TRAVEL

Planning a Legal Trip to Cuba from the US // Travel Restrictions // Rules for Americans

On June 25, 2019
By Kimberly

Getting into Cuba just as the doors close: How we organized a legal trip to Cuba from the US while following all travel restrictions and rules for Americans took a good deal of planning and coordination.

Cuba Opens for Travel

US President Obama opened Cuba slightly for travel in 2015, and immediately we wanted to see this magnificent country. All my life, I have met Cubans in Florida and in the Bahamas and been impressed with their friendliness and resiliency.

In January of 2015, Obama introduced authorization for American to travel to Cuba under 12 specific reasons without obtaining special licenses, and airlines were cleared to fly to Cuba. Some people called this the “Cuban Thaw.” Travel had been restricted since 1963, with President Jimmy Carter making small diplomatic steps in 1977.

While this loosening of travel restrictions began in late 2014, it took a few years for travel companies to obtain their licenses from the U.S. Department of Treasury’s Office of Foreign Assets Control, and people-to-people tours to become established.

Timelines of Cuba opening for American travel vary; I’ve read that people-to-people travel was permitted as early as 1999, and that in 2000, some travel companies already were operating under special licenses.

Brief History of U.S. – Cuba Travel

The Helms-Burton Act of 1996 signed by President Clinton stipulated that U.S. embargo sanctions could only be lifted after Fidel and Raul Castro were no longer in office. In 2009, Obama signed a potential “thaw” for travel.

In 2015 the U.S. and Cuba reopened embassies closed since 1961, and in 2016 Obama visited Cuba, the first U.S. President to visit the island in almost 90 years. Fidel died late in 2016, and Raul stepped down in April of 2018. Cuba’s National Assembly elected Miguel Diaz-Canal as president of Cuba.

From the Council on Foreign Relations, the article U.S.-Cuba Relations covers a brief timeline of the history.

Island Life – History and Accessibility

The Caribbean history feels like my own history as a frequent visitor to the Bahamas, the Florida Keys, and the Virgin Islands, I grew up reading about sailors across the Caribbean, their exploits, adventures and escapes.

We debated for three years about how to travel to Cuba, and about a year ago decided to make a plan. Generally, our dive trip plans are fleshed out about a year in advance, so this time last year, we targeted this summer as our time to head to Cuba.

With flights reasonable and exchange rates favorable, we started thinking that with a two-hour drive to Orlando an a little over an hour’s flight out of Orlando; this trip would be three times quicker than getting to the Florida Keys, and far less expensive. But first, we ran all the options.

The First Plan – by Cruise Ship

So, I started planning. First, I ran all the numbers for heading there by cruise ship. The cruise line that spends the most time in Havana was MSC, with a two-day stop there. Royal Caribbean and Carnival also had stops there.

On their seven-day run, MSC also stopped a few other places, so we could plan some diving at several different destinations.

It sounded like a great plan, except that for our seven days of travel, we would have only two days in Cuba. We wanted more. Our interest was to be on land, longer, meeting more people, learning more history.

Ironically, the Tuesday before we were to fly out on Saturday, travel to Cuba by cruise ship was banned. We flew out the same day we could have been boarding a MSC cruise, so lucky for us we were flying there instead since we would have missed the island entirely.

Plan B – Live-Aboard Dive Boat

Next, I looked into live-aboard dive trips. We eliminated those pretty quickly because they would not give us much time at all on land to see historic sites, interact with people, do any volunteering, or make personal connections with other sailors and divers.

While the live-aboard boats were dive-heavy, with 18 dives scheduled in a week’s time, but we really wanted to spend more time above sea level learning about the people and customs. So, we moved on to the next plan!

Final Plans

Last, I conducted land-based research. Over the course of a couple months, I contacted dozens of travel organizers, dive operators, and other travel professionals.

Eventually, I narrowed it down to four land-based coordinators, then two coordinators, and then, I picked the one with the best communication. Although I knew it probably was not fair to judge any trip organizer on speed of returning emails since Internet access is expensive and sporadic in Cuba, I had to have a tie-breaker. Looking back, I was so fortunate to choose as I did.

Our land-based activities including accommodations, sightseeing, tours, historic visits, scuba diving, tank fills, breakfasts, car rental, drivers, and a million other details were coordinated by CubaDivingNow. I cannot say enough about their commitment to providing a true Cuban experience, and their dedication to customer service. However, I’ll definitely attempt to tell you all about their crew in several future articles!

Fly to Cuba!

With at least a hundred hours of research conducted, several readings of the Code of Federal Regulations, telephone conversations with airline agents, we decided to trust the coordinator, and fly to Cuba.

Yes, we would fly there. On a one-hour flight out of Orlando. It seemed unreal. A country that had been off-limits all of my life suddenly was accessible by a one-hour flight. It seemed impossible.

We made a deposit the with coordinator, booked our flights, took a deep breath, and tried to let it sink in; we were simply going to fly to Cuba.

Flights and Flight Fees

About four months in advance, we booked our flights. The flights cost us about $190 each way, or, $380.03 each which included about $100 in fees. My dive partner is very tall, so we paid an additional “$25 per leg” – that would be leg of the voyage, not leg of the traveler. So, our total flight cost was $430.03 each. I have seen the flights to Cuba from Orlando as low as $134 each way and as expensive as $488.

Unlike long-distance international flight where coach seats are incredibly cramped, the Embraer E190 on which we flew was more of a domestic-route aircraft, and we could have skipped paying extra $50 each for legroom ($25 per flight leg).

There are two seats on each side of one aisle, 25 rows total. The coach seats were quite spacious, and it’s only an hour-long flight. Soon, we would be packed like sardines for hours of travel across Cuba!

The additional fee gained us “Blue Plus” status that allowed us one checked bag not to exceed 50 pounds, extra legroom, and supposedly priority boarding, though the plane is small enough that doesn’t even matter.

Also, apparently, we earned more Jet Blue frequent flyer miles. I did sign up for their True Blue frequent flyer program, and see I have 1,061 points. It looks like the best points deal is 5,000 points one way from Orlando to Havana with a $30.60 in taxes and fees charge – I’ll be flying free soon!

Other Carriers

At this time, it appears American operates 10 daily flights from Miami to Cuba. From Tampa and Fort Lauderdale, Southwest has daily flights. Jet Blue flies from New York in three and a half hours, the most popular route. Here’s How to Fly to Cuba in 2019 which lists a few more options.

For a list of all flights, on Kayak this page shows nine destinations in Cuba but only flights to these six; Havana, Varadero, Holguin, Santa Clara, Camaguey, and Santiago de Cuba. Airlines as varied as Copa from Panama City and BahamasAir from Nassau head to Havana daily.

U.S. citizens have been traveling to Cuba very quietly through the Cayman Islands, Cancun, Nassau, Bahamas, and Toronto, Canada. Whenever I fly through Nassau, I see the flights to Havana on the departures and arrivals boards.

When we returned from Cuba, we were asked if we wanted our passport stamped. That is a holdover from when, to avoid trouble with U.S. Customs, those travelers would ask the Cuban immigration officials to not stamp their passports.

Required Insurance, Visa for Cuba

The price of the flight included the insurance required by the Cuban government, which I believe is about $25 if you are paying for it separately. One of our flight attendants would be eligible to fly there for free, but would need to pay the insurance fee.

Not included in the price of the flight is the visa for travel to Cuba. This is easy – you purchase it at the check-in counter when they weigh your bag and issue your boarding pass. You can pay by credit card. It is $50 per person for a 30-day stay.

I did read recently that different airlines charge different fees for the visa, so keep this in mind if your overall fare plus visa adds to more or less depending on your carrier. American charges $100 at the gate, $85 in advance. Delta, Jet Blue, and Southwest charge $50 at the gate. United charges $75 at the gate. Be sure to look up current rates; these may change.

Passport Requirements

Cuba requires for you to have a full-sized passport, not a passport card. The passport must have at least six months left before renewal, and two pages empty for the entry and exit stamps.

My passport was stamped upon entry into Cuba on one page, and on the next page upon departure. We were asked if we wanted our passports stamped as we exited the country – a courtesy and holdover from when Americans were traveling there surreptitiously.

Luggage on Jet Blue to Cuba

Jet Blue allowed us one check-in bag of up to 50 pounds, overall dimensions not to exceed 62″ which would be length plus width plus height – any shape allowable as long as it fell into those dimensions.

Our rolling bags fit easily under this restriction, and we packed all our dive gear except for regulators in the checked bags. My dive partner put his clothes in his rolling bag as well. I compacted my clothes into a carry on.

We were allowed one carry on bag. The carry on bag has to measure no more than 22 inches in length, 14 inches width, and 9 inches in height. The height of the carry on is very important. I packed my backpack too deep to fit in the overhead, but it did fit under the seat in front of me. I didn’t see anyone else having any trouble.

The last item permitted was a “personal item,” which, on the way there, could be a purse, laptop bag, regulator bag; something of that nature. My dive partner carried his regulator bag, my small purse was in my backpack, so I had no personal item. One of our traveling companions had his smallish backpack from the ScubaPro rolling dive bag set, and another had her purse.

While we were in Cuba we received an email that no electronics larger than a cell phone would be permitted in carry-on luggage, so, anyone planning on carrying their laptop in that category would have had to move a few items around to meet the new restrictions.

Flight Operations Updates including New and updated TSA security screening procedures as well as airport construction are available at this link.

Planning the Details

We fleshed out a plan over the course of several months, and added and subtracted dives. The itinerary changed to coordinate with tours, meetings, and travel schedules.

Several letters in my halting Spanish and the Commodore’s brave English were exchanged, and we added to the schedule a meeting at the Havana Yacht Club to strengthen ties between the St. Augustine Yacht Club, St. Augustine, and the Hemingway International Yacht Club.

The added visit to our fellow yachtsman the Commodore at the International Hemingway Yacht Club finalized our schedule.

Final Itinerary

The final itinerary listed nine nights in four different casa particulars, breakfast included. Also planned: a classic convertible city tour, a walking city tour, a tour of Hemingway’s setting for “The Old Man & The Sea,” several other tours of architectural, archaeological, and historical areas of interest including agriculture of all types, a cenote, and some snorkeling and diving to meet the under-the-sea residents as well.

From our rough itinerary, we really had no idea how much time it would take to travel from location to location, how much Spanish we would end up speaking, or how much access to private citizens we would enjoy.

Then the Mini-Details Began!

Once we finished the overall plan, we researched everything from toilet paper – yes, take wet wipes – electrical service for charging needs, toiletry availability, and expected temperatures. Everyone loaded map apps for getting around and conversion apps for changing from Imperial to Metric and back again for distances, depths, and volumes. We researched what we were allowed to purchase, from whom, and how much we could spend.

I still had a LOT of work to do. On the “to do” list we listed figuring exchange rates, how to deal with money, electrical needs, camera equipment, charging photography devices, assembling toiletries, selecting lightweight hand-washable clothing, shoe considerations, a worthy hat, and a million other plans.

We made lists of things left to do, items we wanted to make sure we took, and items to purchase like more sd cards for all the cameras. Then we assembled a first aid kit, flashlights and batteries, and looked in our closets for our most wrinkle-proof, lightweight, fast-drying summer clothes.

Letting one single tiny detail slip through the cracks could potentially make a lot of headaches and stress for everyone, so we checked, double, triple, quadruple checked every tiny detail.

Communication

Research showed communication would be limited, so we prepared all our family and friends in advance. Upon arrival, we were able to access texts briefly through the house wifi.

The wifi connections seemed to come and go – our casa particulare owner alerted us when it was available, and she and her assistant dropped everything to utilize it themselves when it engaged.

Emails seemed to filter through sporadically, and we could read the subject line to see if it was worth the bother of trying to open them.

We could have purchased wifi access cards for use in several parks, but instead, we took advantage of the lack of communication to totally immerse ourselves in the experience at hand.

Occasionally, our tour guide / dive master would open his cell phone wifi hotspot to us. We were not sure how expensive it was for him to do that, so we limited ourselves to only highly important, brief correspondence.

Money and Spending Restrictions

I wrote “Learning About Exchanging Money for a Dive Trip to Cuba // Minding My CUC’s and CUP’s” before I left. It tells the details you will need to know about conducting currency exchanges; timelines and bank fees. We chose to take Canadian dollars and exchange them for Cuban Convertible Pesos, CUC’s there.

We printed the three-page list of The Department of State list of places Americans cannot spend money restrictions.

What we learned about exchanging currency in Cuba requires an entire article – subscribe to the blog, and you’ll receive a notice when that article goes live. It’s far too much to cover here!

Next time we probably will take American dollars and convert to CUC; we ended up paying more exchange fees than we could have.

Park Sleep Ride Fly Ride Hotel

One detail was to find a park fly and sleep hotel deal, with parking for almost two weeks, and a 24-hour shuttle. I consulted ParkRideFly, ParkRideFlyUSA, ParkToFly, TripAdvisor, Expedia, ParkSleepFly, and StayParkTravel, as well as directly on the hotel websites.

I used my usual conflict resolution / planning grid of a paper with columns for everything essential for choosing a hotel. My categories were: shuttle hours, parking fees, parking days, bed type, distance to airport, total price.

The criteria were first, one that had a shuttle running at 4:30 a.m. since we had to be at the airport at 4:45 a.m., and one that was very close to the airport. We chose the Hilton Garden Inn since it fit both those categories.

Hotel and Parking Considerations

Some items to triple check for booking hotels with the plan of parking there; make sure you know the fees per day of parking, and, if they offer park and fly, double check for how many days they allow you to park. Make sure their shuttle is actually running at the time you need to depart for the airport – I found several that ran 24 hours, and several that did not start service until 6:00 a.m. That would have made an additional taxi necessary.

Comparing sites, this time, on StayParkTravel I found the best overall package deal. The Hilton Garden Inn International Airport special included 14 days of parking, shuttle both ways, and our total bill was $156.38.

Four of us shared a room with two queen beds – other hotels had either one king or two doubles. This hotel had a nice pool, gym, a restaurant on site, and breakfast, which we knew we would miss.

Get to the Airport Three Hours Ahead of Your Flight

Yes. With a 7:45 a.m. flight, we needed to be at the airport three hours in advance to deal with the visa and insurance. You can read all about these Flight Operations Updates including New and updated TSA security screening procedures as well as airport construction

Double checking with Jet Blue, since three hours is more than the two hours we were used to allowing for international flights, we learned that the additional visa and customs lines could be slower, so the three hours was not mandatory, but definitely suggested. I believe since we traveled, it is now mandatory. Check the Flight Operations Updates before you travel.

Gates Close Earlier for Cuba

As it turned out, we did have one hour to spare at the terminal. For this flight, the gates close one hour in advance, so the hour was not wasted. It gave us time to wind down, get one last charge on our phones, and contemplate our goals for the upcoming trip, as well as scope out who was flying to Cuba. We seemed to be the only Americans.

Upon arrival at the curb, we headed straight to the desk. There is no automated, computer check-in for these flights. We checked in, had our bags weighed, purchased our visa, and headed to the next line.

Next was an amazingly long line; through the Homeland Security lines. We saw a total of three dogs working the lines. The queue snaked back and forth, with free lanes in between travelers for the dogs and handlers to walk repeatedly. Dogs passed us two times on each side.

Once through the que, we took the tram to the gate. Surprisingly, we arrived at the gate with only an hour to spare. We had a bite to eat, filled our water bottles, and appreciated one last bathroom stop with toilet seat and paper.

Immunizations, Mosquitoes, and Such

Before traveling, we checked the Center For Disease Control website for updates. CDC reports showed a current watching level 1, 2, 3 for measles, rubella, cholera, zika, and anything that pops up. Ebola, yellow fever, and even monkeypox popped up in different spots on the globe this year.

No immunizations were required, though a recent tetanus shot is always a good idea. One of my friends brought an all-natural geranium and citronella mixture called NoNatz for the gnat, no-see’um, fly and mosquito. It kept off of us even the aggravating teeny gnats, and smells very nice too!

We checked with our mosquito expert who has conducted mosquito research around the globe, and he said Cuba has a good history of mosquito control. We saw it in action later.

Water

For water, some of us brought reusable water bottles. We ended up boiling then filtering water for drinking and ice, and buying a lot of bottled water. Next time, we will take a filtration system and bring Immodium. Three out of four of us had brief to extended stomach issues from the water.

Below, under “Resources,” are some of the government publications I read before our departure.

Hemingway International Yacht Club

We wanted to return the favor of a visit from Commodore Jose Miguel Diaz Escrich of the Internacional Hemingway De Cuba Club Nautico – International Hemingway Yacht Club of Cuba. He visited our St. Augustine Yacht Club in December of last year and spoken about Cuba and the Importance of the Men of the Sea. He now invited us to visit him at his yacht club.

We printed his letters of invitation from the Hemingway International Yacht Club for each of us to carry in case we got separated at customs, and we printed answering invitational letters from our St. Augustine Yacht club.

Then we printed four copies of everything for everyone’s record of what we did in Cuba because we read we must keep them about five years for proof of activities while we were there.

Further Restrictions Announced

We really felt we were making the trip as the doors were closing. In April, further restrictions on travel to Cuba were announced by John Bolton, the national security advisor.

“The Department of the Treasury will implement further regulatory changes to restrict non-family travel to Cuba,” he said. “These new measures will help steer Americans’ dollars away from the Cuban regime.” That was a vague indication that travel by Americans to Cuba would become more difficult.

Then, three days before our trip, on June 5, travel by passenger and recreational vessel including cruise ship, private boat, yachts, and private and corporate aircraft was deemed no longer allowed by the Treasury Department’s Office of Foreign Assets Control, OFAC, as well as part of one of the 12 approved categories; people-to-people.

Now there are 12 categories of authorized travel to Cuba. Choosing one of these categories becomes your “license” for authorized travel.

While we were in Cuba, we heard about Expedia’s fine for assisting people with travel or travel-related services.

Remaining Uncertanties

There is still a lot of confusion about travel to Cuba. A lot has been written about that subject. This LA Times articles covers some of the questions: Myths, facts and gray areas that will complicate your Cuba travel plans. In researching, I attempted to read as much as humanly possible so we not only traveled in the “letter of the law,” but also in the spirit of the current laws.

Articles like Expedia fined for allegedly violating Cuba regulations made me think sometimes although companies believe they are following the letter of the law, sometimes details might be neglected. Expedia settled quickly, paying their fines, and issuing statements that they intended to fully comply with all restrictions.

I even found articles about people traveling to Cuba with possibly not following either the letter or intent of the law. Articles like New York man to pay fine for unauthorized 1998 Cuba visit made me very aware of following both.

While we did drive by a couple places on the List of Restricted Entities and Subentities Associated With Cuba as of April 24, 2019, we were very careful to carry a list of those restricted entities with us and avoided spending at those locations. I had even read about someone going to fill SCUBA tanks somewhere on the island, and realizing they could not pay for fills due to the ownership of that particular location.

Another Option: A Liveaboard!

All Star Liveaboards operates a 125′ scuba diving liveaboard vessel in Cuba; the Avalon II, with 10 passenger cabins featuring individual temperature control and a sundeck with hot tub and bar.

Over 80 dive sites are accessible in the area where Avalon II operates, Jardines de la Reina Marine Park, so up to 22 dives plus two night dives are possible. In the Gardens of the Queen, you can log up to four dives a day!

I worked for years on the windjammer fleet in Maine, and I can tell you that a liveaboard is a very special experience. You have the opportunity to learn so much about the environment and water. Your daily routine begins to flow with the sunrise and sunset and tides, and your commute to the dive sites is also on the water – so your time is spent on, in, or near the water all week.

A liveaboard trip on the Avalon II means all your energy is spent either diving or relaxing on the boat. So, there’s no hotel-hopping, packing and unpacking, or having to come up with a plan for each meal. Avalon II includes gourmet meals, around which there’s sure to be plenty of dive talk and experience sharing from the day’s adventures.

For someone who wants to maximize their time in Cuba for diving; this is the perfect experience.

Summary

You can travel to Cuba under one of the 11 approved categories of travel. Tourism is not allowed. It’s a short flight from Orlando. Shorter from Fort Lauderdale or Miami. Longer from New York. You can bring back $100 in Cuban rum and cigars; up to $500 total in goods. Some references say $800. Research before you go as limits can change.

You cannot spend at military-controlled businesses including hotels and restaurants. The Department of State list of places Americans cannot spend money is currently unavailable.

Our wonderful hosts and organizers: Cuba Diving Now. Mention you heard about them from DeepWaterHappy, and they will save a kiss for me and a hug for you!

Mentioned or Shown in Article

I’m sharing with you some of the travel items we found most useful. Although your price does not change if you do happen to order any of the items mentioned; I might earn a small commission from your purchase, which allows me to continue bringing you great content. Thank you for reading!

Let’s Talk Spanish – this book has some truly useful and truly hilarious phrases!

Bill’s Mystery Ranch backpack – perfect size for packing in a carry-on, then unfolding once you reach your destination. Held our first aid kit, flashlight, and everything else.

My Passport Cover is only available if you cruise a lot on RCCL, however, you can find great ones online here if you want to keep your nationality a bit of a surprise whilst waiting in queues in airports.

Olympus TG-5 Waterproof camera – red – good to 50 feet, great for traveling in case of spills, then excellent for snorkeling. You’ll need the Underwater Housing for diving to depth of 150 feet.

Hydrapak Stash Water Bottle collapses to the size of a hockey puck!

Lifeproof NUUD Series Waterproof Case for iPhone – not the FRE! This case is nearly indestructible – I use it on the sailboat, cycling, on dive boats, and near glasses of ice water and cups of coffee.

The all-natural geranium and citronella mixture I mentioned is called NoNatz for the gnat, no-see’um, fly and mosquito. It kept even the aggravating teeny gnats off of us, and smells very nice too!

What to Read Next

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