The famous southernmost point in Key West Can you spot Cuba

Day trips from Key West to Cuba – can it be done? The short answer is; YES, it can!

Well, there are issues of course, despite the short distance between Key West and Havana, Cuba. The political distance is longer than from the earth to mars.

There are a few ways to travel to Cuba from Key West in 2022 and 2023, but none of them are currently commercial options. So, let me tell you here how to do it!

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1. Chartered flight Day Trips From Key West To Cuba

Day tour from Key West to Havana. You can take a day tour from Key West to Cuba, by chartering a jet!
Jet yourself privately from Key West to Havana in less than an hour

If you’re looking for a hassle-free way to travel from Key West to Cuba, you can actually do a chartered private jet flight!

There are a few companies that offer chartered flights from Key West to Cuba, and they typically depart from the Key West International Airport.

On a day trip from Key West to Havana, you can suddenly go shopping in Obispo street! A shop in a busy Havana street.
A shop in a busy Havana street

The flight time is between 30 and 50 minutes, so it’s a quick and easy way to get to Cuba for a day trip.

Remember Cuban Tourist Card

One thing to keep in mind when booking a chartered flight (or any flight) is that you will still need to obtain a Cuban tourist card beforehand.

Day tour from Key West to Havana. You can take a day tour from Key West to Cuba, by chartering a jet! It takes 30-50 minutes to get you safely to the buzzing Havana only 100 miles away.

If your tour operator does not provide this, it can be done through a Cuban embassy or consulate. You can also buy a visa from an online provider, and have it sent right to your door before your trip.

I use Easy Tourist Card, which normally gets my Cuban tourist card to my mailbox in three days.

Make sure you have your visa before arriving at the airport (unless you can buy it there, or the charter company provides one for you), as you will not be able to board the plane without one.

Parque Central in Havana from above, where you can hail the Old Classic American cars!
Parque Central in Havana from above

Money In Cuba

Another thing to keep in mind is that Cuba is a cash-only economy.

Be sure to bring enough cash, and that needs to be euros or Canadian dollars, to cover whatever you intend to spend while in the country.

The World By Hege in Cuba 2022

One Day In Havana Cuba Itinerary

Take it from a Scandinavian ex-pat living in Havana for almost two years, here are the best things to do in Havana when you have the one day!

I am assuming your flight takes off super early in the morning from Key West so you have the entire day at your disposal!

  • Walking tour of Old Havana
  • Classic American Old Car tour of the wider Havana city
  • Have lunch at El Dandy or Km Zero
  • Walk the Prado Avenue and get some artsy memorabilia
  • Cocktail at Floridita, Hemingways favorite hang-out
  • Take a break on the Malecon and have a Cristal Cerveza
  • Casa de la Musica Havana or Salsa Havana to shake your dancing feet (if you are allowed to stay out late)

Also read: 33+ Legendary Things To Do In Havana! The Ultimate Guide 2022/2023

Prices Chartered Jets from Key West To Cuba

Day trip from Key West to Cuba. You can take a day tour from Key West to Cuba, by chartering a jet! It takes 30-50 minutes to get you safely to the buzzing Havana only 100 miles away.

Price example for a private jet fare from Key West to Havana, Cuba (*before taxes and fees):

A One Way Flight for 3-9 people$5180
A Return Flight for 3-9 peopleEnquire!

2. Charted Boat Trips From Key West To Cuba

Charter a yacht for a day trip from Key West to Cuba
Charter a yacht from Key West to Miami

A slower but fun way to travel to Cuba (if you like the ocean) is by chartered boat.

There are a few companies that offer chartered boat trips from Key West to Cuba, and they typically depart from the Key West marina.

Also read: Amazing Havana Rooftop Bars & Restaurants!

In just one hour you can be walking around in Parque Central in Havana, hailing a classic old American car!
Parque Central Havana

You can do a single-day round trip between Key West and Cuba, so it is actually possible to go on a day trip by boat!

The trip over takes a few hours, and it’s a convenient and fun way to get to Cuba for a day trip even though quite a bit of the day is spent on the boat! If you like boats, well, it probably is perfect.

Day trip from Key West to Cuba by boat!

You can also do multi-day trips by boat to Cuba, where you are able to visit more than one port.

You can contact the provider for information and possible itineraries for a Cuba boat charter!

3. Multi-Day Sail Trips From Key West To Cuba

You can do a multi-day sailing tour starting in Key West, and touring all across Cuba.

If you’re looking for a truly unique way to travel from Key West to Cuba, and travel around Cuba (not just a day trip), sail trips are the way to go!

Sail trips from Key West to Cuba typically depart from the Key West marina. You can check out the various boat types, travel itineraries, and destinations here.

4. Go To Miami And Get A Commercial Flight!

Miami beach, from where you can almos see across to Cuba!

There are flights from Miami to Havana or Varadero every day. This is a lot cheaper than chartering a private jet, and the flight time is around 1 hour.

You still need the Cuban tourist card, and you can buy one at the American Airlines check-in at the Miami International Airport if you don’t have time to order one online beforehand!

Price Example Return Flight Miami – Havana

This is a price example of a return flight Miami – Havana – Miami in one day:

A Return Ticket Miami – Havana 1 person (6 am – 9 pm)$566
A ONE-WAY Ticket Miami – Havana 1 person$298!
Classic old american cars

To-Do List Before Your Day Trip From Key West To Cuba

No matter how you choose to travel, there are a few things to keep in mind when planning your day trip to Cuba.

American Citizens Visiting Cuba

Day trip to Cuba from Key West
Take a day trip from Key West to Cuba just to take a ride in this

First, American citizens will need to obtain the pink tourist card before entering the country, as opposed to the green one that the rest of the world is using.

Make sure you are familiar with the 11 pre-approved reasons for US citizens to visit Cuba. Most US visitors’ travel reason is to “help the Cuban people”. There is no paperwork connected to this, you just need to state your reason if anyone asks.

If you plan on staying at a hotel or casa particular while in Cuba, you also need to make sure it is not on the US restricted list. Most are not, so don’t worry, but it is smart to check before you do your booking.

The view from the rooftop terrace of hotel Gran Bristol in Havana, the capitolio just after sunset!
The Capitolio just after sunset in the center of Havana Cuba

Remember that Cuba is a (mostly) cash-only economy, AND that the US dollar is currently banned since June 2021.

Be sure to bring enough cash to cover whatever you plan on doing while in Cuba, and bring euros or Canadian dollars.

Be respectful of the Cuban people and their culture. Cuba is a wonderful place to visit, and we hope you enjoy your day trip!

Why Day Trips From Key West To Cuba?

Key West street view on a sunny day!
Key West street view

Well, it is a super short distance! And, Cuba is a beautiful island nation, rich in culture, history, architecture, nature, and so much more.

Situated just over 100 miles from the Florida Keys, Cuba has been a popular destination for day trips from Key West since way back.

In fact, in the first half of the 21st Century, the relationship between Cuba and the US was great, at least from a strategic and business point of view.

The Havana malecon is only 100 miles from Key West, if you want to take a day trip from Key West to Cuba you can stroll here!
The famous Malecon boardwalk in Havana

US and Cuba – Before!

The trade was blooming, and lots of American companies had businesses in Cuba, trading in rum, sugar, honey, and more.

During the prohibition period in the US, in the 1920ies and 30ies, there was also an “invasion” of bartenders and bar owners buying and opening bars, restaurants, and clubs in Cuba – where there was no prohibition at all.

The venerable Hotel Nacional in Havana, where the rich and famous of the world used to come to party in the 1920ies and 30ies!
The venerable Hotel Nacional in Havana party scene for the rich and famous of the world in the 1930ies

That, of course, was before Fidel Castro, the revolution, the Cuba crisis, the failed invasion of Playa Giron, and all that.

But back to day trips. Currently, there are no commercial flights, ferries, or cruise ships traveling between Key West and Cuba, due to the tightened sanctions implemented by President Trump before he left office.

He also put Cuba on the dreaded list of “nations that support terrorism” which did not help tourism, but here we are.

Wrap-Up Day Trips From Key West To Cuba

It is not cheap, but you CAN take a day trip from Key West to Cuba, and Havana!

Even if you take the small detour up to Miami, and fly from there, for a price that is a bit nicer. Or come for the weekend instead? Plenty of things to do, you will not regret it!

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