Charter Smarter Newsletter | August 7, 2025
So... Where Do We Charter? Here's the Answer (and Why These Spots Are Hard to Beat)
We get asked this question a lot: “Where exactly do you offer charters?”
It’s a fair one, especially when you're seeing reels of secluded beaches, turquoise water, and luxury catamarans that look straight out of a travel magazine. While we hope the scenery speaks for itself, let’s dive in a little deeper.
We currently offer private, all-inclusive yacht charters in two of the Caribbean’s most exceptional destinations: The U.S. Virgin Islands (USVI) and the British Virgin Islands (BVI).
The British Virgin Islands: A Global Charter Favorite
The BVI is one of the most celebrated yacht charter destinations in the world. With over 50 islands and cays, protected waters, and short sailing distances, it’s the ideal region for a week on the water, whether you're a first-timer or a returning guest.
Expect postcard-perfect experiences like:
Snorkeling the caves at Norman Island
Dining on fresh lobster in Anegada
Swimming ashore to the Soggy Dollar Bar on Jost Van Dyke
Hiking the famous boulders at The Baths on Virgin Gorda
Quiet sunset anchorages in sheltered bays
Everything about the BVI is tailored to smooth, scenic sailing and flexible itineraries. The routes are customizable, the views are nonstop, and the experience is consistently world-class.
The U.S. Virgin Islands: Effortless Travel, Unforgettable Vibes
Chartering in the USVI is the easiest way to get on the water, especially for U.S. travelers. No passport needed, direct flights into St. Thomas, and an equally beautiful set of islands to explore.
Top highlights include:
St. Thomas, the launch point for many charters, with gorgeous anchorages and vibrant beach scenes
St. John, where two-thirds of the island is protected national park with exceptional snorkeling and hiking
Water Island, a quiet spot with fewer crowds and a laid-back feel
You can choose to stay within the USVI or combine it with the BVI for a broader itinerary. Either way, the scenery is spectacular, and the experience is seamless.
Why These Two?
We focus on the USVI and BVI because they consistently deliver what matters most:
Smooth sailing conditions
Diverse and flexible itineraries
Top-tier crews and boats
A balance of relaxation, activity, and natural beauty
These regions allow us to create trips that feel luxurious without being overly structured, adventurous without being difficult, and totally tailored to the group on board.
Thinking About Booking?
Whether you’re dreaming of an anniversary trip, a family getaway, or just a reset with a few friends, these two destinations are the perfect place to start. Let us know what kind of experience you’re after, and we’ll help you find the right boat, the right crew, and the right itinerary.
Did You Catch Our Latest Stunning Yacht Highlight?
If not, now’s the time to hit play.
We recently shared a reel on our socials that gives you a close-up look at Iara, one of our most beautiful sailing catamarans available for charter in the Virgin Islands. She blends effortless comfort with thoughtful design, and offers the kind of all-inclusive experience that takes the stress out of vacation planning entirely.
Iara is a 50-foot luxury catamaran with three spacious guest cabins, each featuring a private bath and full air conditioning. She comfortably hosts up to six guests, making her ideal for families, couples traveling together, or small groups looking for a completely private escape. But what truly sets Iara apart is the crewed, all-inclusive experience. From the moment you step on board, everything is handled: daily five-star meals, unlimited drinks, and personalized service tailored to your group.
It’s the kind of vacation that’s hard to describe in words, which is exactly why we’re showing more of it on video.
Our social content is designed to show, not just tell, what makes chartering a yacht so different from a typical vacation. We'll be posting more walk-throughs, sneak peeks, and yacht highlights in the coming weeks. If you’re not already following us, now’s a great time to start. You’ll get a real sense of what the boats look like, how the spaces flow, and what to expect onboard.
And if you’ve already seen the Iara reel and found yourself wondering what a trip like that might cost, or how to make it happen, we’d love to walk you through the details.
Follow us on Instagram to stay in the loop, and let us know if you'd like more info on Iara or similar yachts. Chartering doesn’t have to feel overwhelming. Sometimes, it really is as simple as showing up and enjoying the ride!
The Anti-Itinerary: What Happens When You Don’t Plan Every Second?
It’s 7:00 AM. You’re not rushing to beat the breakfast buffet. There’s no tour bus idling outside. No back-to-back “must-see” stops. You’re barefoot, coffee in hand, watching the water shift color as the sun comes up over a quiet bay. And there’s only one thing on your to-do list: nothing.
Welcome to the anti-itinerary. This is what life looks like on a private yacht charter through the Virgin Islands.
Let’s Be Honest: Most Vacations Still Feel Like Work
Even luxury ones.
Sure, you might be in a beautiful place. But the mental load stays with you:
What time is dinner?
How far is the drive?
Should we squeeze in one more stop?
Did we pack the sunscreen?
What’s everyone in the group actually in the mood for?
You’re still managing. Still juggling. Still planning.
A crewed yacht charter flips that dynamic on its head. When we say it’s all taken care of, we mean it.
The Itinerary Builds Itself
On a charter, the experience is designed around flow, not obligation.
Yes, you’ll have a general route. But nothing is locked in. Want to linger longer at that secluded beach? Stay the night. Want to skip a port and sail straight to the next island? Done. Your captain adapts the route in real time based on weather, vibe, and what your group is enjoying most.
It’s the rare kind of travel where spontaneity isn’t stressful, it’s the point.
A Private Chef Means No One’s Arguing Over Where to Eat
One of the most underrated parts of the anti-itinerary? The food.
You’re not scrambling for last-minute reservations or navigating unfamiliar menus. Your onboard chef handles everything, based on your preferences, dietary needs, and cravings. You might start the day with tropical fruit and fresh-baked pastries, and end it with grilled mahi and a mango coulis you didn’t even know you wanted.
It’s not just delicious, it’s frictionless.
Your Time Becomes Yours Again
Want to snorkel before breakfast? Nap after lunch? Open that second bottle of wine without worrying about how you’ll get back to the hotel?
It’s all fair game.
There’s no bus schedule. No pressure to get your money’s worth out of a resort. No 6 a.m. wake-up calls because “that’s the only time the tour runs.” It’s just time. Your time. To use how you want.
The Hidden Luxury? Mental Clarity
People book yacht charters for the views, the privacy, the adventure.
But what they remember most?
How light they felt.
The weight of decision fatigue disappears. Everyone relaxes. Conversations get deeper. Laughter gets louder. Phones stay in bags. People sleep better. And for the first time in a long time, no one is performing vacation, they’re just living it.
Let Go of the Schedule. Keep the Experience.
If you’re used to overplanning your time off, this kind of trip might feel unfamiliar at first. But we promise, it’s the right kind of unfamiliar.
Because the best parts of a charter?
They aren’t the bullet points on an itinerary.
They’re the moments you didn’t see coming.
Ready to rethink what travel can feel like? We’ll help you choose the right boat, build your ideal (loose) route, and connect with a crew that gets your vibe.
CHARTER TIP 💡
Flexible Dates? Score a Last‑Minute Deal! If your schedule is open, you could snag significant savings with a last‑minute yacht charter. When a boat has an unbooked week or a cancellation opens up a prime date, many owners offer reduced rates to fill the gap. These opportunities can pop up anytime, especially outside peak season, and are perfect for travelers ready to say “yes” and set sail on short notice.
Jill Bailey
General Sales Manager
