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The sunny Caribbean has over 700 islands, cays, and reefs covering about one million square miles. That is a lot of fun in the sun! People go to the Caribbean for the beautiful surroundings, perfect weather, nature, luxury, and beaches.

Most first-time visitors to the Caribbean head to one of the bigger islands for their first taste of one of the best tropical destinations in the world.

Let’s look at the five biggest islands in the Caribbean, starting with Cuba, the largest one amongst the 13 sovereign island nations and 12 dependent territories.

Cuba

Which Is The Largest Island In The Caribbean?

Cuba is the biggest island country in the Caribbean (and 16th biggest worldwide) and has the most scenic areas of beautiful landscapes that blend into the endless blue ocean.

Cuba is a beautiful Caribbean island with many UNESCO-designated World Heritage sites.If you have a tropical vacation checklist, Cuba could tick them all.

From Old Havana with vintage cars parked on quaint cobbled streets to Playa Paraiso on Cayo Largo del Sur island to Baracoa, the oldest city in Cuba with black sand beaches, your travel expectations are easily exceeded in the best way possible.

Don’t miss Varadero with luxurious all-inclusive resorts in Cayo Coco, where you can see fancy flamingoes and more pristine beaches. Nature lovers must see the Alejandro de Humboldt National Park, which has an abundance of nature and wildlife to enjoy as you hike the scenic trails.

Then there is the charming city of Cienfuegos with its European atmosphere and picturesque old town. Every place in Cuba has the friendliest locals, great food, and weather that makes winter a distant memory.

You will find yourself in paradise as soon as you arrive and your days will be filled with exciting travel experiences balanced with the relaxation that all good vacations are made of.

Hispaniola

Which Is The Largest Island In The Caribbean?

The next largest island in the Caribbean is Hispaniola. Haiti and the Dominican Republic form the Caribbean island of Hispaniola, which covers about 49 thousand square kilometers.

The Dominican Republic is a tropical paradise with stunning beaches, nature, culture and great food, sights, and shopping. The country is one of the biggest producers of cigars on earth and even if you aren’t into smoking them, it is interesting to see how they are made.

Of course, you will spend plenty of time on the beach swimming in the crystal-blue water and soaking up the sun’s rays. The snorkeling and diving are excellent and there are plenty of water sports on the main beaches of the Dominican Republic.

Ecotourism is booming as travelers hear about activities like camping, bird watching, white water rafting, and horseback riding.

The Haiti side isn’t visited so much as it’s considered dangerous for tourists, but it also has a colorful culture, history, and natural beauty.

The National History Park is a UNESCO World Heritage site and has historic monuments and scenic views. The Bassins Bleu Falls are worth mentioning. These deep blue waterfalls get their vibrant color from minerals in the water.

Perhaps in the future, the situation will change and it will become a safe country for travelers again. Until then, we recommend staying on the Dominican Republic side when in Hispaniola.

Jamaica

Which Is The Largest Island In The Caribbean?

Jamaica is the next largest island in the Caribbean. A trip to Jamaica is a summery adventure in the Caribbean with activities that are often a highlight of travelers’ lives.

Imagine swimming with the dolphins or maybe sharks and stingrays if you are looking for a wilder time. Waterfalls are iconic sights in Jamaica and we recommend you check out the gorgeous Dunn’s River Falls.

Following a 90-minute hike, you can jump into the waterfalls where the famous historic land battle happened between the English and Spanish in 1657.

Along with the crash of the ocean waves, Reggae music is another signature sound of Jamaica. You can hear the soulful tunes at many beach bars and when you visit The Bob Marley Museum and Rastafari Indigenous Village.

You can also see the colors associated with reggae all around the island (red, black, gold, and green).

Thrill-seekers can go cliff jumping in Negril and try water sports like kayaking and surfing on 7 Mile Beach.

That is also a great area to stay in with many all-inclusive resorts that have beautiful swimming pools and great services like spa, kids club, dining, and entertainment.

If you prefer a quieter area to stay in, we recommend booking your accommodation around Runaway Bay, also home to the interesting Green Grotto Caves.

Puerto Rico

Which Is The Largest Island In The Caribbean?

This island which is the fourth biggest in the Caribbean is one Americans can travel to without a passport. There are many luxury resorts, including ones offering all-inclusive deals.

You couldn’t be blamed for never leaving your resort because many are thoughtfully set up to include everything you need from spacious rooms, swimming pools, spas, restaurants, bars, coffee shops, and boutique shopping.

Many have nightly entertainment and activities to keep you busy all day long.But if you do venture out, you have beaches galore, including the popular Flamenco Beach, which is often seen in travel magazines and blogs all over the world.

The longest zip-lining ride in the world, as confirmed by The Guinness Book of World Records, is in Puerto Rico. It’s called The Monster and goes for 1.5 miles, so you sure do get a decent ride if you are brave enough.

A tamer time can be had at Old San Juan. The UNESCO World Heritage Site has colorful buildings dating back to the 16th century and museums to visit.

The historic colonial district is very photogenic and interesting and you can easily spend a whole morning or afternoon roaming around.

Trinidad, Trinidad, and Tobago

Which Is The Largest Island In The Caribbean?

Trinidad is the biggest island in Trinidad and Tobago, a very popular Caribbean vacation destination. The capital, Port of Spain, is where many travelers spend a few days exploring before heading off to other areas of the island.

At the Port of Spain, the main attractions include the Queen’s Park Savannah, Emperor Valley Zoo, Royal Botanical Gardens, and the National Museum and Art Gallery, along with shopping, dining, and nightlife.

The cuisine in Trinidad is delicious, with flavors taking in African, Indian, Asian, European, and Latin American influences. You might be enjoying a Spanish lunch, Indian dinner, and of course, the tropical cocktails are always flowing at the beach and bar.

Dive into the street food temptations, resort restaurants, and authentic dining options all around the urban areas of Trinidad and you won’t be disappointed.

If you are in Trinidad in December, you can see the Celebrate Carnival, which is a massive annual street party on Monday and Tuesday before Ash Wednesday.

The vibrant festival attracts people from around the world who want to see the streets full of people in colorful costumes dancing to loud music and celebrating.

 It is a wonderful chance to see one of the best festivals on the global calendar and you will come away with the most amazing collection of photos.

The hiking in Trinidad is great, with many trails leading to beautiful waterfalls. Surfing is also a popular water sport in Trinidad for locals and tourists.

Surf conditions are ideal all year round, with the best waves crashing from November to March. Book a lesson at a surf school, or if you are experienced, you can rent gear and dive right in.

From the largest island in the Caribbean to the smallest cay, there is beauty in every corner.

With so many options when it comes to Caribbean vacations, it pays to have a plan to make sure you see the best areas based on your travel style and interests. There is a high rate of return visitors to the Caribbean because it’s such a wonderful place to visit and so many islands to explore.

Starting with some of the larger islands, you will get a good feel of what the Caribbean is like and probably fall in love with it all at the same time. Trying smaller islands for future trips is a great way to experience many sides of the Caribbean.

Eventually, you will find your favorite areas and the locals will get used to seeing you arrive back there every year when it’s time for your annual vacation.

Visit the Trip Support website to find out more about Trip Support flights, or call our travel experts on #1-855-606-0606 for more information. They are always ready to help our clients plan their next epic vacation.

The face of travel is changing rapidly. We are proudly leading the industry with an innovative and flexible Book Now, Pay Later option.

You can buy the air ticket and vacation packages by putting down a small deposit to secure the services and pay the balance in installments. Flexibility and savings are just some of the benefits of flying with Trip Support.

We don’t check credit scores so this payment Book Now, Pay Later method is available to everyone. You can book now and pay later in installments. There is no credit check with this fantastic pay later option.

You can book now and pay later and go to the Caribbean with Trip Support. Get your pay later flight to the Caribbean by Trip Support today!

Trip Support

The face of travel is changing rapidly. We are proudly leading the industry with an innovative and flexible Book Now, Pay Later option. You can buy the air ticket and vacation packages by putting down a small deposit to secure the services and pay the balance in installments.

Flexibility and savings are just some of the benefits of flying with Trip Support.

We have cheap flights to Rye in Colorado. Book your vacation to Rye and many other wonderful places and pay later with Trip Support. Go ahead and get your pay later flight with Trip Support today!

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