12 Warm Destinations in September in the Caribbean Where Summer Never Ends

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When the rest of the northern hemisphere begins to get cooler and cooler, the Caribbean still offers a lot of sun, sea, and sand. While many of the islands enjoy pleasant weather all year round, September remains an excellent time to explore the region while avoiding the larger winter crowds. It is also a great time to enjoy great hotel deals since the high season is yet to arrive.

Whether you’re into snorkeling, hiking, or simply lounging on the sand, these 12 Caribbean destinations promise a September full of adventure and relaxation.

Saint James, Barbados

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Saint James, on the west coast of Barbados, is known for its golden beaches, calm waters, and reputation for hosting some of the most exclusive resorts in the Caribbean. September temperatures in this parish hover around 86°F (30°C) during the day and cool to 77°F (25°C) at night.

Further, Saint James is a paradise for sun-seekers and water sports enthusiasts. Visitors can enjoy snorkeling in crystal-clear waters and relax under Paynes Bay Beach’s palm trees. A visit to St. James Parish Church, one of the oldest churches in Barbados, will help you appreciate the local culture.

Book a stay at Fairmont Royal Pavilion to surround yourself with luxury. This 5-star beachfront hotel has a beauty shop, an outdoor swimming pool, and offers free airport shuttles.

Santo Domingo, Dominican Republic

Santo Domingo, the capital of the Dominican Republic, lures many tourists seeking an exciting mix of history, culture, and beachfront beauty. In September, the city enjoys average daily temperatures of 88°F (31°C) with nighttime lows around 74°F (23°C). It also boasts a UNESCO World Heritage Site within the Zona Colonial, where historic architecture, cobbled streets, and quaint cafes make for perfect day trips.

There is also plenty of coastline to enjoy, such as Boca Chica Beach and Juan Dolio Beach.

For those seeking top-tier comfort, the El Embajador provides an exceptional experience. This 5-star property is in a privileged location in Santo Domingo and features a lush garden and an inviting pool area.

Negril, Jamaica

Famous for its seven-mile beach, spectacular sunsets, and laid-back vibe, Negril is an unmissable Caribbean destination for September travelers. During this time, the town sees average daytime temperatures around 87°F (31°C), with the evenings dipping to a pleasant 76°F (24°C).

The beaches here are some of the best in the Caribbean, offering soft, powdery sands and warm turquoise waters. Water sports, catamaran cruises, and visits to the Negril Cliffs make Negril a well-rounded getaway.

When in Negril, consider The Royalton Negril, an Autograph Collection All-Inclusive Resort. It is a sophisticated boarding facility with a kids’ club, nine restaurants, and seven bars, all designed to make your stay luxurious.

Grand Cayman, Cayman Islands

The largest of the Cayman Islands, Grand Cayman, is renowned for its pristine beaches, vibrant coral reefs, and luxurious resorts. September temperatures average a balmy 88°F (31°C), with cooling nighttime breezes bringing the temperature down to around 77°F (25°C).

Visitors to this island should not miss Seven Mile Beach, where endless sand and clear waters await. For beach hopping adventures, you can go to Rum Point, Starfish Point, and Cemetery Beach and Reef. All these beaches are drop-dead gorgeous. That aside, diving enthusiasts will love the famous Stingray City, where you can swim with stingrays in shallow water.

The island’s diverse yet comfortable accommodations also allow for fun-filled getaways. The Ritz-Carlton, Grand Cayman is the epitome of luxury. With beachfront rooms, a Greg Norman-designed golf course, and a world-class spa, this 5-star resort is the ultimate choice for a pampered and memorable Caribbean vacation.

Nassau, Bahamas

Which Caribbean Island Should You Visit Bahamas — © Mariakray / Adobe Stock

Over 9.5 million tourists visit the Bahamas. Many of the travelers stop by Nassau, a city popular for its hospitality, beautiful beaches, and favorable weather. September temperatures here average around 85°F (29°C) during the day, with slightly cooler evenings at 77°F (25°C).

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Nassau offers many cultural and recreational activities, including visits to the Pirates of Nassau Museum, exploring the vibrant streets of Bay Street, or relaxing on Cable Beach. The city is also an ideal spot for snorkeling and diving adventures.

Make sure to experience Nassau’s pinnacle of luxury at The Ocean Club, A Four Seasons Resort. Situated along the shores of Cabbage Beach, this hotel offers a refined 5-star experience. Guests can expect high-end dining experiences and access to 8 Balinese-inspired spa villas.

Willemstad, Curaçao

Willemstad, the capital of Curaçao, is a UNESCO World Heritage Site known for its brightly colored Dutch colonial architecture and charming streets. September temperatures in Willemstad average 88°F (31°C) during the day and 79°F (26°C) at night, offering perfect weather for beach activities and sightseeing.

Popular local attractions include Mambo Beach, one of the island’s most famous stretches of sand, and Shete Boka National Park, where visitors can explore dramatic coastal landscapes. Another must-see is the Floating Market, where vendors from Venezuela sell fresh produce and fish directly from their boats. Don’t miss out on Punda; it is a super historic and picturesque neighborhood.

If you want a pampered holiday, consider staying at Curacao Marriott Beach Resort. This 5-star hotel is on a 6-acre (2.5-hectare) oceanfront property.

Noord, Aruba

Noord is a laid-back yet lively town on the northern tip of Aruba. September temperatures in Noord reach 90°F (32°C) during the day and cool down to 78°F (26°C) at night. With its constant trade winds, the destination is ideal for windsurfing, kitesurfing, and other water sports.

A visit to the California Lighthouse offers breathtaking coastline views, while Arashi Beach has soft white sands and calm waters for swimming. If you are a beach lover, more options like Eagle Beach and Palm Beach await. Noord is also home to the Butterfly Farm, a peaceful sanctuary where visitors can walk among thousands of colorful butterflies.

For an unforgettable stay, The Ritz-Carlton Aruba provides a 5-star experience with a posh spa and a casino.

Scrub Island, British Virgin Islands

Scrub Island is a unique holiday destination in the Caribbean. It’s an intimate, quiet escape for those seeking luxury and serenity. In September, temperatures on the island range between 87°F (31°C) during the day and 76°F (24°C) at night, providing ideal conditions for relaxation and adventure alike.

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Visitors can explore nearby islands by boat or enjoy world-class snorkeling and diving in the clear turquoise waters. The island’s secluded beaches, such as Honeymoon Beach, offer peaceful solitude, while activities like sailing and paddle boarding await the more adventurous.

The best part? Scrub Island Resort, Spa & Marina, an Autograph Collection hotel, offers 5-star accommodations with private villas, swimming pools, and spa treatments. This is the ultimate escape for a luxurious and private Caribbean experience.

St. George’s, Grenada

Hidden Beaches in the Caribbean_Paradise Beach, Grenada_Paulo_AdobeStock_223037396 — © Paulo / Adobe Stock

September temperatures in St. George’s hover around 86°F (30°C) during the day and 78°F (26°C) at night, thus perfect for soaking up the sun and exploring the island’s lush landscapes.

Besides being the capital of Grenada, this city has plenty of goodies for tourists. Among the top attractions is the Grenada National Museum, which offers insight into the island’s history. For nature lovers, Grand Etang National Park offers hiking trails through a tropical rainforest, leading to waterfalls like Annandale Falls. After long days of exploration, you can unwind on the nearby beaches like Grande Anse Beach, Magazine Beach, and Morne Rouge Beach.

Beautiful beaches aside, a luxurious stay awaits at Calabash Hotel, a 5-star boutique hotel on L’Anse Aux Epines Beach. It’s a family-friendly accommodation facility and has two high-end eateries.

Port of Spain, Trinidad and Tobago

Port of Spain is a perfect destination to experience the city’s culture, nightlife, and natural beauty. September sees average temperatures of 88°F (31°C) during the day and 77°F (25°C) at night, making it an inviting destination for both relaxation and exploration.

Among the city’s highlights are the Queen’s Park Savannah, the largest open space in the city, and the Magnificent Seven, a row of historic colonial mansions. Nature lovers can head to the Asa Wright Nature Centre, a tropical paradise for birdwatching.

Also, from Port of Spain, you can easily access breathtaking beaches like Maracas Beach.

The icing on the cake is Port of Spain’s comfortable accommodation facilities. Enjoy a luxurious stay at Hyatt Regency Trinidad, a 5-star hotel with a rooftop infinity pool. Its central location makes it a perfect base for exploring Port of Spain.

San Juan, Puerto Rico

San Juan effortlessly blends vibrant culture, historic charm, and stunning beaches to offer visitors a lively Caribbean experience. In September, you can expect average daytime temperatures of 84°F (29°C), with warm nighttime temperatures dropping only slightly to around 76°F (24°C).

The favorable climate allows for strolls in Old San Juan, where cobblestone streets are lined with colorful colonial buildings, or relaxing on beaches such as Condado Beach and Ocean Park Beach.

You can spice up your trip to this city by staying at the Condado Vanderbilt Hotel. It is a Spanish Revival-style accommodation facility that opened in 1919. Aside from the hotel’s beachfront location, it features a full-service spa and an outdoor swimming pool.

Portsmouth, Dominica

For travelers seeking natural beauty and eco-adventures, Portsmouth is an excellent choice. Its popular attractions include Cabrits National Park, home to Fort Shirley, an 18th-century British fort, and the Indian River, where visitors can take boat tours through lush mangroves. The nearby Trafalgar Falls and Boiling Lake are also must-visit natural wonders.

After all the fun and games outdoors, retreat to InterContinental Dominica Cabrits Resort & Spa, an IHG Hotel. This 5-star accommodation facility is set along Douglas Bay and has thatched-roof furnished cabanas where you can enjoy the ocean breeze.

That aside, September temperatures in Portsmouth remain warm, with daytime highs of 85°F (29°C) and nighttime lows of 75°F (24°C). With these warm temperatures, you can spend your days lounging on beaches like Coconut Beach and Ripaton Beach.