• 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

11 Days from £2,399

Dates, Prices & Travel

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.

Sailing Area

offshore sailing route antigua to bahamas
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 sample itinerary only showing some of the possible options for the route. The wind and weather at the time will shape what we can actually do and when.

Join the yacht, sailing & training in Antigua

Crew members join the boat in Antigua. This is one of the Leeward Islands and is full of fascinating culture, wonderful sights and perfect white sandy beaches.

There will be a real sense of excitement for the voyage to come as we help everyone get their belongings packed away and ready to start the sailing lifestyle. After safety briefings and lunch, we’ll slip lines and head out onto the water to learn new skills, revise any existing ones, and get up to speed for the sailing to come. We will practice tacking, gybing, rescuing a casualty who has fallen overboard, and all the other skills we’ll need.

caribbean sailing crew

Antigua to Nevis & St Kitts

The first couple of days, we’ll sail, train and explore around Antigua and we should get a lovely passage to Nevis & St Kitts. It means we start with short distances, lots of training time and a chance to feel at ease on board. There are also some fascinating places to explore each day on the islands.


Offshore passage to Jamaica

Our major offshore passage is a fast and exhilarating sail that, with the powerful trade winds pushing us along, should take around 4-5 days and nights at sea. Our first task is to navigate our way south of the British Virgin Islands. Depending on the wind angle, this first section can have more challenging conditions, but then we turn west for a fast and utterly exhilarating downwind sail past the south coasts of Puerto Rico, the Dominican Republic and Haiti. Cuba lies ahead, so we turn south and make landfall on the north coast of Jamaica.

offshore saling yacht in caribbean

Note: these are true sailing adventures!

These are true sailing adventures that require more than just a presence on board—they demand enthusiasm, teamwork, and a positive spirit from each crew member. To fully embrace and benefit from these experiences, it’s crucial that crew come prepared to contribute actively to the life and tasks on the vessel. Those who step up with the right attitude will find that the rewards are immense. Not only will you gain new skills and face exhilarating challenges, but you’ll also forge deep connections with fellow adventurers and create memories that last a lifetime.

Dates, Prices & Travel

Start Date & Location

February 18, 2025

End Date & Location

February 28, 2025
Montego Bay, Jamaica







Trip Information

Start Date: February 18, 2025

Start Time: 09:00

Start Country: Antigua

Start Port: Jolly Harbour (TBC)

Start Marina: Jolly Harbour (TBC)

End Date: February 28, 2025

End Time: 10:00

End Country: Montego Bay, Jamaica

End Port: Montego Bay

End Marina: Montego Bay

Find Flights For This Trip
Fly Into: Antigua (IATA code: ANU)
Fly Out of: Sangster International Airport (IATA Code: MBJ)

* Flights are not included in the trip price.

Important Notes
Joining the boat
  • You will join the boat in Antigua
  • It is scheduled to be in Jolly Harbour
  • The trip starts at 9:00 AM on February 18 2025, so you will need to be in Antigua by February 17, 2025.
  • You have two options for accommodation on the night before the start date:
    • Stay in a hotel or AirBnB.
    • 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 Montego Bay, Jamaica
  • The boat is scheduled to arrive into Jamaica on the evening of February 27, 2025, and you will need to disembark by 10:00, February 28, 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 from Jamaica 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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