Many people adore fall for its pumpkin-spiced everything, harvest celebrations, and approaching holidays. But if autumn just makes you dread the coming cold, then booking a tropical getaway is a pretty good way to cope. After all, plenty of islands and far-flung hotspots boast summer weather even during the fall and winter months—and they’re only a flight away.
Best Tropical Vacation Destinations for Fall and Winter
Here are eight tropical vacation destinations that deliver great weather and bargains when the mercury drops back home.
Image Gallery
![Treehouse hotel in Jamaica](https://www.smartertravel.com/wp-content/webp-express/webp-images/doc-root/wp-content/uploads/2016/09/Negril-Jamaica-700x500.jpg.webp)
Reggae music, coral reefs, and white-sand beaches are sure to make you forget about bone-chilling weather. Slow down and snorkel in Negril, Jamaica, with unique all-inclusive lodging rather than the giant resorts so many visitors frequent.
Romantic treehouse-style villas at the adults-only Sunset at the Palms will let you relax in the treetops of Jamaica's beloved rainforests—where you can book spa treatments in addition to deep-sea fishing, local market tours, and rainforest river rafting excursions. The aptly-named resort is located at Bloody Bay, which is known for deeply hued sunsets over the Caribbean Sea.
Or, try local boutique lodging like the nearby Cliff Hotel, which offers fall specials on four-night getaways during October. Local flair, Caribbean-inspired food, a cliff-side ocean pool, and sea caves abound reflect the signature warmth of this tropical vacation destination. The waterfront sunsets aren't too shabby, either.
![Treehouse hotel in Jamaica](https://www.smartertravel.com/wp-content/webp-express/webp-images/doc-root/wp-content/uploads/2016/09/Negril-Jamaica-700x500.jpg.webp)
Reggae music, coral reefs, and white-sand beaches are sure to make you forget about bone-chilling weather. Slow down and snorkel in Negril, Jamaica, with unique all-inclusive lodging rather than the giant resorts so many visitors frequent.
Romantic treehouse-style villas at the adults-only Sunset at the Palms will let you relax in the treetops of Jamaica's beloved rainforests—where you can book spa treatments in addition to deep-sea fishing, local market tours, and rainforest river rafting excursions. The aptly-named resort is located at Bloody Bay, which is known for deeply hued sunsets over the Caribbean Sea.
Or, try local boutique lodging like the nearby Cliff Hotel, which offers fall specials on four-night getaways during October. Local flair, Caribbean-inspired food, a cliff-side ocean pool, and sea caves abound reflect the signature warmth of this tropical vacation destination. The waterfront sunsets aren't too shabby, either.
![](https://www.smartertravel.com/wp-content/webp-express/webp-images/doc-root/wp-content/uploads/2016/09/Rarotonga-Cook-Islands-700x500.jpg.webp)
When it's winter in the Northern Hemisphere, summer is at its peak in the Cook Islands—home to South-Pacific gems like Rarotonga. This remote tropical vacation destination is dominated by volcanic mountains, thatched-roof cabanas, and bright blue coastal waters that most visitors access via once-weekly flights from LAX.
The island life on Rarotonga in the Cook Islands will get the best of you, especially at eco-tourism retreat Ikurangi—glamp-worthy outdoor villas nestled amidst organic gardens, teetering palm trees, and lush mountain slopes. But this isn't ordinary camping by any standards: Fine dining delivered to your lodging, leisurely cycling on included bike rentals, and isolated beaches are sure to keep you busy.
![](https://www.smartertravel.com/wp-content/webp-express/webp-images/doc-root/wp-content/uploads/2016/09/Capetown-South-Africa-700x500.jpg.webp)
A Southern-Hemisphere summer destination that's slightly easier to get to, South Africa's famed port city of Cape Town and its surrounding wine regions are always a good idea in the final and first months of the year. Hike Table Mountain for far-reaching waterfront views; go whale watching or enjoy a safari; and taste local wine, chocolate, honey, and olive oils in the nearby coastal town of Hermanus. South Africa is as romantic as it is adventure-packed.
![](https://www.smartertravel.com/wp-content/webp-express/webp-images/doc-root/wp-content/uploads/2016/09/Antigua-700x500.jpg.webp)
For a family-friendly Caribbean getaway, Antigua's pristine tropical beaches have a unique and pirate-filled history that birthed picturesque cathedrals, squares, markets, and lookout points. The Blue Waters Resort & Spa includes private villas and a spa in addition to a kids' club full of activities—in case the aqua-blue ocean and infinity pool doesn't keep them busy enough. The Blue Waters offers flash sales and seasonal discounts on its website.
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A Southeast-Asian paradise worth splurging on, Borneo has beaches, wildlife reserves, hiking, and palaces that make this tropical vacation destination the stuff of your wildest dreams. Spot exotic animals like orangutans and pygmy elephants on a rainforest safari, or simply lounge on the beach all day.
Winter travel means low-season and sparser crowds thanks to monsoon season—but don't let it scare you. It may rain a little every day on Borneo, but sun often dominates the morning and early afternoon. Luxurious oceanfront villas at Pangkor Laut or Gaya Island are likely to be more affordable during the fall and winter than the higher-demand mid-year months.
![](https://www.smartertravel.com/wp-content/webp-express/webp-images/doc-root/wp-content/uploads/2016/09/Maui-Hawaii-700x500.jpg.webp)
Consistently named the top island in Hawaii by a host of major travel publications, Maui's untouched beauty offers the perfect tropical vacation destination for families and couples alike—especially in winter, which is the optimal time to whale watch and spot sea turtles.
The southwestern coast of Maui is well-traveled while still retaining its natural beauty, with rentals and villas (rather than high-rise resorts) offering all the comfort of home within sight of the ocean. Splurge on luxe residential-style lodging like the Andaz Maui, or book an ocean-front apartment with local charm.
![](https://www.smartertravel.com/wp-content/webp-express/webp-images/doc-root/wp-content/uploads/2016/09/Havana-Cuba-700x500.jpg.webp)
Winter is arguably the best time to go to Havana. It's during these months that the heat and humidity of hurricane season lifts, and visitors take to the understated locale to unplug and enjoy Cuban food, retro cars, idyllic beaches, and rousing baseball games.
Group tour providers like Intrepid Travel and Smartours offer government-certified "People-to-People" tours that are pre-approved as legal options for American visitors. (U.S. citizens traveling to Cuba need to fall into one of 12 travel categories in order to visit.) Guided tours will let you travel worry-free, with transport and hotels pre-booked—a huge advantage when experiencing Cuba's limited Internet access.
![](https://www.smartertravel.com/wp-content/webp-express/webp-images/doc-root/wp-content/uploads/2016/09/Mazatlan-Mexico-700x500.jpg.webp)
Colorful Mazatlan, Mexico, sits on 20 miles of sandy beaches. Once a tourist-trap city (the first resort town on Mexico's Pacific coast), its center is experiencing a resurgence of old charm—refurbished store fronts, gastronomic and craft-beer festivals, historic art galleries, theaters, and the world's third-largest carnival.
Winter months remain temperate in Mazatlan, and historic hotels like the boutique Casa Lucila, once a local family's mansion, have rates at surprisingly low price points. And the average hotel is well below $100. Head to Mazatlan during the holiday season for Mexico's Dia de los Muertos or Christmas celebrations, or for week-long Carnival in February. All make for a warm tropical vacation destination with an added cultural boost.
Editor's note: Be advised that the State Department recommends "travel in Mazatlan should be limited to Zona Dorada and the historic town center" due to crime in other areas.
More from SmarterTravel:
- 8 Places to Say Goodbye to Summer 2016
- 10 Places You Never Knew You Could Afford in 2016
- 10 Insanely Affordable Destinations for Fall 2016
Associate Editor Shannon McMahon writes about all things travel. Follow her on Twitter and Instagram.
We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.
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