Key West To Cuba
* Please be advised, as of right now the U.S Government requires U.S citizens to have special permission to visit Cuba. Any and all U.S charters to Cuba must be approved by the U.S Government prior.
Info About Cuba Charters
Directly across the Straits of Florida from Key West lies the island of Cuba. Only 90 miles away, yet a million miles from any country you’ve ever visited. Call Key West Charter Boat or fill out a quote form. We’ll introduce you to several travel options for journeying Cuba, from single-day round trips to excursions lasting a week or longer. Or if you prefer, fill out a quote form. Either way, Charter Boat to Cuba is an experience you don’t want to miss.
State-of-the-art power yachts from Key West to Cuba allow you to spend a day wandering through plazas of Havana and be back in the United States by nightfall. For a more leisurely voyage, employ the professional services of a certified captain and sail to Cuba on a 65-foot catamaran, making stops at Matanzas, Santiago de Cuba, Cienfuegos and other culturally rich ports around the island.
Charter QUOTES
FAST RESPONSE
Charter Flights From Key West To Havana Cuba
Flights from Key West to Havana Cuba are available for both private and public charter. The aircraft in use is the reliable twin engine turboprop Britten-Norman BN2T Turbine Islander. The aircraft has seating for up to 9 passengers. Private charter flights from Key West to Cuba are available to depart any day of the week you like. To reserve we need a minimum of 24 hours notice to file and get clearance for the flight to Cuba.
Our public scheduled flights from Key West to Havana are scheduled for every Monday, Wednesday and Friday. Departing at 8:00 AM and returning at 6:00 PM. Many travelers make online bookings directly through our site, simplifying their travel preparation while ensuring everything is pre-approved and confirmed before departure. Each ticket includes airfare, visa handling, and Cuban government taxes, making the process straightforward and efficient.
Havana in a Day Itinerary
A day trip to Cuba from Key West provides you with a chance to experience the culture and history of the city Havana in the shortest time possible. This means that when you are traveling from Key West you will have to get up early to catch your short flight and be ready to tour the city of Havana throughout the day.
Here’s an itinerary breakdown of your day in Havana Cuba.
- 7:15 AM: Check in at Key West International Airport (EYW).
- 8:00 AM: Flight departs Key West.
- 9:00 AM: Arrive at Jose Marti International Airport (HAV) in Havana, Cuba where you meet your local guide and driver.
- 9:30 AM: Depart Havana International Airport and travel to “Finca Vigia”, Ernest Hemingway’s house and now museum. View Key West-registered boat “Pilar”.
- 11:30 AM: Visit the fishing village of Cojimar, where Hemingway would depart on fishing expeditions.
- 12:00 PM: Lunch at “Paladar” (privately-owned restaurant) in Cojimar.
- 1:30 PM: Visit Old Town Havana Hemingway literary landmarks including:
- “Ambos Mundos” hotel, where Hemingway frequented and whose room is maintained as a free museum.
- “La Bodeguita del Medio” restaurant and bar favored by many writers and poets, including Hemingway.
- “La Floridita” restaurant and bar that claims to be the birthplace of the daiquiri, Hemingway’s favorite drink.
- Shop for crafts directly from local vendors at a local market.
- 4:00 PM: Meet driver at “Parque Central” for return to HAV.
- 5:00 PM: Flight departs HAV.
- 6:00 PM: Arrive at EYW.
As soon as you arrive, the old world charm of Havana welcomes you, and takes you on a magical journey to a land seemingly frozen in time.
A walking tour of Old Havana is on the schedule, this will give you a chance to experience the rich culture and historical atmosphere of the city as well as visit points of interest like Hemingway’s house along with his favorite places. Cuban cuisine also has a significant impact on the Key West food culture, and this trip enables you to taste that connection.
Whether you are interested in history, food, or culture, Havana has a lot to offer to everyone.
Public Flight
Per Person- Airfare
- Visa & all required documentation
- All US & Cuban government taxes
- Transportation & guide in Cuba
- Entry to all museums & points of interest
- Lunch & drinks
Private Flights
Private Custom Itineraries- Airfare
- Visa & all required documentation
- All US & Cuban government taxes
- Custom Itineraries
- Day Trips / Multi Day Trips
- Transportation & guide in Cuba
Walking Tour of Old Havana
Old Havana on foot is a time machine, every stone that completes the streets reveals a part of the city’s fascinating history. Start at the oldest square in Havana, the Plaza de Armas, where you can feel the history in every stone. The tour then proceeds to Plaza Vieja, another lively square that is famous for music and colorful buildings.
There is no way you can visit Old Havana without visiting El Floridita, the birth place of the Daiquiri. Also other famous bars like La Bodeguita del Medio which was Hemingway’s favourite joint. Utilizing local tour guides and drivers to conduct the tours is helpful in enhancing the tour experience and at the same time, helps the community through their tips.
Local Cuisine and Restaurants
Cubans love their food and eating is a big part of the culture which is why food is one of the best ways to experience Havana. Eating at privately owned restaurants, such as Paladar, helps the local population and is a popular place amongst visitors. These eateries serve typical Cuban fare, for example, ropa vieja, a shredded beef preparation that is common in Cuban cuisine.
Lunch during the excursion is usually inclusive of food from a locally owned Cuban restaurant which makes the experience even more local. The street foods such as tostones which are fried plantains served with different sauces are a mouth-watering reminder of the vibrant food culture in Havana.
Local Markets and Vendors
A trip to Havana is not complete without a visit to the local markets. One of the best markets in Havana is Mercado de San José where one can mingle with the locals and buy handcrafts. These markets are well stocked with various items that are hand crafted special souvenirs such as jewelry, textiles and art. Buying the products from the artisans helps in preserving the traditional arts and crafts that supports Cuba’s creative industry.
Cuban History & Island Info
Circumnavigating Cuba has been popular since Christopher Columbus first set foot here in 1492. The famous explorer liked the tropical paradise so much, he claimed it in the name of Spain. Five centuries later, Ernest Hemingway felt the same, planting his flag and living in the outskirts of Havana for over twenty years.
On a Key West to Cuba charter boat trip, you can discover the island’s colorful history for yourself. No place in the world has quite the same blend of cultures and traditions. You’ll appreciate why Cuba’s nickname, Pearl of the Antilles, is a particularly accurate moniker. Being on Duval street is nice by why not have an authentic Cuban experience instead?
Cubas Untouched Beauty
Fortunately, Cuba still has much of the extraordinary raw beauty Columbus so appreciated— endless pristine beaches of pure white sand, sparkling turquoise waters, verdant, rugged mountains. Guided excursions into the interior can be arranged on the spur of the moment locally or planned in advance by Key West Charter Boat.
The food alone is justification enough to visit this island nation of eleven-million people. In addition to the exceptional regional fare, be sure to order the national dish of Cuba, ropa vieja. Local adaptations aside, ropa vieja is made of shredded flank steak in an aromatic tomato sauce base, served with black beans, yellow rice, plantains, and fried yuca—nearly always accompanied by beer.
The gastronomic masterpiece is both delicious and affordable, costing approximately nine Cuban pesos ($9.00 U.S. dollars) per serving. No wonder so many people return to Cuba year after year for vacation.
Ernest Hemingways Secret Retreat
Hemingway journeyed to Cuba for several reasons, not least of which was the world-class fishing. The warm waters of the Gulf Stream flow the entire length of the island’s north side, attracting spectacular Sailfish, Black Fin Tuna, Mahi Mahi, Wahoo, and a diverse assortment of other sport fish.
Key West Charter Boat can put you in the fighting chair of a sport fishing yacht trolling Cuban waters in a matter of a few hours. Surprisingly, Key West to Cuba distance is substantially shorter than Miami’s proximity to the Bahamas. Journey to the southern coast of this internationally acclaimed fishing destination and you’ll be in the Caribbean Sea, where the daily catch could easily include mammoth Tiger and Hammerhead sharks.
Cuban Culture
No Key West to Cuba trip would be complete without spending at least a day in Havana. Once a playground for the rich and famous, Hollywood starlets and business tycoons were found here nightly, gambling in casinos and taking in a show at the world-famous Tropicana Nightclub. Havana in the 1950s was an “anything goes” town of fame and occasional infamy. Today the high life has disappeared, old-world charm lingers.
Stroll the streets of Old Havana and you’ll feel a mixture of cultural influences that are uniquely Cuban, from the conservative architecture of a Spanish cathedral to plazas lined with brightly colored building facades. Stop along the way and sample some of the city’s famous street food, including Tostones—deep-fried plantains served with a variety of dipping sauces.
Any walk through Old Havana is sure to pass under clotheslines strung between apartment buildings and have an encounter with at least one vintage 1950s-era Ford or Chevy automobile, still in operational condition and often used as taxis.
The Richness Of Cuban Culture
In Cuba, music feels like it’s a religion of its own, as sacred and loved. Some of the finest musicians you’ll ever hear can be found playing in places like Plaza Vieja and Plaza de Armas. So do what the locals do: sit, enjoy a cup of Cuban coffee, and partake in a little people watching.
Whether you travel from Key West to Cuba on a Hemingway excursion, fishing expedition, or simply to tour and experience a magnificent jewel of the Caribbean, you’ll discover Cuban citizens to be welcoming and engaging. For additional information about Key West to Cuba trips, either by sea or day trips by Air Key West, call Key West Charter Boat today.
Planning Your Trip
There are a few things that one needs to make sure of when planning a trip to Havana.
- Having a passport
- Having a Visa
- Declare an OFAC list item (i.e Support for the Cuban People )
- Do not spend money at Cuban government owned businesses
- Keep receipts for proof to US customs
- Proof of Insurance
- Know location of US embassy and phone number
- Inform family and friends of where you will be staying
- Cuba compatible cell phone
- Bring Plenty of Cash US Dollars or Cuban Pesos
- Check the weather
- Bring Purified Water Bottle
- Bring sunscreen
- Bring Mosquito repellent
- Bring rain poncho or umbrella
- Bring Toilet Paper
Document checks at the air and seaports are standard for U.S. citizens going to Cuba. Upon return to the United States expect customs to conduct a larger than normal interview and inspection in regards to your trip to Cuba.
Safety concerns and the weather are among the most important factors to consider when planning your trip to Cuba. If staying overnight please locate a non government, privately owned boutique hotel that has reputable reviews. This not only keeps you in compliance with US laws and regulations but also helps the local economy of the Cuban people.
For passengers on the day trip flight please remember to meet your driver by 4:00 PM to secure your ride to the airport for your 5:00 PM departure.
Booking and Scheduling Tips
Book your trip as far in advance as possible! Trips must be booked at least 48 hours in advance to ensure that proper paper work goes through as well as your tour and transportation are properly arranged.
To inquire for a potential booking please fill out the trip request form seen on this page. Or feel free to call or email us at any time.
Our Cuba Charter Flight was absolutely stunning, to say the least. We took our plane all over Cuba, visited fabulous beaches & explored local villages. Amazing.
If you want to experience something like no other, charter a boat a plane to Cuba. Our trip to the island was like a step back in time, not to mention beautiful.
Gallery
Gallery
Frequently Asked Questions
How long is flight from Key West to Havana
A flight from Key West to Havana typically takes about 1hr to complete the 105 mile flight. The Havana day trip flight departs Key West once a day.
How long is the boat ride from Key West to Cuba?
A boat ride from Key West to Cuba normally takes 3-4 hours depending on sea conditions.
Can you go to Cuba from Key West?
Yes you can travel from Key West to Cuba. Key West airport is the hub for many departures. You can go for a Havana day trip or for as many nights as you please.
Is Key West 90 miles from Cuba?
Yes, Key West is 90 miles away from the Cuban coast. However the capital city of Havana is 105 miles away.
What's the fastest way to travel from Key West to Cuba?
By air Key West to Havana Cuba is only about an 1 hour flight.
Is there a ferry from Key West to Havana?
No, there is not a ferry to Cuba from Key West.
How do you get from Key West to Havana?
The best way to go from Key West to Havana Cuba is by air. Boat charters are also available under certain government sanctioned purposes.
Is Key West closer to Havana or Miami?
Key West is actually closer to Cuba than it is to Miami. 90 miles to Cuba vs 150 miles to Miami.
Is it possible to see Cuba from Key West?
No it is not possible to see Cuba from Key West Florida. If you are in a plane you can spot Cuba once you’re 40 miles away. From a boat you can spot Cuba when you are 15 Miles away.
Can you go to Cuba for the day from Key West?
Yes! You can take a day trip to Cuba from Key West. A Havana day trip is a legal day trip that departs Key West airport heading to Jose Marti International Airport multiple times a week. Fill out an inquiry form or give us a call to discuss.
What do United States citizens need to travel to Cuba?
American tourists are not allowed to visit Cuba for tourism reasons. United States citizens who travel to Cuba must declare a reason other than tourism from the State Departments OFAC list. A United States citizen will also need a valid passport, visa and proof of insurance.
Do you fly out of Key West International airport for a Havana day trip?
Yes, the Havana day trip flight departs Key West International airport on a weekly basis. Round trip flights to visit Cuba from Key West airport, will land in Havana at Jose Marti International airport. These legal day trips to Havana are bookable in both scheduled trips and private charters.
Are there cultural and historical connections between Key West & Cuba?
Yes there are many cultural and historical connections between Key West Cuba & the rest of the Florida Keys. This can be seen as you walk through the streets of Key West where many privately owned restaurant businesses were started by Cuban entrepreneurs. Key West Cuba.
Is Cuba Still Communist?
Cuba is a socialist state, in which the role of the Communist Party is enshrined in the Constitution. Cuba has an authoritarian government where political opposition is not permitted.
What time should I check in for my flight from Key West to Cuba?
Passengers should arrive at Key West Airport for check-in by 7:00 AM for a day trip.
Is it legal to travel from Key West To Cuba?
Travel from Key West to Havana is legal under specific guidelines set by the U.S. government.
What should I bring with me on my trip to Cuba?
Travelers should pack basic toiletries and over-the-counter medications due to shortages in Cuba.
Should I bring Cash or Card with me to Cuba?
Cash is required for travel in Cuba; U.S. credit and debit cards are not accepted due to sanctions.
Where should I stay in Cuba?
U.S. law generally prohibits staying at government-owned hotels in Cuba, requiring the use of private accommodations.
Do US citizens need a visa to go to Cuba?
A Cuban Tourist Card (visa) is required for entry into Cuba.
What customs forms do I need to do?
The D’Viajeros form is a mandatory online customs and health declaration that must be completed before arriving in Cuba.
Do I need to keep records of my trip for US customs?
U.S. law requires travelers to keep records of their trip for up to five years to prove compliance with U.S. regulations.
Which OFAC category is the most commonly used?
The most common authorized travel category is ‘Support for the Cuban People’.
What is the population of Havana Cuba?
Havana had a population of 2,137,847 inhabitants in 2022.
Book Now
&
$ave
Best Charters Best Prices



































