• 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

The Grenadines are made for exploring under sail. A long chain of islands stretches south through the warm Caribbean, from St Lucia towards Grenada.

Most passages are short enough to keep things moving, with a new island, bay or anchorage usually somewhere ahead. You will be on the helm, trimming sails, navigating between reefs and helping work out where to head next. It is proper sailing, with the reward of making landfall somewhere remarkable at the end of almost every passage. We go ashore by RIB, wander through small waterfront communities, find local bars and restaurants, swim from the yacht and spend the evenings at anchor.

Bequia is an island that still earns its living from the sea in the traditional way, with boatyards, ferries and fishermen. Mustique is the oddity, immaculate and faintly improbable, a little world of its own. Mayreau and Canouan are rougher around the edges, with village roads dropping to the water and evenings centred on a handful of bars by the shore. Then come the Tobago Cays, low and bright beyond the reefs. We anchor in the lee, swim off the boat and spend the afternoon in water clear enough to watch turtles as they swim past us.

There is something of a small expedition about the whole trip. We are working our way through a scattered island chain, with the yacht taking us to places that are awkward or impossible to reach any other way. It is adventurous without being intimidating, hands on without being relentless, and hugely rewarding. You get real sailing, beautiful anchorages, plenty of time ashore and the satisfaction of travelling through the Caribbean under sail rather than simply visiting it.

Want to join?

Most people join solo, although friends, couples, and families fit in well. You will be part of a small team from the moment you arrive, living and sailing together as a working crew rather than as passengers. Rubicon 3 is Europe’s number one rated adventure sailing company, with thousands of sailors trusting us to give them real involvement and solid instruction in remarkable places. Use the Dates and Prices button to see when this trip runs. It also gives clear guidance on travel, including where to fly and when and where to meet the boat.

 

Sailing Area

Grenadines sailing area map
Grenadines sailing route map
The Yachts

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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 journey south through the Windward Islands takes its own shape. The weather, the trade winds and the mood of the crew all play a part, so the exact route is never fixed in stone. Some days we may push further south, others we may linger in an anchorage that is simply too good to leave. That freedom is part of the point.

Below are some of the places we may find along the way.

sailing crew in caribbean

St Lucia: Setting South

We begin in St Lucia, with the twin Pitons rising above the southern coast and the Windward Islands stretching away beyond them.

Depending on the conditions, our first night may be beneath the Pitons themselves or tucked into Marigot Bay, surrounded by steep green hills and mangroves. From here we turn south, leave St Lucia astern and begin working our way down the island chain.

St Lucia Pitons

Bequia: An Island Built Around the Sea

Bequia is a place that earns its living from the water. Wooden boats sit in the harbour, fishermen work along the waterfront and old boatbuilding traditions remain part of island life. We can anchor off the village, head ashore by RIB and wander without needing much of a plan. There are small bars, beach cafés, workshops and steep roads climbing into the hills. It is the sort of place where an afternoon vanishes.

Bequia street scene

Canouan: Hills, Reefs and Quiet Anchorages

Further south, Canouan rises behind a fringe of coral reef and pale beaches. We’ll take the RIB ashore and can walk up into the hills for views across the Grenadines, with islands scattered across the sea in almost every direction. Back aboard, the evening is often wonderfully memorable with dinner on the deck, a quiet anchorage, warm air and a sky full of stars.

Canouan

The Tobago Cays: Inside the Reef

The Tobago Cays feel like the point where the journey really leaves normal life behind. A great horseshoe reef encloses a group of tiny uninhabited islands, with brilliant blue water, coral gardens and turtles feeding in the shallows. We can anchor inside the reef, swim from the yacht and explore with masks and fins as sea turtles float by. Magical.

Caribbean turtle

Union Island: The Southern Outpost

Beyond the Cays, Union Island rises sharply from the sea with 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. We love this island!

Union Island

Petit St Vincent: The Edge of the Grenadines

Near the southern edge of our journey lies Petit St Vincent, a tiny island with white sand and fringed with reef. The beaches are empty except for the occasional pair of seabirds lifting off the shore. We can head ashore and explore for a wonderful afternoon.

RIB landing on beach

Mayreau: Tiny, Quiet & Perfect

Mayreau is a very simple island, with a single village that sits along a ridge and a small church looking out across the blue sweep of the Tobago Cays. We can 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: A Different Caribbean

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 can anchor off Macaroni Beach and walk through the small village covered in flowering bougainvillea.

mustique

Dates, Prices & Travel

Start Date & Location

January 5, 2027
St Lucia

End Date & Location

January 14, 2027
St Lucia

Price

£2,399

Deposit

£999

Availability

Available

Trip Information

Start Date: January 5, 2027

Start Time: 09:00

Start Country: St Lucia

Start Port: Rodney Bay

Start Marina: Rodney Bay Marina

End Date: January 14, 2027

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 05 2027, so you will need to be in St Lucia by January 04, 2027.
  • 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 13, 2027, and you will need to disembark by 09:00 Janaury 14 2027.
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:

Start Date & Location

January 18, 2027
St Lucia

End Date & Location

January 27, 2027
St Lucia

Price

£2,399

Deposit

£999

Availability

Available

Trip Information

Start Date: January 18, 2027

Start Time: 09:00

Start Country: St Lucia

Start Port: Rodney Bay

Start Marina: Rodney Bay Marina

End Date: January 27, 2027

End Time: 12:00

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 18 2027, so you will need to be in St Lucia by January 17, 2027.
  • 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 morning of Wednesday 27th January 2027 and you will need to leave by 1200.
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:

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