A Trip of a Lifetime in St. Vincent & The Grenadines

45 feet of freedom, seven islands of color, and one unforgettable adventure.

Published: Friday, January 2, 2026 9:00 am
By: Melanie Kyle

Some trips feel like a vacation. Others feel like a story you’ll tell for the rest of your life — the kind that starts with a grin and ends with, “You had to be there.” Our recent Trip of a Lifetime Giveaway delivered exactly that: a week of warm trade winds, reef-fringed anchorages, and the kind of island-hopping itinerary that makes sailors fall in love with the Grenadines all over again.

The Trip of a Lifetime is our biggest adventure of the year — an all-expenses-paid sailing vacation that sends two winners from the U.S. and two winners from Canada on an unforgettable Caribbean escape, made possible entirely through the generosity of our sponsors. This year, our floating home was a 45-foot catamaran from Horizon Yacht Charters — roomy, steady, and built for the rhythm of Caribbean days. Its wide beam became our porch for morning coffee, our front-row seat for sunsets, and our gathering space for the nightly ritual of reliving the day: the best snorkel, the smoothest tack, and the moment someone spotted a sea turtle and suddenly the whole crew was pointing and laughing like kids.

With St. Vincent & The Grenadines spread out like stepping stones across sapphire water, we set out with a plan that balanced iconic anchorages with time to actually be there. Our route: St. Vincent → Bequia → Mustique → Canouan → Tobago Cays → Mayreau (two nights) → Bequia (final night). If you’ve ever wondered what the “perfect Grenadines sampler” looks like, this was it.

St. Vincent: The Gateway to the Grenadines

We began on St. Vincent, the rugged, soulful heart of the country with green mountains rising steeply from the sea, a coastline that hints at volcanoes, and rainforest hikes just inland. St. Vincent feels less polished than some of its southern neighbors, and that’s part of the charm. It’s real, lived-in, and full of energy.

There’s something ceremonial about provisioning and casting off from the main island. The first day carries a special buzz — checking lines, stowing fresh fruit, pointing out landmarks as they slide astern. The boat shifts from “dockside base” to “moving world,” and suddenly you remember why sailors chase horizons in the first place.

Bequia: A warm welcome and a sailor’s pace

Our first stop was Bequia, and just like that, the trip’s tempo clicked into place. Bequia is the kind of island that meets you with a smile: friendly faces, a relaxed waterfront, and the unmistakable vibe of a place that has welcomed sailors for generations.

It’s the perfect first stop because it offers comfort without feeling crowded. You can shake out your sea legs, find your favorite cockpit spot, and settle into the routine: anchor down, mask on, dinghy ready, music low, worries gone. Evenings here feel designed for strolling — sand between your toes, a breeze off the anchorage, and the gentle glow of boats at rest.

When we cast off for Mustique the next day, the passage reminded us that even paradise can come with a little spice. The swells were big enough that it wasn’t exactly an “easy” ride, but the time flew, especially when our guest Scott landed a gorgeous bluefin tuna. Dinner tonight? Check.

Mustique: Where the breeze feels a little more glamorous

Mustique is all polished beauty and famously private corners. Even arriving by water feels different, like you’ve drifted into a postcard where everything is slightly more vivid: the sea a deeper blue, the hills a little greener, the shoreline dotted with tucked-away beaches.

And then we did something that still makes us laugh: we headed to Basil’s Bar to see if they could cook up the epic fish we’d just caught. Basil’s is Mustique’s iconic, come-as-you-are hangout perched right over the water in Britannia Bay — a laid-back, open-air spot where yachts pull in, barefoot lunches turn into sunset drinks, and the night can quietly (or loudly) become a party.

Now back to that tuna. Picture this: someone carrying a 15-pound tuna in a reusable plastic grocery bag, barefoot, walking into a beautiful waterfront spot where celebrities are known to frequent. Yep, that was us. And it instantly became one of those stories we’ll never forget. The chef at Basil’s cooked our tuna to perfection, and if you ever find yourself on Mustique, it’s a must.

Canouan: Clean lines, clear water, and calm confidence

From Mustique we sailed to Canouan, where the Grenadines begin to feel even more like a chain of secret lagoons and reef-protected bays. Canouan has a tidy, composed feel — an island that blends natural beauty with a touch of refinement.

We pulled into Sandy Lane Yacht Club and couldn’t believe our luck: we had the marina basically to ourselves for the evening, with just one other boat sharing the seawall. We wandered through the little shops, ordered fresh-baked bread to pick up the next morning, and topped off provisions.

Next stop: Shenanigans Beach Club. We were greeted by attentive staff and, somehow, had the place entirely to ourselves for a few hours. We swam in the pool, took dips in the ocean, and sampled some of the yummiest cocktails of the entire week.

For sunset, we headed to Scruffy’s Bar — hands down the best place to take it all in. The beach lined with tiki torches, the soft glow, the ocean breeze… the ambience was five-star. Dinner brought us back to Shenanigans, and we invited the crew from the other boat to join us. The night turned into an easy, happy shared meal, complete with helping celebrate a birthday.

And the next morning? A small joy that felt huge: a proper shower. Sandy Lane’s facilities may honestly be some of the nicest bathrooms we’ve ever seen on a charter.

Tobago Cays: The dream you’ve been picturing

Then came the moment everyone talks about — Tobago Cays. If the Grenadines are the greatest hits album of Caribbean sailing, Tobago Cays is the title track.

The water here doesn’t just look clear — it looks lit from within. Protected by a horseshoe reef, the anchorage feels like nature built a private swimming pool for sailors. And the snorkeling? It’s the kind that resets your brain. Coral gardens. Schools of fish flickering like confetti. And yes — turtles everywhere. The Tobago Cays are known for their turtle population, and all you have to do is jump in to understand why.

That evening we went ashore for our lobster dinner — and when we say lobster dinner, we don’t mean white tablecloths. We mean a picnic table in the sand, a makeshift kitchen, and local fishermen bringing fresh lobsters to be grilled up to perfection. Simple, salty, and absolutely magical.

Mayreau: Two nights to truly sink in

After Tobago Cays, we headed to Mayreau — and stayed two nights, because some places deserve more than a passing hello.

Mayreau has a sweetness to it, a small-island intimacy that makes you instantly slow down. The second night is what really made it special. With an extra day, the crew stopped checking the clock. Mornings stretched. Someone lingered over coffee. Someone else found shade and a book. People snorkeled again not because they hadn’t yet, but because they couldn’t resist.

It’s one thing to visit paradise. It’s another to feel like you belong there for a moment — like the anchorage recognizes you, like the breeze is familiar, like you could stay one more day and nobody would question it.

Back to Bequia: The perfect final chapter

For our final night, we returned to Bequia, closing the loop the way all good voyages do — back to a place that now felt even more like home. This time, we were finally able to visit Sargeant Brothers Model Boat Shop (it had been closed during our first pass-through).

I was especially eager to see what all the hype was about, and it did not disappoint. Sargeant Brothers is a can’t-miss stop for anyone who loves the sea. This family-run workshop is known for crafting beautifully detailed, hand-built model boats — each one a tribute to Bequia’s deep boatbuilding traditions. Whether you’re after a classic Caribbean schooner, a local fishing boat, or a custom keepsake that captures your own vessel, it’s the kind of place where you can watch the craftsmanship up close and leave with a piece of island maritime heritage.

I happened to leave with a beautiful hand-carved ship that now has a proud place on display in my family room — one of the best souvenirs I’ve ever brought home.

The last evening aboard always carries that quiet mix of gratitude and disbelief: the week flew, the memories are already stacking up, and somehow you’re already planning the next trip in your head.

What this giveaway really gave us

Yes, it was a stunning route. Yes, it was a beautiful boat. But the heart of the Trip of a Lifetime wasn’t just the scenery — it was the reminder of why we sail: to unplug, to explore, to laugh at how little we actually need, and to wake up each day in a new corner of the world with the ocean right outside the hatch.

St. Vincent & The Grenadines has a way of doing that to people. It doesn’t just show you a good time — it gives you back a version of yourself that’s calmer, brighter, and a little more alive.

And if that isn’t a trip of a lifetime, we don’t know what is.