September through November is typically considered the rainy season in some of the Caribbean islands.
However, you won’t have to worry about anything other than a few cloudy days and the occasional shower.
Plus, October is a fantastic time to experience the islands' different cultures, thanks to all the season’s arts and music festivals.
Our list of the best island vacations in October will help you find the best Caribbean islands to visit during the fall.
What’s more, October is considered the low season in the Caribbean, which means prices are also lower than the rest of the year.
They don’t spike up again until mid-December.
Less crowd plus cheaper rates guarantee an unforgettable vacation, don't you think?
Let’s talk about some of the best tropical vacations in October below.
Weather in the Caribbean During October
October tends to be pretty warm, with afternoon highs being around 77- and 87-degree F (25- to 31-degree C).
The humidity levels of summer still linger on most islands, too. On average, you will experience rain about 12 days out of the month’s 31 days.
There may be the possibility of a hurricane, but don’t let that dissuade you from booking your best beach vacations in October.
Typically, you can travel to Aruba, Bonaire, and Curacao. They are the southernmost islands in the Caribbean and are considered to be outside the hurricane zone. Have a lovely vacation on Kees OBX Rentals with your family and friends.
The Bahamas is also a great destination for your October trip. The crowds are lesser, and the weather is fairly pleasant with some scattered rains.
If you are still concerned about the possibility of a big storm, look into getting yourself a travel insurance coverage.
They aren’t too expensive and can help relieve the stress of booking your trip.
Best Island Vacations in October
There are more than a few islands in the Caribbean that are ideal for relaxing during the fall.
The key is finding out which Caribbean island has best weather in October.
Here are the best islands to visit in October:
The high season in the Bahamas begins around November or early December.
This means booking your holiday during October will be beneficial, as there will be fewer tourists and no premium pricing.
Even the temperatures remain fairly pleasant at around 80 degrees F.
This is perfect for those interested in swimming or sunbathing on the beach on the island’s breathtaking turquoise waters.
That said, we must warn you that the Bahamas sits inside the Caribbean island’s hurricane belt, so there is always a possibility of strong winds and heavy rains.
On the upside, though, this typically occurs during the start of November.
The islands of Grand Bahama, which is home to Freeport, the popular cruise port, and the Abaco chain, witnessed the devastating Hurricane Dorian back in September 2019.
When this Category 5 storm made landfall on these islands, it wiped out everything and even took numerous lives in its wake.
Keep that in mind when planning when to go to the Bahamas.
Tourism makes up a huge portion of the island’s income.
Additionally, there is a lot to see and experience here. All of the locals are always welcoming of the visitors, too.
Special Events in October
We recommend heading to the Bahamas during the second week of October.
October 12th is Discovery Day on this island. It marks Columbus’ landing in 1492 and is one of the island’s national holidays.
This is celebrated on the adjacent Monday or Friday if the holiday falls on the weekend.
Since Columbus made his first landfall on the island of San Salvador in the Bahamas, this holiday carries special weight for the locals.
Around this holiday, Bahamas’ McLean’s Town on the Grand Bahama hosts its Annual Conch Cracking Festival.
This festival dates back to the early 1970s, and it involves more than just a conch cracking contest.
It serves up a conch buffet with every imaginable iteration—grilled, steamed, fried, fresh, and poached.
Other Off-Season Advantages
While the Bahamas may appear to be more inviting in the winters, your holiday can be more enjoyable if you head there during October, the off-season month.
For starters, the beach and swimming pools will have less crowd and, in some cases, you may even have it all to yourself.
High-end resorts offer jaw-dropping summer sales to fill up their property, which means you can live like a king without breaking the bank.
If that’s not enough, you can enjoy a meal at luxurious restaurants without having to wait in line. There's also no need to wait for a rental car.
This lets you enjoy the best Bahamian attractions—sand, sea, surf, and lots of sunshine—without all the fuss that comes with crowds.
Best of all, flights run pretty light, and the fares are much more reasonable.
All of these reasons make the Bahamas an excellent destination for a holiday in October.
Saint Lucia tends to have a higher chance of rain during October due to its mountainous setting.
Still, these showers will pass quickly and what follows are clear blue skies with a gorgeous green landscape.
The fall also brings in the island’s premier food event called the Food and Rum Festival.
Here, you will find homegrown chefs, like Shorne Benjamin and Nina Compton, join food critics, wine connoisseurs, rum distillers, and other chefs from all around the world for rum and wine tastings, cooking demonstrations, reggae and calypso music, and chef dinners.
October also marks the Creole Heritage Month.
This is a celebration of Saint Lucia’s French Creole ethnic, cultural, and artistic heritage through theatrical and musical performances.
There are also seminars and lectures, street fairs, art exhibits, and most importantly, mouth-watering food.
This celebration culminates during the last weekend of October, with the celebrations of the International Creole Day, also known as Jounen Kweyol, in communities throughout the island.
October is a great month to visit Aruba because the island hosts the Eat Local Restaurant Month.
Throughout the month of October, you are encouraged to visit over 65 restaurants that offer pre-fixed lunches and dinner.
These local restaurants take special care to incorporate all the authentic regional cuisine in their menus.
If you are considering spending your Halloween holiday on this island, we highly recommend carrying an awesome costume along with you.
Halloween is a very big deal in Aruba.
Most of the resorts and hotels are decorated and turned into haunted houses.
You will also find spooky monsters, zombies, and ghosts roaming all over the beaches.
For the party-goers, enjoy your nights at different clubs, bars, and lounges across the island, as they celebrate themed Halloween parties.
For the little ones, they can visit the hotels and resorts along the main drag in Oranjestad for their Trick-or-Treat custom.
If you plan to extend your holiday and stay in Aruba through to November, you can enjoy the annual Island TakeOver Festival.
This is a four-day urban and electronic music festival of pool parties, beach parties, international DJs, and even a big concert.
In the past, these big concerts have featured international artists like Bad Bunny and J Balvin as headliners.
Make sure to visit the Aruba Art Fair, as well, where you can bring home a unique keepsake from one of the 200+ exhibitors.
This is a three-day event filled with hands-on workshops, performances, art tours, and children’s art classes.
Turks and Caicos
Turks and Caicos in October bring calmer waters and less-oppressive temperatures.
This encourages sport fishermen to take to the ocean to catch the in-season wahoo, tuna, spiny lobster, mahi-mahi, and sailfish.
If you’re a foodie and seafood interests you, you should plan a trip around late October.
This month features major culinary events, like the Caribbean Food and Wine Festival.
Here, you will find chefs from all over the world celebrate with five days of food fairs, gourmet dinners, and tastings.
Push your return journey to November if you wish to partake in two major events.
First is the Turks and Caicos Unity Festival, which features fashion shows, concerts, and a battle of the bands.
The other major event is the Conch Festival, which honors the island’s national symbol through unique and traditional dishes, such as conch chowder, conch empanadas, and conch fritters.
For those on a family vacation, you will surely love Museum Day at the Turks and Caicos National Museum.
Here, you and the little ones can participate in free games, drinks, food, live music, prizes, and performances by local school kids.
Trinidad and Tobago
Cycling fans must visit Trinidad and Tobago at the start of October to participate in the Tobago International Cycling Classic.
Here, you will find several amateurs and professional riders battling it out on challenging terrains, all while the patrons enjoy the races against the backdrop of Caribbean festivities.
The famous Tobago Blue Food Festival takes place in mid-October, too.
This festival focuses on Dasheen, a root vegetable. This is also known as Taro and turns blue when cooked.
The festival is celebrated with a farmer’s market, live entertainment, tours of Dasheen farms, and crayfish catching competitions.
About a third of Trinidad and Tobago’s population trace their heritage back to India, which is why the sacred Hindu tradition of Diwali, the celebration of light, is celebrated here, too.
The date of this festival is calculated according to the position of the moon and the Hindu lunar calendar, so it can occur at any time between mid-October to mid-November.
Diwali is a five-day festival that features the lighting of lamps filled with coconut oil to welcome Goddess Lakshmi, also known as the Goddess of Light.
The main event occurs on Diwali Night and is celebrated with singing, dancing, light displays, and lots and lots of Indian food.
Make sure to holiday in the Grand Cayman to enjoy the Cayman Cocktail Week held in October.
You will be able to enjoy pre-fixed menus of lunches and dinner, pop-up bars, cocktail tours, cocktail competitions, and even Champagne and oyster parties.
Families with kids can enjoy Pirates Week, where thousands of people gather to watch a mock pirate invasion, parades, fireworks, costume contest, and more.
If you are an avid scuba diver, Grand Cayman is the perfect destination for you.
This island is considered one of the best diving spots in the Caribbean.
The waters will offer you ample opportunities to get up close to the region’s colorful sea life.
1. Which Caribbean island has best weather in October?
The best beach vacations in October are those islands where the skies are blue almost every day of the month.
Bonaire, Aruba, and Curacao, all Dutch colonies, lie below the hurricane belt.
As such, there is little worry of any tropical storms.
Instead, you can expect bright shining shores all through October.
2. Is it OK to go to the Caribbean in October?
Not only is it OK to go to the Caribbean in October, we actually encourage you to do so.
Sure, the Caribbean islands experience rains with thunderstorms and heavy showers around this month.
Yet, even with this wet weather, there is a lot of sunshine to enjoy with balmy evenings, warm seas, and a lot of daylight.
This is the reason why the Caribbean islands are considered among the best tropical vacations in October.
3. What’s the average temperature in October in the Caribbean?
The average temperature tends to be around 80 degrees F with about 150mm of rainfall.
Farther south, the temperatures go a bit higher, reaching 86 degrees F with 180mm of rainfall.
As such, this is where you will find the best islands to visit in October.
Holidaying in the Gems of the Caribbean
These best island vacations in October will help you make the most of your fall trip to the Caribbean.
Even if it’s off-season, there is still a lot to experience in the islands throughout this month.
In fact, we highly recommend going there in October if you are on a tight budget. This will ensure you get the best deals, lack of a crowd, and more to experience!