Best Experiences in the Caribbean for Everything on Your List

For being comprised of such small islands, the Caribbean offers a diverse range of fun and adventure from water sports to rainforests. The hard part about visiting the area is figuring out where to go and what to do. Fortunately, each island is branded with its own unique strengths and beauty. Here’s how to tackle Caribbean excursions, one island at a time:

1. The Best Caribbean Island for Sailing

There’s something about the Caribbean breeze and being on vacation that makes you feel completely invincible. After a day in the sun, you feel like you can walk right out onto the water. The next best thing is gliding across the water on a beautiful 44′ sailing yacht for a few hours of sailing. Grab your snorkel gear and dive right in during a snorkel stop for warm, clear waters and colorful fish darting in and out of dazzling coral. After your fill of snorkeling, guests are served a home cooked, gourmet lunch before making your way back to St. Thomas.

If you’re worried about getting seasick try a kayak tour in St. John, instead. This takes you out to the uninhabited island of Henley Cay where birds call and wildlife plays. In fact, we wouldn’t be surprised if we saw a Disney princess saunter out and start singing along in unison. And while you’re daydreaming about living the island life, take a moment to breathe in the vibrant nature of the area from your unique vantage point by kayak.

2. The Best Caribbean Island for Walking Tours

You know that scene you keep playing back in your mind where you wear gauzy white clothes blowing in the wind, walk among colorful flowers and twittering birds at sunset, and dance with wild abandon to live jazz? Well, that version of you exists in Cuba. It turns out you’re drinking cocktails on rooftop restaurants and kicking back in a convertible for a sunset ride.

Cuba is a powerhouse destination of culture, architecture, and history that’s ideally explored by an Old Havana walking tour. Visitors walk through the historic Plaza de Catedral and Plaza del Cristo. You’ll also wind over to the harbor to see Plaza de San Francisco where the main trade hub in Cuba once thrived. End the night dining on Cuban sandwiches, fresh plantains, and dancing the evening way at a Cuban jazz club.

NOTE: Due to the recent travel ban issued on June 4, 2019 by the U.S. government, these excursions are no longer available for purchase on shoretrips.com. We will study these new regulations. Although the US State Department allows travelers who have purchased (prior to June 5th) at least one portion of their Cuba trip to continue without restrictions, we will let you know if this matter changes. 

3. The Best Caribbean Island for Seeing Nature

In theory, the idea of unwinding all day in the hot Caribbean sun feels absolutely divine, but in reality, many of us are still stuck in overdrive from our busy lives. That’s why you may need something that’s more than a sleepy little island. Fortunately, you can combine water sports, sun, and fun with culture and art with the rich diversity of Puerto Rico.

Although you can drive around the entire island of Puerto Rico in a handful of hours, there is more to see and do than you’ll likely have time for. Discerning rum aficionados flock to the Bacardi Rum Factory for a history lesson (and sips) of local rums while travelers of all ages explore the expansive El Yunque rainforest. For history lovers, the Spanish forts of El Morro and San Cristobal give visitors an education on the island. But we saved the best last, and this one will blow your mind. Save a night for the bioluminescent bay in Puerto Rico where you can kayak your way through a glowing bay that looks positively electrified by the mystery of the night.

4. The Best Caribbean Island for History Buffs

The Caribbean is the perfect spot to sneak in some history lessons in between all of that glorious beach time and water sports. Curacao fits the bill with sandy beaches, snorkeling, and kayaking along crystal clear waters. But this little island is also big on historical stops.

Take a tour of Curacao’s local museum with a slave ship replica and learn more about the days of slave trading routes. But even seasoned history buffs are surprised to hear about Curacao’s Jewish Quarter and the stunning Mikveh Israel Synagogue dating back to 1732. Afterward, make a stop at the Jewish Historical Museum preserving religious and cultural artifacts on the island.

5. The Best Caribbean Island for Native Experiences

It’s tough to zero in on a single native experience that earns the title of best in the Caribbean. After all, many of the islands boast their own incredible customs and traditions that visitors scarcely see. But a tour through native Dominica brings guests up close and personal to its true, long-standing locals.

Travel along the coast to the Carib Indian Village of Kalinago Barana Aute. This is the spot where native Caribs work on canoe building, basket weaving, and herb collection before embarking on a storytelling or cultural performance. You’ll walk away with a greater appreciation for Dominica’s most sacred traditions and marvel at how much there is to see, do, and learn no matter your age.

6. The Best Scuba Diving and Snorkeling in the Caribbean

You may think “beach” when you hear “Cayman Islands”, but scuba diving enthusiasts hear something else entirely. Do an experiment, say “beach”, and watch them get glassy-eyed and sweaty as their adrenaline starts pumping. Yep. All they’re thinking about is scuba diving and seeing more stingrays.

Start with Grand Cayman for its phenomenal scuba diving tours in areas like Trinity Caves, Big Tunnels, Orange Canyon, and North West Point Drop Off along with others. Or you can hop on a catamaran for a boat ride out to the Stingray City sandbar and marvel at friendly stingrays that are so warm to visitors that you can actually hold them. Afterward, guests take a short jaunt over to Starfish Point for calm waters and a chance to see the bright red starfish called the Cayman Sea Star.

7. The Best Horseback Riding in the Caribbean

Riding horseback along the water with the wind in your hair isn’t just a fantasy, it’s totally doable in Jamaica. This island is bursting at the seams with natural wonders and breathtaking landscape. Over in Ocho Rios in Jamaica, visitors explore rainforests, waterfalls, and discover plenty of chances to fulfill those wind-whipping in the hair montages playing in your head while horseback riding.

Indulge your fantasies in a horseback riding tour in Ocho Rios that combines horseback riding, history, and shoreline views. You’ll hear about old plantations and the history of the island from horseback along the water’s edge. Fortunately, horseback riding works up an appetite, so make time for fresh plantains, saltfish, and freshly squeezed limeade.

8. The Most Kid-Friendly Island in the Caribbean

We’re pretty sure the Caribbean was somehow designed with kids in mind. The sheer volume of sand, salt, and sun make it a prime destination to just roll the kids on the beach along with the towels and toys. However, some Caribbean islands are kid-friendlier than others with just the right mix of adventure and relaxation.

Turks and Caicos is an ideal spot for kids who love marine life from dolphins to green turtles and stingrays, but need to get away from crowded beaches. Kids can do nothing but play in the sand and look for seashells all day, or hop in the water for a snorkeling tour in Grand Turk before indulging in a tropical feast. It doesn’t hurt that there’s also plenty of Caribbean rums waiting for the visiting grown-ups to pour and enjoy.

9. The Best Place to Swim with the Dolphins in the Caribbean

Swimming with the dolphins has been every kid’s dream since they saw whatever Free Willy or Flipper reboot that Hollywood released. And we admit it. We feel it, too. Dolphins just seem to beckon us directly into the water to solidify a new lifelong friendship. And as you probably know, there are tons of places for dolphin experiences in the Caribbean, but we think the Bahamas offers the best dolphin experience in the Caribbean.

Guests ride out by boat to “Sanctuary Bay” in the Bahamas before taking a dip in the water with eager and friendly dolphins. Hugging and kissing your new marine friends is welcome and the moment is captured by a professional photographer. And, yes, go ahead and re-share that post every time Facebook reminds you of its annual anniversary. The whole dolphin experience is the stuff that tugs on your heart-strings.

10. The Best Caribbean Island for Birding

You simply can’t go anywhere in the Caribbean without a vibrant, colorful parrot landing on your shoulder as you sip a delicious rum-based drink and take in the sunset while pondering life at sea. Okay, not really, but it just feels like it should be true.

What is true is that the Caribbean is a birder’s paradise with tours that bring you up close and personal to your feathered friends. Bonaire is the perfect island for a tour to see colorful flamingoes and unique salt flats. Or, navigate a glass bottom kayak through the mangroves for a completely unique vantage point. As you bob up and down gently on the water, listen for those tropical birds calling your name… We still hope that parrot shows up, though.

Which islands have you already visited, and which ones are calling your name?

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