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A First Class Day At Sea Aboard
Anguilla Sailing Charter... Tradition


Sailing is deeply weaved into the fabric of Anguilla. It's the island's national sport and a key aspect to the island's biggest holidays (ex., Carnival, Anguilla Day, Easter Monday). Considering that Anguilla is surrounded by the sea, it makes perfect sense to spend plenty of time on it.

One of the most special ways to experience the Caribbean Sea? By climbing aboard Tradition Sailing Charters...

See the video above for a full look at the Tradition Sailing experience.

The Vessel

anguilla card emblem

Anchored in Road Bay in Sandy Ground, Tradition is a timeless beauty.

True to her name, she is a classic sailboat, a 50' Carriacou sloop, or to be more precise, a "gaff rigged West Indian sloop built in 1978" as owner Laurie Gumbs says.

There She Is!
tradition sailing charters anguilla

Tradition is no stranger to the waters surrounding Anguilla. Back in the day she was a cargo boat. Sailing up and down the Leeward and Windward Islands between St. Barths and Grenada (her home), she transported cigarettes, spices, rums and anything else that people needed to have sent between the islands.

Tradition Sailing
sailing anguilla

You can just imagine the riveting tales told by those those who've sailed her.

Laurie Gumbs and Deborah Vos have several of their own, having sailed her to St. Barth, Antigua, Montserrat, and even down to her home in Carriacou, Grenada.

Timeless Tradition
tradition sailing charters anguilla

She has seen all corners of the Caribbean, cut through high seas and survived many an adventure.

Painted red with white trim, her all wood structure creates an especially classic feel. She is a dream!

An afternoon on her is delightful. Her deck is wide and open, with plenty of space. And, being able to be part of her adventures is truly special.

tradition sailing charters anguilla

Your Hosts

Tradition is owned by Laurie Gumbs. He is Anguillian born and bred, and a familiar face if you visited his bar The Pumphouse, back in the day.

When aboard Tradition Sailing Charters, he is your Captain for the day. An experienced sailor with a watchful eye and serious concern for safety, yet with a warm, fun, relaxed personality, he is the ultimate Captain.

Laurie Gumbs
laurie gumbs anguilla

At his side is Deborah Vos. We all call her "Deb" and to say it simply, she is the coolest. Originally from Canada, I met Deb on the Picton Castle when it was anchored in Anguilla back in 2008. It is a three masted tall ship out of Nova Scotia that does a year long circumnavigation. After sailing the world, today, Deb calls Anguilla home.

She has real experience sailing in the roughest of conditions. Knowing that, I always feel safe when she is on board.

Deborah Vos
deborah vos anguilla

Beyond her experience on the water, she has spent a lot of time in the hospitality industry. She is so attentive and does everything to make your day absolutely indulgent. She is a wonderful host!

The #1 Anguilla Activity

Together, Laurie, Deb and their team operate a most comfortable and indulgent charter on a historic boat.

Raising The Main Sheet
tradition sailing charter main sheet anguilla

The experience is reminiscent of the Caribbean of yester-year.

Wide Open Deck Space
tradition sailing charter deck space

Tradition offers a variety of charters, including...

Their full day "Prickly Pear Lobster Lunch Day Sail" has grown to be the #1 Anguilla activity on TripAdvisor.

It's not hard to see why...

The Journey

It all begins at your meeting point, the wharf in Sandy Ground at 9am. Here, Laurie scoops you up and brings you to Tradition. As soon as you board?

Deb graciously offers you a "Morning Mimosa."

Morning Mimosas
morning mimosas on tradition sailing charter

We always oblige!

As you sip and take in the surrounding beauty of Sandy Ground, the Tradition team prepares the sailboat.

The work and strength that goes into it is incredible!...

Raising The Jib
tradition sailing charter main sheet anguilla

The team raises the sails, Laurie provides the history of Tradition followed by a safety briefing, and then?...

It's all smooth sailing to Anguilla's outer island, Prickly Pear where lunch, snorkeling and swimming await.

As you cast off the mooring, and as the wind dances in your hair, you are left without a care in the world.

The sails full...

The sound of the sea...

The wind propelling you forward...

It's a liberating feeling to be powered by nothing other than the breeze!

Prickly Pear in The Distance
prickly pear anguilla in the distance

Once the boat is sailing steady, the whole team makes sure you are well taken care of.

Another mimosa? Rose? Rum punch? It all flows freely aboard Tradition!

Full Cooler!
full cooler of drinks aboard tradition anguilla

Drink in-hand, there is nothing else to do but sail on...

To get a feel for the sail, here's a 30 second video clip of a day at sea with Tradition...


Pretty Prickly Pear

One very short hour later, Prickly Pear emerges in the distance.

Arriving at Prickly Pear
sailing anguilla

The offshore cay is made up of two small islands, Prickly Pear East and West. Their landscape is similar to Anguilla's. Rugged and arid, they are both small islands, surrounded by crystal clear, blue seas.

You approach the two islands from behind. As you head for the channel between them, the sailing can get tricky. Laurie and Deb stand on guard as you make your way through the passage.

On the other side?

Nothing But Bluuuue!
blue water of prickly pear anguilla

Endless beauty!

The bay is large, clear and protected by a long reef you can see in the distance. There, big waves break.

Inside lies this calm body of water, perfect for snorkeling, swimming and relaxing.

The tranquil seas take your breath away in a million shades of blue. The color is something out of a movie. Take a look...

Pure azure waters!
sailing anguilla

sailing anguilla

Prickly Pear is only home to two buildings, Johnno's restaurant and Prickly Pear Restaurant. The rest of Prickly Pear is inhabited by a large population of Brown Boobies, and that's about it!

Bluuuetiful Seas
rum punch anguilla

As Laurie and Deb put Tradition on a mooring, you can't help but gaze out at pristine Prickly Pear in the distance. Palm trees swaying, the white, sandy beach looked so inviting.

Tradition provides everything you need for enjoying a relaxing Prickly Pear beach day. Noodles? Check. Snorkel equipment? Check. Cooler packed with drinks? Check, check, check!

On shore the Tradition team ensures you have beach umbrellas, chairs, towels and plenty of refreshments. The service is truly 5 star in every way.

Prickly Pear Beach
prickly pear beach

Lunch Time

When your stomach begins to growl, you couldn't have a prettier view...

View from Prickly Pear
prickly pear restaurant anguilla

Lunch is served at Prickly Pear Restaurant. Its perch overlooking the beach and the clear sea makes it one of the most spectacular spots in Anguilla's waters.

What's for lunch?

The BEST BBQ Lobster!
prickly pear lunch

The smell of grilled seafood wafts through the air and before you know it, Deb places your lunch before you. A sumptuous, juicy lobster, this one goes down as one of our all time favorites. The delicacy is bathed in a super rich garlic butter sauce laced with hints of orange and Malibu. Each bite is sinfully delicious!

The meal also comes with crisp coleslaw, tasty sautéed potatoes and savory rice and peas.

Note: This is called a "Lobster Lunch Day Sail," but should you desire fish, ribs or chicken, they offer that, too.

After lunch...

The Beach Beckons
prickly pear anguilla

Returning to Sandy Ground

After beaching, floating, snorkeling and snoozing, Sandy Ground calls you home.

Sailing Back
sailing back to anguilla

With the sun kissing your face, the afternoon sail back is always blissful.

Deb knows how to make a perfect afternoon even better...

Fresh Watermelon & Homemade Chocolate Chip Cookies
deb chocolate chip cookies

Bellies full, the waves lull you into a sleepy state...

Nap-Eye View
looking up at the full sail on tradition sailing charter

It's more than 5 miles from Sandy Ground to Prickly Pear. You always travel them far too quickly ;-)

Back in Sandy Ground with Tradition Sailing Charters
tradition sailing charters anguilla

Every time is a blissful time aboard Tradition. Their trips to Prickly Pear just may be the most blissful of all.

Truly an Anguilla must-do, there are few experiences that compare to afternoons like these with Tradition!

Contact Laurie & Deb

tradition sailing boat

Tradition offers a variety of charters. From day time cruises (price includes snacks, drinks and lunch), to sunset sails (includes drinks and hors d'oeuvres), to custom private charters (during the day or at moonlight), they do it all, and with class and grace.

They are an Anguilla Card Partner. Save 10% when you book your trip with your Anguilla Card.

More on Tradition

For more details, you can reach Tradition by phone here: (264) 476-7245, or via email: traditionsailing@gmail.com or info@tradition-sailing.com

Tradition's Official Website


More Memories Aboard Tradition