Saratoga which is right in the mix of all of Havana. It’s also the hotel that many celebrities stay at.

8 Hotels in Havana according to Vogue: Click Here

Where to stay in Cuba according to Conde Nast: Click Here 

Food and Evenings Out:

Get ready to enjoy some plantains, rice, beans and mojitos!  The food is great and many of the restaurants source their ingredients from the gardens nearby.  It’s as organic as you can get!

Here’s where I went:

Lunch on Day 1: 304 O’Reilly

Dinner on Day 1: Motivo’s / Razones

Lunch on Day 2: NAO

Dinner on Day 2: Porto Habana

Lunch on Day 3: Casa de Confianza (in Vinales at their farm)- absolutely must go here!!! Amazing!!!!!!!!

Dinner on Day 3: El Cocinero followed by Fabrica de Arte (Anthony Bourdain went here) these two places amazing. El Cocinero is very hip and reminded me of a place in TULUM. Go to roof deck to sit at table and/or get a drink at roof!! Great music.  Lines long at Fabrica de Arte post dinner so try to do earlier dinner and get to Arte early (they are next door to eachother).  

Bar on Day 3: Espacios Tapas Bar & Restaurant

Lunch on Day 4: Ajiaco Cafe (in Cojimar) – cooking class – amazing and farm next to it where they source food do tour of farm! My favorite.

Dinner on Day 4: Habana 61

Bar on Day 4: Kilometro Zero

*I will post some photos soon on these locations!  

My Itinerary:

Day 1:

Explored the neighborhood of Vedado, Havana the richer neighborhood of Havana where there are large homes with beautiful architecture.  I watched the sunset on the Melecon and drank some local rum! Highly recommend a night watching the sun and having a drink on the Melecon, most locals do this.  There’s also a beer garden across from the Melecon in Vedado that I visited too.

For dinner I visited a local paladar, a privately owned restaurant, and went to a local jazz club.


History of paladares:

Day 2:

Today I visited Callejon de Hammel, took a classic car ride around Havana, did a walking tour of Old Havana, explored the Plaza de Armas, Plaza de la Catedral, Plaza Vieja and Plaza de San Francisco and finally took a salsa dancing class!  


Callejon de Hammel:

Salvador Gonzalez:,

Neighborhoods of Havana:

Old Havana: and


Day 3:

My favorite day!  I went to Vinales, Cuba.  A bit of a drive from Havana but worth it!  First I stopped at Las Terrazas, a small community and nature reserve.  I then went on to Vinales and  toured a beautiful organic farm (Casa de Confianza) and had lunch overlooking the mountains of Vinales! I also was able to visit a local cigar farm and smoke a cigar! Dinner was at El Cocinero which was amazing.  Very hip spot and reminded me a lot of Tulum, Mexico.  Definitely head to the roof for a drink and some music before or after dinner!  I then headed over to Fabrica de Arte (Anthony Bourdain went here).  There are long lines long at Fabrica de Arte so try to do an earlier dinner and get to Arte early (they are next door to each other).  I ended up later in the evening at Espacios Tapas Bar & Restaurant.  This is also the night I learned of the death of Fidel Castro along with the rest of Cuba!  


Cuban Cigars:

Anthony Bourdain’s experience at Fabrica de Arte:

Day 4:

Today I visted a Cigar factory (Partagas Cigar Factory) and I highly recommend you doing this as well!  It’s incredible to see first hand the process that goes into making each cigar and I had no idea that they were carefully hand rolled one by one by a local Cuba and not done by machinary.  The experience of being in a factory and seeing people at work was also eye opening.  I won’t reveal much as I’d like people to see this on their own!  I then took a cooking class in Cojimar at Ajiaco Cafe  and toured the local garden nearby where they source much of their ingredients.  The day ended visiting Fusterlandia and shopping for souvenirs.

Cuban cigar history:

Different factories:

Brief overview of Cuban food history: and


Jose Fuster:’s-irrepressible-Gaudi-restyles-Jaimanitas

Extra Information:


There is no relationship between U.S, financial institutions and Cuba therefore credit cards will not work.  You NEED cash and it’s important to get this from the airport when you arrive in CUBA.


There is no internet or cell phone usage in Cuba.  WiFi is available through Government owned hotels in Cuba and they offer internet cards for 1 hour uses (cost around $2 CUC – $10 CUC depending on the hotel).  The cards SELL OUT so buy a few at once so you have a stash.  


Do NOT drink the water.  Use bottled water for everything including brushing your teeth.

Offline maps

Download offline map app from the app store and download Havana.  

Handing Out Supplies

Bring items to give away to people in Cuba – they will appreciate it!  Cubans do not have access to many drug store like items like advil, bandaids, first aid items, OTC drugs, toothpaste, etc.  Also, you could bring candies and hand them out to children on the streets – I did this and the kids LOVED IT!  You can even pack clothes you plan on donating in the USA and bring that to hand out when you leave (plus that leaves you with less in your suitcase for all the rum and cuban cigars you buy!)


Definitely encouraged for service people like your tour guide and translator!

Pack in your bag daily:

A snack (nuts, granola bar, etc), toilet paper (you will thank me for this at one point), hand sanitizer, and sanitary items (for the ladies).




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