Sail Helios

12/08/2026

If you love The Beach Bar, more bags coming out soon !

06/08/2026

Bags made from a Spinnaker

04/08/2026

Another new bag

03/08/2026

⛵ A New Chapter Begins!

To all of our friends, guests, and fellow sailing enthusiasts—

After many wonderful years on the water, Captain Jay is shifting his full attention to St. John Sailsack Co. and Caribbean Canvas Co. From now on, you’ll find him turning reclaimed sails into handcrafted bags and accessories right here on St. John.

If you’re visiting the island, stop by the shop, see where retired sails get a second voyage, watch the bags being made, and say hello to Capt. Jay!

While Helios is retiring from the charter business and will now be used only for personal sailing adventures, we’d love to recommend some great local captains for your day on the water.

Our Recommended Charters

📍 Cruz Bay
⛵ Morningstar Charters
🌐 http://morningstarcharter.com
📞 340-626-8743

🚤 Just Right Charters (56’ Sea Ray)
🌐 www.justrightvi.com
📞 (340) 643-9690

📍 Coral Bay
🚤 Flyaway Charters
🌐 www.flyawaycharters.com
📞 (340) 693-8180

⛵ Mandolin Sailing Charters
📞 (340) 727-5339

Thank you to everyone who has supported us over the years. We look forward to seeing you at St. John Sailsack Co., where every handcrafted bag tells the story of a sail that found a new life.

See you around the island!

— Capt. Jay & the St. John Sailsack Co. Team

2 to 6 individual passengers or single groups up to 12. Laid back relaxed fun atmosphere. Enjoy our Captained sailing/ snorkeling or sunset Sails, both Bayside & Oceanside. Let 30 years of experience on the reefs and waters around Key Largo set you free to discover. Enjoy the beauty of the Florida K...

19/05/2025

Helios has a new mainsail. Check out StJohn Sailsack Co to get a bag made from the last one!

⛵️❤️ Big news from Cruz Bay! ❤️⛵️
Helios, the beautiful Hinckley that’s become part of so many St. John love stories, just got a brand new main sail. The sail that came down has seen countless sunsets, weddings, and island adventures—many of them officiated by the one and only Captain Jay.

We’ll be turning this storied sail into a limited run of Sailsacks. If you have a connection to Helios or her captain, now’s your chance to carry a piece of her legacy. ⛵️ Reach out and let us know to reserve a sailsack from this sail for you!

PS: If you’re dreaming of your own island wedding or private charter, we can’t recommend Helios enough. Just ask our tribe—she’s magic.

30/11/2024

“I am such a summer person. Just give me a quiet spot with a breathtaking view, a cool drink in my hand, a warm sea breeze on my skin, and the soothing sounds of waves crashing and I will be in all my glory.” — Unknown

Book your Day Sail, Wedding, Elopement, Vow Renewal or Engagement, on a Classic Hinckley Sou’wester 48’ Book online @ https://buff.ly/3QxMW5n sailing out of Cruz Bay St John USVI
Text or call. 340-244-3290

29/11/2024

“My soul is full of longing for the secret of the sea, and the heart of the great ocean sends a thrilling pulse through me.” — Henry Wadsworth Longfellow

Book your Day Sail, Wedding, Elopement, Vow Renewal or Engagement, on a Classic Hinckley Sou’wester 48’ Book online @ https://buff.ly/3QxMW5n sailing out of Cruz Bay St John USVI
Text or call. 340-244-3290

28/11/2024

“The best memories are those the waves can never wash away.” — The Diary of a Nomad

Book your Day Sail, Wedding, Elopement, Vow Renewal or Engagement, on a Classic Hinckley Sou’wester 48’ Book online @ buff.ly/3QxMW5n sailing out of Cruz Bay St John USVI
Text or call. 340-244-3290