Timing
When to go
Three calendars overlap on every Caribbean trip: climate, Atlantic hurricane season, and the US school year. The planner on the home page stacks all three. This page is the reference.
Hurricane season
Official season is June 1 through November 30. More than three-quarters of Atlantic hurricanes form between mid-August and mid-October, with September 10 as the long-run statistical peak. That is a basin fact, not an island fact — Curaçao is not Jamaica.
Jan
Off
Feb
Off
Mar
Off
Apr
Off
May
Off
Jun
low activity
Jul
building
Aug
high
Sep
peak
Oct
high
Nov
low activity
Dec
Off
Storm risk by island
| Island | Relative risk | Note |
|---|---|---|
| Jamaica | high | In the main hurricane belt. Peak risk is August through October, with western Jamaica historically more exposed in late season. |
| Saint Lucia | moderate | Eastern Caribbean exposure peaks mid-August through September. The Pitons stay lush because this island gets more rain than Barbados or Curaçao. |
| The Bahamas | high | Exposed to recurving Atlantic storms, especially September and early October. Nassau is easier to reach but sits in the belt. |
| Barbados | low | Far enough south that direct hurricane hits are uncommon compared with Jamaica or the Bahamas. Still in official season June–November. |
| Antigua | moderate | Leeward Islands take Cape Verde systems in August and September. Dickenson Bay is on the calmer west coast. |
| Grenada | low | Southern Caribbean, near the edge of the belt. Direct hits are rarer than in Jamaica, Antigua, or the Bahamas. |
| Curaçao | very low | Sits south of the main hurricane belt. Direct hits are historically rare, which is why Curaçao is the usual recommendation for August–October travel. |
| Saint Vincent | low | Southern Windwards, similar to Grenada and Barbados: official season still runs June–November, but climatological risk is lower than Jamaica or the Bahamas. |
| Turks & Caicos | high | In the hurricane belt and exposed to storms that recurve toward the Bahamas. Grace Bay is still one of the best swimming beaches in the brand. |
US school holidays & busy season
Caribbean “high season” is mid-December through April because North America is cold. On top of that, Christmas week, Presidents’ Day, spring break, summer break, and Thanksgiving move both airfares and occupancy. District calendars vary; these are the windows that actually change the quote.
Winter break / Christmas week
2026-12-18 → 2027-01-04 · extreme
The most expensive week of the Caribbean year. Minimum stays are common. Book butler inventory far ahead.
Martin Luther King Jr. weekend
2027-01-15 → 2027-01-18 · elevated
Short-stay bump, especially from the East Coast into Jamaica and the Bahamas.
Presidents’ Day week
2027-02-12 → 2027-02-15 · high
A favorite couples window. Honeymoon and Valentine’s demand stacks on top of the long weekend.
Valentine’s week
2027-02-12 → 2027-02-16 · high
Sandals honeymoon demand. Overwater and swim-up butler suites go first.
US spring break window
2027-03-06 → 2027-04-12 · high
Families fill Beaches. Sandals stays busy with couples taking school-holiday weeks. Peak inside this window is mid-March.
Easter / Passover week
2027-03-26 → 2027-04-05 · high
Overlaps the late spring-break rush. Beaches Turks & Caicos is especially tight.
Memorial Day weekend
2027-05-28 → 2027-05-31 · elevated
Last easy long weekend before hurricane season. Good value relative to winter.
US summer break
2027-06-05 → 2027-08-22 · high
Family peak at Beaches. Sandals is quieter than Christmas but July is busy. August–early September is the storm-risk tradeoff for lower rates.
July 4th week
2027-07-02 → 2027-07-06 · high
A pricing spike inside summer. If you can shift a week later, rates usually ease.
Labor Day weekend
2026-09-04 → 2026-09-07 · elevated
Peak hurricane-season weekend. Curaçao, Barbados, and Grenada are the lower-risk islands.
Labor Day weekend
2027-09-03 → 2027-09-06 · elevated
Peak hurricane-season weekend. Curaçao, Barbados, and Grenada are the lower-risk islands.
Thanksgiving week
2026-11-21 → 2026-11-29 · high
Hurricane season is ending. A popular couples week with high airfares from hub cities.
Thanksgiving week
2027-11-20 → 2027-11-28 · high
Hurricane season is ending. A popular couples week with high airfares from hub cities.
Winter break / Christmas week
2027-12-17 → 2028-01-03 · extreme
The most expensive week of the Caribbean year. Book the room category you actually want, not a placeholder.
Value windows we like
Late April – early June
Spring break is over, hurricane season has not peaked, and families are still in school. One of the best couples windows.
Early June
Hurricane season has started on paper, but storm activity is usually low. Rates beat winter by a wide margin.
Late August – October (south islands)
Cheapest air and rooms of the year. Use Curaçao, Barbados, Grenada, or St. Vincent if you want to cut storm exposure.
First three weeks of November
Season is winding down, Thanksgiving has not hit yet. A quietly excellent couples window.