Five Caribbean Destinations under $650 Round Trip from Toronto This Fall

Escape the brisk autumn wind of Toronto and head to one of these sunny Caribbean destinations for less than $650 return.

Hopper Editors - Oct. 26, 2017

Torontonians considering booking an autumn getaway this summer would do well to remember the ice storms and snow blizzards of last year’s winter. In fact, they’d do well to remember the ice storms and blizzards of Toronto’s winters from time immemorial. That may just be enough to get destinations like the Caribbean back into the fore for travel in the fall, when the pearly sands and turquoise reefs that glisten on the pages of travel brochures are only made better with the added bonuses of low-season hotel rates and ebbing tourist crowds.

Here are five destinations that are easily accessible from Toronto this autumn, all for under $650 return! These deals were all found using the recently launched Hopper Flight Explorer and were valid on the day of publication. The Hopper Flight Explorer makes it easy to search for cheap tickets to states, provinces, countries, regions and even whole continents, so we suggest travelers check it out for current prices to Caribbean destinations from Toronto.

Find deals on flights from Toronto to the Caribbean using the Hopper Flight Explorer and see which destinations are on sale right now!

1. Fly to Montego Bay, Jamaica, for less than $450 round trip

Do you find yourself pining for that perfectly concocted mojito? Perhaps longing for a lounge on a sunbed by a pool? Are luxurious resorts, swim-up bars and world-class concierge service your thing? Then look no further than this indirect flight connection with Delta Air from Toronto’s Pearson International Airport to Montego Bay, Jamaica – where clusters of the Caribbean’s best hotels cling to the glimmering sands of the shore. Incidentally, there’s also a nonstop flight with WestJet, taking just over four hours and costing a smidgen more for the ride.

2. Fly to Nassau, Bahamas, for less than $475 return

Photo by derekskey via Flickr.

OK so this is a pseudo-Caribbean pick, readers will have to forgive us the Bahamas because of their bountiful offering of autumnal attractions. Glazed over by the trade winds of the Atlantic, the cays and islets around Nassau enjoy a steady stream of hot weather well into October and November. Granted there’s the chance of tropical storms, but much less so than in Florida, and who could deny that the low-season here makes the brilliant white-sanded beaches more tantalizing than ever?

3. Fly to San Juan, Puerto Rico, for less than $450 round trip

Forget the Victorian Gothicism of Casa Loma and the modernist spire of the CN Tower, think instead of the cannon-blasted castles of Puerto Rico, which dot the coastal cliffs all around San Juan Bautista. They include the UNESCO-attested El Castillo San Felipe del Morro – which helped cement Spanish rule here for almost three centuries – and the Castillo de San Jeronimo – which resisted the onslaught of English invaders in the New World. Coupled with the surf swells and beaches of this tropical American island, this all makes $450 sound like a great deal for this fall, wouldn’t you agree?

4. Fly to Aruba for less than $600 round trip

Photo by WanderingtheWorld ( via Flickr.

Aruba presents a perfect Caribbean getaway this fall, as it's far south enough to miss most of the season's hurricanes – it's just a few miles off the coast of Venezuela – which means travelers can book with confidence that they won't have to rearrange their travel plans. Once in Aruba, travelers can explore the island's quaint capital city of Oranjestad and its colorful shop houses, or they can simply lounge at an all-inclusive resort and enjoy the island's white-sand beaches. Both WestJet and Air Canada offer non-stop flights from Toronto straight to Aruba, which means you're only 5.5 hours from paradise.

5. Fly to Saint Martin for less than $650 return

If you found yourself languishing in the orange and yellow hues of GTA parks last fall, feeling the long nights and crispy days of winter had come all too soon, then why not extend your party season with a trip to fun-loving Saint Martin, where the casinos, cocktail bars and beach shacks ooze energy right through the fall. Cheapest tickets on the route tend to be with US Airways and Air Canada, who operate an indirect flight to the island’s Princess Juliana International with a stopover in Philly.

Find more deals to Caribbean destinations from Toronto using the Hopper Flight Explorer!

Tweet these deals!


}(document, 'script', 'twitter-wjs');

Get the Hopper app to find the best deals.
You could save up to 40% on your next flight!