Tradition Sailing Anguilla

Tradition Sailing Anguilla Authentic Caribbean Adventures on a Classic West Indian Sloop.
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We at Tradition have heavy hearts as we share the sad news of the loss of Brennon Gumbs, who passed away on December 18,...
25/01/2025

We at Tradition have heavy hearts as we share the sad news of the loss of Brennon Gumbs, who passed away on December 18, 2024. Brennon was an irreplaceable part of the Tradition family from the very beginning, joining us as our first crew member when we launched Tradition Charters 15 years ago.

Brennon wasn’t just there for the hard work—like those early annual maintenances in Carriacou, where we rolled up our sleeves in the shipyard and discovered the island’s simple joys together.

In the early days, Brennon was the face of Tradition, featured in our first promotional materials. And while we lovingly called him our “onboard curmudgeon” in our crew profile on the website, his warmth, humor, and genuine spirit left an indelible mark. Brennon wasn’t just a crew member—he was the heart of our team during charter seasons, bringing laughter, exceptional service, and unforgettable moments to every sail. Guests loved his sharp wit and hospitality, and he had a way of making every moment aboard Tradition truly special.

Over the past 15 years, even after Brennon moved on to other projects, he and Laurie kept in touch in a way that was uniquely theirs. They would constantly message each other whenever they spotted funny business signage, a hilarious malaprop, or anything that was certain to amuse them both—which was quite a lot. That shared humor and connection were just another example of the joy Brennon brought into the lives of everyone who knew him.

More than anything, Brennon helped shape the soul of what we are today—dedicated to excellence, personalized service, and the bond of an outstanding crew. His humor, dedication, and kindness are woven into the very fabric of our story.

We feel this loss deeply, and our hearts are with his family and the many friends who loved him.

Rest easy, Brennon. You’ll always be part of Tradition’s story, and you’ll forever be missed.

When a sunset sail mood sets in, Tradition is your girl. (Weather permitting☝️) Sunsets are magnificent every day but ta...
23/01/2025

When a sunset sail mood sets in, Tradition is your girl. (Weather permitting☝️) Sunsets are magnificent every day but taking it in with kindred spirits from the wooden deck of classic Caribbean sailing sloop is nonpareil. ❤️

Thanks to Tira G. for the capture!




“Sometimes, the most productive thing that you can do is to step outside and do nothing… relax and enjoy nature.” Melani...
22/01/2025

“Sometimes, the most productive thing that you can do is to step outside and do nothing… relax and enjoy nature.” Melanie Charlene

As displayed by some guests on Tradition’s Prickly Pear Lobster Lunch Day Sail. The nature is extra special out here, and accessed by a breathtaking sail to and from. ❤️

Shared Prickly Pear sail days are Tuesdays, Thursdays, and Saturdays. Join us!




The place to be on a cold winter day! ❤️⛵️💦Join us for a gorgeous sail and quality time at Little Bay on Wednesdays and ...
20/01/2025

The place to be on a cold winter day! ❤️⛵️💦

Join us for a gorgeous sail and quality time at Little Bay on Wednesdays and Fridays.




Behold a smörgåsbord of seafaring delights. ❤️ Tradition’s evening sailing option is intimately timed around the sun set...
16/01/2025

Behold a smörgåsbord of seafaring delights. ❤️ Tradition’s evening sailing option is intimately timed around the sun setting over the water and a finale under the stars.

Photo thanks to Mark N.




You might call this the authentic ocean lover’s dream scenario… Classic sailing sloop ✔️, snorkel gear ✔️, floatation no...
14/01/2025

You might call this the authentic ocean lover’s dream scenario… Classic sailing sloop ✔️, snorkel gear ✔️, floatation noodles and ring ✔️, offshore marine protected area ✔️, inviting ocean water ✔️, time to enjoy it all ✔️. Like candy! ❤️

Join our shared Prickly Pear Lobster Lunch Say Sails on Tuesdays, Thursdays, and Saturdays.




We’re Hiring! Join the Crew of Tradition! 🌊Deckhand Position Available ⛵️Are you passionate about sailing and ready for ...
13/01/2025

We’re Hiring! Join the Crew of Tradition! 🌊

Deckhand Position Available ⛵️
Are you passionate about sailing and ready for an exciting opportunity to work on the water? Tradition, Anguilla’s premier day sail charter, is seeking a deckhand to join our dedicated and hardworking crew!

About the Role -
Seasonal Sailing: Work with us November through July, with an option to join our maintenance period in Carriacou, Grenada during August.
Customer Interaction: Deliver outstanding customer service while engaging with guests for 6+ hours per charter.
Physical Readiness: Tackle physically demanding tasks (e.g., lifting up to 50 lbs/22.7 kg, standing for extended hours).
Team Collaboration: Help prepare the boat, assist during charters, and pitch in with occasional kitchen duties.

What We’re Looking For -
✔️ Sailing Experience (mandatory)
✔️ STCW Certification (mandatory)
✔️ Strong Communication Skills – A sense of humor is a huge plus!
✔️ Team Spirit – We work closely as a crew, so being a team player is essential.
✔️ Bonus Skills: Experience with rigging, oil changes, or engine maintenance is a big advantage.

How to Apply:
Email us at [email protected] with your resume, a brief introduction about yourself and your sailing journey, and highlight any experience with engine maintenance and rigging.

Join the adventure and become part of our amazing crew! 🌟







Enjoy a flashback photo from twelve years ago, looking across the salt pond, over Sandy Ground, and to Tradition on her ...
12/01/2025

Enjoy a flashback photo from twelve years ago, looking across the salt pond, over Sandy Ground, and to Tradition on her mooring in Road Bay. She stands out during the day. ❤️

Today the sea is rolling and not as flat, and there are more boats accompanying Tradition in the bay. Happy Sunday to all!




Salty souls are welcome to take Tradition’s tiller when the conditions are right... whether experienced or not. On this ...
11/01/2025

Salty souls are welcome to take Tradition’s tiller when the conditions are right... whether experienced or not. On this particular sunset sail we had a seasoned captain take the helm. ❤️

Tradition’s Sunset Sailing cruise is on Mondays, Wednesdays and Fridays.

Photo thanks to Mark N.




Set sail with us for cozy and delicious moments on Tradition’s heritage deck. Freshly made hors d’oeuvres and fine Frenc...
09/01/2025

Set sail with us for cozy and delicious moments on Tradition’s heritage deck. Freshly made hors d’oeuvres and fine French imports pair with our premium drinks and the sunset mood… Mondays, Wednesdays, and Fridays. 🥂




When it’s plunge time at Little Bay, the rewarding feeling is indescribable. 💦 Tradition’s spacious deck and flat gunwal...
07/01/2025

When it’s plunge time at Little Bay, the rewarding feeling is indescribable. 💦 Tradition’s spacious deck and flat gunwale make it easy and the scenery of Little Bay is alluring. We’ve got what you need to snorkel, float, stay hydrated, and dry off. The sail back is also a winner. Join us on Wednesdays and Fridays for Tradition’s Little Bay Half Day Sail and Snorkel Adventure! ❤️⛵️




It’s freshly grilled, it’s local and it’s even sweeter after a morning of sublime sailing on a classic…The lunch feast o...
04/01/2025

It’s freshly grilled, it’s local and it’s even sweeter after a morning of sublime sailing on a classic…

The lunch feast on Tradition’s Prickly Pair Lobster Lunch Day Sail excursion is one of many memorable highlights of a magnificent day. Join us Tuesdays, Thursdays and Saturdays. Reserve through our website or call or email Deb at 264-476-7245, [email protected].




Ready for a ton of fun for all of our sailors at Prickly Pear! 💦 And ready for a fresh, local lobster feast too!  🦞🍹 Res...
28/12/2024

Ready for a ton of fun for all of our sailors at Prickly Pear! 💦 And ready for a fresh, local lobster feast too! 🦞🍹 Reserve your spot, we sail there on Tuesdays, Thursdays and Saturdays! ❤️⛵️




May all your needs be met and your heart filled with gratitude. ❤️ Happy Boxing Day!
26/12/2024

May all your needs be met and your heart filled with gratitude. ❤️ Happy Boxing Day!




Winter sunset sailing on Tradition feels perfectly warm and soulful. Join us from 4:30pm to 7pm on Mondays, Wednesdays a...
23/12/2024

Winter sunset sailing on Tradition feels perfectly warm and soulful. Join us from 4:30pm to 7pm on Mondays, Wednesdays and Fridays for the authentic and inspiring experience. 🧀🍷❤️⛵️




The start of a fabulous day of sailing, special moments, and adventure… Tradition’s morning starts are Tuesdays, Wednesd...
21/12/2024

The start of a fabulous day of sailing, special moments, and adventure… Tradition’s morning starts are Tuesdays, Wednesdays, Thursdays, Fridays, and Saturdays between our Prickly Pear Lobster Lunch Day Sail and our Little Bay Half Day Sail and Snorkel Adventure. Come sailing with us on a classic West Indian sloop and treasure the unique experience. See our website for available dates or to book your spot! ❤️⛵️




Mood lighting for the post-sunset sail back to Sandy Ground… Warm and lovely red, of course. ❤️
18/12/2024

Mood lighting for the post-sunset sail back to Sandy Ground… Warm and lovely red, of course. ❤️




Your ride…A classic West Indian sloop and the water around Prickly Pear is a sight to see. Tradition’s red is the cherry...
16/12/2024

Your ride…

A classic West Indian sloop and the water around Prickly Pear is a sight to see. Tradition’s red is the cherry on top. ❤️⛵️ https://tradition-sailing.com




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