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5 Best Caribbean Islands for First Timers

We've rounded up five of the best Caribbean islands for first timers and explain why each of these destinations is perfect for any Caribbean vacation.

First impressions often last, so if you’re planning your first Caribbean vacation, you want to make sure it’s a great one.

But with so many islands to choose from, where do you start?

To make it easier for you, we've rounded up five of the best Caribbean islands for first timers. We'll explain why each of these destinations is perfect for any first Caribbean vacation.

Let's get started!

Saint Kitts and Nevis

best caribbean island first timers saint kitts

First on our list is the twin-island nation of Saint Kitts and Nevis.

Why is it perfect for first timers? To start, its location is conveniently centralized in the Caribbean Sea, making it easy to get to from most major hubs.

Plus, the islands are well connected by ferry and cruise ships, so you can explore both in one go.

Additionally, no first-time trip to the Caribbean would be complete without indulging in a bit of marine life. Luckily, Saint Kitts and Nevis boast some of the best Caribbean snorkeling and diving opportunities, making it an ideal destination for aquatic adventurers.

Pro Tips

  • The port in Basseterre (Saint Kitts) is where you can find many friendly taxi drivers who can take you to the island's top attractions.
  • Taxi service is also available from Basseterre and Robert L. Bradshaw Airport to the Sea Bridge ferry terminal, connecting Nevis.
  • While Frigate Bay is one of the most popular spots on Saint Kitts, you should also check out Shipwreck Beach Bar and Carambola Beach Club for a more scenic and relaxed atmosphere.
  • On Nevis, Pinney’s Beach is the most popular with tourists and locals alike. Be sure to try the local beach bars and grills for a true Caribbean experience!

Saint Lucia

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Next up on our list of the best Caribbean islands for first timers is the stunning island nation of Saint Lucia.

If breathtaking scenery and tranquil waters are what you’re after, then this is the place to go.

Indeed, Saint Lucia gave us Hawaii vibes in the Caribbean and is sure to take your breath away! From its beautiful beaches and rainforests to the iconic Pitons (pictured above), it's one of the best Caribbean islands, period.

Whether you arrive by boat in Castries (the capital) or by plane at Hewanorra Airport, you MUST brave the 1.5 or 1-hour drive, respectively, to Sugar Beach.

Located at the foot of the majestic Pitons, this incredible (public) beach is an ideal spot for snorkeling, paddleboarding, or just relaxing in one of several water hammocks offered by the ritzy Viceroy Hotel.

Pro Tips

  • You don't need to be a guest of the Viceroy Hotel to take advantage of Sugar Beach. Just expect to pay high prices for food and drink unless you bring your own.
  • The hike to Sugar Beach from the hotel entrance is quite steep, so be sure to wear comfortable shoes or check with the Viceroy concierge about shuttle services.
  • Toraille Waterfall, located near Soufriere, is one of the only waterfalls in the Caribbean that you can swim in, so why not take a dip?
  • When exploring Saint Lucia, make sure to visit Pigeon Island National Park for sweeping ocean views and a peek into the island’s rich history.

Puerto Rico

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Let's move on to our third best Caribbean island for first timers: Puerto Rico!

Puerto Rico is the ideal choice if you're looking to combine a Caribbean experience with a bit of city living in San Juan.

The island offers plenty to explore, from its unique culture and history to its pristine beaches.

While in Old San Juan, don't miss the grassy and windswept El Morro (pictured above), where you can do as the locals and fly a kite!

Truly, this is such a fun experience, well worth the 10 to 15 dollars you'll spend for a basic kite from one of the vendors along the fort. If you're new to kite-flying, ask one of the locals for help with tying it properly to avoid a nasty crash-landing.

Pro Tips

  • Check out El Jibarito in Old San Juan for tasty traditional Puerto Rican dishes like mofongo and alcapurrias!
  • For some of the best beaches in the Caribbean, venture east to Fajardo where you can take ferries to Vieques and/or Culebra Islands.
  • Explore the vibrant Plaza Las Americas, the largest mall in the Caribbean, for unique shopping and dining.
  • El Yunque National Forest is a stunning rainforest to explore, featuring multiple waterfalls and hiking trails. It's technically free to enter, though there's a $2 fee per vehicle.

Dominican Republic

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Fourth on our list of the best Caribbean islands for first timers is the Dominican Republic.

The DR, as it's affectionately known, is one of the best all-around Caribbean destinations, great for first-time visitors who want to experience a little bit of everything.

With its expansive and varied topography, the DR stands as the largest Caribbean island on this list, offering a wealth of activities to indulge in. From exploring its colonial architecture in Santo Domingo (the capital) to windsurfing in Cabarete (Puerto Plata) to horseback riding in Constanza, there's something for everyone!

Of course, we can't mention one of the best Caribbean islands without giving a nod to the DR's impressive suite of all-inclusive hotels. Many of these resorts sit along the white-sand beaches of Bavaro and Punta Cana. And with rates as low as $125 per night for a five-star resort, you can easily make the most of your vacation budget!

Pro Tips

  • All-inclusives can be fun, but if you're looking for a local experience, head to the vibrant beach towns of Cabarete or Las Terrenas (you can fly into the Puerto Plata International Airport).
  • If you're looking for what is arguably the best beach in the Caribbean, head to Punta Rucia near Puerto Plata, then hire a local dinghy to take you to Cayo Arena sandbar and explore the mangroves on your way back!
  • In Santo Domingo, make sure to check out La Zona Colonial for its cobblestone streets, lively music scene, and colorful colonial architecture.
  • For a one-of-a-kind adventure, you won't want to miss the 27 Waterfalls of Damajagua, a natural water park where you can slide down smooth rocks and cliff jump into natural pools!

Saint Martin (Sint Maarten)

best caribbean destinations saint martin

Last but certainly not least on our list of the best Caribbean islands for first timers is Saint Martin.

This gorgeous dual-nation island (the French control the north side, while the Dutch govern the south side) is a great choice for travelers looking for a laid-back vacation, with an eclectic mix of shopping, dining, and sightseeing opportunities at reasonable prices.

On the Dutch side, you'll find the popular Maho Beach, where you can catch planes take off and land at Princess Juliana International Airport. There's also Great Bay Beach near Phillipsburg, where you can rent a chair and umbrella for the day from a local vendor at a low cost.

The French side is equally charming, with amazing dining spots like Lolo's and L'Auberge in Grand Case and incredible turquoise beaches like Orient Bay Beach, offering lots of fun water activities such as kitesurfing, parasailing, and jet skiing.

Pro Tips

  • We recommend renting a car to explore the island, as taxis can be quite expensive.
  • Marigot Market, Front Street, and Maho Village are great spots for shopping.
  • Be sure to check out Pinel Island (just off of Orient Bay), an uninhabited islet that's home to amazing marine life and perfect for a day trip!
  • Visit the Loterie Farm on the French side for an incredible zip-lining experience.

Recap of the Best Caribbean Islands for First Timers

If you're narrowing down your list of best Caribbean destinations:

  • Saint Kitts and Nevis is a great choice for history buffs.
  • Saint Lucia is perfect for nature and view lovers.
  • Puerto Rico is ideal for those looking to combine city living with beach time.
  • The Dominican Republic offers something for everyone, from all-inclusives to outdoor adventures.
  • And Saint Martin is the place to go for a laid-back vacation, with great shopping and dining to boot.

No matter which island you choose, your first time in the Caribbean will be an unforgettable experience! So get out there and start exploring these best Caribbean islands.

For more travel tips, hacks, and inspiration, be sure to check out the rest of our blog.

Happy travels! 💙🏖️🌴⛵☀️

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