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Caribbean island activities not to miss on your all inclusive vacations
As the leaves turn and the temperature drops, a familiar thought seems to creep into every Canadian workplace: “Why are we here and not at the beach?” Yeah, been there. Fall’s the sweet spot of Caribbean travel that only the savviest of vacationers know about. As crowds subside in October and November, you're greeted with warm weather, not the struggle of navigating a hectic crowd. For Canadians, this translates to more room to chill and unbeatable deals on all inclusive vacations you daydream about in Tuesday morning meetings. Plus less wait time for your drink order.
If you’re feeling a fall getaway to any of these Caribbean islands, consider our picks for must-try activities down south.
Cuba: Where vintage cars meet pristine beaches
Cuba's like that picture-perfect rom-com destination – except it's real life. Cuba all inclusive resorts offer exceptional value during the fall months, with temperatures hovering around a comfortable 25-27°C, which is basically Canadian summer. Start with Varadero Beach, a legendary 22-kilometre stretch of white sand that consistently ranks among the Caribbean's top beaches. Then lose yourself in Old Havana, a UNESCO World Heritage Site where every cobblestone street tells a story. The Catedral de San Cristóbal is also worth the walk, even in sandals. Don't miss Trinidad, another UNESCO gem that'll make you feel like you've time-travelled to the 18th century, but with better plumbing. The fall bonus? These usually busy locales are now reserved for travellers who know that timing is everything.
Jamaica: More than just (excellent) reggae and rum
The atmosphere on the island in fall is uniquely relaxed and you can take full advantage with lower prices and less crowds at Jamaica resorts. Average highs hit 29°C with a Caribbean breeze that somehow makes everything better. Everyone needs to see Dunn's River Falls and climb the terraced cascades for stunning jungle views. Seven Mile Beach in Negril, too, as it’s the kind of showstopping beach you come back for. Travel inland and you’ll find the Blue Mountains, where Jamaica's famous coffee grows – and yes, the tour includes tastings of the delicious java. With Jamaica celebrating 70 years of tourism in 2025, it’s clear to see that this island is loved – and Jamaica gives it right back to travellers with its signature blend of Caribbean charm and natural beauty.
Dominican Republic: The Caribbean's overachiever
The Dominican Republic is always having a moment, but the countless visitors each year proves this place genuinely delivers. Punta Cana resorts put you within easy access of beaches like Saona Island, where the turquoise water and white sands are so vivid they seem unreal. Take time to explore Santo Domingo, the oldest European settlement in the Americas. It’s basically history with beach access and significantly better Wi-Fi than most historical sites. For active travellers, Damajagua Waterfalls offers natural water slides that'll make your local at-home water park seem quite tragic. Fall here means temperatures around 25-29°C with significantly less rainfall than summer – perfect for those adventure tours you've been promising yourself that you'd actually do instead of just saving to your Pinterest travel board.
Freeport, Grand Bahama: Paradise with a duty-free shopping bonus
Just off Florida's coast, Freeport, Grand Bahama offers easy access to that tropical vibe, the Bahamas all inclusive experience and that sweet, sweet duty-free shopping. Gold Rock Beach, part of Lucayan National Park, offers some of the most spectacular secluded beaches that you'll find, while Deadman's Reef features shallow waters perfect for snorkelling with colourful coral and friendly sea life – the kind of underwater beauty that lobsters sing about. When you need a break from all that relaxing, Port Lucaya Marketplace provides a vibrant commercial hub where you can rub elbows with the locals. November brings cooler breezes and seven to eight hours of daily sunshine, making it ideal for outdoor activities that won’t leave you drenched in sweat.
The smart traveller's secret
Let's be honest – when our Canadian weather starts its annual cool down, there's something deeply satisfying about boarding a plane and getting the heck out of dodge. Plus, you get access to unique seasonal experiences you'd miss during peak times. The beginning of sport fishing season in Grand Bahama, golfing in Punta Cana with milder temperatures and cool sea breezes, cultural events like Jamaica’s Treasure Beach Food, Rum & Reggae festival or the International Havana Ballet in Cuba.
Fall Caribbean travel isn't only about escaping another Canadian winter (though that's certainly a perk). It's also about experiencing these incredible destinations with better weather than at home, fewer crowds and off-season pricing that makes it feel like you’re getting more than you bargained for (in a good way). Explore our fall packages and discover the Caribbean for less.
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