When the northern hemisphere turns cold and grey, there are dozens of sailing destinations around the world at their absolute best. Whether you’re after the classic Caribbean trade winds or something a little further off the beaten track, this guide covers the top places to sail in December, January and February, with the honest weather and conditions data you need to plan your trip.
| Destination | For who | Skill level | Best yachts | Pros | Cons |
|---|---|---|---|---|---|
| BVI & USVI | First-timers, families, party sailors | Beginner to intermediate | All types | Best infrastructure in the Caribbean, sheltered waters, legendary spots | Very busy (and pricey) over Christmas and New Year |
| St Martin / Sint Maarten | Couples, sailors wanting seclusion | Beginner to intermediate | All types | Excellent sailing radius, quieter feel, nearby islands like Anguilla and St Barths | Less sailing infrastructure than BVI |
| Guadeloupe & Martinique | French speakers, honeymooners, families | Beginner to intermediate | All types | French culture in a Caribbean setting, great provisioning, strong charter fleet | Very popular during French school holidays |
| St Lucia | Sailors seeking dramatic scenery, island-hoppers | Beginner to intermediate | All types | Stunning landscape, great position for multi-island itineraries | Fewer charter bases than BVI or Martinique |
| The Bahamas | American sailors, divers, nature lovers | Beginner to intermediate | All types | Easy from Florida, incredible diving, festive atmosphere in December | Occasional cold fronts in Jan/Feb; less accessible from Europe |
| French Polynesia | Adventurers, remote destination seekers | Intermediate to advanced | Sailing catamarans, sailboats | Pristine atolls, very low tourist density, unique landscapes | Far from most origins, boats book out fast, more expensive to reach |
| Thailand | Asia travellers, beginners, foodies | Beginner | All types | Calm seas, easy access from almost anywhere, incredible food and culture | Light winds (not ideal for performance sailing), very touristy on land |
| Australia (Whitsundays / NSW) | Bucket-list sailors, divers, families | Beginner to intermediate | All types | Southern hemisphere summer, Great Barrier Reef, world-class scenery | Whitsundays technically in low/rainy season Dec-Feb |
| The Seychelles | Couples, luxury charterers, Indian Ocean fans | Beginner to intermediate | Catamarans, motor yachts, sailboats | Stunning islands, reliable trade winds, excellent snorkelling | Expensive; crowded during Christmas and New Year |
| The Maldives | Honeymooners, divers, sailors from Asia/Middle East | Beginner | Catamarans (shallow atolls) | Peak dry season, flat calm seas, warm water, close to India/UAE | Limited sailing culture, less variety in sailing routes |
| UAE / Dubai | Middle East residents, luxury charterers | Beginner | All types | Most comfortable time of year, world-class marinas, unusual destination | Light winds, not a traditional sailing destination |
| Mauritius | European sailors seeking an alternative, honeymoon couples | Beginner to intermediate | All types | Exotic Indian Ocean setting, strong trade winds, beautiful nature | Wettest season Dec-Feb; peak weeks very expensive |
Sailing in winter: not always the most comfortable in the Northern hemisphere
When winter hits hard in the Northern hemisphere, which is usually between December and February for most places, sailing can become quite challenging.
Not only are temperatures harsh, but the elements can be a bit wild too: wind, rain, heavy swell and other hazards that make sailing unpleasant and quite often (very) dangerous.
Obviously, this is not exactly the kind of weather where you want to lay in a bathing suit on the deck of your catamaran with your friends or family.
For these reasons, many otherwise popular sailing destinations are almost off limits between December and February. This includes a good part of the Mediterranean, especially destinations on the European side.
But should you stop your winter sailing dreams and wait for next summer to rent the yacht of your dreams? Absolutely not.
In fact, there are many destinations around the world that come into their prime precisely during these months. Some might even be closer to where you live than you’d expect.
Where are the sailing destinations where you can have sun during the winter months?
The basic rule is simple: when it’s winter in the Northern hemisphere, it’s summer in the Southern hemisphere. So one obvious answer is to go south.
But since there aren’t many southern destinations that rival the Mediterranean playground for sailing infrastructure, you’ll want to look closer to the equator. Then it’s just a matter of checking the rainy seasons of those tropical locations and avoiding them.
Ask 10 sailors where to go in winter and the answer will be 9 out of 10 times: “go to the Caribbean”. And they’re right. All Caribbean islands are at their best during these winter months: dry season, reliable trade winds, and well clear of hurricane season.
But there are plenty of other sailing destinations with equally good weather and conditions in winter that are NOT necessarily in the Caribbean. Both lists are covered below.
The best Caribbean sailing destinations for December to February
The Caribbean is the benchmark for winter sailing, and for good reason. Warm temperatures, steady trade winds, calm seas and a festive atmosphere across the islands make it hard to argue with. Here are the destinations that consistently claim the hearts of sailors during these months.
The British & US Virgin Islands: a classic winter escape for yacht enthusiasts
The British Virgin Islands (BVI) and the US Virgin Islands (USVI) are the most popular sailing destinations in the entire Caribbean, and the winter months show exactly why.
The two archipelagos sit side by side and are easy to sail between. Over 60 islands in the BVI alone, sheltered anchorages, consistent trade winds and legendary spots like The Baths on Virgin Gorda or the Soggy Dollar Bar on Jost Van Dyke make this area close to perfect for a week on the water.
December is a particularly sweet spot: the weather is warm and settled, and you arrive just before the Christmas rush drives prices up and anchorages fill. Trade winds blow at a reliable 10-15 knots from the east-southeast, temperatures sit around 26-27C, and seas are generally calm. Early December is also a great time to catch the tail of the BVI Autumn Regatta season.
January is peak season. The trade winds strengthen slightly (15-20 knots, occasionally more), which makes for excellent sailing but can mean a few rolly anchorages on exposed shores. Water temperature stays around 26C. The famous New Year’s Eve celebrations at Great Harbour on Jost Van Dyke carry well into January, and the island’s social scene is at its liveliest.
February offers some of the best conditions of the year: the winds are steadier and more predictable than December, the Christmas crowds have thinned, and the trade winds remain consistent at 12-18 knots. Sea state is typically the calmest of the three months. Many experienced sailors consider February the single best month to charter in the BVI.
If you’ve never been to the Caribbean, starting with the BVI or USVI is rarely a bad decision.
- Location: Northern Caribbean
- Spoken Language: English
- Recommended Yachts: All types of yachts are suitable
St Martin & Sint Maarten: an exclusive destination for a calm winter escape
Saint Martin and Sint Maarten share one island but two distinct identities: French on one side, Dutch on the other. Both are excellent bases for a winter charter.
The real draw is the sailing radius. From St Martin you’re a short hop from some of the most secluded spots in the northern Caribbean. Anguilla, Saint Barthelemy and St Kitts are all within reach, ideal for day trips or longer itineraries. Trade winds blow steadily at 12-18 knots from December through February, with temperatures averaging 27-28C. Seas are generally moderate and well-suited to both novice and experienced sailors.
St Martin has a reputation for secludedness and authenticity that sets it apart from the busier Caribbean hubs. If a quieter, more intimate winter sailing experience is what you’re after, this island is worth serious consideration.
- Location: Northern Caribbean
- Spoken Language: French (Saint Martin) / Dutch (Sint Maarten)
- Recommended Yachts: All types of yachts are suitable
Guadeloupe & Martinique: the two trusted Caribbean destinations for French-speaking sailors
Guadeloupe and Martinique are French overseas departments, so administratively you’re in France when you step ashore. The climate, however, is pure Caribbean. December through February is their dry season: temperatures hover around 27-29C, trade winds blow at a consistent 15-20 knots, and the seas are lively without being challenging.
French mainland sailors have been making the pilgrimage here for decades. Christmas, New Year and school holiday periods are predictably busy, but the sailing infrastructure is excellent across both islands: well-stocked marinas, good provisioning and a strong charter fleet. If you want French culture woven into a Caribbean setting, these two islands deliver it better than anywhere else.
- Location: Caribbean
- Spoken Language: French
- Recommended Yachts: All types of yachts are suitable
St Lucia: a rising favourite in the Caribbean region
St Lucia may not be the Caribbean’s most famous island for mainstream tourists, but among sailors it’s rapidly earning a top-tier reputation.
The sailing conditions during winter are excellent: trade winds averaging 15-20 knots, warm air temperatures around 28C, and sea temperatures around 27C. Its geography is dramatic from both land and sea, with the iconic Piton peaks dominating the horizon as you approach by boat. St Lucia also sits in a strategically brilliant position: with Martinique to the north, St Vincent and the Grenadines to the south, and Barbados reachable on a good day’s sail to the east, it works naturally as a hub for longer Caribbean itineraries.
If you’re planning Christmas or New Year afloat in the Caribbean, St Lucia is far from a second-tier choice.
- Location: Caribbean
- Spoken Language: English and Creole
- Recommended Yachts: All types of yachts are suitable
The Bahamas: a great playground only a short sail away from the US
The Bahamas has always been the natural winter escape for American sailors, close enough that you can sail directly from Florida to the Exumas or the Abacos without a transatlantic adventure. Technically sitting just north of the Caribbean proper, the archipelago tends to get overlooked by European visitors. Their loss.
December marks the start of the dry season: daytime temperatures around 24-27C, seas at around 25C, and the trade winds beginning to establish from the northeast at 10-15 knots. January and February see the winds strengthen slightly (15-20 knots is common) and conditions become more consistently settled. Sea state in the protected waters between the islands is generally calm and ideal for island-hopping. The famous Junkanoo Festival, a spectacular parade of colour, music and dance, kicks off on Boxing Day and again on New Year’s Day, making late December a particularly festive time to be in the Bahamas.
One note: the Bahamas can see occasional cold fronts pushing south from the US in January and February, bringing brief periods of stronger northerly winds. These pass quickly and are part of the sailing texture of the destination rather than a reason to avoid it.
- Location: North of the Caribbean
- Spoken Languages: English, Bahamian Creole
- Recommended Yachts: All yachts are suitable
Great sailing destinations in Winter that are NOT in the Caribbean
The Caribbean may get all the headlines, but it’s far from the only option. If you’re sailing from Europe, the Middle East, Asia or Africa, several of these destinations are actually closer and, in some cases, less crowded during peak weeks.
French Polynesia: a remote archipelago that you can sail all year round
French Polynesia is a destination on the rise, and it’s not hard to see why: near-perfect weather across five major archipelagos, countless atolls to explore, and a natural environment largely untouched by mass tourism.
December through February falls in the austral summer, which means warm, humid conditions with temperatures around 28-30C, occasional tropical showers, and light to moderate winds of 10-15 knots. This isn’t the driest period of the year (that’s May to October), but the conditions are still very pleasant and the marine life is exceptional. Water temperatures stay around 28C.
For something genuinely different over Christmas or New Year, French Polynesia is a compelling choice, especially if you’re based on the US West Coast, where flight connections are relatively straightforward.
Pro tip: demand consistently exceeds available boats in French Polynesia. Book well in advance.
- Location: Pacific Ocean
- Spoken Languages: French
- Recommended yachts: Sailing catamarans and sailboats
Thailand: a South East Asian paradise dry during the Northern hemisphere winter
Thailand is one of the most reliable winter sailing destinations outside the Caribbean. December through February is the dry season on the Andaman Sea side (Phuket, Phi Phi, Krabi), with almost no rainfall, temperatures around 28-30C, and gentle easterly winds of 8-15 knots. Sea conditions are calm and beginner-friendly, and water temperatures hover around 27C.
Despite its fame as a land destination, Thailand is also a serious sailing playground with calm waters and plenty of islands that aren’t overrun by mass tourism. The combination of dramatic limestone scenery, outstanding food and easy logistics makes it the most accessible Asian winter sailing option, well connected from Europe, the Middle East and Australia alike.
- Location: South East Asia
- Spoken Language: Thai
- Recommended Yachts: All kinds: motor yachts, catamarans, sailboats
The Whitsundays and the rest of Australia: a huge playground that works all year round
If you’ve always wanted to sail Australia, winter in the northern hemisphere is the right time to do it. December, January and February are full summer down under, and conditions vary depending on where you sail.
The Whitsundays, the undisputed star of Australian sailing, are warm (averaging 29C) with winds from the east-southeast at around 15 knots. Technically this falls in the low season due to higher humidity and occasional tropical showers, but it’s not a monsoon: showers tend to be brief and the sailing is still excellent. The NSW coast around Sydney is drier and sunnier during these months, and also increasingly popular for winter charters, with temperatures around 24-26C and reliable sea breezes in the 10-18 knot range.
- Location: Oceania
- Spoken Language: English
- Recommended Yachts: All kinds
The Seychelles: an exotic destination for some tropical sun from December to February
The Seychelles is one of the Indian Ocean’s finest sailing grounds, and December through February is one of its best sailing windows. The northwest monsoon brings warm temperatures around 29-30C, light to moderate winds of 10-15 knots, and generally calm seas between the islands. You may see some short rain showers, but the trade winds are blowing reliably and conditions are very pleasant for a catamaran or sailboat charter.
Christmas and New Year bring a wave of visitors, so if you’re looking for that same weather and warmth with fewer people, booking for late January or February is a smart move. Many sailors make the Seychelles a regular fixture: once you’ve island-hopped through Mahe, Praslin and La Digue, it’s hard to go back to anywhere else in the Indian Ocean.
- Location: Indian Ocean
- Spoken Languages: Seychellois Creole, English, French
- Recommended yachts: Everything: catamarans, motor yachts and sailboats
The Maldives: a perfect and sunny playground for a winter yacht trip
The Maldives are better known for overwater bungalows than yacht charters, but don’t let that fool you. December through February is peak sailing season here: the northeast monsoon delivers dry, sunny skies, temperatures around 28-30C, gentle winds of 10-15 knots, and calm, flat seas. Water temperatures are a constant 28-29C. For a catamaran exploring the shallow atolls, these conditions are close to ideal.
The Maldives also have a strong geographical advantage: they’re comfortably reachable from India, the UAE and the rest of Asia, and not dramatically further than the Caribbean for Europeans. A winter charter here is a legitimate alternative to the more obvious choices.
- Location: Indian Ocean
- Spoken Languages: Dhivehi, English, Arabic
- Recommended Yachts: Catamarans to navigate the shallow atolls
The United Arab Emirates: December to February is a pleasant season to charter a yacht in Dubai
The UAE, and Dubai in particular, makes a genuinely good winter sailing destination. These months are the most comfortable of the year, with temperatures of 22-26C, calm seas, and light winds of 8-12 knots. It’s not the most wind-blessed sailing environment, but the scenery and infrastructure are excellent and the marinas are world-class.
Beyond the Dubai marina scene, there’s more to explore along the UAE coast than most visitors realise. If you want to discover that part of the Middle East from the water rather than a hotel room, a winter charter here is an unusual and rewarding choice.
- Location: Middle East
- Spoken Languages: Arabic, English
- Recommended Yachts: All yachts are suitable
Mauritius: a great option in the Indian Ocean for a warm sailing winter trip
When it’s cold and dark in Europe, seasoned sailors know it’s time to head to Mauritius. December through February falls in the austral summer: temperatures of 28-30C, warm seas around 27C, and trade winds of 15-20 knots. It’s the wettest period of the year, so expect some tropical showers, but they’re generally short-lived and interspersed with plenty of sunshine.
Christmas and New Year bring a spike in demand and prices. Book those weeks well in advance, or consider arriving just before or after the peak to get the same weather with far less competition for anchorages and marina berths. For those looking for something different from the Caribbean or the Seychelles, Mauritius is one of the Indian Ocean’s most exotic and rewarding alternatives.
- Location: Indian Ocean, close to Madagascar
- Spoken Language: Mauritian Creole, French and English
- Recommended Yachts: All types of yachts are suitable
Still unsure about your next winter sailing vacations? Get in touch with our team to get your questions answered or receive a free quote.
