The high season stretches from December to April, when the weather generally stays mild and dry with rare storms and temperatures hover between the mid-70s and the low 80s. Accommodation rates and crowds hit their peak during the winter—though most of the islands around the Tobago Cays stay exclusive and pricey year round. The tradewinds are also at their peak during the winter, making this a prime time for an island-hopping bareboat cruise.
As with most of the Caribbean, the summer low season runs from June to October, which also coincides with when hurricanes blow in. While the average temps are higher in summer, it’s generally just by a few degrees, topping out in the high 80s. This is also the wettest time of year, especially in July, when most days see at least some rainfall. The bonus of the early summer months (June to August) and the shoulder season (May and November) is that some accommodations and charters offer reduced rates. Another bonus in late June? Vincy Mas—or St. Vincent’s Carnival—is in full swing, and the street party that crowns the end of this 12-day festival is one of the largest and wildest in the Caribbean.