• Wave icon Trip Type: Coastal
  • 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:


Experience Required:

10 Days from £2,199

Dates, Prices & Travel

Sailing and exploring the paradise islands between St Lucia & Antigua

Take part in this majestic 12-day sailing adventure through the heart of the Caribbean, exploring the enchanting islands of St. Lucia, Martinique, Dominica, Guadeloupe, and Antigua. You’ll be sailing in the warm trade winds, arriving in a new destination every day. You’ll get to explore the islands and discover the beauty spots that often can’t be reached by land. You can anchor under the insta-famous Piton of St Lucia, enjoy the fusion of French and Caribbean culture in Martinique, explore the Indian river and jungles of Dominica, wander the magical beaches and islands of Guadeloupe and enjoy all the energy and beauty that comes with Antigua. On this route no prior sailing experience is needed. The expert Rubicon 3 instructors will ensure you are fully involved in helming, navigating and trimming sails, giving you all the tuition you need.

Ready for the trip of a lifetime with Europe’s #1 rated adventure sailors?

Rubicon 3 expeditions are genuine sailing adventures rather than luxury sailing vacations. You will be off the beaten track, possibly out on the open ocean depending on the route you choose and sailing to and exploring remote and beautiful places. The expert Rubicon 3 instructors will train you and ensure you are fully involved in all aspects of the experience, including navigating, helming, trimming sails, cooking and looking after the yacht. As a true sailing adventure, it is much less predictable (& much better!) than a packaged experience, with itineraries planned day by day and shaped by local circumstance and weather. To take part in the adventure, crew must come with the right attitude, an open mind and a desire to be fully involved.

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 to and when and where to join the boat.


Sailing Area

Leeward sailing area
Leeward Islands sailing 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 adventure is genuine: a Rubicon 3 sailing vacation in the Leeward Islands has no set itinerary. The skipper, mate and you, the crew, will look at the wind and the weather at the time and make a plan for your time on board – and that plan will likely change a few times during the expedition! You may discover a fantastic place and want to spend an extra day exploring, or the wind is from the wrong direction, so you sail somewhere off the initial plan. Making the adventure up as we go is all part of the magic of these trips in the West Indies.

Where are the Leeward Islands

The Leeward Islands are a group of islands in the Lesser Antilles chain of the Caribbean Sea. They are located southeast of Puerto Rico and north of the Windward Islands, separated by the Dominica Channel. These unspoilt, tropical islands are among the most captivating and picturesque in the Caribbean and the ideal destination for a mix of holiday and adventure. To the north, you have the US Virgin Islands and BVIs, St Kitts and Nevis, Sint Martin /St Martin/St Maarten, and St Barts.


Caribbean beach anchorage

Our route explores the southern islands, including St Lucia, Martinique, Dominica, Guadeloupe and Antigua. These are a little more off the beaten track, and gems like Dominica are ones you will never get to see on an average yacht charter.

This stretch of the Leeward Island chain is also purely coastal sailing, with around 40 miles between each island being the furthest distance we have to make. It means we will stop and discover somewhere new daily, including fascinating towns and communities, spectacular scenery rich in jungle, volcanoes, coral reefs, quiet anchorages and perfect white sand beaches. 

Allied to the trade winds, the sun and warm Caribbean sea make this a magical location for an adventure on a sailing yacht!

St Lucia

This beautiful island is celebrated for its dramatic Pitons and rainforests, including the renowned Edmund Forest Reserve and the captivating Diamond Falls Botanical Gardens. The island has a storied past marked by Franco-British rivalry, now reflected in the colonial charm of Castries and the historical richness of Pigeon Island National Park. Sulphur Springs Park is a one-of-a-kind drive-in volcano we must try if we can.

st lucia pitons


Martinique, 30 miles north of St Lucia, is steeped in history and natural beauty. The island was first settled by the Arawaks, followed by the Caribs, and was discovered by Columbus in 1502. It became a French colony in 1635, and its history is deeply intertwined with the sugar trade and the era of slavery, leaving a significant cultural impact. We can explore the haunting ruins of Saint-Pierre, once known as the “Paris of the Caribbean,” destroyed by the 1902 eruption of Mount Pelée. The island’s capital, Fort-de-France, features historic sites like Fort Saint-Louis and the Schoelcher Library. The Balata Gardens and Les Salines beach offer stunning natural escapes, while the Château Dubuc ruins echo the island’s colonial past. Martinique is an island full of natural wonders, colonial history, and vibrant Creole culture.


caribbean turtle


Dominica, known as the “Nature Island” of the Caribbean, is a tropical paradise with a world-famous coral reef. The island’s rainforests, home to the Morne Trois Pitons National Park, a UNESCO World Heritage site, offer incredible hiking trails leading to the Boiling Lake and Trafalgar Falls. It has nine volcanoes, including Morne Trois Pitons and Morne Diablotins, although all of these are currently considered dormant volcanoes. The history of this Caribbean Island is marked by indigenous Kalinago people and later European colonization, which is reflected in its culture and seen clearly in the historic capital, Roseau. The island’s volcanic terrain also creates many natural hot springs, like those in Wotten Waven, where you can swim and rest under a lush green palm tree.

Dominica anchorage


Guadeloupe is an archipelago of islands, perfect for nature lovers with its relaxed atmosphere and mesmerizing blend of natural beauty and rich history. The two islands of Basse-Terre and Grande-Terre offer quite diverse experiences. The small island of Basse-Terre is home to the Guadeloupe National Park, featuring the La Soufrière volcano and the Carbet Falls. Grande-Terre has beautiful secluded beaches like Plage de la Caravelle and charming towns like Sainte-Anne. Guadeloupe’s history, influenced by the Caribs and its colonization by France, is most evident in its Creole culture. The Memorial ACTe museum in Pointe-à-Pitre offers profound insights into the region’s past, particularly the history of slavery. With its captivating mix of natural wonders, colonial heritage, and lively Creole traditions, Guadeloupe is a beautiful place to discover.

Beach market


Antigua, a jewel in the Eastern Caribbean, has 365 beaches, one for each day of the year, with favorites like Dickenson Bay and Half Moon Bay offering crystal-clear waters and perfect white sands. The island’s rich history is highlighted in Nelson’s Dockyard in English Harbour, a beautifully restored naval dockyard and UNESCO World Heritage site, reflecting its importance during colonial times. Antigua’s capital, St. John’s, is home to the baroque St. John’s Cathedral and vibrant local markets. Shirley Heights offers a spectacular lookout point for panoramic views and is well known to all sailors.

antigua shirley heights

The Sailing Season in the Leeward Islands

The season for sailing yachts in the Leeward Islands runs from January through to April. The dates for this year can be found in our Dates & Prices tab. We usually arrive in this region in mid-December, having sailed the Atlantic Ocean in the ARC. The best time to sail and explore these islands is January to April, with steady trade winds and no risk of hurricanes (which come through June to November).

sailing crew in caribbean

The difference between Rubicon 3 and a yacht charter

This is not a luxury yacht charter vacation but a proper sailing adventure. Sailing with Rubicon 3, unlike a leeward islands yacht charter company like Sunsail or Moorings, means you’ll have a far more authentic and in-depth experience.

Landing rib on beach
  1. Tailored Experience: Unlike standard leeward islands yacht charters, every day, the Rubicon 3 team work hard to tailor the experience to your specific 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 snorkelling or fishing, we look to help you achieve it.
  2. Expert Knowledge: Yacht charter companies will send you off with minimal instruction. Rubicon 3 have 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. Unlike other yacht charter destinations, the Leeward Islands, in particular, offer places off the beaten track, such as Dominica.
  3. Learning Opportunities: 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 not just as a vacation but also as a learning opportunity.
deserted island in the caribbean


Dates, Prices & Travel

Start Date & Location

February 4, 2025
St Lucia

End Date & Location

February 13, 2025







Trip Information

Start Date: February 4, 2025

Start Time: 09:00

Start Country: St Lucia

Start Port: Rodney Bay

Start Marina: Rodney Bay Marina

End Date: February 13, 2025

End Time: 10:00

End Country: Antigua

End Port: Jolly Harbour

End Marina: Jolly Harbour

Find Flights For This Trip
Fly Into: St Lucia (IATA Code: UVF)
Fly Out of: Antigua (IATA Code: ANU)

* Flights are not included in the trip price.

Important Notes
Joining the boat
  • You will join the boat in St Lucia.
  • It is scheduled to be in Rodney Bay Marina.
  • The trip starts at 9:00 AM on February 4 2025, so you will need to be in St Lucia by February 3, 2025.
  • You have two options for accommodation on the night before the start date:
    • Stay in a hotel or AirBnB in St Lucia.
    • 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 Jolly Harbour, Antigua
  • The boat is scheduled to arrive into Antigua on the morning of February 13, 2025, and you will need to disembark by 12:00 on February 13, 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 Antigua 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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