Caribbean · Island Collection
From Saint Barths glamour to Turks & Caicos calm, your island, your way.
About Caribbean
Luxury Gallery
Tap any image to expand
Where You'll Stay
A shortlist of favourites, we'll match the right one to your travel style and celebration.
Chic beachfront resort
Serene pavilions on Providenciales
Private island with family villas
Sample Itinerary
Every WorldKey itinerary is bespoke. Use this as a starting point, we'll shape yours around dates, pace and the people traveling with you.
Day 1
Fast-track arrival, private transfer to your staffed villa, welcome dinner prepared by your private chef.
Day 2
Morning snorkel with a marine biologist, afternoon spa at your villa, sunset cocktails on the terrace.
Day 3
Private catamaran to a neighbouring island for a beach picnic and swimming with turtles.
Day 4
Short charter flight to St. Barths or Anguilla for a change of scene and a legendary lunch.
Day 5
Private yoga on the sand, beach barbecue with local musicians, and a last dip under the stars.
Packages & Highlights
Choose the pace that fits your trip and download a tailored highlights PDF drawn from this destination's stays, experiences, and day-by-day plan.
Price range · shown in USD
$3,200 – $17,500 USD / guest
Ranges span smart mainstream fares & 4-star hotels up to top-suite & private-jet luxury. Exchange rates fluctuate daily. Verify today's rate with a trusted source:
Verify on XE.com4 – 5 nights
A curated first taste, the icons, one signature stay, the moments no first-timer should miss.
6 – 8 nights
Our most-loved balance, deeper immersion, layered stays, and the private access we're best known for.
9+ nights
The full expression, every highlight, every stay, and the rare experiences that turn a trip into a story.
Every package is a starting point, we tailor dates, pace, and inclusions around your party.
Signature Experiences
Private yacht day to Tintamarre or the Tobago Cays
Barefoot beach dinner with local musicians
Reef snorkel with a marine biologist
Seasons & Ranges
Slide across the months to compare temperature ranges and rainfall. Highlight a season to see how it stacks up against the rest of the year.
Use ← → to move between months, Enter to pin details, Esc to clear.
Twelve-month climate summary for Caribbean. Warmest month: Jul at 89°F. Coolest month: Jan at 71°F. Wettest month: Sep with 6.7 in. Driest month: Mar with 1.8 in. Recommended travel window: Dec, Jan, Feb, Mar, Apr. Use the arrow keys to move between months. Press Enter or Space to pin details, Escape to clear.
Twelve months of climate normals. Arrow left and right to move between months. Home and End jump to January or December. Enter or Space pins a month for detailed read-out. Escape clears the selection.
Hover a month
Temperature range
Tap or hover a bar
Rainfall
Peak 6.7 in
Highest month of the year
Season averages
Highlight a season
Compare against the year
Bars show the average low-to-high temperature range; blue bars show monthly rainfall. Sparkles mark our recommended travel window.
| Month | Season | High | Low | Rainfall | Humidity | Recommended |
|---|---|---|---|---|---|---|
| Jan | Winter | 82°F | 71°F | 2.6 in | 75% | Yes |
| Feb | Winter | 83°F | 71°F | 1.9 in | 74% | Yes |
| Mar | Spring | 84°F | 72°F | 1.8 in | 73% | Yes |
| Apr | Spring | 85°F | 73°F | 2.4 in | 73% | Yes |
| May | Spring | 86°F | 75°F | 3.9 in | 75% | No |
| Jun | Summer | 88°F | 77°F | 3.4 in | 75% | No |
| Jul | Summer | 89°F | 78°F | 3.3 in | 74% | No |
| Aug | Summer | 89°F | 78°F | 4.4 in | 75% | No |
| Sep | Autumn | 88°F | 77°F | 6.7 in | 77% | No |
| Oct | Autumn | 87°F | 76°F | 6.2 in | 78% | No |
| Nov | Autumn | 85°F | 74°F | 4.5 in | 77% | No |
| Dec | Winter | 83°F | 72°F | 3.3 in | 76% | Yes |
Plan by dates
Choose your travel dates and we'll estimate likely conditions in Caribbean based on long-term monthly climate normals.
Pick a start and end date above to see estimated conditions.
A concise briefing from your WorldKey advisor, visa guidance, weather notes, and the ideal lead time to secure the finest addresses.
Download travel guide (PDF)Passport & documentation
Most islands offer visa-free entry for U.S., Canadian, U.K., and EU passports for 30 – 90 days. Requirements vary by island, your advisor will confirm any pre-arrival forms (e.g., ED cards, health declarations) for each stop on your itinerary.
Best window · December – April
Trade-wind warmth all year; December–April is the classic dry, low-humidity season for beaches and yacht days. Warm and tropical year-round (78–88°F). December through April is the reliably sunny high season; hurricane season officially runs June through November, with the highest activity August through October.
Lead-time guidance
Presidential villa weeks over Christmas, New Year, and Presidents' Week fill 10 – 12 months ahead. Late spring and early December are the best value windows and can be secured 3 – 4 months out.
Elegant resort wear, reef-safe sunscreen, and a light rain shell if traveling in shoulder months.
Entry rules and seasonal conditions can change. Your WorldKey advisor will confirm the latest visa, health, and documentation requirements for every traveler in your party before ticketing.
The next ideal window is December–April 2026. We'll email you when it's time to secure your suites, your suggested lead time is prefilled.
Verified Guest Stories
Browse verified reviews from guests who booked luxury escape trips with WorldKey, and imagine your own story.
Read Luxury Escape Reviews“The Maldives itinerary was pure poetry. Seaplane at dawn, private sandbank picnic, star-lit dinner in the lagoon.”
Tailored Quote
A few thoughtful questions to help your WorldKey advisor design an unforgettable trip to Caribbean.
Your journey, prefilled
Caribbean, Island Collection
Add to your brief
Caribbean Trip Planning FAQ
Clear answers on timing, cost, accommodations, and what to expect when you request a bespoke Caribbean quote from WorldKey Travelers.
Share your dates and wishes, a WorldKey advisor will craft a personalized Caribbean itinerary and reply within one to three business days.
You May Also Like
Curated with the same eye for detail as Caribbean, start dreaming about where you'll wander next.