• Wave icon Trip Type: 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

36 Days from £5,499

Dates, Prices & Travel

Sail the Atlantic: Cuba – Bermuda – Azores – Scotland

Join the crew for an unparalleled adventure that promises to be the voyage of a lifetime. Join the yacht in Havana, Cuba, for a breathtaking sail across the Atlantic Ocean. This extra special route takes us north to Bermuda, to the volcanic archipelago of the Azores, and finishes on the beautiful west coast of Scotland. Imagine starting your voyage in the historic and colorful streets of Havana, where the rhythm of salsa and the aroma of Cuban cigars set the perfect mood. Our sail north to Bermuda takes us to a world of crystal-clear waters and pink sand beaches, and an island full of mysterious legends. The adventure then continues to the Azores, where volcanic landscapes and rich greenery are a wonderful change of pace from the salt, sea and sun as we cross the ocean. The voyage concludes in the rugged highlands of Scotland, a world of ancient castles and rich cultural heritage.

This is an RYA Yachtmaster Ocean qualifying passage for those who sign on as a watch leader.

Ready for the adventure of a lifetime with the offshore sailing experts?

Rubicon 3 are renowned as the offshore sailing experts, renowned in the sailing world for our extensive experience, comprehensive training, dedication to discovery, and fantastic sailing adventures. Our expert team, highly experienced sailors in ocean passage making, the Arctic, North Sea, and Norwegian Sea, offer hands-on instruction in all aspects of offshore sailing, catering to those new to offshore sailing and more seasoned sailors.

Our selection of unique bucket lists and less-traveled routes sets us apart, ensuring offshore sailing that’s both exhilarating and full of discovery. Our ethos is an unwavering commitment to safety and environmental sustainability, ensuring every voyage respects the sailors and the sea. Additionally, we are as focused on individual skill-building as a sailing school so that everyone is fully involved in every aspect of the passage. This holistic approach built Rubicon 3’s reputation as the go-to experts for anyone seeking the highest level of offshore sailing.

Want to join?

Go to the Dates & Prices button to see this trip’s dates. It will also give you information on connecting travel, including where to fly and when and where to join the boat.

Sailing Area

Cuba to scotland atlantic 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.

This is a selection of some of the special places we can visit on this Atlantic crossing. As with any long-distance ocean passage, the actual route and itinerary will be dictated by the wind and weather at the time, so other than the start and end points, none of these can be guaranteed, but we’ll be aiming for them!

Havana, Cuba

Old Havana, a UNESCO World Heritage Site, is a treasure trove of colonial architecture, culture, and rich history. Get here early and stroll through the cobblestone streets lined with their colorful buildings, and explore iconic landmarks such as Plaza Vieja, El Capitolio, and the famous Malecón. The lively atmosphere is enhanced by street musicians, local markets, and classic cars, making it a perfect introduction to Cuba’s captivating capital.


Bermuda’s stunning crystal caves are a natural wonder featuring dramatic stalactites and stalagmites reflected in crystal-clear underground lakes. There is a guided tour that offers great insight into the geological history and formation of these breathtaking caves.

Horseshoe Bay Beach is renowned for its pink sand and turquoise waters, and is one of Bermuda’s most picturesque spots. It’s ideal for swimming, snorkeling, and simply relaxing after our first long passage of the crossing.

St. George’s Town is a UNESCO World Heritage Site, and gives a great glimpse into Bermuda’s colonial past. We can wander through its narrow streets, visit the historic St. Peter’s Church, and learn a bit more about the island’s history at the Bermuda National Trust Museum.

The Azores (Faial Island)

Our most likely stop in the Azores isHorta, the main town on Faial Island. It is renowned for its picturesque marina, an iconic stop for transatlantic sailors. The marina’s walls are adorned with colorful murals and paintings left by sailors from around the world, creating a great atmosphere. After a long passage, it is lovely to stroll along the waterfront, maybe visit the Horta Museum to learn about the island’s maritime history, and have some R&R.

Peter’s Café Sport: A legendary meeting spot for sailors and visitors alike, Peter’s Café Sport is a must-visit landmark in Horta. Established in 1918, this iconic bar is famous for its ambiance, nautical memorabilia from passing yachts, and its signature gin and tonics.

Capelinhos Volcano: If we have time, you may be able to explore the dramatic landscape of the Capelinhos Volcano, the site of a volcanic eruption that occurred between 1957 and 1958. The eruption created an otherworldly terrain of ash and lava, adding a new landmass to the island.

The Isle of Mull, Scotland

We will likely make landfall on the colorful capital of the Isle of Mull, Tobermory. It is famous for its brightly painted buildings along the waterfront. We can explore the charming streets, visit its famous malt whisky distillery, and likely enjoy fresh seafood after our sea rations! If we have time we could look to visit Duart Castle, perched on a cliff overlooking the Sound of Mull or have a hike up Ben More, the island’s highest peak, with stunning views from the top.

sailing in the arc

Pre departure activities

In the build up to departure, we take time to get out sailing and really work with the crew to build skills, develop as a team and answer as many questions as we can. It means that when we finally set sail for the big crossing, you are as prepared as possible.

navigating at sea with sextant

Daily Routine at Sea

Life at sea quickly settles into a routine governed by the elements and the necessities of sailing. Each day is structured around watches, navigation checks, sail adjustments, and some boat maintenance. You’ll have day watches and night watches, when you will see star scapes unlike any you have ever seen before. When you’re not on watch, you can rest, read, gaze out over the endless horizons and spectacular sunrises and sunsets and immerse yourself in the experience of being out in the middle of the Atlantic Ocean.

under sail

Helming and Navigation

Helming, or steering the boat, is a shared responsibility, with crew members taking turns to keep the yacht on course. Modern navigation aids complement traditional methods, ensuring the yacht remains on the best path across the Atlantic. GPS, chart plotters, and weather forecasting tools are used to make well informed decisions and it’s fun to get the sextant out and learn how to navigate just using the Sun and stars.

ocean sunset

Trimming Sails and Keeping Watch

We need to keep moving as quickly and efficiently as we can, so trimming sails to suit the wind conditions is a constant task that requires attention and teamwork. Efficiency and speed depend on correctly setting the sails, a skill you will be honing with your ever-increasing experience and knowledge. Keeping watch always involves more than just watching for other vessels; it’s about monitoring weather changes and sea conditions and keeping us going fast and well.

cooking at sea

Cooking and Meals

Meals are always central events of the day, providing not just welcome food but a chance for all the crew to come together, chat and share experiences. Cooking at sea, in a confined and moving space, challenges crews to be creative with limited ingredients. It’s fun and becomes ever more fun to see what can be made with the remaining food.

Relaxing and Leisure

Despite the demands of sailing, there is plenty of time for relaxation and introspection. The vastness of the ocean offers a unique backdrop for reading, contemplation, or simply enjoying the solitude and beauty of the ocean. Watching dolphins play in the bow wave or marveling at the unobstructed view of the stars at night are experiences that stay with sailors long after the crossing is over.

arriving in the caribbean under sail

Dates, Prices & Travel

Start Date & Location

April 4, 2025

End Date & Location

May 9, 2025







Trip Information

Start Date: April 4, 2025

Start Time: 09:00

Start Country: Cuba

Start Port: Havana

Start Marina: Havana Port

End Date: May 9, 2025

End Time: 10:00

End Country: Scotland

End Port: Oban

End Marina: Oban Marina

Find Flights For This Trip
Fly Into: Havana (IATA code: HAV)
Fly Out of: Glasgow (IATA code: GLA)

* Flights are not included in the trip price.

Important Notes
Joining the boat
  • You will join the boat in Havana, Cuba
  • It is easy to get there from the airport
  • The trip starts at 9:00 AM on the start day, so you will need to be in Havana on or before Thursday April 03 2025.
  • You have two options for accommodation on the night before the start date:
    • Stay in a hotel or AirBnB in Havana
    • 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 Oban, Scotland by 10:00 am on May 09 2025
  • It is around a three hour train ride to Glasgow and its airport. Full details here.
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 back from St Lucia 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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