• Wave icon Trip Type: Coastal, Offshore
  • Speech bubble icon Instructors: 2
  • People icon Crew Size: Max 9 (10 for ocean)
  • Cake icon Ages: 18-70 ish
  • Pin icon Region: Caribbean & The Americas

Adventure Rating:

Low to some

Experience Required:
Low to some

11 Days from £2,499

Dates, Prices & Travel

Adventure sailing vacation: Cuba Explorer

Welcome to Cuba, an island nation rich in history, culture, and natural beauty. Get ready for some of the most beautiful beaches in the world such as Playa Sirena, vintage cars and spectacular colonial architecture. Cuba is an intoxicating mix of history, Latin American and Caribbean culture, vast mountains and mangroves. Beyond its physical attractions, Cuba’s real soul lies in its people – so warm, welcoming, and proud of their heritage, and with a shared sense of community and resilience that is truly inspiring. This expedition starts on Cuba’s southwest coast and finishes in its iconic capital, Havana.

Sail with the Experts in Off the Beaten Track Sailing Exploration

Rubicon 3 are the leading experts in off-the-beaten-path sailing adventures, renowned for taking on some of the most secluded and spectacular sailing adventures around. Our reputation is built on extensive experience, rigorous training, and a real dedication to exploring uncharted territories. The expert Rubicon 3 crew, with their hard-won experience in navigating through remote area, offer hands-on instruction in sailing, welcoming both novices and seasoned sailors looking for new challenges.

These are unique adventures that navigate away from the usual routes, giving the chance of exhilarating sailing experiences brimming with discovery. At the heart of our ethos is a deep commitment to safety and environmental stewardship, ensuring that every journey respects both the participants and the untouched natural environments we explore. This comprehensive approach has ensured Rubicon 3’s status as the go-to people for those seeking the ultimate sailing adventure off the beaten track.

Want to join?

Go to the Dates & Prices button to see the dates for this Cuba sailing holiday. It will also give you information on connecting travel, including where to fly and when and where to join the boat. Please note a Cuba Tourist Card will likely be needed. See here for details. Why not combine this with the Jamaica to Cuba expedition that comes just before it to make the ultimate Cuba sailing adventure?


Sailing Area

cuba explorer sailing area map
cienfuegos to havana sailing route map
The Yachts
Key Information
What’s included
  • All food and accommodation on board

  • All fuel & berthing fees

  • Your own bunk and storage area

  • Use of oilskins

  • Use of lifejacket

  • Sailing tuition

  • RYA Competent Crew (supplementary fee)

What’s Not included
  • Your connecting travel to & from boat

  • Sailing & travel insurance

  • Meals you choose to eat ashore

  • Alcohol

  • Visas where required

  • Discretionary tip

Interested in dates & availability?

To see when this trip runs, its start and end locations, price to join the crew and availability, click on the ‘Dates, Prices & Travel’ button up top.

Discretionary tipping of the Rubicon 3 crew

The trip price is 5% less than we would normally charge. This is to allow you at the end of your adventure to offer a combined 5-10% tip to the Rubicon 3 skipper and mate if you feel they have delivered exceptional performance. This tip is entirely discretionary. See our FAQs here.

Got some questions?

Joining a big sailing adventure is a big thing, so don’t be surprised if you have lots of questions before you book. Who else joins, what to expect, and so many more queries are entirely normal. The home page has loads of info on this (scroll to the bottom), there are our FAQs and never hesitate to contact us by email, phone or live chat. The team are here to have a chat, discuss options, answer questions and help make sure you get on the exact right sailing trip for you.

A brief history of Cuba

Before the arrival of Spanish explorer Christopher Columbus in 1492, the island was inhabited by the Taíno and Ciboney peoples, whose influence is still evident in Cuba’s cuisine, tobacco farming, and some words in the Spanish language. The Spanish colonization made Cuba a hub for the sugar and slave trades, leading to wonderful architecture in places such as La Habana (the capital Havana) which shaped its social and economic foundations. The 19th and early 20th centuries were marked by struggles for independence from Spain, culminating in the Spanish-American War in 1898 and Cuba’s formal independence in 1902. The mid-20th century saw a pivotal moment in Cuban history with the 1959 revolution led by Fidel Castro, which transformed the island into a socialist state, aligning closely with the Soviet Union during the Cold War. It continues to face economic sanctions and a degree of global isolation. The island’s history has led to a population hardened by resilience and resistance. Victualling, facilities and rules all change rapidly in Cuba. This is true off-the-beaten-track adventure and you have to be ready to accept what comes. Below is a selection of some highlights.


Cienfuegos, known as the “Pearl of the South,” is a city celebrated for its French neoclassical architecture and gentle maritime atmosphere. Having likely stopped at wonderful islandssuch as Cayo Guano and Cayo Sal en route, the city is a real change. It’s heart, Parque José Martí, is surrounded by remarkable buildings like the Tomas Terry Theater and the Catedral de la Purísima Concepción, showcasing the city’s rich cultural heritage. A stroll along the Punta Gorda, extending into the bay, reveals a wide range of architectural styles and offers stunning sea views, particularly at sunset. The nearby Palacio de Valle is an architectural marvel with its intricate Moorish designs, offering insight into the city’s luxurious past. The city is a real mix of architectural elegance, historical depth, and natural beauty, making it a quintessential Cuban experience.


Passage from Cienfuegos to Cayo Largo

It is around 70 miles from Cienfuegos to Cayo Largo, so we may do this overnight under the Caribbean stars, allowing us to arrive at this Cay in daylight hours. With so much coral around, mangroves and shifting sands, this is always wise in this part of the world. It’s an exciting and exhilarating sail that will really set you up for what is to come

offshore saling yacht in caribbean

Cayo Largo

Cayo Largo del Sur, commonly known as Cayo Largo, is part of the Canarreos Archipelago. Cayo Largo is renowned for its natural beauty, boasting some of the most beautiful beaches in the Caribbean. Playa Sirena, Playa Paraiso, and Playa Blanca are among the most popular, offering miles of soft, white sand and crystal-clear waters. The beaches are ideal for sunbathing, swimming, and enjoying breathtaking sunsets. The island’s surrounding waters are teeming with marine life, making it an excellent spot for snorkeling and diving. The coral reefs are home to a really diverse array of fish, sea turtles, and other marine species. There are often guided diving and snorkeling tours, which often include visits to shipwrecks and beautiful coral formations. The Sea Turtle Hatchery (Centro de Rescate de Tortugas Marinas) is a great place to learn about sea turtles and the conservation work being done to protect them. Depending on the season, you might also have the chance to witness turtle hatchlings making their way to the sea.

cayo largo

Cayo Rosario

Cayo Rosario has a good anchorage and is an uninhabited jewel within the Canarreos Archipelago, not far from Cayo Largo. It is world-renowned for its beaches and crystal-clear waters, and coral reefs. It is surrounded by some of the most spectacular coral reefs in the Caribbean, making it a paradise for snorkeling and diving. The waters around the island are teeming with a variety of fish, sea turtles, and other marine species.. it is only accessible by boat from Cayo Largo and has no facilities, making it a true deserted island. It is a rare escape into a world where the beauty of the natural environment is meticulously preserved.

caribbean turtle

Isla de la Juventud

Isla de la Juventud is Cuba’s second-largest island and located about 50 miles south of the mainland. It is a unique mix of history, natural beauty, and culture. Historically significant as a penal colony during both Spanish rule and later under Cuban governance, it gained notoriety for housing Fidel Castro in the Presidio Modelo, an abandoned panopticon-style prison, after his initial uprising. Isla de la Juventud is also renowned for its stunning natural landscapes, including beaches, forests, and the world-class Punta Frances Marine National Park. It encompasses a significant portion of the island’s southwestern coast, providing protection to a wide array of ecosystems, including mangroves, sea grass beds, and coral reefs. These ecosystems are home to an impressive biodiversity, including endangered species such as sea turtles and black coral. Puerto Frances itself has a beautiful beach we can enjoy.

cuba street

Cayo San Felipe

Cayo San Felipe is one of the lesser-known gems in the Canarreos Archipelago. This small, secluded island is part of the pristine and ecologically significant area that is cherished for its unspoiled natural beauty. itis famous for its rich biodiversity, including mangrove forests,  coral reefs, and an abundance of marine life. The island itself is largely uninhabited and this has helped protect its beaches, coral reefs, and the variety of wildlife that calls it home.

flamingo cuba

Maria La Gorda

Maria La Gorda is located in the westernmost part of Cuba, in the Guanahacabibes Peninsula, which is a UNESCO Biosphere Reserve. This area is renowned for its exceptional natural beauty, both above and below the water. Maria La Gorda is particularly famous among diving enthusiasts for its clear, warm waters, vcoral reefs, and a rich variety of marine life, making it one of the premier diving destinations in the Caribbean. This is a haven for colorful tropical fish, sea turtles, and various types of coral. The visibility is often excellent, allowing divers and snorkelers to have a clear view of the underwater wonders. Besides diving, Maria La Gorda is an excellent place for bird watching, hiking, and enjoying the serene beauty of Cuba’s natural landscapes.


Passage to Havana

We finish with one of the classic passages, navigating the 180 miles from the western edge of Cuba to Havana, its capital city. This is a real teaser. A little offshore, the powerful Gulf Stream can be picked up and will power you north east – but with the prevailing ENE winds, it can be a bouncy ride. Stick close to shore and you have the SW running current that slows you down. We will sail through the night under the stars, arriving into Havana as the end to this huge adventure.

The difference between Rubicon 3 and a yacht charter

This is not a luxury yacht charter vacation on a private yacht but a proper sailing adventure. 

  1. Tailored Experience: Unlike many yacht charters, the Rubicon 3 team works daily to tailor the experience to your interests and skill level. Whether you’re interested in learning advanced sailing techniques, exploring off-the-beaten-path destinations, or focusing on particular activities like snorkeling or fishing, we look to help you achieve it.
  2. Expert Knowledge: Yacht charter companies will send you off with minimal instruction. Rubicon 3 has extensive local knowledge and expertise. We can find hidden gems, secluded anchorages, and the best spots that might be off the radar of the charter companies. This insider knowledge significantly enhances the sailing adventure. 
  3. Learning Opportunities: Sailing in Cuba with Rubicon 3, you don’t need any previous sailing experience. If you’re interested in learning about sailing, navigation, or seamanship, the expert Rubicon 3 instructors ensure a hands-on, educational experience. This is ideal if you see your sailing trip as a vacation and a learning opportunity.


Dates, Prices & Travel

Start Date & Location

March 18, 2025
Cienfuegos, Cuba

End Date & Location

March 28, 2025
Havana, Cuba







Trip Information

Start Date: March 18, 2025

Start Time: 09:00

Start Country: Cienfuegos, Cuba

Start Port: Cienfuegos

Start Marina: Cienfugos

End Date: March 28, 2025

End Time: 10:00

End Country: Havana, Cuba

End Port: Havanna

End Marina: Marina Hemmingway

Find Flights For This Trip
Fly Into: José Martí international Airport (IATA Code: HAV)
Fly Out of: José Martí international Airport (IATA Code: HAV)

* Flights are not included in the trip price.

Important Notes
Joining the boat
  • You will join the boat in Cienfuegos, Cuba.
  • It is scheduled to be in Cienfuegos Harbour.
  • It is easy to get here from José Martí international Airport.
  • The trip starts at 9:00 AM on March 31 2025, so you will need to be in Svalbard by March 30, 2025.
  • You have two options for accommodation on the night before the start date:
    • Stay in a hotel or AirBnB in the Cienfuegos.
    • Alternatively, you can stay onboard the boat from 6:00 PM on a bed & breakfast basis. Select this option during your booking process.
Leaving the boat
  • You will leave the boat in Havana, Cuba.
  • The boat is scheduled to arrive into Havana on the evening of April 10, 2025, and you will need to disembark by 10:00 AM, April 11th, 2025.
General Notes
  • We have a very strong track record of meeting the scheduled end date, with only a few exceptions over a decade of sailing and across hundreds of thousands of miles of sailing.
  • You cannot stay on the boat after the trip end date.
  • Once you have booked, we will connect you up with other crew so you can liaise regarding connecting travel, meet up in advance etc.
  • If you have any questions, don’t hesitate to get in touch.
5-Point Pre-Booking Checklist

Before you finalize your booking, we suggest you run through our pre-booking checklist:

  1. Check Flights: Make sure you have found the right flights for your trip. Book them as soon as you have booked your Rubicon 3 trip.
  2. Travel Insurance: Once you’ve booked your trip with us, buy some sailing travel insurance. Read our full guide here.
  3. Passport Validity: Ensure your passport is valid for at least six months beyond your planned return date. Some countries require this for entry, so it’s crucial to check and renew your passport if necessary.
  4. Visas: Most sailors will not require any visas for this trip. However, if you are concerned, check any visa requirements for both your destination and any transit countries. If you do need a visa, processing times can vary, so it’s advisable to apply well in advance of your trip.
  5. Vaccinations and Health Checks: There are no vaccinations required for this trip. Make sure you have an acceptable level of fitness and agility. You can read our guide here. This is for the safety of all on board.
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