Cuba Travel Journal

“Cuba does not adapt to you. YOU must adapt to Cuba.”

Last Updated: June 2017

Welcome to the Speakeasy Guide to Cuba. This information was complied by the first group of Speakeasy members to visits Cuba in April, 2017. It contains a ton of useful tips and ideas to make your stay in Cuba more enjoyable, regardless of whether you are going solo, or with a tour group.

Below are the Speakeasy Members that went on the trip. Feel free to reach out to any of them if you have any questions or need clarification about something:

  • Chad Massaker, Founder & Head Aficionado, Speakeasy
  • Roger Pisaneschi, Head of Speakeasy in Palm Beach Florida, Board Member of the Inner Smoke Ring
  • Tiffani Hollis, Board Member of the Inner Smoke Ring
  • Faye Sykes, Board Member of the Inner Smoke Ring
  • Cindy Lynch, Member
  • Bob Spano, Member


First Speakeasy Group to Visit Cuba


Last Updated: 2017/06/27

  • The tour provided by Smooth Draws Cigar Tours is a very cigar oriented, and, by extension, a guy-oriented trip. That being said, about 1/2 the members on our first trip were women and all very much enjoyed the experience. We even converted never/seldom cigar smokers to women more appreciative of a good, hand-rolled Cuba cigar. However, if you would rather spend more time shopping and seeing historical stuff, the SmoothDraws trip may not be your best first choice. But you will still get a TON of cultural information on the Smooth Draws trip.
  • All of our members that were on the first trip, 1/2 of which were women, all reported feeling safe once in Cuba, despites concerns prior to going. The cities are also very clean.
  • If you go solo, have backup plans for everything. And have backups for those backup plans.
  • The key to a good experience is a lot of patience, flexibility and having backup plans, back means of transport, etc.
  • If doing the guided tour, we recommend adding a day to your trip as a free, unguided day.
  • Stay with your group while touring Havana or loudly announce your need to stop, use the bathroom, shop, whatever. It’s easy to get separated.
  • Also, insist on getting the actual street address to your hour or hotel the second you arrive, so if you do get lost, you know how to get “home”.
  • Street signs are located on every corner but are small, stone obelisks that are low to the ground and sometimes hard to read. A picture of one is below.

Cuban Street Signs


Last Updated: 2017/06/27

Cuban 20 CUC

The major legal currency for Cuba is the Cuban Convertible Peso, CUC. It’s what you exchange your foreign currency for and make all your purchases with in Cuba. Most tourists will only ever deal with CUC. For international exchange purposes 1.00 Cuban Convertible Peso = $1.00 USD.

The second legal currency in Cuba is the simple and lowly Cuban Peso, CUP, which is rarely used by the vast majority of tourists, but it’s still something you should know about as it is perfectly legal for tourists to use it. For example, you can pay the ride in old taxies anywhere in Cuba in CUP. They cost between 10 CUP and 20 CUP per person depending on the distance and destination. However, you can pay for the service in CUC as well. Just be aware that there is no way to pay 10 CUP in CUC, so that will cost you 50 centavos CUC, which is 12 CUPs. You can also use CUP in local shops where Cubans buy their provisions.

These foreign currencies are accepted Cuba:

  • Canadian Dollars CAD
  • Pound Sterling GBP
  • Mexican Pesos MXN
  • Danish Krone DKK
  • Norwegian Krone NOK
  • Swedish Krona SEK
  • Japanese Yen JPY
  • Euro EUR.
  • Swiss Francs CHF
  • US Dollars USD (additional 10% surcharge mentioned above.)


  • We recommend trading in your US dollars for a foreign currency BEFORE trading in for CUCs to avoid the 10% penalty that the USD incurs.
  • The Smooth Draws Cigar Tours Guys will let you send them money in advance of the trip so that they can handle the exchange for you before you arrive. If you send them a check, DO NOT reference Cuba anywhere on the check (in the memo line, etc.). The bank will most likely hold the check and ask you a bunch of compliance related questions as they are required to do with all financial transactions that are related to Cuba.


Last Updated: 2017/06/27

Stonegate Credit Debit Card Works in Cuba

UPDATE 2017/06/19: Statement from Stonegate CEO Regarding Trump Changes:

At this point we do not know if there will be an impact to our current credit card and debit card program with Cuba. We are going to have to wait for the Treasury to address this as they implement the President’s program. We are hopeful that the program will remain in place but it is too hard to tell at this point.

Dave Seleski
Stonegate Bank
President / CEO

No card issued by a bank that has any connection with the United States will be accepted in Cuba, except Stonegate Bank, located in south Florida. Credit Cards issued in other major countries should work fine where credit cards are accepted.

If you opt to get a Stonegate credit or debit card (which we recommend) you will need to call the bank and get the application from them. It is a  very specific card that you have to apply for.  Note that the 10% exchange penalty (see Currency tab) does not apply to transactions paid for by this credit/debit card. These cards may also be used at ATMs to withdraw CUCs.

Credit cards are generally only accepted at the large, state-owned institutions, such as hotels, restaurants, etc. Anywhere you see an actual Point of Sale system can probably take credit cards.

PRO TIP: We went to places where they made claims that their credit card machines are no working that day. You should push back on this and tell them all you have is a credit card and that you don’t have any CUCs on you. Stay persistent for at least a few tries. If they continue to persist that they cannot take credit cards, it might be legit. Cuba’s internet access is not super stable.


Last Updated: 2017/05/14

Not having working internet while on the island and no phone at dinner was nice. No one really missed having access to the Internet. However, if you must have it, we provide information on that below.


You will not need a travel adaptor while in Cuba. All power outlets are U.S. standard NEMA receptacles.


Internet cards are sold in in 1 hr increments at various convenient stores through major cities such as Havana. You can purchase a $2 card for 1 hour or a $10 card for 5 hours. A sample card can be seen below.

Cuba Internet Card

Many Trip Advisor reviews claim that there are several hotels with free WiFi. We visit 2 hotels while there and neither had Internet that we could see. 


Currently, you cannot just buy a SIM card in the country and swap it out wth your phone like you would in Europe. You have to purchase a local mobile phone and a card with minutes on it. You’ll type in a special code each time you want to make a call. A sample card is below.

Sample Cuba Telephone Calling Card






Last Updated: 2017/05/14

It’s a long travel day with a 2 hour flight and lots of waiting in line. Purchase several snacks at the airport once passed security.

Alcohol choices are VERY limited. If you want Bourbon, Scotch, Tequila, high end wines or beer, purchae as much as you can at Duty Free once past security

Put any torches in checked baggage preferabbly. Make sure to empty them first.

Tropical attire is a MUST have. Columbia, Ex-Officio, etc. All linen or wicking materials make all the difference in the world.

For a 5 day 4 night trip, plan to bring no less than $1000, if you are a cigar smoker and going on factory tours.

Plan to spend $200 on tipping if going on a guided tour ($20 per day for the tour guide, $5 for driver, and the rest for various other things)

Bring extra cigarettte lighters as a backup in case your torches do not make it through the aiport and on to the plane

Bring tons of Gatorade or some other kind of electrolyte dissolvable drinking powder

Bring a MicroFiber Travel Towl

Pack Extra Toilet Paper

Bring a small portable notebook as a travel journal

Make sure to pack coolers of water into the cars everday. You house most likely has a cooler

We need a day packing list:

Bring Mixers for Drinks

Pack a wide brim hat WITH a chin strap (need it for the convertible

Download enough movies / TV shows for 4 hours of flight and 4 hours of airport wait time (at least) Flight DID have onboard movies in the headrest

Save some CUCs for the duty free store on the way home. This is where you should buy any rum that you plan to take home.

Each piece of art is “taxed” at the Cuba airport before leaving the country. $3 per item. The stamp does add authenticity to the items however.

Plan to arrive at the aiport to return home at leat 3 hours before the flight. You cannot do online check and will need to get your boarding pass from the Gate agents. Don’t forget to have your signed Visa out too once you get to security

Pack a 10″ portable fan

Pack a Scottivest (might be able to replace a backpack)


Last Updated: 2017/05/14


Last Updated: 2017/05/14



Last Updated: 2017/05/14


Last Updated: 2017/05/14

We were told by more than 1 tour guide that Cuban people generally have no problem screwing over their family and friends to get ahead. They are very opportunistic. So any thoughts that Cuban’s do not understand capitalism, despite being a communist country for decades, may be unfounded, even if only at a basic level.

Older citizens are afraid to re-model their homes in fear that the government will take it away from them if they make it too nice looking.


Last Updated: 2017/05/14


Cuba just has recently allowed their citizens to start and own their own business which has paved the way for a boom in the hospitality/tourism space. This ability to start a new business was right around the time Obama started lifting travel restrictions.  Also, as a result of the increased tourism, the cost of cars and houses used by tourists has more than tripled in the past 2 years. It turns out that this move by Obama might have been more strategic than originally thought. China has been making massive inroads into Latin countries and Cuba is a little too close to home. So the move to open Cuba was also most like born out of a necessity to curb Chinese influence.

Cuba has issues servicing their debt and has gone through debt restructuring deals with almost all countries which are creditors to the island. For example, Cuba still has not paid China for a ton of construction equipment, buses, and cars that they sent over a few years back. Putin wrote off 90% of their debt just last year… about $32 billion.

Because it is an island, many basic needs must be imported. It’s not uncommon to walk into a grocery store and find that they are our of basic things like toilet paper and cooking oil, only to find that weeks later there are whole aisles devoted to cooking oil. When supply is high, Cuban’s must stock up because they never know when the next shipment is coming in. Stocking up can be had to do with a ration card seen below.

Cuban Ration Book

This is why we tell you to bring extra rolls of toilet paper on the packing list. The houses that we stayed in had plenty, but when were out and about, we found that we had to pay for toilet paper if we wanted to use a public restroom. 

Finally, we saw a lot of new construction cranes while there which lends credence to the notion that 2017 and early 2018 truly is the magic window of time with which to visit Cuba before it becomes commercialized / Americanized.

The Future

Short term, Cuba is most likely to buckle under economic pressures, (increased tourism demand will exceed their initial abilities to scale). So things might get worse before they get better. But, if they can find a way to stabilize, make enhancements that tourists from other countries take for granted – such as cheap, pervasive internet and telephone access,  and, they can scale with the pace of demand, the future looks every bright.

None the less. companies seeking to do business in Cuba must be very risk-tolerant if they are to have a chance of succeeding.

Interesting Side Note:

Cuba has never cashed a single rent check for Gunatonimo Bay. They consider us illegal occupiers.



Last Updated: 2017/05/14


Last Updated: 2017/05/14

The Smooth Draws Tour company has asked that we keep the addresses, names and contact information of the homes that we stayed at confidential. I will make this information available to Speakeasy members only and upon request. Email to get it.

However, we can provide pictures and walkthroughs of these homes.

As you can see, the homes are palatial and well secured via high walls, automatic gates, camera systems, etc.