December to March · Warmth instead of winter
Sailing in Winter: Sailing Trips in the Sun
When the boats are out of the water at home, the best sailing season begins in the Caribbean, the Canary Islands and Thailand. Here you will find all sailing trips from December to March that start in warm sailing areas. You book a berth and sail with a skipper.
Updated: 11 November 2026 · Redaktion toernfinder.de
from 51 providers compared
The essentials at a glance
Season
December to March, most departure dates in January and December
Duration
Usually one or two weeks
Most common departure ports
Phuket, Le Marin, Quinta do Lorde, San Miguel and Arrecife
Requirements
No sailing licence required
Week-long trip per person
usually 700–1,450 €
Current winter sailing trips in the sun
Here you can see all sailing trips that start no earlier than 1 December and end no later than 1 April, departing from the south: roughly level with Sicily and Athens or further south. Your enquiry goes directly to the provider.
Where can you sail in winter?
Where winter is the dry season or the climate stays mild. Most winter sailing trips take place in the Caribbean and on the Atlantic islands.
Caribbean
High season
From December to April is the dry season, and the trade winds blow steadily. Martinique, the Grenadines and Antigua are the major sailing areas.
Cabin Charter in the Caribbean →Canary Islands
mild, short flight
Around 20 degrees in winter and a good four hours' flight away. The trade wind often blows strongly between the islands.
Cabin charter in the Canary Islands →Cape Verde Islands
Trade winds and open sea
Long legs between the islands, plenty of wind and hardly any other yachts. Better suited to sailors with some experience.
Cabin charter in Cape Verde →Thailand
Dry season
In the Andaman Sea off Phuket, December to March is the best time for sailing, with calm weather and warm water.
Cabin charter in Thailand →Madeira
around 19 degrees
Mild climate all year round. From Funchal you can head to the Desertas or across to Porto Santo.
Cabin charter on Madeira →Across the Atlantic
Trade wind route
From November to January, many yachts sail from the Canary Islands or the Cape Verde Islands to the Caribbean.
Cabin Charter on an Atlantic Crossing →How warm is it when sailing in winter?
In Thailand and the Caribbean, daytime temperatures from December to March are between 29 and 34 degrees. In the Cape Verde Islands it is 24 to 25 degrees, and in the Canary Islands and on Madeira around 20 degrees, with chilly evenings there.
| Sailing area (measuring station) | Dec | Jan | Feb | Mar |
|---|---|---|---|---|
| Canary Islands (Santa Cruz de Tenerife) | 22 °C, 43 mm | 21 °C, 32 mm | 21 °C, 35 mm | 22 °C, 38 mm |
| Madeira (Funchal) | 20 °C, 100 mm | 19 °C, 103 mm | 19 °C, 87 mm | 20 °C, 64 mm |
| Cape Verde Islands (Sal) | 25 °C, 2 mm | 24 °C, 5 mm | 24 °C, 4 mm | 25 °C, 1 mm |
| Caribbean (Guadeloupe) | 30 °C, 137 mm | 29 °C, 84 mm | 29 °C, 64 mm | 29 °C, 73 mm |
| Thailand (Phuket) | 32 °C, 62 mm | 32 °C, 23 mm | 33 °C, 26 mm | 34 °C, 59 mm |
Average daily maximum air temperature and average monthly rainfall. Long-term averages from the national weather services, measured at one typical location in each case.
- Caribbean: Water temperature around 26 degrees. It still rains fairly often in December; February and March are the driest months.
- Canary Islands: Air temperature around 21 degrees, water around 19 degrees. You will need a warm jacket for night passages and evenings.
- Southern Mediterranean: In Sicily, Malta or southern Greece, winters are mild but often windy, and not warm enough for swimming.
If you would rather sail in the north in winter, you will need very different clothing. You will find tips in the article Sailing in Winter: Clothing and Safety.
What should you look out for on a winter sailing trip?
Above all, the flight and the wind. Many sailing trips in the Caribbean last two weeks, as the long journey out would otherwise hardly be worth it.
- Book your flight early: Flights to the Caribbean and the Canary Islands are most expensive over Christmas, New Year and the carnival school holidays.
- Trade winds: In winter, the Caribbean has steady easterly winds, often force 4 to 6 on the Beaufort scale. There is also a swell between the islands.
- Sun protection: The sun in the tropics is very strong even in winter. Pack sun cream, a hat and a long-sleeved shirt in your kit bag.
- Entry requirements: An ID card is enough for the Canary Islands and Madeira. For the Cape Verde Islands, Thailand and most Caribbean islands you will need a passport, in some cases with online registration before travel (as of November 2026).
- Hurricane season: In the Caribbean it officially ends on 30 November. The dry season with steady trade winds then begins.
You can also find sailing trips over the New Year period on Sailing over Christmas and New Year's Eve.
Törnfinder data
Winter Sailing Trips in Numbers
Analysed: all winter sailing trips in the sun published on Törnfinder. As of: 12.11.2026.
Most common departure ports
- 1Phuket32 trips
- 2Le Marin31 trips
- 3Quinta do Lorde25 trips
- 4San Miguel20 trips
- 5Arrecife17 trips
47 %of trips last 7–8 days
76 %are round trips, start and finish in the same port
17 %take place on a traditional ship or tall ship
49different departure ports
40countries on offer, led by Spain and Martinique
150 nmcovered by a typical week-long trip
As of 12.11.2026: Törnfinder lists around 340 Winter sun trips from 51 providers. 47 % last 7–8 days, 76 % are round trips with the same start and end port and 17 % take place on a traditional ship or tall ship. Most trips start in Phuket, Le Marin and Quinta do Lorde, and most departures are in January and December. A week-long trip usually costs 700–1,450 € per person.
How these figures are calculated
The analysis covers all sailing trips published on Törnfinder that take place between 1 December and 1 April and start in the south, with a start date from today onwards; the figures are recalculated twice a day. Prices are the providers' figures per person; offers for a private yacht charter with skipper, which are charged per boat, are not included in the prices. “Typically” refers to the middle half of the offers; the cheapest and the most expensive quarters are left out. The departure harbour is the port of departure named in the listing, and a round trip is a sailing trip with the same departure and destination harbour. The texts on this page are written and checked by the editorial team of toernfinder.de.
In which months do most winter sailing trips start?
In February and March. There are fewer dates in December, and over the holidays the bunks go quickly.
When the trips start
Most Winter sun trips start in January and December. Trips are available from December to March.
105
Jan87
Feb58
Mar0
Apr0
May0
Jun0
Jul0
Aug0
Sep0
Oct0
Nov88
DecAll winter sailing trips in the sun published on Törnfinder for the next twelve months. As of: 12.11.2026.
What does a sailing trip in winter cost?
Most common are week-long trips, usually 700–1,450 € per person, with a day on board costing around 130 € on average. On top of that comes the flight, which is considerably more expensive to the Caribbean than to the Canary Islands.
| Trip duration | Price per person (usually) | per day | Dates |
|---|---|---|---|
| 7–9 days, week-long trip | 700–1,450 € | around 110 € | 165 |
| 10–15 days | 1,600–2,400 € | around 130 € | 157 |
| 16 days or more | 1,650–4,150 € | around 130 € | 8 |
| Week-long trip on a traditional vessel | 2,950–3,900 € | around 440 € | 26 |
"Usually" means: the middle half of all offers falls within this range; the cheapest and most expensive quarters are not included. Click on the duration to see the corresponding trips.
On top of the trip price come travel costs and usually the ship's kitty for food, harbour fees and diesel. The box shows what typically belongs in it.
What's included in the price and what goes into the crew kitty
Included in the trip price
- Your bunk on board
- The vessel
- The skipper
Usually via the crew kitty
- Food
- Hafengeld
- Diesel
Usually around 150–300 € per person per week, depending on what the group agrees, for example whether restaurant visits are included. On some boats, meals are already included in the price.
It is best to clarify in advance with the provider exactly what is included.
Countries with the most trips
With the usual weekly price and the next departure. Each card shows the matching trips there.
Spain
81 trips
next departure 02.12.2026
week usually 790–810 € per person
Show trips →Martinique
78 trips
next departure 04.12.2026
week usually 3,250–3,950 € per person
Show trips →St Vincent and the Grenadines
56 trips
next departure 12.12.2026
week from 4,500 € per person
Show trips →Popular trip types
Besides classic crew trips, these trip types are offered most often here.
Mileage-building
23 trips
Long passages with night sailing, many miles in a short time.
next departure 05.12.2026
week usually 700–800 € per person
Show trips →Sail training
11 trips
Learn to sail on board, from the basics to the exam trip.
next departure 20.12.2026
week usually 790–1,000 € per person
Show trips →Event sailing
5 trips
By ship to Hanse Sail, Kiel Week and other harbour festivals.
next departure 05.12.2026
week from 1,450 € per person
Show trips →Frequently asked questions about winter sailing
Short answers to the questions that come up most often before a winter sailing trip.
Where can you sail in winter?
In the Caribbean, the Canary Islands, the Cape Verde Islands, Madeira and Thailand. It is warm there in winter, or at least mild. In the Mediterranean there are only a few sailing trips in winter.
Which trips does this page show?
All sailing trips on Törnfinder that start no earlier than 1 December, end no later than 1 April and depart from the south, roughly level with Sicily and Athens or further south. Trips in northern Europe are not included.
Where is it warm enough for sailing in January?
In Thailand, with around 32 degrees by day, and in the Caribbean, with around 29 degrees. In the Cape Verde Islands it is around 24 degrees, in the Canary Islands around 21 degrees.
What does a sailing trip in winter cost?
Most common are week-long trips, usually 700–1,450 € per person. Flights and the onboard kitty come on top.
How long does a winter sailing trip in the Caribbean last?
Usually two weeks, because the journey there is long and many sailing trips link several islands. In the Canary Islands, week-long trips are the norm.
Do I need a sailing licence?
No. On a cabin charter, the skipper runs the boat. You book a berth and sail as part of the crew.
Find your winter sailing trip
In the trip list you can set the dates yourself and filter by sailing area and duration.