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Caribbean sailing holiday: The Windward Islands

Caribbean sailing holiday: The Windward Islands

Coastal Sailing




A true sailing adventure in the southern Caribbean as we sail through the spice-laden Grenadines, with rainforests, volcanoes, coral reefs and tropical fish.

This is the Caribbean of days gone by, with deep turquoise waters, hidden anchorages and tropical islands lined with white sand beaches and soaring green mountains. Sailing from St Lucia to the Grenadines, you'll be exploring little-known isles that are off the beaten track. Bequia and Mayreau in the Grenadines are magical stopovers, as are the open-air markets of exciting St. George’s. This truly is a part of the Caribbean that remains authentic and unspoiled. Throughout, you’ll be fully involved, getting top class training and constantly building your sailing skills and experience.

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These are the available dates and routes. To book your place, please select the dates from the drop-down above the ‘Add to Cart’ button.


  • Start date / place: December 23 2022. Rodney Bay, St Lucia
  • End date / place: January 03 2023. Rodney Bay, St Lucia
  • Full price: £2,159
  • Deposit: £540


  • Start date / place: January 09 2023. Rodney Bay, St Lucia
  • End date / place: January 20 2023. Rodney Bay, St Lucia
  • Full price: £2,049
  • Deposit: £5512


  • Start date / place: December 23 2023. Rodney Bay, St Lucia
  • End date / place: January 03 2024. Rodney Bay, St Lucia
  • Full price: £2,159
  • Deposit: £540


Please see ‘TRAVEL – GETTING TO & FROM YOUR TRIP’ tab for advice on start and end points.



All crew must produce a negative Covid-19 test result within 72 hours before the start date.

This is non-refundable. On making payment, your berth is guaranteed.

Paying the balance
The balance of the invoice can be paid at any time. It must be received by Rubicon 3 90 days before the trip start date or your place will automatically be cancelled. We will remind you of the date nearer the time.

Cancellations and moving trips
Our expedition sailing yachts only have between 7 and 10 berths on them. When you book, you are committing to take one of these places. Due to these very limited numbers, we will often have turned away someone else who would have liked the berth. Unlike many other holidays, please understand this gives us little if any flexibility to make changes or to move trips. We will always endeavour to assist you (& the earlier you tell us the better), but unless we can find someone else to take your place, we usually cannot move your booking.

This is a typical itinerary for one of our sailing holidays in the Grenadines. What makes an adventure holiday so special however is that there is no fixed itinerary. The wind and the weather ultimately shape what’s possible each day but everything is very flexible within that.

A day of sail training to get everyone up to speed

As ever on Rubicon 3 trips, there’s no previous sailing experience required to get fully involved. Every Rubicon 3 trip encompasses a full ‘learn to sail’ course and today your skipper and mate will guide you through all the basics. You’ll learn about points of sail,  tacking, gybing, reefing and even how to recover a casualty over-board.

For those who have sailed before, this is all great revision and a chance to develop as a crew. If it sounds a lot, don’t worry as you have the rest of your time onboard to practise and develop your skills!


St Lucia

Breathtakingly beautiful and dominated by its world-famous Pitons, St Lucia is an almost perfect Caribbean island of jungles, white sand beaches, coral reefs and hidden bays

Carriacou and Tyrell Bay

The beautiful island of Carriacouis about 25nm north of Grenada and we pass the tiny Ronde Island on our way. We’ll drop anchor in Tyrell Bay. Known as the land of the reefs, this is a gorgeous hideaway, where you can swim or snorkel in clear waters amongst turtles, nurse sharks and golden eels. There is a backdrop of exotic coral reefs, a long white sandy beach and some further R&R!


The paradise island of Mayreau is accessible only by sea. Breath-taking, awe-inspiring, and pristine are three words that come to mind when one thinks of the island of Mayreau.  Some may call Mayreau Island “the place that time forgot”.

This is also the smallest inhabited island in the Grenadines. We’ll probably anchor in the beautiful Saltwhistle Bay, where we can swim and kayak into Half Moon Beach. If you hike to the top of the hill you’ll have spectacular views of the Tobago Cays and on the return, we’ll maybe have a few sundowners at the Saltwhistle Bay Beach Club.

The Tobago Cays

The Tobago Cays are well known as a jewel in the crown of the southern Caribbean. They are five uninhabited, beach-ringed islands that surround an amazing, sandy-bottomed lagoon.

Tobago Cays are part of a national park and wildlife reserve and the five beautiful islands are undoubtedly the main attraction.  With perfect clear turquoise waters and white sandy beaches, the Tobago Cays are simply paradise.


sailing whitsundays

There are so many adventures to be had on these gorgeous islands. There are hiking trails that criss-cross the islands of Petit Rameau and Petit Bateau, where you can walk among an abundance of tropical flora, fauna.  Snorkelling and diving in the Tobago Cays is also a  spectacle to behold!   We can swim with turtles, get up close to an octopus and see the thousands of colourful fish weave their way through the coral.

There are no restaurants on these islands, but those that frequent the Tobago Cays will tell of an even more enticing dining option: fully prepared barbecue dinners on the beach! It’s only optional but it’s very special! Our time here will give you memories for a lifetime.


Canouan is a  beautiful hook-shaped isle that has some of the most brilliant beaches in the entire Grenadines chain. There are some incredible beaches on its eastern side that are completely inaccessible by land and, weather permitting, we will be able to reach them in our RIB.


This island is the haunt of the rich and famous due to its stunning beaches and amazing blue sea. The island is privately owned and there are nearly 100 incredible mansions covering the island. Perhaps we’ll spend the evening at Basil’s Bar, famous for sitting on stilts over the Caribbean Sea.


Now we can sail to Bequia, known as the Nantucket of the Caribbean. We should find space in Port Elizabeth, Admiralty Bay. The island is a real mix of the modern and the traditional, with lots of local sailors and their hand-built boats. The brightly coloured rooftops and exotic trees sit amongst lovely restaurants and shops.

Only a short walk away from the hustle and bustle of the busy harbour and shops you can find the beautiful, secluded and as yet totally unspoiled, Princess Margaret beach.   You could go on a tour around the island, with a local guide which is absolutely fascinating and you will have amazing views from places such as Mount Pleasant.

Petit St Vincent

We now sail south, passing by Petit Tabac and Palm Island and between the sand islets Mopion and Punaise, and head east into another wonderfully sheltered anchorage on the north side of Petit St. Vincent. Paisley of green amid swirls of turquoise seas,

Petit St. Vincent, universally known as PSV, is a 115-acre volcanic island fringed with pristine beaches.  It is also home to the Cousteau dive centre and we will hopefully spend a couple of days here to try some scuba diving (beginners welcome) Diving here is a fantastic experience; keep your eyes peeled for colourful coral, fascinating fish and majestic eagle rays.


  • You should join the boat in Rodney Bay, St Lucia at 0900hrs on the start day.
  • You will disembark the boat in Rodney Bay, St Luciaat 1200 hrs on the last day.


  • St Lucia has two airports. Hewanorra International Airport (IATA code: UVF) is the main international airport but you can also fly into Castries (IATA code: SLU)



These adventure sailing holidays are open to everyone aged 18 years and over. If you are aged 70 or over, or have any concerns about your health, we ask that you get a doctor’s note before booking. This is just to make as certain as possible that you will be okay out on the water.


We provide the foul weather clothing, life-jackets and all other technical equipment you will need. You need to bring a sleeping bag and some waterproof boots.

See more information and the full kit list here


We believe that as many people as possible should be able to head out to sea and have a great adventure. However, it is essential for everyone’s safety that you are in a fit enough state to be on board. Ability to complete the five exercises below is a pre-requisite for joining as a crew member. They are not designed to be physically taxing and almost everyone should be able to complete them. Rather they are in place to check that you have the stability and basic physical condition to be on-board. If when you join the vessel the skipper believes you are not capable of completing these exercises, you will probably not be allowed to embark. If you have any doubts at all about your ability to complete these exercises safely, you must contact your doctor before attempting them.

Fitness to sail


Four weeks before your trip start date, you will be sent final joining instructions. At this time you will be asked to complete our medical declaration. At the time of booking, it is your responsibility to be sure that you will be able to pass all the criteria at the start date of your trip. If you cannot pass the criteria you will probably be refused permission to board.

See the Medical Declaration here


  • All crew must have adequate travel insurance in place for your sailing holiday.
  • We strongly recommend that you arrange insurance as soon as you book. This ideally will cover you for any mishaps, medical or otherwise, in the build-up to your holiday so that should you have to cancel, you can reclaim your fees.
  • Please note we will not refund your money or cancel your invoice due to medical issues that disqualify you from joining your trip.
  • For our latest guidance on travel insurance, please read here.


For a full explanation of what to expect with the various trip ratings please click here.


  • Foul weather clothing to keep you dry in any conditions.
  • Fladen immersion suits. These will keep you warm in even the coldest, windiest conditions.
  • Ocean-spec lifejackets. These are the best on the market.
  • All on-board food and snacks.
  • Daily sailing lessons and tuition from two highly experienced instructors.
  • RYA sailing qualifications where applicable.


  • Your travel to and from the start and end points.
  • Travel insurance (see our travel insurance page here)
  • Any alcohol – but feel free to bring your own or buy some along the route
  • Any meals you eat ashore


Everything’s included except for flights, travel insurance, a sleeping bag and some waterproof boots. There are no hidden extras.

  • These expeditions have small numbers of people on board. When you book, you are committing to being a part of the crew.
  • These are genuine adventure sailing holidays and you will be helping sail the boat, planning where we go, navigating, cooking and keeping the boat clean and tidy
  • When you book, the deposit is non-refundable. It is possible to cancel subsequently, however you may still be liable for the balance of the invoice, depending on how close you are to the start date when you cancel.
  • Please ensure you have read and agreed to the T&Cs and read the Trip Notes before booking.