Don’t want to say goodbye to summer? Try these 6 tropical fall getaways

Fall gets a lot of love from people who celebrate the cooler temperatures, changing leaves, and spooky stories. But if you’re the type of person who has always loved summer, you might be dreading the change of seasons which means cooler days are just around the corner. The good news is that there are plenty of destinations where you can turn a classic fall getaway into a warm, tropical getaway. Imagine endless beaches, warm breezes, swaying palm trees and clear skies.

And, bonus: Crowds tend to be smaller and prices are usually lower at these locations during the fall. You should consider hurricane season in many of these destinations, which runs through the end of November. But if you plan it right, you can enjoy an amazing tropical fall vacation with the whole family or just the adults. Here are my picks for ideal tropical getaways to visit this time of year.

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1. Grand Cayman, Cayman Islands

Grand Cayman is home to Seven Mile Beach, one of the most beautiful beaches in the Caribbean. You’ll find many of the island’s best hotels located along the stretch of white sand on the island’s west coast, as well as spots like Bonny Moon Beach Club, which offers cabanas and beachside food and drink service during the day and DJs, stargazing and other events after sunset. And you’ll be able to enjoy it all with fewer people but still pleasantly warm weather.

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Apart from the beaches, this island also has a wild side, but is still family friendly. Visit the Cayman Turtle Center to learn all about the gentle sea creatures and other local wildlife or book a tour of the National Trust for the Cayman Islands’ blue iguana conservation facility, dedicated to restoring the endangered reptile population on Grand Cayman and preserving the island’s biodiversity. Artificial coral reef created by the sinking of the ship USS Kittiwake is the place to see stingrays, reef and nurse sharks, as well as all kinds of tropical fish.

Where to stay in Grand Cayman for a fall getaway

Kimpton Seafire Resort + Spa offers oceanfront views of Seven Mile Beach and is home to Library by the Sea, named the best bar in the Caribbean by North America’s 50 Best Bars. The Westin Grand Cayman Seven Mile Beach Resort & Spa is located along the famous beach, and on-site dive operator Red Sail Sports helps guests explore the crystal-clear waters around the island. And The Ritz-Carlton, Grand Cayman is always a great choice for a special trip with the family.

2. Key West, Florida

Fall is the ideal time to visit Key West. There is less humidity in the air, and this is the perfect season to explore the spooky side of the island. But there are plenty of things to do here if you’re not into spooky stuff or traveling with little ones, like visiting The Key West Butterfly & Nature Conservancy, riding the legendary Conch Tour Train, and strolling around Harry S. Truman’s Little White House.

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The Key West Aquarium celebrates its 90th anniversary in 2025 and is home to more than 250 specimens of fish, sharks and four of the five species of turtles. On November 1, the Elizabeth Bishop House & Garden opens to the public, allowing visitors to see the fully restored house where the American poet lived and wrote during the 1930s and ’40s and a garden featuring more than 80 plant species, including 50 species native to the Florida Keys. Plus new flights from Allegiant Air and Breeze Airways make it even easier to reach the southernmost point in the continental US

Where to stay in Key West this fall

A multimillion-dollar renovation at the Doubletree by Hilton Grand Key Resort Key West has given the property’s accommodations, restaurants and pool areas a fresh, island-inspired look. The new Blue Flamingo Resort has a fun tropical vibe, and Southernmost Beach Resort offers a variety of ways to stay for a family vacation or adults-only trip.

3. Miches, Dominican Republic

About 90 minutes north of Punta Cana, Miches is an up-and-coming destination in the Dominican Republic that’s the perfect place for a tropical fall getaway. Imagine lush tropical forests, beautiful waterfalls, and palm-fringed beaches and lagoons, all with few visitors.

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The secluded Playa Esmeralda beach is known for its white sand and turquoise waters, while Montaña Redonda offers sweeping views of the area. Horseback riding and guided ecotours help visitors explore the region’s impressive natural landscapes.

Where to stay in Miches for a fall getaway

The new All-Inclusive Zemi Miches Punta Cana Resort, Curio Collection by Hilton offers accommodations inspired by the native Taíno people of the Caribbean and an array of family-friendly activities and amenities. The eco-friendly Club Med Miches Playa Esmeralda features a “village” for families and adults, and the new Secrets Playa Esmeralda Resort & Spa is a luxury spot for an adults-only getaway.

4. Maui, Hawaii

A trip to Maui is always a good idea, and even better in the fall, when the number of visitors has started to decrease but the days are still comfortable. Many fun events also take place on Maui this time of year, such as the Hawaiʻi International Film Festival, the Hawai’i Food and Wine Festival, and the Aloha Classic windsurfing competition.

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In addition to spending lots of time in and by the water, you can also check out the Maui Chocolate Tour at the Cacao Farm Tour and the new Treehouse Luncheon at Ku’ia Estates and the new immersive Planting Experience from the Maui Pineapple Tour. To learn more about the island’s history and culture, visit Mele: A Hawaiian Music Experience at Maui Ocean Center’s Sphere Theatre, where dancers and musicians bring Hawaiian songs and stories to life.

Where to stay in Maui this fall

Royal Lahaina Resort & Bungalows recently completed a multi-million dollar revitalization of the entire property with the opening of a new beachfront spa and Mana Up Market highlighting locally made products. Wailea Beach Resort – Marriott also recently unveiled a resort-wide refresh and new Signature Oceanfront Villas, and the Grand Wailea, A Waldorf Astoria Resort launched its new Keiki Club, led by Forbes-trained childcare brand itavi and offering culturally immersive daily programs and experiences.

5. Granada

Head underwater this fall in Grenada, known as the “Wreck Diving Capital of the Caribbean.” More than a dozen shipwrecks can be found near the island in the eastern Caribbean Sea, including a 600-foot cruise ship. Bianca C it’s called “Giant from the Caribbean.” Snorkelers can explore Grenada’s Underwater Sculpture Park, home to coral fish, seahorses, rays, starfish and other marine life.

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Autumn is a great time to visit Annandale Falls and the Seven Sisters with fewer people around and finding plenty of space to relax at Grande Anse Beach and Bathway. And Belmont Estate is a must-visit for anyone with a sweet tooth to learn more about organic farm-to-bar chocolate making.

Where to stay in Grenada for a fall holiday

The luxurious Spice Island Beach Resort is a highly praised place for an all-inclusive holiday. Royalton Grenada, An Autograph Collection Resort is another great option for an all-inclusive family vacation, offering a kids’ club, an on-site dive shop for scuba and snorkeling tours, and a variety of activities to keep the whole family busy. Silversands Resort at Grand Anse Beach Grenada has a new Kids Club with fun features like a “Reading Tree.”

6. St. Maarten

Expanded air service from JetBlue Airways, Southwest Airlines, and American Airlines makes planning a tropical fall getaway to St. Louis a breeze. Maarten easier than ever. The weather is still ideal for visiting the island’s 37 beaches, but you won’t have to share the sand with as many people as at other times of the year.

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Head to Maho Beach to watch the jets land at Princess Juliana International Airport or book a snorkeling excursion to Île Pinel. Loterie Farm’s private nature reserve offers hiking trails and the Jungle Kids Adventure Park for young visitors. Or explore the world’s steepest zip line at the island’s Rockland Estate.

Where to stay in St. Maarten for a tropical fall getaway

Sonesta Maho Beach Resort, Casino and Spa offers a special children’s water park, kids club and youth zone for a fun family vacation. The two-bedroom villa at Simpson Bay Resort, Marina & Spa includes a kitchen and plenty of space for the whole crew, and the JW Marriott St. Maarten Beach Resort & Spa is a good choice if relaxing is on the agenda.

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