Hey, I'm Captain Jonathan. I'm lucky enough to sail these waters just about every day the weather lets me, and I've had the same happy conversation with hundreds of guests down on the Esperanza boat ramp — the ones who planned every other detail of their Puerto Rico trip but weren't totally sure what a sailing charter in Vieques actually involves.
So here's the friendly, no-fluff version: everything I'd tell you over a coffee before you book. A few honest bits most tour sites skip, too.
Here's the thing people fall for: the quiet. The moment the sails go up and it's just water against the hull and the boat leaning gently into the breeze — that's the good stuff. It's slower than you might expect, and that's kind of the whole point. You're not being shuttled from A to B. You're sailing, letting the wind do the work while Vieques drifts by.
If you've never done it before, that first hour has a way of rearranging your idea of a good day on the water. And if you have? You already know. 🌬️
This is the quirky part I love telling people: Just Today runs on 100% wind and solar — no diesel, no fumes, no engine rumble. We pulled out the old diesel motor, put in a full electric drive, and now generate every watt we need from solar panels and a little wind generator (the dinghy's electric too).
Practically, it means we sail with the weather instead of powering through it — which honestly just makes for a calmer, quieter, better day. And it keeps our little corner of the Caribbean cleaner, which everyone out here can get behind. If you're curious how the whole setup works, I geek out about it on the eco sailing page.
Every sail is private — your group of up to four, plus me. That's not about being fancy; it's about being comfortable. Four people is the cozy little number where everyone gets a great seat, a turn at the wheel if they want it, and a day that bends to your pace instead of a schedule.
Traveling with family, celebrating something, or just want a mellow afternoon with your favorite people? Perfect. You can meet the boat (and me) over on the boat & crew page.
You can sail here year-round, and honestly both seasons are lovely — they just have different personalities:
Winter (roughly December–April): The Caribbean trade winds show up in full force. Livelier, more spirited sailing if you want the boat really moving — though stronger wind also means a bit more bounce. If you're wind-curious, this is a fun one.
Summer (roughly May–November): Softer breezes, calmer water, and an easygoing ride. Great if you're bringing kids, you're brand new to boats, or "relax" is higher on the list than "adventure." The island's quieter this time of year, too.
A few days before your sail the forecast gets reliable, so I'll give you the real scoop on what to expect. I'd always rather set you up right than promise a flat-calm day the wind isn't going to deliver.
No fancy marina here — we do it the island way, and it's part of the charm. You'll meet me at the Esperanza boat ramp, hop into the electric dinghy right off the beach (bring shoes that don't mind getting wet 👟), and we'll putter out to Just Today. Quick safety chat, sails up, and off we go to find the calm, quiet stretches of coastline along the south side of the island.
From there, it's your day. Sail, swim, float, snorkel off the boat, or just kick back with a drink and watch Vieques roll by from an angle you don't get from shore. Morning half-day sails, or the sunset sail — which, I'll be honest, is really hard to beat. You're shore-to-shore the whole time, never far from that ridiculously green coastline.
The hospitality side is all handled. Your charter comes with responsibly bottomless premium drinks — wine, champagne, beer, plus sodas, sparkling and filtered water, and coconut water — served in real glassware, along with Turkish-style beach towels and little waterproof bags for your things. Want to bring snacks? Give me a heads-up and I'll have a cooler on ice ready to go.
What to bring yourself:
Sun protection: hat, sunglasses, a sun shirt, and reef-safe sunscreen
Swimsuit and shoes that are happy to get wet
A photo ID
A change of clothes if you like
Something for seasickness if you're prone to it (more on that in a sec)
One rule that isn't mine to bend: no marijuana of any kind, including legal medical. The boat and I are federally licensed by the U.S. Coast Guard, and under federal law it's still a no-go. All the details live on the Q&A page.
I'd rather mention this now than have you find out at anchor. This is open-water sailing, so there'll be wind, waves, and real motion — especially in winter. If you get queasy at all, chat with your doctor about the right remedy before your trip. It makes a world of difference. Here's the full weather and motion sickness policy.
And since there are no docks, you'll need to be steady enough to get in and out of a dinghy and climb a five-foot ladder onto the deck. Not sure if that's doable for you or someone in your group? Drop me a message and we'll figure it out together — no pressure either way.
You can check live availability and current seasonal pricing for the sunset, half-day, and full-day sails right here: Book Now. Weighing your options, or dreaming up something special — an anniversary, a proposal, a custom trip? Just say hi. It's a one-boat, one-captain operation, so the person you're chatting with is the same person who'll be sailing you. 🙂
Sail, relax… it's Just Today.
Fair winds, Captain Jonathan
Do I need any sailing experience? Nope, none. I handle everything. Want a turn at the wheel? Great. Want to stay in the shade with a drink? Also great.
How many people can come? Up to four guests, and the whole boat is yours — you'll never share it with strangers.
What's the best time of year to go sailing in Vieques? Winter brings stronger trade winds and livelier sailing (with a bit more motion); summer is calmer and gentler, which is lovely for families and first-timers. Both are wonderful — it just depends on the day you're after.
Can I still swim and snorkel? Absolutely. You can hop in and snorkel right off the boat — the sailing's the heart of it, but the water's yours to enjoy.
Where do we meet? At the boat ramp on the east end of El Malecón in Esperanza. From there it's a short electric-dinghy ride out to the sailboat.
What if the weather looks iffy? I keep a close eye on the forecast and I'll always give you the straight story. See the cancellation and weather policy for how it all works.