Open to all
Croisière Formation FFV dans les Grenadines
Martinique · Caribbean
Next: 7 - 14 November 2026
15 dates in 2026 & 2027
€1,490
December to April · By the berth
Winter Sun Sailing Holidays
A winter sailing holiday, one berth at a time. Join a skippered yacht for Christmas, New Year or a break in the Caribbean season. Choose an island-hopping cruise, a training week or an offshore passage, and check the experience level before you book.
- Vetted operators only
- Secure booking
- Trusted by 50,000+ sailors
Logged in the SailTies app
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As seen in
Winter trips with dates
39 trips sailing in warm water between December and April, from £170 per person.
- 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
- Intermediate & Advanced
The Atlantic Threshold: Gibraltar to the Canaries
Gibraltar & Spain · Europe
Next: 1 - 9 January 2027
1 date in 2027
€800
- Advanced5.0
Uphill to Brazil - 2200 NM Blue Water Passage
Martinique & Brazil · Caribbean
Next: 6 - 24 January 2027
1 date in 2027
€4,900
- Open to all5.0
RORC Transatlantic Race
Spain & Antigua & Barbuda · Europe
Next: 7 - 20 January 2027
1 date in 2027
€7,100
- Beginner5.0
Catamaran Bareboat certification
British Virgin Islands · Caribbean
Next: 10 - 17 January 2027
4 dates in 2027
$4,050
$4,50010% off
Hear when new winter sun trips list
Leave your name and email to get Mike's monthly email. It's where we announce new trips, so you'll hear when winter sun trips list.
Prefer to talk it through?
Christmas sailing holidays
Christmas week on a yacht, booked as one berth. Every trip here is at sea on Christmas Day, so you don't need a whole boat or a group to go. Meals, celebrations and time ashore depend on the trip, so read the itinerary.
- Beginner & Intermediate
St Lucia Christmas Cruise
St. Lucia · Caribbean
19 - 26 December 2026
1 date in December
€1,520
€1,90020% off
- Open to all5.0
The Grenadines - Caribbean Christmas
Grenada & Martinique · Caribbean
20 December 2026 - 2 January 2027
1 date in December
€3,200
€3,80015% off
- Intermediate & Advanced
The Final Push Outwards: Sardinia to Gibraltar
Italy & Gibraltar · Europe
24 - 31 December 2026
1 date in December
€800
Want more choice?
Hear when Christmas trips list
New Year sailing holidays
Trade the usual New Year plans for days on the water. Every trip here is at sea on 1 January, from island-hopping cruises to longer passages. The trip page tells you where you join, where you finish and how much sailing is involved.
- Open to all5.0
The Grenadines - Caribbean Christmas
Grenada & Martinique · Caribbean
20 December 2026 - 2 January 2027
1 date in December
€3,200
€3,80015% off
- Intermediate & Advanced
The Atlantic Threshold: Gibraltar to the Canaries
Gibraltar & Spain · Europe
1 - 9 January 2027
1 date in 2027
€800
Want more choice?
Hear when New Year trips list
Where winter trips start
Every winter sun trip with dates, by the port it leaves from. Tap a pin to see the trip.
Where to sail for winter sun
The Caribbean is the heart of the season, with warm water further afield too.
The Caribbean season
Island-hopping cruises, training weeks and regattas give you different ways to sail through winter. Pick the route and pace that suit you, not just the sunshine.
The Canaries
The closest winter sun to the UK. Trips here are often offshore legs to or from the islands rather than holiday weeks, so check the itinerary.
Brazil
Coastal cruising and longer voyages for a different winter escape. Check the route and watch-keeping requirements on each departure.
Southern Africa and the Indian Ocean
Sailing adventures that follow a route rather than sheltered holiday cruising. Check each departure's itinerary and level.
Which winter suits you?
A first sailing holiday
Look for a cruise or training trip that welcomes beginners. Ask what you'll learn and how much you'll take part on board.
A Caribbean race
Join a regatta crew for a more active winter break. Experience and practice-day requirements vary by boat and event.
A longer passage
Choose offshore sailing for the journey itself. Watch systems, night sailing and longer periods at sea are part of it.
How booking works
Choose your winter
Compare the dates, route, experience level and what is included.
Book one berth
Choose your place on the boat, not a whole-yacht charter.
Get ready to join
Read the operator's joining instructions, travel details and kit list.
Sail and log it
Meet your crew and keep your track, photos and miles in the free SailTies app.
Before you book your winter escape
The right boat for you
Compare experience levels, cabins and what the itinerary asks of you. A sunny destination doesn't make every passage a beginner trip.
Know the full cost
Read what's included before paying. Flights, transfers and shared costs on board may be extra; the operator's terms set out the details.
Ask before you go
Ask our sailing team about the route, travelling alone and choosing a trip that suits you.
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.”
Photos & videos from our sailing trips
Taken by the people who were there, attached to the reviews they left.
Gift vouchers
Give a winter escape
A SailTies gift voucher works on any trip we list, Caribbean weeks and ocean passages included. Choose the amount, add a message, and send it now or on the day.
They choose the trip and the dates.
Another way aboard
Looking for a free crew place?
Some yacht owners welcome crew who help sail and share costs. Crew Match connects skippers with sailors looking for their next boat.
The free SailTies app
Keep your winter on record
Record your track, crew, photos and daily log in the free SailTies app as you sail. Keep the miles and the memories long after you're home.
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.
Read the story
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.
Read the story
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.
Read the story
Winter sun sailing FAQs
Where can I sail for winter sun?
The Caribbean is the main winter sailing destination. Trips in the Canaries, Brazil, southern Africa and the Indian Ocean show here too when they have dates. They can be cruises or offshore passages, so check the itinerary rather than assuming every trip is a beach holiday.
When is the winter sun sailing season?
This page lists trips sailing between 1 December and 30 April, and moves on to the next season each May. Weather and conditions vary by destination, so read the operator's trip details before choosing your dates.
Can I book a Christmas sailing holiday on my own?
Yes. You book a berth, not the whole yacht. Choose a departure that includes Christmas Day and check the cabin arrangement, experience level and joining instructions on the trip page.
Are there New Year sailing holidays?
Yes, when operators list them: the New Year section above shows every trip at sea on 1 January. Each trip's itinerary explains where you sail and what is included; celebrations, meals and time ashore are not assumed.
Can beginners join a winter sun sailing trip?
Some cruises and training trips welcome beginners, while offshore passages and racing trips may ask for experience. Look for Beginner or Open to all on the trip card and check any requirements before you book.
Is 50 too old to start sailing?
Age alone doesn't decide which trip is right for you. Consider your mobility, fitness, comfort on a moving boat and what the itinerary asks. Tell the operator about any concerns and ask what taking part on board involves.
Where is the nearest winter sun sailing to the UK?
The Canaries are closer to the UK than the Caribbean. Trips there are often passages rather than holiday cruises, so check the departure and itinerary.
What does a winter sailing holiday cost?
Prices depend on the route, length, boat and what the operator includes. Each trip shows its price per person. Check flights, transfers, food and any shared costs on board before booking; don't assume a trip is all-inclusive.
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