The Grenadines

Grenada • Carriacou • Tobago Cays • Bequia • Saint Lucia

The Trip

The Caribbean, one anchorage at a time.

Ten days sailing north through the Grenadines, from Grenada to Saint Lucia. A small group on a big catamaran, with a few hours on the water each day.

Every night we drop anchor somewhere quiet, swim off the back of the boat and cook dinner together. Most days we sail for two or three hours. The rest of the day is yours. Snorkel with the turtles in the Tobago Cays, or read on the trampoline until it's time to swim again.

No experience needed. Just curiosity.

Next departure: January 9 - 19, 2027

The Essentials.

Everything you need to know before you come aboard.

Ten days, one way. We start in Grenada and finish in Saint Lucia.
The route depends on wind and weather, and Joaquin plans each day in the morning. Places we hope to stop: Carriacou, Mayreau, Petit Tabac and the Tobago Cays, Mustique and Bequia.
Most days are two or three hours of sailing, and we anchor every night.
This trip passes through three countries: Grenada, Saint Vincent and the Grenadines, and Saint Lucia. We handle the clearance along the way. You'll need your passport on board.
Capped at 8 guests. Four of us on board with you, running the boat and the kitchen.
Joaquin, captain. Grew up in a family of sailors. Skippers the 1,500-mile passage between Mallorca and the Canaries. This experience means you can fully disconnect knowing you’re in very good hands!
Audrey, the other half of Sailing Alisios. Makes sure the trip is clear ahead of time, answers your questions, helps you plan, etc.
Josee, host. Left Alabama in a van after high school and hasn't really stopped. Freedives whenever there's water. Also hosts our Western Canaries trips.
Quinn, host. Didn't grow up travelling. Has said yes to almost everything since.
Machango, a 2021 Lagoon 46 catamaran.
Catamarans sit flat on the water. No heeling, a lot more space and a lot less seasickness. If your stomach is the reason you've never tried sailing, this is the boat to start on.
Four double cabins, each with its own bathroom and shower. A watermaker on board, so you can rinse off properly after every swim. A big outdoor table for long dinners, and a flybridge with cushions that fills up around sunset.
We strong recommend packing in soft bags only. Hard suitcases don't fit in the cabins - and we want you to have as much room as possible!
€3,000 per person, sharing a double cabin. (roughly €300 a day).
Included
- Ten days on board, with linens and towels
- All meals on board, cooked by us + food costs
- Water, coffee and tea
- Fuel, plus anchoring and marine park fees
- Safety equipment
- Paddleboards and snorkelling gear
- Dinghy rides to shore
- A pre-trip WhatsApp group
- A few surprises
Not included
- Flights to Grenada and home from Saint Lucia
- Airport transfers
- Customs and entry fees [CONFIRM]
- Meals and drinks ashore
- Alcohol and personal spending
- Travel insurance
Dietary needs? Let us know when you enquire.
None needed. Joaquin handles the navigation. Want to take the helm, trim a sail or learn how to anchor? He'll show you. Would you rather lie on the trampoline? Also totally fine!
Winter in the Caribbean is warm and steady. The trade winds blow from the east most days, and the water stays around 27°C. Expect the odd squall. Twenty minutes of rain, then sun again.
The route adapts to conditions, and Joaquin makes conservative calls.
A note on seasickness: it’s rarely something people deal with here. The water is generally calm and the passages are short, so most people feel completely fine. We still recommend picking up some Biodramina before departure, just in case. And if you do need a slower start to the day, that’s always completely fine.
Ready to go? Fill in the interest form and we'll get back to you ASAP. A deposit secures your spot. The balance is due before departure.
Cancellation: full refund if you cancel 30 or more days before departure. Within 30 days, the deposit is non-refundable. If we have to cancel, you get a full refund or a new date.
This is a one-way trip, so you'll need one-way flights. Wait until your spot is confirmed before you book them.

Meet your Grenadines team

Joaquin Escolar - Captain

Joaquin is the captain. He grew up in a family of sailers and learned these skills before anyone gave him a certificate. These days he skippers the 1,500-mile passage between Mallorca and the Canaries. This experience means you can fully disconnect knowing you’re in very good hands!

Audrey Henderson - Crew

Audrey is the other half of Sailing Alisios. She makes sure the you find the right trip for you, and looks after everything that happens before you step on board, so she's probably the one who answered your first message. This time she's coming along.

Josee Steelman - Host

Josee grew up in Alabama. After high school, she moved into a van and started travelling around the US. That turned into backpacking abroad and a real love for new cultures and new people. You’ll usually find Josee freediving or sailing. Bringing like-minded people together is her favourite.

Quinn DeVita - Host

Quinn spends most days somewhere between the ocean and the mountains, or beep bopping around the world. Quinn didn't grow up travelling, so everything since has come from saying yes to opportunities and staying open to wherever life leads. That mindset shapes every trip Quinn hosts.

Come sailing with us

How the trip unfolds.

Departure

The Spice Isle, then north.

Meet on the boat in Grenada. Settle into your cabin, learn your way around and get the first swim in before dinner. We sail north the next morning.

The Southern Grenadines

Small islands, smaller towns.

Carriacou is quiet in the way most of the Caribbean used to be. From there we clear into Saint Vincent and the Grenadines and keep moving north, one short hop at a time.

The Tobago Cays

Turtles, reef and crystal clear waters.

A handful of uninhabited islands inside a horseshoe reef. We anchor behind it, snorkel with the turtles over the seagrass and probably stay longer than planned. Petit Tabac and Mayreau are a short sail away.

Arrival

Bequia, Mustique and the Pitons.

Bequia's harbour is full of boats from everywhere, and its little town is the best stop for a walk ashore. Then comes the longest sail of the trip, across the channel to Saint Lucia with the Pitons ahead of us. Last swim, last dinner on board.

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You’ll love this trip if...

You'd like your winter to not feel like winter.
Short sails and long swims sound about right.
You've always wanted to try sailing but worried about seasickness. This is the boat for it.
You're coming on your own and want a small group that actually feels like one.