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Caribbean sailing holiday: St Lucia, Grenada & the Grenadines

Caribbean sailing holiday: St Lucia, Grenada & the Grenadines

Coastal Sailing




A true sailing adventure in the southern Caribbean as we sail through the spice-laden Windward Islands, 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 Grenada, 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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This is a typical itinerary for a 14-day trip from Grenada to St Lucia (If you’re sailing from St Lucia to Grenada just reverse it!) Some trips may be a slightly different length. 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.

Day 1: Welcome on board in Grenada

Join the yacht between 1200h and 1800h in Grenada. Today is all about settling in, meeting the crew and finding your way around your home for the forthcoming sailing holiday. Grab a cold beer, enjoy the Caribbean sun and swim in the sea. Grenada is a stunning island and today you can just relax and enjoy it.

Day 2: 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! Tonight we’ll likely anchor in Dragon Bay, where you can dive on the incredible underwater sculptures.

Day 3: Sail to Carriacou and Tyrell Bay

Today it’s a lovely 4-5 hour sail north, using the easterly trade winds to get to the beautiful island of Carriacou. This is 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!

Day 4: Sailing and exploring in Mayreau

We can now use the morning for a leisurely sail on the open water to the paradise island of Mayreau, 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.

Days 5-6: 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.

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.  Snorkeling 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.

Day 7 : Canouan

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.

Day 8: Mustique

It’s a sail to Mustique next. 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.

Day 9: Bequia

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.

Day 10-11: 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.

Days 12-13: Passage to St Lucia

Finally, it’s time to check out of the Grenadines and set off for an exciting blue water sail north to St Lucia. It will take us a full day to get there. By the time we arrive, it will be night time and we will anchor by the Pitons, with a starlit sky and the magical sounds and scents of the island drifting out to us.

Day 14: Clean ups, debriefs and goodbyes

The end comes all too soon, and it’s time to put the boat back to how we found her, exchange pictures, reminisce about the trip and bid farewell to the yacht and new found friends. You’ll be free to disembark at 1200h and take a flight home that afternoon.


  • You should join the boat in Rodney Bay, St Lucia or Grenada after 1200 hrs on the start day. It is good if you can join us as close to 1200 hrs as possible, but if your flight or ferry gets in later than this, that is fine. We will ask you closer to the time to let us know your travel details.
  • You will disembark the boat in Grenada or St Lucia by 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)
  • Grenada’s airport is Maurice Bishop International Airport (IATA code: GND).



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. We really urge you not to spend any extra money unless you are sure you want to! You need to bring a sleeping bag and some waterproof boots.

See more information and the full kit list here


We are committed to helping as many people as possible have an amazing sailing holiday and experience the magic of the sea. Our skippers and mates have medical training and the boats have some medical supplies and equipment on board. However, the reality is that once on board access to professional medical assistance is going to be slower than if you were on land. If we are offshore it may be some days. For this reason we ask you to check through the medical disclosure form below before you book. If you answer yes to any of the questions, you should get in touch with us before you book. It will probably still be fine but it’s good to make sure. You will be asked to submit the form electronically 14 days before the start date, ensuring that we have the most up to date information.

See the Medical Declaration here


  • It is essential that you have adequate travel insurance in place for your sailing holiday.
  • We strongly recommend that you arrange insurance that covers you for any medical mishaps in the build up to your holiday so that should you have to cancel, you can reclaim you fees.
  • Please note we cannot refund your money or cancel your invoice due to medial issues.
  • For our latest guidance on travel insurance, please read here.


Mostly day sailing, shorter mileage and more time to head ashore and explore.


  • 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.

    Terms & Conditions