• Wave icon Trip Type: Coastal, Offshore
  • Speech bubble icon Instructors: 2
  • People icon Crew Size: Max 9
  • Cake icon Ages: 18-75
  • Pin icon Region: Caribbean & The Americas

Adventure Rating:

Low to some

Experience Required:
Low to some

12 Days from £2,799

Dates, Prices & Travel

Adventure sailing vacation: Jamaica to Cuba

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 the north shores of Jamaica and a wonderful 100-mile passage in the powerful trade winds to the south coast of Cuba, giving the crew the perfect mix of sailing and adventure.

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 Cuba Explorer that comes just after it for the ultimate Cuban sailing adventure?



Sailing Area

sailing jamaica to cuba area map
jamaica to cuba 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.

Offshore sail from Jamaica to Cuba

We set sail from the north coast of Jamaica for a passage across a stretch of the Caribbean sea to the south coast of Cuba. It is around 110 miles, so will take us around 18 hours. If the timing work out, we’ll set off really early in the morning, under the stars, and experience sunrise out on the ocean followed by a wonderful passage in the powerful trade winds, arriving late tat evening into the intoxicating atmosphere of Santiago de Cuba.

offshore saling yacht in caribbean

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

santiago de cuba

Santiago de Cuba

Santiago de Cuba, the island’s second-largest city, is a melting pot of Afro-Caribbean culture, revolutionary history, and vibrant musical traditions. Nestled against a backdrop of the Sierra Maestra mountains, this city buzzes with energy and is famed for its significant historical sites, such as the Castillo del Morro, a UNESCO World Heritage fortress that offers panoramic views of the Caribbean Sea. The city’s heart is Parque Céspedes, where the Cathedral of Santiago de Cuba stands, surrounded by colonial-era buildings echoing the city’s rich past. Santiago is also the birthplace of numerous Cuban music genres, making it a fantastic place to experience live son, salsa, and trova performances. The Santa Ifigenia Cemetery is a must-visit, housing the tomb of José Martí, a national hero.

portillo cuba

Marea Del Portillo

Marea del Portillo is a hidden gem located in the Granma Province on the southern coast of Cuba. Unlike the typical white sandy beaches Cuba is famous for, Marea del Portillo boasts distinctive dark volcanic sand. This secluded area is surrounded by the majestic Sierra Maestra mountains, creating a stunning contrast between the turquoise waters and the lush greenery of the hills. This is an excellent spot for scuba diving and snorkeling. The nearby coral reefs are home to a vast array of sea creatures, and the clear waters provide perfect visibility for underwater activities. The area is also known for several sunken ships, adding an element of mystery and adventure. Due to its remote location, Marea del Portillo remains relatively untouched by mass tourism.

jardin de la reina

Jardin De La Reina

The Jardines de la Reina archipelago was given its name by Christopher Columbus during his second voyage to the New World in 1494. Columbus was so impressed by the beauty of the 75-mile-long tropical islands that he believed them to be the most beautiful he had ever seen in all his travels. Highlights are a dive at the “Octopus’s Garden,” renowned for its vibrant coral and diverse marine life. Divers can also get up close with nurse sharks at “Shark’s Friend,” explore the shallow “Coral Labyrinth” teeming with juvenile fish, and we can all enjoy a sunset dinner at anchor, surrounded by untouched mangrove islands. Sometimes we can try kayaking through mangrove forests, rich in birdlife and juvenile marine creatures. There is La Boca de Anclitas and The Black Coral Wall, along with The Galleon a site merging amazing history with natural beauty.

trinidad cuba


Trinidad is a UNESCO World Heritage site that has beautifully preserved colonial architecture, cobblestone streets, and a vibrant cultural scene. Walking through Trinidad is like stepping back in time, where every corner offers a glimpse into the 19th century, from the historic Plaza Mayor to the Museo Romántico and the Palacio Cantero. The city is also a hub for traditional Cuban music and dance, with numerous live performances in its bars and open-air venues, especially at Casa de la Musica. Beyond its rich history and cultural offerings, Trinidad is surrounded by natural beauty, including the tranquil Ancon Beach, perfect for sunbathing and snorkeling, and the nearby Escambray Mountains.

flamingo cuba


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.


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 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 17, 2025
Montego Bay, Jamaica

End Date & Location

March 28, 2025
Cienfuegos, Havana







Trip Information

Start Date: March 17, 2025

Start Time: 09:00

Start Country: Montego Bay, Jamaica

Start Port: Montego Bay

Start Marina: Montego Bay

End Date: March 28, 2025

End Time: 10:00

End Country: Cienfuegos, Havana

End Port: Cienfuegos

End Marina: Cienfuegos

Find Flights For This Trip
Fly Into: Sangster International Airport (IATA Code: MBJ)
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 Montego Bay, Jamaica.
  • It is scheduled to be in Montego Bay.
  • It is easy to get here from Sangster International Airport.
  • The trip starts at 9:00 AM on March 17 2025, so you will need to be in Jamaica by March 16, 2025.
  • You have two options for accommodation on the night before the start date:
    • Stay in a hotel or AirBnB in Montego Bay.
    • 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 Cienfuegos, Cuba
  • The boat is scheduled to arrive into Cuba on the evening of March 27th, 2025, and you will need to disembark by 10:00 AM, March 28th, 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. However, given the nature and distance of ocean crossings, we can’t guarantee it and recommend booking flexible onward travel or at least allowing an extra day in your itinerary as a precaution.
  • 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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