The Best Short Trips from Cuba to the Caribbean

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Letztes Update: 24. May 2021

If you’re already in Cuba, why not explore the whole Caribbean?

If you want to see not only our beloved Cuba, but also make a trip to other countries of the region, then here is the ultimate list of prices and destinations for you!

Because in the end the problem with holidays in the Caribbean is not what you pay once you are in the country, but always the long, costly flight – at least from Europe. And if you are already in the Caribbean, then you can also visit other countries 🙂

Since there has been at least a little change recently and some new airlines have appeared that land in Cuba, it now makes sense to fly to the other Caribbean countries. A few years ago only the flight to Cancun was affordable, everything else was too expensive. Today we already find some flights for less than 200,- Euro, e.g. to San José in Costa Rica or to the Cayman Islands. And of course to Florida: many flights for less than 100,- Euro.

No “No-Frills” Airlines in Cuba

In general, however, flights in the Caribbean are far from being as cheap as in Europe or the US mainland. Only the routes to the USA and Mexico are cheap, the rest is, with a few exceptions, much more expensive than we are used to.

For the DomRep or Haiti we have to pay between 200 – 300,- Euro per flight, with a little luck we can get to Panama or Jamaica for the same price. Aruba, Martinique or Guadeloupe are only available starting from 400,- Euro upwards – and these are prices we also pay for the flight directly from Germany!

However, with companies such as Sunrise Airways (DomRep) or JetBlue (USA), there are some “No-Frills” airlines that have the region in their sights. So let’s hope that there will be some changes in the Caribbean airspace in the future!

Where Do The Prices Come From?

I researched in May 2019 for flights going in September 2019, that’s low season, there should be cheap offers for that time slot. Why September? in September, I’ll be teaching at the summer school of the Humboldt University and the University of Havana again and a side trip might fit quite well!

Of course there are always changes, different offers and sometimes the flights are not reasearchable via flight search engines. Cubana for example doesn’t show up on these websites because of the embargo (and doesn’t have a  working website as well), but even holiday airlines like TUI aren’t always in these search engines with their regular flights.

So it may well be that you find better – or higher – prices for the routes, depending on the offer. Also, I might have missed some connections. But, as you know already: write a comment or an email and I update the article with your input 🙂

Direct Flights From Cuba to the Caribbean

And here are my findings! Short instruction on how to use the table: by clicking on the column header you can sort the table, e.g. by country or by price. Use the search function to find special destinations.

Warning: USA only as Cuban, relative or with special reasons – all thanks to Trump!!!

The cheapest flights from Cuba go to the USA and that pretty much from all Cuban airports. Unfortunately, it has become problematic with the flights Cuba-USA since the Trump presidency.

There are actually only these reasons that allow you to fly from Cuba to USA or vice versa:

• Visit relatives,
• Humanitarian, cultural activities etc. (see below)

The German Federal Foreign Office writes about it:

“Tourist travel directly from the USA to Cuba is prohibited under current US regulations. This also applies to German [=all non US] travellers. Direct trips from the USA to Cuba are only allowed under one of the 12 categories defined by the US authorities, such as cultural, economic, scientific and religious activities, but also trips to support the Cuban people and private visiting trips. So far, there are no experiences available for checking the purpose of travel stated by the travellers. Changes may occur at short notice”.

Further details you find on the following websites:

• Customs and Border Protection (CBP),
• Department of the Treasury – Office of Foreign Assets Control (OFAC)
• US-Botschaft in Havanna
• American Airlines.
• German Federal Foreign Office

The usual experiences on the internet are, however, that you can easily meet the 12 conditions for a Cuba trip to and from the USA – especially if you are not from the US – since it will be difficult for the US authorities to check your receipts for a proper itinerary if you are in Europe. But you better check  exactly, e.g. with your embassy – and don’t rely on me on this topic 😉

Ferries? Not Yet!

Actually it would be so easy: get on a boat and go to the other islands. Unfortunately I haven’t found any real alternatives yet. From the US there are connections to Cuba, but thanks to Trump everything is uncertain. Cruise ships had the permission and that was recalled just start of June, so for an extended ferry service we still have to wait. As it doesn’t have to be ferries from the US, maybe some other connections are coming – but I don’t see that coming, either.

Do you have any experiences or news about ferries to Cuba? The ferry would definitely be an ecological alternative to the plane. And I also hate flying, gives me a headache :/

Explore the Caribbean

In September I’m in Cuba again with enough vacation to test some things out, so I will take a look at what is possible – and update you.

You are missing some flights in my list? Of course there are more flights to the region, but they are not direct flights. For example, you can fly from Havana to San Juan in Puerto Rico via Fort Lauderdale for 140,- Euro with one transfer in less than 6 hours. So, if you don’t mind a stopover while flying, there are even more possibilities.

I’ll be happy if you’d share your experiences with us on trips to the entire Caribbean! I’m sure many of our readers will also be interested to hear news from you 🙂

Saludos desde Berlin,
Dietmar

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