Sail with Picante Tobago: Behind the Scenes of a Soca Music Video

Some days in Tobago feel like a movie – and this was one of them. I spent a full day aboard Sail with Picante Tobago doing behind-the-scenes photography for Rich Rasta’s music video Drop D Anchor. The day also featured Luna (Melika Gillard), a Trinidad & Tobago-based professional dance artist, choreographer, and Soca performance powerhouse, known for her electrifying stage presence, work with top Caribbean artistes, and her mission to empower women through dance.

This post walks you through the entire shoot day- from Mount Irvine Bay to the Nylon Pool – while also giving you a real look at what it’s like to sail with Picante.

Starting the Day at Mount Irvine Bay

We began the day on the resort side of Mount Irvine Bay, capturing opening shots with calm waters and soft morning light. After wrapping those scenes, we relocated to the public side of Mount Irvine Bay near Anchor Bar and Grill, where the logistics of the day really kicked into gear.

We were welcomed by the Picante owner—genuinely friendly, approachable, and hands-on. He shared his contact number with us directly and made it clear that if anything came up throughout the day, we should reach out immediately. That level of care makes a difference, especially on long excursions.

Because the Picante catamaran is moored offshore, we made several trips by zodiac to transport guests, crew, and filming equipment from shore to the boat. While this added extra steps, everything ran smoothly thanks to an organized and patient crew.

Keep in mind, it is considered a “wet entry” hopping into the zodiac so be prepared to get a little wet on your lower half. Proper etiquette is to remove your shoes that you do not get sand in the boat.

First Impressions of Sail With Picante

Once aboard, we were warmly welcomed by the crew members. All crew were incedingly friendly, knowledgeable and genuinely enjoyable to be around – exactly the kind of energy you want on a long day at sea.

Their calm confidence made the entire experience feel smooth and well-managed, even with a packed itinerary. One of the captains, Marcello, quickly became a favourite and ended up becoming a character in the music video.

We were given time to settle in, enjoy a tour of the catamaran, and go through a clear safety walkthrough before setting sail.

Sailing from Mount Irvine Bay to the Nylon Pool

Because Sail With Picante operates a large catamaran, the route to the Nylon Pool is different from the quick trip taken by glass-bottom boats. Instead of cutting straight across, we had to sail farther out to sea and around the reef, which took about 45 minutes from Mount Irvine Bay.

On this particular day, the sea was rough. A few people in our group chose to lie down inside the hull, where motion is felt less. I do recommend taking a Gravol before sailing if you are prone to sea sickness or it’s a particular rough day.

Despite the conditions, the sail itself felt adventurous and very “real Tobago,” not overly polished or rushed.

Arriving at the Nylon Pool

After navigating around the reef and making the longer sail from Mount Irvine Bay, we finally arrived at one of Tobago’s most iconic natural attractions: the Nylon Pool.

Located in the middle of the sea, the Nylon Pool is a natural, shallow sandbank with crystal-clear turquoise water so calm and shallow that you can stand waist-deep far from shore. It’s often described as “a pool in the ocean,” and once you see it in person, you immediately understand why.

The water here is exceptionally clear, shifting between pale aqua and soft blue depending on the light. On a day like ours—with clouds moving quickly and the sea still active beyond the reef—the contrast made the Nylon Pool feel even more surreal. Calm, glassy, and almost glowing, it felt like stepping into another world.

Apparently if you remain calm, they don’t sting. Would you try this?

Why the Nylon Pool Is So Special

What makes the Nylon Pool truly unique is its location and natural formation. Protected by surrounding coral reefs, the area remains shallow and sheltered even though it’s completely surrounded by open sea.

It’s also deeply tied to local folklore—many Tobagonians will tell you that swimming in the Nylon Pool brings youth and good luck. Whether or not you believe the legend, there’s no denying that time seems to slow down here.

A Floating Studio in the Middle of the Sea

With the Picante anchored nearby, the Nylon Pool became our floating studio for the day. The catamaran provided a stable base while still allowing easy access in and out of the water via the zodiac.

Between shots, people drifted, laughed, lounged, and took in the moment. Even with a full production happening around us, the energy here remained calm and unhurried—something that’s hard to find on more crowded boat tours or stressful sets.

The Clear Kayak Shot

The opening shot of the music video was a vision Rich had long before the video ever premiered. To bring it to life, a clear kayak was transported by jet ski from Store Bay to the Nylon Pool, ensuring we captured the scene exactly as imagined.

With the catamaran anchored nearby, Luna lay back in the clear kayak, headphones in, softly singing along to the track while floating over the shallow, crystal-clear water. The stillness of the moment contrasted beautifully with the vastness of the sea around her, making the Nylon Pool feel even more otherworldly.

Capturing It All From Above

To fully do the Nylon Pool justice, the scene was filmed from the air. A drone hovered above the shallow water, carefully positioned to capture the scale, symmetry, and clarity that make this location so iconic.

Watching the drone operators work was a reminder of how much precision goes into moments that look effortless on screen. Between coordinating movement, light, and wind, every shot required patience and timing—especially with equipment being launched and recovered directly over the water.

Life On Board the Catamaran

The rest of the day was a busy blur as we worked to get a variety of shots on board. The lighting was a dream on this day so I couldn’t resist snapping photo after photo. The crew was incredible and ensured we had everything we could possibly need.

Time to Cool Down

With the hot sun shining on leading lady Luna, Rich attempts to cool her down by fanning her with the Picante’s cushion.

Driving the Boat

Rich provides Luna instruction on how to drive the boat, she plays along.

But this isn’t Luna’s first time driving a boat! She takes the wheel with a fierce attitude.

There’s never been a happier steering wheel, catching a wine from the whining boss.

Luna’s Time to Shine

Giving Luna her moment to showcase her incredible dance moves and core strength was a highlight of the day. The boat was moving and shaking a lot, making each step, jump, and spin much more challenging than it looked on camera.

Yet, as always, Luna made it appear effortless. Her poise, energy, and precision turned the Picante deck into her stage, and every move perfectly captured the rhythm, joy, and cinematic beauty of the day. Watching her dance on a swaying catamaran was not just impressive—it was inspiring.

Lounging on the Trampoline Nets

One of the best ways to relax on a catamaran like the Picante is on the trampoline nets at the front of the boat. These netted “hammocks” stretch between the two hulls, letting you feel the breeze, hear the water below, and soak up the sun—all while floating just above the sea. The crew set up the shade canopy to provide some relief from the hot Tobago sun.

Rich and Luna got some amazing shots singing the track while lying back together on the nets.

Luna Gives Rich a Dance Lesson

While Rich is undeniably a talented vocal artist, his footwork isn’t quite as polished—so naturally, Luna stepped in. As a professional dancer and teacher, she took it upon herself to show him a few moves, guiding him across the deck and demonstrating steps with patience and flair. The moment was full of laughs, playful corrections, and good-natured teasing.

Hammock Fun Beneath the Trampolines

The Picante catamaran had a hammock suspended beneath the trampoline nets, offering a one-of-a-kind way to lounge over the water. You could lay back while partially submerged in the turquoise sea —a perfect mix of relaxation and adventure.

And then came the unforgettable moment: Rich jumped straight into the water… fully clothed. Without missing a beat, he climbed into the hammock and continued singing as if nothing had happened. Everyone on board was shocked—and thoroughly entertained—by his fearless energy.

Lunch on Sail With Picante

Lunch was catered and casual, which made sense given our filming schedule. Everyone ate when they could rather than sitting down all at once.

The meal included fish, rice, and salad—simple, healthy, and full of flavor. Cold water, gingerale, sprite and coke were available to drink throughout the cruise. I was so hungry by the time I took a break to eat, I missed getting any shots of my meal, sorry!

If you’re booking a private Sail With Picante tour, you can opt for a more formal sit-down lunch experience instead.

A Sweet Break: Snow Cones at the Nylon Pool

No trip to the Nylon Pool is complete without spotting the iconic snow cone boat. On this day, Blend Isles Delights came by just as we were finishing the drone shots, bringing a splash of color and a sweet treat to the middle of the ocean.

One of the drone operators was celebrating his birthday on this day and so obviously he had to get a (rum spiked) snow cone. How can you not love Tobago?

That’s A Wrap!

After a full day of sailing, shooting, and creating unforgettable moments, we filmed the final scenes of the music video aboard the Picante. There was a tangible sense of accomplishment in the air—everyone had given their all, and the footage reflected it.

From Luna’s flawless movements to Rich’s fearless energy, from drone shots over the Nylon Pool to candid moments on deck, every frame captured the magic of Tobago. The crew, captains, and cast took a moment to soak it all in, laughing, cheering, and celebrating the successful shoot.

Heading Back

Once filming wrapped and we had a moment to soak it all in, we were ready to set sail again. We made our way back to the mooring in Mount Irvine Bay.

After a long and busy day, I was so excited to reach to shore, get home and review my pictures!

Is Sail With Picante Tobago Worth It?

Absolutely.

Sail With Picante offers one of those bucket-list Tobago experiences that feels equal parts adventure and relaxation. They now operate under new ownership, offer a variety of sailing experiences, and truly care about their guests.

The sunset cruise is next on my list—it looks incredible and is perfect if you want something more relaxed than a full day sail.

Final Thoughts

Whether you’re visiting Tobago for the first time or looking for a unique way to experience the island, Sail With Picante Tobago is an experience you don’t want to miss.

Be sure to check out Rich Rasta’s “Drop D Anchor” music video, and I hope you enjoyed this behind-the-scenes look at a day sailing Tobago.

Thank You to Everyone Who Made It Happen

No creative project like this happens without an incredible team, and this song and shoot was no exception. A huge thank you and shout out to everyone who made this song and music video come to life:

• Rich Rasta – Song Writer, Singer, Actor
• Badjohn Republic, Kyle Phillips – Mix and Master
• Rodney Alexandar – Live Bass
• Karyce Phillips – Background Vocals
• Luna – Actress, Dancer
• J3TLG – Video Editing, Filming
• Master B Pixel Studio – Drone Videography
• Cardinal North Studio – Photography
• Picante Crew