Caribbean Yacht Charters: Why Winter is the Best Time to Set Sail
Destination guide · Caribbean
Frosty mornings, icy winds, and dark afternoons by four. Or a warm deck, a steady trade wind, and a turquoise anchorage all to yourself. Caribbean yacht charters turn the British winter into the best sailing season of the year.
This guide covers why winter is the time to go, where to sail from our six Caribbean bases, and the two ways to sail the Caribbean with Seafarer: your own yacht, or a flotilla in the British Virgin Islands.
In short
Winter is the best time for Caribbean yacht charters. The dry season runs from around December to April, with steady trade winds, warm sea, and the Atlantic hurricane season (June to November) behind you. Seafarer offers bareboat charters from six Caribbean bases: the British Virgin Islands, Tortola, St Martin, Antigua, Grenada, and Martinique. You can also join our two-week BVI flotilla, which sets sail on 13/02/2027.
6
Caribbean charter bases
Dec–Apr
the Caribbean dry season
14 nights
on our February 2027 BVI flotilla
£6,050
per yacht for 14 nights on the BVI flotilla
Winter sun
Why winter is the best time for Caribbean yacht charters
While the UK shivers, the Caribbean enjoys its finest sailing weather. Winter brings sunshine, lower humidity, and reliable breezes, so you can spend your days hopping between islands and your evenings at anchor under the stars.
Steady trade winds
North-easterly trade winds blow reliably through the winter, often a little fresher around Christmas, for lively, consistent sailing.
The dry season
December to April is the driest, sunniest time of year, with lower humidity than the summer months.
Warm water
The sea stays warm all winter, perfect for snorkelling over reefs and swimming straight off the boat.
Outside hurricane season
The Atlantic hurricane season runs from June to November, so winter charters avoid it entirely.
Where to sail
Where to sail in the Caribbean
Each of our Caribbean bases has its own character, from the easy island hops of the Virgin Islands to the French flair of Martinique.
Northern Caribbean
British Virgin Islands
Our BVI base is at Scrub Island Resort. A week takes in Norman Island, Cooper Island, The Baths on Virgin Gorda, North Sound, and Jost Van Dyke. Short, line-of-sight hops make it ideal for a first Caribbean charter.
Tortola
The heart of BVI sailing. From our Tortola base, Norman Island, Jost Van Dyke, and their famous beach bars are an easy sail away.
St Martin
One island, two cultures, French and Dutch. Expect excellent restaurants, boutique shopping, lively nightlife, and white sand beaches. See St Martin charters.
Eastern and southern Caribbean
Antigua
Said to have a beach for every day of the year, plus Nelson’s Dockyard, a UNESCO World Heritage Site in English Harbour. See Antigua charters.
Grenada
The Spice Island, with rainforest, waterfalls, and quiet anchorages, and the Grenadines to explore to the north. See Grenada charters.
Martinique
French Caribbean style, with rum distilleries, coral reefs, and wonderful food. See Martinique charters.
Sail with Seafarer
Two ways to sail the Caribbean with Seafarer
Whether you want the freedom to plan your own route or the company and support of a flotilla, there’s a Caribbean sailing holiday to suit you.
Bareboat yacht charter
Six bases · your own route
- Choose from the BVI, Tortola, St Martin, Antigua, Grenada, or Martinique
- Plan your own itinerary and pace
- Check live availability online
- The skipper should hold an ICC or equivalent, and we can arrange the ICC assessment
BVI flotilla
Two weeks · from 13/02/2027
From £6,050 per yacht for 14 nights
- Starts and finishes at Hodges Creek Marina, Tortola
- Anegada, Virgin Gorda, Jost Van Dyke, and Norman Island
- Lead crew support, plus a punch party and a beach party
- Cabins on the lead yacht from £1,995 per person
New to flotillas? Read our first-timer’s guide.
Freedom
Why choose a Caribbean yacht charter?
A yacht charter gives you something a resort never can: a new island, beach, or anchorage almost every day.
- Your own pace: stay an extra night where you love it, or move on when you’re ready.
- Places only boats reach: quiet coves, reefs, and remote anchorages such as Anegada’s coral atoll.
- Great for groups: share a yacht with family or friends and enjoy a holiday together.
- Book with confidence: every holiday that includes flights is ATOL protected.
Plan your trip
How to book your Caribbean yacht charter
- Check availability: search live availability online, or call our team on 020 8324 3118.
- Choose your holiday: pick your base, yacht, and dates, or a place on the BVI flotilla.
- Add the extras: flights, transfers, and anything else you need, all arranged by our team.
Common questions
Caribbean yacht charters: your questions answered
When is the best time for a Caribbean yacht charter?
December to April. It’s the dry season, the trade winds are steady, and it falls outside the Atlantic hurricane season, which runs from June to November.
Which Caribbean destination is best for a first charter?
The British Virgin Islands. The islands sit close together and you can usually see your next stop, which makes navigation easy and passages short.
Do I need qualifications to charter a yacht in the Caribbean?
Yes, to skipper a bareboat yacht you’ll need suitable qualifications and experience. Our team can confirm what each base requires. If you’d rather not skipper, you can book a cabin on the BVI flotilla’s lead yacht.
Can I join a flotilla in the Caribbean?
Yes. Our two-week BVI flotilla sets sail from Tortola on 13/02/2027, with lead crew support and a route that takes in Anegada, Virgin Gorda, and Jost Van Dyke.
Escape the winter
Plan your Caribbean sailing holiday
Tell us when you’d like to sail and who’s coming, and we’ll help you choose between a yacht charter and the BVI flotilla.
Call or email us
Monday to Friday 09:00 to 19:00 · Saturday 09:30 to 17:00
Book with confidence. Seafarer has run sailing holidays since 1995, and every payment you make to us is financially protected: ATOL licence 9511 for holidays with flights, ABTOT member 5660 for holidays without.
