• 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
Introductory

Adventure Rating:
Introductory

None

Experience Required:
None

10 Days from £2,399

Dates, Prices & Travel

Discover the insanely beautiful Grenadines between St Lucia & Grenada

The Windward Islands are the Caribbean as it used to be: beautiful, welcoming and much less touched by mass tourism. We’ll sail between islands where jungle still blankets the hillsides, anchorages are quiet and the pace of life is unhurried. The trade winds are steady and reliable, giving you perfect sailing conditions, but the distances are short enough that you can be in a new world every day.

St Vincent rises steeply from the sea, volcanic and dramatic, with hidden bays and waterfalls deep in the rainforest. Bequia is all colourful markets, small wooden boatyards, and a community that still lives by the rhythms of the sea. The Tobago Cays are pure paradise: five tiny islands inside a turquoise lagoon, ringed by coral and home to grazing turtles and vivid reef fish. Mustique blends pristine beaches with understated charm, while Union Island’s jagged peaks dominate the skyline. St Lucia’s Pitons, rising straight from the water, mark one of the most iconic landfalls in the region.

Days here are simple and rich, swimming off the boat, snorkelling over coral gardens, exploring small fishing villages, or sitting down to a lobster barbecue on the beach as the sun sets. This is hands-on adventure and sailing in its truest form: taking the helm, trimming sails, and navigating through one of the most special corners of the Caribbean. Most people join solo, average ages are 30-70 and no experience is needed (you’ll get world class training and full involvement) just the appetite for adventure and the desire to get involved.

Want to join?

You’ll be sailing with Rubicon 3, Europe’s #1 rated adventure sailing company. 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

Grenadines sailing area map
Grenadines sailing route map
The Yachts

Can't see the video? You may need to adjust your cookie preferences here.

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 with PLB

  • All 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 crew 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

We’ve priced this trip 5-10% lower than we otherwise would to allow you the option, at the end of your adventure, to offer a discretionary tip to the Rubicon 3 skipper and mate if you feel they’ve provided exceptional service. A combined tip of 5-10% is suggested but is entirely at your discretion and based on your satisfaction with their performance. See our FAQs here.

Got Questions? We’re Here to Help!

We get it – joining a major sailing adventure is a big decision, and it’s natural to have lots of questions before you book. Wondering who else will be onboard? What the experience will be like? These and many more questions are completely normal. While our homepage and FAQs provide loads of info, we know sometimes it’s best to talk it through. Don’t hesitate to contact us by phone, email, or live chat (at the bottom of the screen). Better yet, we’d suggest you schedule a call. Most crew who join do and find it really useful. We can discuss your options, answer every question, and make sure you’re booking on the perfect trip for you.

Every trip through the Grenadines is different. Our route is shaped by the wind, the weather, and the preferences of the crew at the time. No two journeys are ever the same, and that’s exactly how adventure sailing should be. Below are some of the highlights we may explore along the way.

sailing crew in caribbean

Setting Sail from St Lucia – Gateway to the Windward Islands

We start and end in St Lucia, where its icnonic twin Pitons stand like sentinels over the southern coast. The first night, we may anchor beneath the towering Pitons themselves, or slip into the calm shelter of Marigot Bay, a perfect natural harbour ringed by mangroves and palm trees.

St Lucia Pitons

Bequia – The Old Mariner’s Island

Once a hub for whalers and boatbuilders, Bequia harbour is full of brightly painted wooden boats that rock gently on their moorings while fishermen mend nets under the shade of sea almond trees. Pastel houses line the waterfront, and narrow streets wind up into the hills where you’ll see goats grazing between coconut palms. We can tie up or drop anchor, wander through the village, chat with locals, eat fresh mangoes, buy handmade jewellery, or stop to sample grilled snapper at a small beachside café. The air here is always heavy with the smell of salt and hibiscus and you’ll quickly fall in love with it.

Bequia

Canouan – A Quiet Escape

Further south, Canouan is fringed with coconut palms and coral reefs. It has quiet anchorages where pelicans dive and waves break gently on powdery white sand. Ashore, a single road traces the island’s coast. We can take the RIB ashore, hike up the grassy hills for wide open views across the Grenadines chain, and that night lie back under a sky filled with stars, the boat rocking softly in the warm Caribbean breeze.

Canouan

The Tobago Cays – A Protected Paradise

Sailing deeper into the Grenadines brings us to the Tobago Cays, a cluster of uninhabited islets encircled by a horseshoe reef. Here, the water is always shifting from turquoise to deep blue. Sea turtles glide through the seagrass beds while schools of reef fish dart between brilliant corals. We might swim with stingrays, snorkel over coral gardens, or simply relax in the warm shallows and explore ashore. As night falls, we’ll be at anchor in the lee of the reef, cooking dinner aboard, and sitting beneath a sky crowded with stars.

Caribbean turtle

Union Island – The Volcanic Outpost

Beyond the Cays, Union Island rises sharply, its jagged green ridge line cutting against the horizon. In Clifton Harbour, brightly painted market stalls sell fresh limes, bananas, and coconuts, while fishermen unload their catch at the docks. The scent of grilling fish fills the sea air, with simple beach bars and reggae music spilling out into the warm evening. Further inland, goats pick their way through the brush and small farms dot the hillsides.

Union Island

Petit St Vincent – The Edge of the Grenadines

Near the southern edge of our journey lies Petit St Vincent, a tiny private island wrapped in white sand and fringed with reef. The beaches lie empty except for the occasional pair of seabirds lifting off the shore. We can swim ashore, explore the coastline on foot, or simply sit back and take in the stillness.

RIB landing on beach

Mayreau – Tiny, Quiet, Perfect

On the return north, Mayreau offers a moment of real simplicity. The island’s single village sits along a ridge, its modest church looking out across the blue sweep of the Tobago Cays. We anchor in Salt Whistle Bay, where a crescent of white sand wraps around the anchorage and coconut palms lean out over the water.

mayreau

Mustique – The Private Island with a Public Face

Mustique adds a different feel to the adventure. Though long associated with royalty and rock stars, the island remains remarkably peaceful. Empty beaches stretch for miles, sea turtles poke their heads above the waterline, and dirt roads weave quietly through the hills. We may anchor off Macaroni Beach and then walk through the small village where island staff ride bicycles beneath flowering bougainvillea. The charm of Mustique lies in its simplicity.

mustique

Returning to St Lucia – Full Circle

As we sail north once more, the familiar shape of St Lucia’s twin Pitons rise ahead, their sharp green slopes reaching skyward from the deep blue sea. The final sail brings us full circle, back to where we began. The Grenadines offer a world of their own and as we tie up once more in St Lucia, you will have that unmistakeable sense of having just discovered a very special part of the world indeed.

Caribbean beach bbq

Final thoughts…

Sailing here is warm, easy and as close to the ‘dream’ as it gets. Almost everyone joins solo, so it’s a fun and engaging way to travel, average ages are 30-65 ish and it’s usually a 50:50 mix of men and women. There is absolutely no expectation to know anything.You’ll be fully involved and get top quality training. Click ‘Dates & Prices’ to secure your place!

Dates, Prices & Travel

Start Date & Location

January 6, 2026
St Lucia

End Date & Location

January 15, 2026
St Lucia

Price

£2,399

Deposit

£999

Availability

Available

Trip Information

Start Date: January 6, 2026

Start Time: 09:00

Start Country: St Lucia

Start Port: Rodney Bay

Start Marina: Rodney Bay Marina

End Date: January 15, 2026

End Time: 09:00

End Country: St Lucia

End Port: Rodney Bay

End Marina: Rodney Bay Marina

Find Flights For This Trip
Fly Into: Hewanorra International Airport (IATA Code: UVF)
Fly Out of: Hewanorra International Airport (IATA Code: UVF)

* 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 January 6 2026, so you will need to be in St Lucia by January 5, 2026.
  • 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 Rodney Bay, St Lucia
  • The boat is scheduled to arrive into St Lucia on the evening of January 14, 2026, and you will need to disembark by 09:00 January 5 2026.
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 St Lucia 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.
Add Trip Extras

Sub total:

Start Date & Location

January 20, 2026
St Lucia

End Date & Location

January 29, 2026
St Lucia

Price

£2,399

Deposit

£999

Availability

Available

Trip Information

Start Date: January 20, 2026

Start Time: 09:00

Start Country: St Lucia

Start Port: Rodney Bay

Start Marina: Marina TBC

End Date: January 29, 2026

End Time: 10:00

End Country: St Lucia

End Port: Rodney Bay

End Marina: Marina TBC

Find Flights For This Trip
Fly Into: Hewannora St Lucia (IATA code UVF)
Fly Out of: Hewannora St Lucia (IATA code UVF)

* 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 January 20 2026, so you will need to be in St Lucia by January 19, 2026.
  • 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 Rodney Bay, St Lucia
  • The boat is scheduled to arrive into St Lucia on the evening of January 28, 2026, and you will need to disembark by 10:00 Janaury 29 2026.
General Notes
  • 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.
Add Trip Extras

Sub total:

You May Also Like

  • Norway coast
    Offshore

    Across the Norwegian Sea: Norway to Iceland

    Sail and explore the rugged, magical coast of Arctic Norway before embarking on a 700-mile offshore passage across the Norwegian Sea to Iceland. Navigate through remote islands, glaciers, and historic fishing villages, sailing under the continuous daylight of the Midnight Sun before heading off across the open ocean for a five-day crossing to Iceland, crossing the Arctic Circle on route Watch for whales, sea eagles, and the Arctic horizon stretching endlessly ahead. One of the great offshore sailing adventures.

  • sailing yacht svalbard
    Offshore

    Polar Explorer: Norway to the Wilds of Svalbard

    12 Days from £2,999

    Embark on a breathtaking sailing adventure from Norway to Svalbard. Discover majestic glaciers, encounter Arctic wildlife, and experience the magic of the polar regions. Join us for an unforgettable journey through some of the most pristine and remote landscapes on Earth.

    Quick Buy This product has multiple variants. The options may be chosen on the product page View
  • st maarten regatta header
    Coastal

    St Maarten Regatta

    11 Days from £2,499

    Join this exhilarating, week-long regatta, mixing none-too-serious but competitive yacht racing with wonderful Caribbean culture and events ashore.

    Quick Buy This product has multiple variants. The options may be chosen on the product page View