When to travel south from Montreal: the month-by-month calendar
The best window for the Caribbean runs from January to April, and April offers the best balance of weather, crowds and price. The months to avoid are September and October for most destinations, but two of them run in reverse and are actually visited at that point. This calendar says what to choose, and above all what to avoid, depending on where you are going.
The question "when should we go" almost always gets the same soft answer: winter. That is true and useless, because January in Puerto Plata and January in Punta Cana are not the same week of holiday, and because the cheapest month is not the one people assume.
The overview
| Period | Caribbean weather | Crowds | Relative price | Our view |
|---|---|---|---|---|
| January | Dry, warm, the most reliable of the year | Very high | High | Perfect conditions, book far ahead |
| February | Dry and warm, sea slightly cooler | Peak during March break | The highest of the year | The school break week is the most in-demand of the calendar |
| March | Dry, warm, very stable | High early, easing late | High then moderate | Late March is an excellent compromise |
| April | Still dry, sea warmed through | Moderate | Moderate | Our first recommendation of the year |
| May | Rains begin, heat rising | Low | Low | Good value, except that sargassum is starting |
| June and July | Hot and humid | Moderate, families on holiday | Moderate | Peak of Caribbean sargassum beaching |
| August | Hot, humid, hurricane risk begins | Moderate | Moderate | Watch closely |
| September | The wettest, hurricane peak on the 10th | Very low | The lowest of the year | The month to avoid almost everywhere |
| October | Still wet, high hurricane risk | Very low | Very low | Avoid, except on Costa Rica's Caribbean coast |
| November | Rains ending, good weather returning | Low | Low | One of the best values of the year |
| December | Dry and warm | Low early, peak at Christmas | Two opposite realities | The 1st to the 18th is excellent; after that it is the most expensive |
What is the best month to travel south?
April. The rains have not started, the sea has warmed all winter, the school break and Easter have usually passed, and prices come down. It is the month our advisers take for themselves.
Two other windows are worth knowing, because they give high-season conditions at low-season prices.
- Late November. The rains are over in most destinations, the hurricane season closes on the 30th, and Christmas pricing has not yet arrived.
- The first two weeks of December. January weather, November crowds. The switch happens around 18 December, and it is abrupt.
Which month to avoid, destination by destination?
This is where generic calendars mislead. The worst month is not the same everywhere, and two destinations run on an inverted calendar.
| Destination | Best window | Month to avoid | Why |
|---|---|---|---|
| Cancún and Riviera Maya | December to April | September | Rainfall peak, hurricane peak and residual sargassum at once |
| Punta Cana | February to April | September and October | Rains and hurricane season |
| Puerto Plata | June to September | November and December | Inverted calendar: northeast trades hit the mountains |
| Samaná | January to March for the whales | No dry season | Double Punta Cana's annual rainfall |
| Jamaica | January to April | September and October | Twin rainfall peaks, in May and October |
| Costa Rica, Pacific | December to March | October | The wettest month on the Pacific slope |
| Costa Rica, Caribbean | February-March and September-October | December and July | No defined dry season on that slope |
| Bahamas | December to April | September | Rain and hurricane peak |
| Barbados | February to April | October and November | The two wettest months of the year |
| Aruba | All year | None | 450 mm of rain a year, November the wettest |
| Puerto Vallarta | December to April | September | Maximum rain and the Pacific hurricane peak |
| Los Cabos | November to May | September | The likeliest month for a Pacific hurricane |
Remember the two inversions. "December in the Dominican Republic" is excellent in Punta Cana and dreadful in Puerto Plata. "October in Costa Rica" is the worst moment on the Pacific and one of the best on the Caribbean coast.
The months that shape the calendar here
January, high season at its peak
The month when the urge to leave is strongest and the conditions are best. Nothing to fault in the weather. Plenty to say about availability: the good hotels on the good dates book four to six months ahead, which means September or October for January.
March break, the tightest week of the year
One week, every family in the province at once, and supply that does not stretch. It is when prices climb most and choice closes fastest. Six to nine months ahead is not excessive. Shifting departure by two or three days from the peak Saturday often moves the bill visibly.
April, the best week of the year
Good weather, warm sea, crowds gone, prices down. The only trap is Easter, which moves from year to year and drops a high-season week into the middle of the month.
September and October, to avoid for travelling and to seize for booking
They are the worst months to travel in the Caribbean and the best months to buy. Tour operators launch their winter programmes then, with the best season-launch promotions of the year. In short: do not go in September, book in September.
December, two months in one
From the 1st to the 18th it is one of the best windows of the year: January weather, November prices, quiet hotels. From the 19th everything changes. Christmas and New Year form the most expensive period of the calendar, with minimum stays imposed at several properties and mandatory festive dinner supplements rarely highlighted at booking.
Should you fear hurricane season?
The Atlantic season runs from 1 June to 30 November, with a statistical peak on 10 September. A trip between January and April sits entirely outside it, and the question does not arise.
For this year, one figure reverses the usual advice. El Niño is strong, and it inverts the two ocean basins. NOAA forecasts a seventy-five percent probability of a below-normal Atlantic season and a seventy percent probability of an above-normal Pacific one. Mexico's Pacific coast is therefore more exposed than the Caribbean this year.
The East Pacific also opens its season on 15 May, two weeks before the Atlantic, which almost no travel calendar mentions.
If you do travel in season, the useful protection is not the choice of month but cancellation and interruption insurance, taken out when you book.
And the sargassum, when?
The belt forms in January and February, reaches its maximum extent in June, drives the Caribbean beaching peak in June and July, then declines until November. The quietest window runs December to March, which happens to coincide with the high season here.
A trip to the Caribbean in May, June or July calls for a serious check on the beach, and for choosing a sheltered or leeward area rather than one exposed to the east. The destination-by-destination detail is in our 2026 sargassum guide.
When should you book?
- Christmas, New Year and March break: six to nine months ahead. It is a question of availability rather than price.
- January, February and March outside the break: four to six months.
- April and November: three to four months is enough.
- Low season, May to October: two to three months, and last minute becomes workable if your dates are flexible.
Last minute is a bet that is mostly lost in high season. It works when you will accept any destination and any hotel, which is not most families.
Ten strategies for paying less covers how the calendar drives the bill, and our destination comparison helps you match one to your dates.
Having your dates checked by an adviser
An adviser sees operator programmes before they go public, knows the weeks when a destination fills, and knows which dates on the Quebec school calendar push prices up this particular year. That is not the kind of information a booking site will give you.
Talk to an AquaTerra adviser at 1 866 628-6241.
Voyages AquaTerra holds a Quebec travel agency licence. Booking through an agency licensed in Quebec gives access to the Fonds d'indemnisation des clients des agents de voyages (FICAV), which covers certain specific situations; the conditions are set out on opc.gouv.qc.ca. Weather data, seasonal forecasts and air services cited here were verified on 4 September 2026.
