The Caribbean is easily one of the most accessible areas of the world to visit from the United States. From most major cities in the US, you can find reasonably short, nonstop flights to many different Caribbean destinations. But, should you visit the Caribbean during the fall?
This time of year is hurricane season, so understandably, that makes people question whether to visit this gorgeous area of the world during September, October, and November. That being said, I find the fall to be one of the best times to visit the Caribbean. Keep reading to learn about the best Caribbean islands to visit during the fall season.
When is hurricane season in the Caribbean?
The hurricane season in the Caribbean runs from June 1 to November 30 every year. The last place you’d want to be during hurricane season is stuck on a tiny island with limited infrastructure – I completely get that. That being said, there are a few great ways to visit the Caribbean without really having to worry about the hurricane season.
Some islands in the Caribbean are outside of what’s called the “hurricane belt.” This means that the path that hurricanes take avoids these islands. I’ll talk about which islands are outside the hurricane belt shortly. Others, despite being in the hurricane belt, still make for a wonderful fall vacation.
How to Prepare Yourself to Travel to the Caribbean in the Fall
Before we go over the best islands to visit in the Caribbean during the fall, it’s important to talk about how to prepare yourself properly. Traveling to the Caribbean this time of year has lots of benefits, but that doesn’t mean you shouldn’t prepare for the worst-case scenario.
First off, hotels and airlines are typically very understanding and accommodating when bad weather, like a hurricane, is headed towards them. If you happen to plan a trip and a hurricane happens, airlines and hotels will often issue travel waivers to allow you to switch the dates of your trip so you’re unaffected by the weather. The ability to stay flexible is really important here because it could be a matter of pushing your trip off by 2-5 days.
The most important thing you can do when planning a trip to the Caribbean in the fall is purchase travel insurance. Travel insurance is one of those things you hate spending money on, but you’ll thank yourself when you have it and you need it. I would recommend getting a quote from World Nomads for travel insurance.
10 Best Caribbean Islands to Visit During Fall
A few criteria make a Caribbean island a good spot to visit during the fall months of September, October, and November. Most of these criteria are based on where each island is located geographically, whether it be outside the hurricane belt I mentioned above, or it just happens to be located in an area that typically gets less hurricane action. Keep reading to see which islands in the Caribbean are best to visit during fall!
Aruba easily makes the number one spot on this list. Not only is the island absolutely gorgeous, but it’s the most popular island on the list of Caribbean islands outside of the hurricane belt. Aruba sits outside of the hurricane belt, tucked in the Southern Caribbean. It’s closer to South America than you’d expect – less than 20 miles away from Venezuela.
Access to Aruba by air is really convenient. There are nonstop flights from many major airports in the USA, including New York, Philadelphia, Charlotte, Atlanta, Chicago, Houston, Miami, and Dallas. You can also reach Aruba on nonstop flights from several destinations in Europe and South America, largely due to Aruba’s affiliation with the country of the Netherlands.
There are tons of great resorts in Aruba, so there are plenty of options to choose from for your vacation. Aruba is also home to Flamingo Beach, where you can feed and interact with flamingos on a private island. Whether you decide to spend your vacation sitting on the beach or renting a car and seeking out adventure, Aruba has a little something for everybody.
Like Aruba, Curaçao is another island that’s entirely outside of the hurricane belt, making it a great destination for your fall vacation to the Caribbean. This island is known for its excellent scuba diving, so it attracts divers all year long.
Curaçao is slowly making its way into more popularity, but it’s not quite as accessible as its neighbor, Aruba. You can get nonstop flights to Curaçao from New York and Miami year-round, so you’ll likely have to connect unless you’re coming from one of these destinations.
Over the last few years, more and more resorts are opening up in Curaçao, making it more of a vacation destination compared to a diving destination like it has been for decades. Make sure to rent a car to be able to explore all the island has to offer. Don’t forget to spend some time in Willemstad, which is the island’s capital, which doubles as an UNESCO World Heritage Site due to its pastel-colored buildings and colonial architecture.
Bonaire is another island that exists outside of the hurricane belt, making it one of the best Caribbean islands to visit during fall. Together with Aruba and Curaçao, these three islands make up the ABC Islands (Aruba, Bonaire, Curaçao). Not only are they geographically close together, but they’re all overseas territories of the Netherlands.
Of all the ABC Islands, Bonaire is the most difficult one to get to. There are daily nonstop flights at certain times of year (primarily winter) from Miami, but outside of that, you can’t get here on a daily nonstop flight from anywhere in the USA. Miami has 3x weekly flights to Bonaire during the fall, and other airports offer weekly service, typically on Saturday or Sunday.
The island does have some beautiful, untouched beaches. However, Bonaire is another excellent island for water sports, such as scuba diving and snorkeling. I would probably recommend looking into Aruba or Curaçao over Bonaire if you’re not a scuba diver as these other islands have more to offer for people with varied interests.
Barbados is the first island on this list to technically be within the hurricane zone. The reason I say technically is because yes, it’s within the hurricane zone. However, it’s on the very edge of the hurricane zone, making it an island that very infrequently sees hurricanes. It still can get them, but it’s typically something that maybe happens once a decade versus several times a year, like other islands.
The island of Barbados is quite pretty easy to get to and has several nice resorts. You can fly to Barbados nonstop from places in the United States like New York, Miami, and Boston, with airports like Newark and Washington DC offering seasonal service.
Barbados is located offset from lots of other Caribbean islands which all form a line. Because of its location, the eastern side of Barbados is on the Atlantic Ocean, making the water a bit rougher, but great for surfing. The western side of the island is best for beaches where you can just sit and relax.
5. Saint Lucia
Saint Lucia is easily one of the best islands in the Caribbean. It’s truly a couples paradise because it has some of the most intimate, romantic resorts in the Caribbean, several of which are all-inclusive resorts. There’s even a resort in St. Lucia with overwater bungalows, which is super rare outside of Bora Bora and the Maldives.
St. Lucia is one of the easier islands to get to on this list. You can fly nonstop to the island from Newark, New York, Atlanta, and Miami, among other airports which offer seasonal service.
Of all the islands in the Caribbean, St. Lucia is one of the best. Not only is it naturally stunning at every turn, but there’s a lot of different things you can do. There are endless gorgeous beaches on the island and it has some of the best snorkeling and scuba diving in the region. One of the most striking parts of St. Lucia are the Pitons, located on the island’s southwestern corner. If you’re looking for something active to do, you can actually hike these mountains. If you’d prefer something more relaxing, I’d recommend a full-day boat tour of the island to go snorkeling and see these gorgeous mountains from the water.
Grenada is easily one of the most underrated islands in the Caribbean. Similar to Barbados and St. Lucia, Grenada is technically part of the hurricane zone. Grenada is the furthest south of these three islands, so it rarely sees any hurricane activity, making it one of the best islands in the Caribbean to visit during fall.
This island remains pretty untouched because of its lack of nonstop flights. Both New York and Miami offer daily nonstop flights to Grenada, so chances are you’ll be flying through one of these two cities. Despite the extra stop to get to Grenada, I can promise you it’ll be worth the journey.
While Grenada has a few really nice resorts, the best of Grenada exists off the resorts. Grenada is known as the Spice Island, due to the island’s booming spice industry. Make sure to either do a tour of the full island or rent a car and explore on your own.
7. Saint Vincent & the Grenadines
Saint Vincent and the Grenadines is one of the least visited islands in the Caribbean. Like several islands on this list, it’s technically within the hurricane zone but rarely sees any hurricane activity. As you might be able to guess by the name, this island nation is a group of 32 islands known as the Grenadines.
St. Vincent and the Grenadines is one of the more difficult islands to visit on this list of the best Caribbean islands to visit during the fall. You can fly nonstop to the main island of St. Vincent from New York and Miami. However, the flights aren’t offered daily. From St. Vincent, you can reach the outer islands by boat.
One of the best things to do in St. Vincent is to get on the water. This chain of islands is known for sailing, and for good reason. Visit other islands here, such as Bequia, Canouan, and Mustique. There are some excellent hotels in St. Vincent and the Grenadines, but as you can expect, they’re a bit difficult to get to, making them that much more special.
8. Trinidad & Tobago
Trinidad & Tobago is another great Caribbean island to visit during the fall. This island country is made up of two islands – one is Trinidad and one is Tobago. Both islands and beautiful and full of things to do. If you can, I’d recommend spending some time on both islands.
Despite being a less common “vacation” island in the Caribbean, Trinidad & Tobago is quite easy to get to. The airport is located on the island of Trinidad and has several nonstop daily flights from Miami and New York. Some other cities over nonstop service several times a week, so make sure to check from your local airport.
Both islands have an incredible culture that you can easily experience as a tourist. Trinidad is naturally the more visited island, considering it’s the location of the international airport. However, I highly recommend making a trip over to Tobago as this island has some of the most beautiful beaches in the Caribbean.
Some people might be surprised to see Jamaica on this list because it’s right in the middle of the Caribbean. That being said, I still think Jamaica is one of the best islands to visit in the Caribbean during fall. It’s technically within the hurricane zone, but its location is very unique compared to other islands in the Caribbean.
Jamaica is kind of tucked in between a bunch of other islands, which almost act like a barrier from major weather storms such as hurricanes. It’s not at all immune from hurricanes, but I find that for its location, it gets way less activity than other islands.
Jamaica is easily one of the most accessible islands on this list. You’ll be able to find daily nonstop service to Jamaica from several airports, such as Newark, New York, Atlanta, Miami, Ft. Lauderdale, and Orlando, among several others. You can 1-3x weekly from other airports as well.
Aside from its beauty, Jamaica has some of the best and most popular cultures in the Caribbean. There are several different areas of the island with beautiful resorts, from Montego Bay to Negril to Ocho Rios and beyond. Jamaica is a great place to escape the resort and see the beautiful nature this island has to offer.
10. Cancun / Riviera Maya
I know what you’re thinking – Cancun isn’t an island and it’s not part of the Caribbean. You’re absolutely right about that. However, the Yucatan Peninsula of Mexico, which is the home to popular areas such as Cancun, Riviera Maya, and Tulum, is often lumped together with the Caribbean due to its location on the Caribbean Sea. And even though it’s not technically an island in the Caribbean, I think it deserves a spot on this list of the best Caribbean destinations to visit during fall.
Similar to Jamaica, Cancun is well within the hurricane zone. That being said, due to its location tucked in between the Caribbean Sea and the Gulf of Mexico, it doesn’t have nearly as much hurricane activity as a lot of other areas in the Caribbean.
Cancun is very accessible from several cities in the United States, with nonstop flights from Atlanta, New York, Miami, Boston, Detroit, Los Angeles, Seattle, and dozens more. Regardless of whether you’re visiting Tulum, Cancun, Riviera Maya, Playa Del Carmen, etc, you’ll want to fly into the Cancun airport. There’s an airport currently being built near Tulum, but that isn’t set to open until 2023.
There are literally hundreds of absolutely incredible all-inclusive resorts in Mexico, especially in this area of Mexico. Whether you decide to stay at an all-inclusive resort or in a hotel in Tulum, I highly recommend leaving your resort at least one day and getting to experience all Mexico has to offer. From beautiful cenotes in Tulum to Chichen-Itza, which is one of the Seven Wonders of the World, the Cancun area has so much to see and do.
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Maddie is the traveler behind A One Way Ticket. She has been traveling internationally for over 10 years and has visited 75+ countries on 6 continents. In addition to traveling herself, she’s been helping others plan their own travel for 6+ years. Maddie eats, sleeps, and breathes travel and loves to help others discover that same wanderlust!