A Beginner’s Guide to Adventure Travel in the Eastern Caribbean

I recently took a cruise through the Eastern Caribbean—and because I’m all about adventure, I chose a few high-octane offshore experiences to keep me busy. (Cruises aren’t just for relaxation, you know.)

But what if you don’t feel ready for the extreme stuff yet? What if you’ve never done any of those things and, as a complete beginner, have no idea what to expect—and the thought of trying it makes you a little nervous?

Or what if you’re in the company of complete beginners to adventure travel, and you want to keep them happy—while giving them a gentle, loving shove towards the thrilling activities you enjoy doing? How would that work?

If the Eastern Caribbean was my first taste of adventure travel, here’s how I’d get started, making the most of the unique opportunities in every port.

1. Where to Find Adventure in Grand Turk

Swim in the Insanely Blue Waters of Grand Turk (And I Really Do Mean Insane)

Over 600 miles from Miami in the southwest of the Bahamas, the Turks and Caicos island chain is a scatter of over 300 islands, all but two of them uninhabited. The main island, Grand Turk, was the first stop on my Eastern Caribbean Cruise. Legend has it that it was also one the first port of call for Christopher Columbus in the New World—and who could blame him with a view like this?

Grand Turk Adventure Travel
Catamaran cruising on the island of Grand Turk

Grand Turk is surrounded one of the world’s most stunning coastlines, featuring white sands, glowing azure waters and its very own coral reef. For all these reasons, it’s an ideal place for aspiring deep-sea swimmers and divers to get started—and you’ll find plenty of options to choose from.

If you feel ready to get deeper in every sense, Cockburn Town houses plenty of experienced dive operators. If you want an all-inclusive package booked in advance on your cruise, try this one.

Note: for safety reasons, there’s a minimum skill requirement for scuba—you need to have taken a dive within the last two years, and to have your C-Card that shows you previously took a basic course of training.

Paddle A Boat into The Living Heart of The Island

This is the next best thing to getting in the water—particularly because Grand Turk’s kayaks have glass bottoms, allowing you to see everything down there. The island’s kayaking tours usually head to the fertile mangroves, because that’s where the most dazzling wildlife can be found, flitting from branch to branch overhead or darting right under your kayak in a flash of colors.

There are no prior certification requirements for kayaking. However, it may be a relatively leisurely pace, but it’s still a significant workout for the upper body, especially since you’ll be paddling along for at least a couple of hours.

This tour departs from the Cockburn Town’s cruise ship terminal and takes 3 hours.

2. Adventure Activities in Old San Juan, Puerto Rico

Battle San Juan’s Fierce Atlantic Waves with A Surfboard

The northern edge of San Juan, containing the historic center of the city going back to colonial times, is on a spit of land that sticks out into the Atlantic Ocean—and for that reason, it’s a great place to grab a board and dive into the waves.

If you’ve never surfed before, getting started is simple: you paddle out on a longboard, wait for a big wave, stand up—and then you fall off.

Now repeat this two hundred times, or until your body starts to adapt to your not-so-elegant juggling act between buoyancy, gravity and your sense of balance. It’s instantly fun—and yet the learning curve is brutal enough to keep you busy all day (and indeed for the rest of your life).

Surfing lessons are a popular shore excursion on major cruises to San Juan—and you’ll also find local surf schools offering tuition at local beaches including Escambron, which is just down the coast from Old San Juan.

Walk Around Old San Juan In Record Time…If Your Legs Can Take It

If riding the Atlantic seems like too much hard work, try going for a walk instead—with an adventurous twist.

A brisk walk round Old San Juan (Puerto Rico’s oldest settlement) requires a good pair of legs. A complete lap of the old city is at least a three-hour hike, without factoring in stops for sightseeing and refreshments. This tour of the ancient fortresses of the old city is rated “Difficult” for a reason—it’s a place of 500-year-old cobblestones, uneven surfaces and occasionally treacherous steps. It’ll stretch you, guaranteed.

Under normal circumstances, Old San Juan is a multi-day adventure—so getting around it in just a few hours would be a good challenge that will raise a healthy sweat.

Adventure Travel in Puerto Rico
The streets of Old San Juan, Puerto Rico

3. Where to Go for Adventure in St. Maarten

In country-hopping terms, the remote island of St. Maarten is a terrific value. To the north, it’s Sint Martin and French; to the south, it’s St. Maarten and owned by the Netherlands. The smallest nationally divided island in the world is a popular stop-off for cruise ships and the home of some truly unique adventurous activities—including a nerve-wracking one that’s become world-famous…

Stand on Maho Beach, Where Planes Fly So Low You Can Reach Out And Touch Them

There’s no airport in the world like Princess Juliana International. The main runway starts less than a hundred feet beyond the end of Maho Beach —and when the planes fly over, they’re just a few seconds from touchdown, and so low (less than 100 feet) that you feel like you can reach out and touch the wheels…

Planes landing on Maho Beach is an adventure in itself!
Look out…above?

While you won’t see any of the BIG planes touching down these days, there are plenty of Airbus flights to scare the living daylights out of you.

But that’s only one side of the story. Takeoff is even more of a rush—the hot air from the aircraft’s jet engines blasting through the chain-link fence and over Maho Beach, up to 120 miles an hour, fast enough to roll you down the beach and into the sea, if you don’t lay flat or hang on to something.

Adventure Travel in the Eastern Caribbean
“Jet blast or departing and arriving aircraft can cause severe physical harm resulting in extreme bodily harm and/or death.”

If you’re on a cruise, there will be a shore excursion to the beach in time for a takeoff or landing (it’s virtually guaranteed, since this is such a famous tourist spot). If you want to do it yourself, check out local bars for details—many of them display airline timetables so you can pick the perfect moment to stand on the beach and feel very small…and very scared.

Hurl Yourself into Space and Ride the Steepest Zip-Line in the World

Zip-lining is about adrenaline. There’s no way around this. Sure, you could spend years gently easing yourself into zip lining, doing longer and longer runs. Or you could just embrace the true spirit of adventure and start with the steepest, most thrilling zip-line in the world, right here on St. Maarten. I know which I’d choose.

It starts easily enough. There’s a brand-new chairlift called the Sky Explorer (formerly the Pirate Sky Ride) that takes you all the way up Sentry Hill to the highest point on the island, inevitably called the Crow’s Nest. From there, all you have to do is swallow your fear, say a prayer and clamber onto the Flying Dutchman zip-line, which plunges at a world-record 42-degree angle towards the forest canopy below. You’ll cover half a mile in your secured harness chair, descending nearly 1,000 feet at speeds of up to 50 miles an hour. Permission to shriek is granted.

The Flying Dutchman is part of many organized shore excursions (including this one), which feature transportation to and from the Rockland Estate. Expect the whole trip to take 4-5 hours.

4. Where to Find Adventure on St. Kitts

Walk Between Oceans at Frigate Bay

Like St. Maarten, St. Kitts is a meeting of two worlds. Not only is it one-half of a country (with Nevis, its neighboring island), it’s also where the Atlantic Ocean meets the Caribbean Sea—and you can certainly feel it when you’re on the ground. North Frigate Bay is where the Atlantic waves thunder against the shoreline, while South Frigate Bay, where the Caribbean makes its last gasp, is noticeably warmer and more sheltered.

It’s a good place for a beginner’s hike—whether along each mile-long bay or in a wide loop. If your legs are feeling up for a bigger challenge and if time allows, take a hike up Mount Liamuiga, a dormant volcano with the charming former name of “Mount Misery.”

The view from Timothy Hill Overlook, St. Kitts
The Atlantic Ocean on the left, the Caribbean Sea on the right.

Ride the Atlantic Winds—Or Be Blasted into the Sky

With great Atlantic waves come terrific opportunities for watersports—and St. Kitts caters for every kind.

Of the most exciting options available, windsurfing is probably the easiest to pick up (don’t be fooled by appearances—modern boards are light and stable, and sails are surprisingly easy to handle). Next up the excitement ladder (and requiring a higher level of physical fitness), try kitesurfing, where you’re dragged high into the air in a series of heart-stopping leaps and descents that end when you smack your surfboard back onto the water. And if you’re really adventurous, take to the air, on twin jets of pressurized water, better known as flyboarding.

Don’t worry, it’s not as tough as it first looks.

OK, I Need to Tell You Something

I did something sneaky. I said I’d give you a list of complete beginner’s activities, and instead, I listed things any seasoned adventurer would happily spend all their time on.

This was deliberate. I want to make an important point about adventure travel.

My philosophy on adventure is simple and unchanging: it’s not about the activity, it’s about you. Being a beginner is fine, we all start there—but it’s easy to get trapped into always feeling like a beginner. Feeling like you’re not ready, or you’re not allowed, in some impossible-to-measure way.

Those are the things that stop people from having real adventures.

So, prepare, yes. Get qualified, by all means. Do your research—of course, every time.

But there are no “beginner adventures.” Not really. There’s no ladder of adventurousness to climb before you’re allowed to do something properly exciting. Your favorite adventurers didn’t do that. They just saw something, said, “I want to do that,” and they went and did it.

In the end, adventure is a mindset. So, forget the idea of a “beginner’s guide” to anything adventurous. Just go do it.

This post was created for Away We Go with Carnival, the destination for getting in the getaway state of mind. Head on over.

About the Author

Jeremy Scott Foster

Jeremy Scott Foster is an adventure-junkie, gear expert and travel photographer based in Southern California. Previously nomadic, he’s been to ~50 countries and loves spending time outdoors. You can usually find him on the trail, on the road, jumping from bridges or hustling on his laptop working to produce the best travel and outdoors content today.
  1. We found the beach where Princess Juliana International by complete accident. Was one of my favorite parts of the trip!

  2. Excellent article and really informative at the same time. It’s great to read something fresh. You take remarkable pictures. Sadly, I have never get the opportunity to tour these lovely places, but willing to. Hope my time will come soon.

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