Offshore Sailing in the Caribbean

Iconic offshore sailing in the Caribbean from Antigua to Jamaica

Join the crew for one of the great offshore sailing passages as we sail 1000 miles downwind in the warm, powerful trade winds from Antigua to Jamaica. Beginning with coastal sailing and training around Antigua & Nevis & St Kitts, this iconic route will then set off into the Caribbean Sea for one of the great downwind trade wind routes. Leaving the Virgin Islands to our north, along with Puerto Rico, we then sail off the south coast of the Dominican Republic and Haiti before making landfall in Jamaica. For those who love warm, fast, exhilarating offshore sailing, with some exploration too, this is simply unbeatable!

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, and a dedication to adventure and discovery. Our expert team, highly experienced sailors in ocean passage making, offer hands-on instruction in all aspects of offshore sailing, catering to both those new to offshore sailing and more seasoned sailors.

What sets us apart is our selection of unique, bucket list and less-traveled routes, ensuring offshore and ocean sailing that’s both exhilarating and full of discovery. At the core of our ethos is an unwavering commitment to safety and environmental sustainability, ensuring every voyage respects both 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 the dates this trip runs. It will also give you information on connecting travel, including where to fly and when and where to join the boat.

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

We’ve priced this trip 5-10% lower than we otherwise would to allow you the option, at the end of your adventure, to offer a discretionary tip to the Rubicon 3 skipper and mate if you feel they’ve provided exceptional service. A combined tip of 5-10% is suggested but is entirely at your discretion and based on your satisfaction with their performance. See our FAQs here.

Got Questions? We’re Here to Help!

We get it – joining a major sailing adventure is a big decision, and it’s natural to have lots of questions before you book. Wondering who else will be onboard? What the experience will be like? These and many more questions are completely normal. While our homepage and FAQs provide loads of info, we know sometimes it’s best to talk it through. Don’t hesitate to contact us by phone, email, or live chat (at the bottom of the screen). Better yet, we’d suggest you schedule a call. Most crew who join do and find it really useful. We can discuss your options, answer every question, and make sure you’re booking on the perfect trip for you.