Charter Smarter Newsletter | June 12, 2025
DESTINATION HIGHLIGHT: GRENADINES
Skip the Summer Travel Madness. Sail Here Instead.
Let’s be honest: summer travel can wear you out before you’ve even reached your destination. Airports are packed, hotels are fully booked, and those dreamy island escapes? More like crowded hotspots.
But there’s a better way to do summer — one that swaps the frenzy for freedom, and the noise for nature. Welcome to the Grenadines, a quiet chain of 32 picture-perfect islands tucked into the southern Caribbean.
And if you're looking for the sweet spot? August, September, and October offer a prime opportunity to explore the Grenadines with space to breathe, beautiful weather, and a sense of ease that’s hard to find elsewhere this time of year.
Why the Grenadines…and why now?
1. Fewer crowds, more freedom
High season in the Caribbean typically runs from December through April, which means by late summer, the Grenadines are pleasantly peaceful. Anchorages are wide open, beach bars have a more local feel, and the entire experience feels more personal — and a lot less rushed.
This is the time of year when you can find yourself on a beach with no one else in sight, dine in tucked-away restaurants without a wait, and experience the islands as they were meant to be — unhurried and uncrowded.
2. A playground of islands to explore
Each island in the Grenadines has its own personality. You might start in Bequia, a charming sailing hub with colorful waterfront shops and friendly faces at every turn. Then move on to Mustique, where understated luxury and pristine beaches await.
From there, sail into the Tobago Cays, a national marine park with brilliant coral reefs and shallow, clear waters where you can swim alongside sea turtles. Continue on to Mayreau, Canouan, and Union Island — each offering something different, from lively local culture to remote, tranquil anchorages.
The sailing routes are short and scenic, meaning you’ll spend more time exploring and less time in transit. Whether you’re hopping between beaches, snorkeling untouched reefs, or enjoying a sunset cocktail on deck, every day offers something new.
3. More value, less hassle
Chartering in the Grenadines during August through October can offer more flexibility in both planning and pricing. With fewer boats in the water and less demand on charter services, it's often easier to customize your itinerary, book your preferred dates, and even take advantage of more favorable rates.
4. Breathtaking natural beauty
There’s a raw, untouched quality to the Grenadines. These aren’t overdeveloped islands lined with high-rise resorts. Instead, you’ll find white-sand beaches backed by swaying palms, fishing villages that feel frozen in time, and bays so clear you can spot starfish on the ocean floor.
Late summer and early fall bring lush, vibrant landscapes — the greenery pops, the sunsets are dramatic, and the water is warm and inviting. Afternoon rain showers can roll through briefly, but they often give way to crisp skies and glowing golden hours.
5. A slower, more intentional pace
Everything in the Grenadines moves at a gentler rhythm — and that’s especially true during this time of year. With fewer people and less pressure to “beat the crowds,” your days are truly your own.
Want to linger longer in a favorite bay? No problem. Craving an extra beach day before moving on? It’s your call. This kind of freedom is what makes chartering here such a different experience — it’s not just a vacation, it’s a chance to reset your internal pace and get back to what feels good.
Curious what a week might look like?
We’ve put together a free sample itinerary with stops at some of our favorite anchorages and island hideaways — designed to help you visualize what your Grenadines charter could be. Whether you’re new to yacht vacations or a seasoned sailor, this guide will give you a feel for the flow, the sights, and the pace that make the Grenadines one of the most magical charter destinations in the Caribbean.
When to go?
Ideal months: August, September, and October
Expect: Warm breezes, vibrant greenery, stunning water clarity, and wide-open space — both at sea and onshore
This window gives you the freedom to enjoy the islands without competing for moorings or making dinner reservations days in advance. It’s one of the best times to explore at your own pace, with fewer boats, more flexibility, and everything that makes sailing so satisfying.
The bottom line.
You don’t have to wait for winter to take that bucket list charter. The Grenadines are calling — and late summer into early fall is one of the most underrated times to answer.
No crowds. No stress. Just unforgettable sailing, vibrant scenery, and all the space in the world to unwind.
Lights, Camera, Catamaran: Join Our 2025–2026 Creator Crew
Welcoming New Brand Ambassadors for the 2025/2026 Season
Are you a savvy content creator and believe your followers/audience would have an interest in booking our yacht vacations earning commission? If so, we invite you to apply to be a Charter Smarter brand ambassador and enjoy either a discounted or fully comped 5-night, 6-day luxury charter through the Virgin Islands. It's an excellent opportunity to enjoy our exceptional yachts, create super unique content, earn commission and capture yacht life from the inside to generate bookings. Our program's offering and more details will be provided via email after receiving your application.
Applications for July 2025 and the 2026 charter season are now open. If you’re a thoughtful visual storyteller with a strong point of view and an engaged audience, we’d love to hear from you.
Not Selected This Time? No Worries! There's still an Opportunity to Stand Out .
Even if you’re not chosen for the hosted experience, you can still book a charter and use the trip as a way to build your brand to generate commission through our VIP Exclusive Rewards Program, no matter how small the following. From luxury lifestyle reels to behind-the-scenes client-facing content, there’s no better backdrop for creators and professionals who want to stand out in a saturated feed.
Stay in the Loop
This won’t be our only opportunity. We’re building a growing network of collaborators and brand advocates, and we’d love for you to be part of it when your account is approved in the future. So stay tuned by following us on Instagram at @charter.smarter
Trending Now on Social: Yacht Vacation vs. Resort
A Quick Look at Why More Travelers Are Choosing to Sail
If you're still deciding between a traditional resort stay and something a little more... mobile — you're not alone. One of our recent Instagram posts is getting a lot of attention, and it breaks it down simply.
Top 3 reasons a yacht vacation might just win out?
Gourmet meals, tailored to you
Forget buffets. Onboard, your chef builds a menu around your dietary preferences — whether that’s gluten-free, vegan, or just extra rum cake.A crew that acts like your private travel guide
Think concierge service, but barefoot. Your crew knows the islands inside and out and can show you the quiet beaches, hidden snorkel spots, and best bars with no wait.No need to choose one destination
Why stay in one place when you can wake up somewhere new every day? Island-hopping means variety, spontaneity, and no packing or unpacking.
Whether you’re already booked or still dreaming, this post sums up what makes life onboard different — and in many ways, better.
Watch the full reel here:
👉 Top 3 Reasons a Yacht Vacation Beats a Resort
CHARTER TIP 💡
Try not to do too much research in advance. Our crew live and work these islands and waters every day, and know how to be flexible with changing weather, local events, and other things that might alter the itinerary. Research is great, but flexibility and trusting the experts to lead you in the right direction, based on your preferences, is even better. The crew may take you to places you have never even heard of. And isn't it always fun to be surprised?!
Sit back, relax, and let us show you the time of your life!
Jill Bailey - Charter Concierge & General Sales Manager
