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Caribbean Adventure Sailing Holiday

Caribbean Adventure Sailing Holiday

Coastal Sailing




Two weeks of sailing and exploring in the beautiful Grenadines. Explore Mustique, dive in the Tobago Cays and wander through rainforests and perfect white beaches.

Set amid tropical seas between the islands of St Vincent and Grenada, these tiny emerald-clad volcanic islands are a gorgeous alternative to the Caribbean's larger islands further north. They are renowned for their untouched beauty and natural landscapes. Gorgeous villages, tropical rainforests, powdery white-sand beaches and lighter winds make them a perfect sailing ground and our current absolute must visit place! Throughout, you’ll be fully involved, getting top class training and constantly building your sailing skills and experience.

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Route Map Image

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: St Lucia. December 21 2020
  • End date / place: St Lucia. January 02 2021
  • Full price: £2,299
  • Deposit: £920


  • Start date / place: St Lucia. January 04 2021
  • End date / place: St Lucia. January 15 2021
  • Full price: £1,999
  • Deposit: £800


  • Start date / place: St Lucia. January 18 2021
  • End date / place: St Lucia. January 29 2021
  • Full price: £1,999
  • Deposit: £800


  • Start date / place: St Lucia. February 15 2021
  • End date / place: St Lucia. February 26 2021
  • Full price: £1,999
  • Deposit: £800


  • Start date / place: St Lucia. March 01 2021
  • End date / place: St Lucia. March 12 2021
  • Full price: £1,999
  • Deposit: £800


  • Start date / place: St Lucia. December 23 2021
  • End date / place: St Lucia. January 05 2022
  • Full price: £2,299
  • Deposit: £920


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



This is 40% of the trip price and 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 this sailing holiday in the Grenadines. What makes these adventure holidays so special however is that there can be no fixed itinerary. The wind and the weather ultimately shape what’s possible each day!

(If you are joining us on this trip for Christmas and New Year’s Eve, it is an amazing experience and with so many option from where to choose for the big days, we will make the plans with the crew once you all join. Happy days!)

Joining day

Join the boat and get your belongings packed away and relax. There’s plenty of things to do in the future but right now it’s about relaxing, finding your way around the boat and enjoying the surroundings. After lunch, we’ll start to show you the boat, issue lifejackets and oilskins and teach you the most important skills when on board.

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 sailing 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 on board to practise and develop your skills. We’ll most likely finish the day anchored by the stunning Pitons, the world-famous symbol of St Lucia.

Downwind sailing to Bequia in the Grenadines

We’ll leave St Lucia and it’s a full day’s sailing as we head the 75nm or south to Bequia, known as the Nantucket of the Caribbean. We should find space in Port Elizabeth, Admiralty Bay and here we’ll have to do the usual check-in formalities. Bequia 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. You could go on a tour around the island which is fascinating and you will have amazing views from places such as Mount Pleasant.


After a day exploring Bequia, we have a lovely morning sail to Britannica Bay on Mustique, passing La Soufrière, a 4,000 foot high active volcano, as we go. Mustique 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.


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.


We can now sail southwest for about 25nm to the paradise island of Mayreau, accessible only by sea. 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.

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 wonderful sheltered anchorage on the north side of Petit St. Vincent. A 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) and explore this wonderful island.

Union Island

Next we take a short sail to Union Island with its dramatic volcanic mountains. We’ll anchor at Clifton harbour. There are lots of bars, restaurants and Internet cafes here and the picturesque town, Clifton, has lovely markets where we can re provision the yacht with local specialities. In the centre of the anchorage is the the man-made Happy Island with a fairly spectacular bar!  The next morning maybe you can get rid of the cobwebs and hike Mount Taboi, nearly 1,000 feet above sea level with breathtaking views.

Passage to St Lucia

Having checked out of the Grenadines at Union island, we’ll sail north again and let the yacht stretch her legs in the trade winds. It’s a good 75nm north back to St Lucia, so a wonderful last day of sailing that will stretch past sunset and when we finally arrive in Rodney Bay, everyone will be glowing and ready for a wonderful evening ashore to celebrate the last night.

Clean up and goodbyes

It’s always a surprise how quickly the time vanishes and we spend the last morning doing the boat clean up, packing away our kit, signing log books and saying cheerios to firm friends who, just two weeks ago, were unknown to us. We disembark at 1200hrs.


  • You should join the boat at 1100hrs on the start day. It is important you are not late.
  • You will disembark between 0700 and 1200hrs on the end day.
  • For the exact start and end locations, please see the ‘Dates & Prices’ tab



    • St Lucia has two airports. Hewanorra (IATA code UVF) or Castries (IATA code: SLU). The closest one to Rodney Bay is Castries, but most international flights come into Hewanorra. From Hewanorra you can take a taxi to Rodney Bay (about $60 USD) or one of the local busses (about $5 USD)


    These adventure sailing holidays are open to anyone aged 18 – 70 years. No previous sailing experience is required for this route


    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 you 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.


    • Oilskins
    • 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 can be earned 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.