Caribbean
30 Trips
Sailing trips & holidays
The sailing you've always wanted to do
Single berths and cabins on fully crewed boats, run by operators we know. Long weekends through to ocean passages.
Logged in the SailTies app
- 50,000Sailors
- 187,000Voyages
- 18.2mNautical miles
- 185Countries
As seen in
Where do you want to sail?
Explore our sailing grounds. Somewhere is always in season.
- Caribbean
MediterraneanMediterranean
22 Trips
Atlantic OceanAtlantic Ocean
12 Trips
- Americas
Americas
16 Trips
ArcticArctic
United KingdomUnited Kingdom
13 Trips
Southern Africa and Indian OceanSouthern Africa and Indian Ocean
4 Trips
What kind of sailing trip are you after?
Explore collections built around what you want out of the trip.
Featured
Mile builders · 32 Trips
Qualifying passages for your Yachtmaster logbook.
Somewhere you can only reach by boatSomewhere you can only reach by boat · 33 Trips
Anchorages, islands and inlets with no road in.
Solo travellerSolo traveller · 98 Trips
Trips with single berths still open. No boat, no crew, no limits.
RacingRacing · 28 Trips
Crew places on classic offshore and inshore races.
TrainingTraining · 17 Trips
RYA courses and practical qualifications afloat.
Long weekendsLong weekends · 20 Trips
Three or four nights, one flight, back for Monday.
Once in a lifetimeOnce in a lifetime · 33 Trips
The passages people plan their year around.
Not sure what you're ready for?
Four levels, in plain language, so you can rule trips in or out without guessing.
Level 1
BeginnerBeginner · 80 Trips
No experience needed. The crew will teach you what you need as you go.
Level 2
IntermediateIntermediate · 22 Trips
You have sailed before and can take a watch with someone alongside you.
Level 3
AdvancedAdvanced · 13 Trips
Night watches, heavy weather and passages where you are relied on.
Levels 1-3
Open to allOpen to all
Mixed crews, where experience is welcome and inexperience is fine.
Sailing trips leaving soon
Get on a boat within days. Less time scrolling, more time on the water.
- Advanced4.8
RYA Yachtmaster Prep Course & Exam
United Kingdom · Europe
Next: 16 - 21 November 2026
1 date in November
£1,150
- Open to all4.8
ARC Atlantic Crossing
Spain & St. Lucia · Europe
Next: 18 November - 20 December 2026
1 date in November
£10,000
- Open to all
ARC Atlantic Crossing – Canary Islands to Saint Lucia
Spain & St. Lucia · Europe
Next: 22 November - 13 December 2026
2 dates in 2026 & 2027
£7,495
- Open to all
Croisière Formation FFV dans les Grenadines
Martinique · Caribbean
Next: 28 November - 5 December 2026
14 dates in 2026 & 2027
€1,490
- Intermediate & Advanced
Atlantic Rally for Cruisers (ARC)
Spain & St. Lucia · Europe
Next: 29 November - 18 December 2026
1 date in November
£6,110
- Open to all
Wind & Waves Seminar
U.S. Virgin Islands · Caribbean
Next: 3 - 7 December 2026
2 dates in December
$3,850
- Beginner & Intermediate
St Lucia Christmas Cruise
St. Lucia · Caribbean
Next: 19 - 26 December 2026
1 date in December
€1,520
€1,90020% off
- Open to all5.0
The Grenadines - Caribbean Christmas
Grenada & Martinique · Caribbean
Next: 20 December 2026 - 2 January 2027
1 date in December
€3,200
€3,80015% off
Book with confidence with SailTies
A team of sailors who have your back
We will help you pick the right trip and be there if anything unexpected happens.
Every operator vetted
We only list operators we know personally or have been recommended by past customers. All trips are checked before they go live.
Terms published upfront
Cancellation and refund terms shown on every trip page before you pay a deposit.
Talk to a sailor
Our team sail, and they'll tell you honestly what a trip is like and whether it's right for you.
Sailing trip reviews from the boat
Reviews can only be left by sailors who were on the boat.
Trusted by 50,000 sailors
Kirsty Sutherland
August 2026
Great sailing, lovely crew
“Perfect introduction to non-stop ocean sailing, and night watches. We were blessed with plenty of solar/celestial activity, but most of all a professional and friendly crew who were generous with their time and expertise, and very lovely and thoughtful on top.”
Jay Baum
July 2026
An amazing training opportunity at a world-famous racing event
“I'm a resonably experienced club sailor with some racing experience on smaller keelboats. When I realized I would be visiting the south coast during the Round the Island Race, I went looking for a chance to join a crew. I didn't want to over-sell my experience, and finding a new class of boat (for me) and an organizer like Tim (who was looking to make the event a training day in which we would all have a chance to learn and practice our skills) was the perfect fit. With an experienced skipper and a crew with diverse sailing sailing backgrounds, we worked well together and helped each other in our various roles. Tim focused on communication and timing, making sure we knew what to do, and what to do next. Finishing in in the top half of our class was a proud moment considering we all met for the first time at 5am on race day.”
Andrew Buchan
July 2026
Fantastic sail
“Quite simply, it was a fantastic day. Tim was brilliant, as was everyone else on board. It was great to rotate responsibilities throughout the day, giving everyone the chance to experience all aspects of sailing. It was a fantastic way to pick up new sailing tips, build confidence, and have a great deal of fun along the way. I would highly recommend these sails!”
Dan Fullerton
July 2026
RTI 2026
“The day was absolutely brilliant, Tim who organised the event did an exceptional job, Richard the Skipper was a local so knew the Solent like the back of his hand so the boat sailed well at all times, Niomi who ran the bow definitely knew her stuff and when there was a problem sorted promptly so we could still sail competitively. To say none of us as crew had meet before hand everyone got on and did there rolls and helped others out if people where struggling a bit. By the end of the day everyone could do everything and do it well. I would definitely recommend Seatrails as a company. Hopefully I will sail with them again.”
Always on the lookoutJoin Mike's list
Mike Pickering chooses the operators and approves every trip with a simple test: is this something we'd want to sail ourselves.
He sends a short email when he feels there are trips worth personally telling you about.
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Sailing guides
Guides and stories from our skippers and crew.
6 min readWhat to Pack as Crew on a Sailing TripFind Sailing Crew
What to Pack as Crew on a Sailing Trip
Crew on a sailing trip need one soft bag, non-marking shoes, three clothing layers and good sun protection. The boat usually supplies the safety gear.
4 min readHow to Join a Sailing Crew With No ExperienceFind Sailing Crew
How to Join a Sailing Crew With No Experience
You can join a sailing crew with zero experience. Plenty of skippers want enthusiastic beginners, as long as you're honest, fit enough, and willing to follow instructions.
4 min readHow to Find Sailing CrewFind Sailing Crew
How to Find Sailing Crew
Sailors who find crew fastest are specific about what they offer, use more than one channel and reply within a day. Here is how to do it.
Photos & videos from our sailing trips
Taken by the people who were there, attached to the reviews they left.
Gift vouchers
Give the gift of sailing
A SailTies gift voucher works on any trip we offer, from a first taster day to an ocean crossing. Choose the amount, add a message, and send it now or on the day.
Send it on Christmas morning: pick the date and we'll email it at 8am.
Questions people ask before booking a sailing trip
Can I book on my own?
Yes, and most people do. Trips are sold by the berth, so you join a crew rather than needing to bring one. Cabins are shared with someone of the same sex unless you book a whole cabin.
Do I need sailing experience?
It depends on the trip, and every listing says which level it is written for. Beginner trips assume you have never sailed; advanced trips assume you can stand a night watch without supervision.
What's included in the price?
The berth, the skipper and crew, and the running of the boat. Flights, insurance and most meals ashore are not. Every trip page lists what is and is not included before you pay.
What happens if I need to cancel?
The operator's cancellation terms are published on the trip page before you pay a deposit, so you can read them before you commit. They vary by operator and by how close to departure you cancel.
What if the weather is bad?
The skipper decides the route, and changing it is normal seamanship rather than a problem. Trips are very rarely cancelled outright; when they are, the operator's terms say what happens.
Who are the operators?
Independent charter businesses and skippers we either know personally or have been recommended by past customers. Their registered business details are available upon request. All trips are checked before they go live.
The SailTies community
From the logbooks
SailTies is the leading digital logbook and sailor network. These are stories from the sailors who use it.
Three Volcanoes and a Cracked Shroud: Racing Offshore with Robert Šarić
A cracked shroud 250 miles from the Rolex Middle Sea Race finish, three volcanoes in one campaign, and why Robert Šarić of Veruda Sailing School trains his crews on the Adriatic.
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Seven of Thirteen: Elouise Pemberton's Challenge Fleet Quest
A Tall Ships bursary put Elouise Pemberton to sea at 19. Twenty years on she is working through all thirteen Challenge yachts, logging every mile on SailTies.
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46 Legs Round Britain: Jenny Whelan's Voyage with Dogsail
Jenny Whelan sailed 46 legs and 1,800 nautical miles around Britain with her partner Pete, their dog Svea, and an AI chatbot, logging every leg on SailTies.
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