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Exclusive Private Escapes

Indulge in your very own private adventure and romance on azure seas. We’ll sail you to pristine snorkeling sites and breathtaking reefs where dolphins swim and sea turtles dwell.

Half Day Sailing, Snorkelling & Lobster Lunch

Join us for a magnificent sail to where a tropical paradise awaits. It’s a day of indulgence that begins the moment your feet touch the deck of Tradition and only ends when we wave you goodbye.

Deluxe Champagne and Tapas Sunset Cruise

Our Deluxe Champagne & Tapas Sunset Cruise is an inspired blend of spectacular scenery & stunning sunsets, a delicious selection of tapas on deck of our historic trading vessel, and the splendor of sailing under the stars.

A Classic West Indian Sloop

This vacation, create a new tradition…

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Luxury and Adventure.

Book online or call +1.264.476.7245 to reserve your amazing tropical experience.

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What others say about us

BooZoo
“Trust me….you REALLY want to do this”
5 of 5 starsReviewed May 31, 2013

Even if your plan for Anguilla includes nothing more than: beach, pool, beach bar, dinner, repeat….you must fit in a trip on the Tradition. Step aboard the beautiful 50′ Carriacou sloop and be greeted with warm muffins and cold champagne. They offer day trips to Prickly Pear, half day trips to Little Bay and Sunset cruises. We took the half day charter to Little Bay. My wife and I had the added benefit of being the only guests booked….hello private charter! We were immediately impressed that they went ahead with the charter with just the two of us.

The crew, headed by Capt. Laurie, were professional, capable and terrifically hospitable. Deb, Brennon and Erica took great care of us. Beer? Yes, please. Wine? Sure. Rum punch? Why not. Sailing, swimming, sunning….just a fantastic morning. Around 12:15, Deb announced that the charter was “officially” over. They didn’t have an afternoon trip, so she asked if we were in any hurry to get back. Um, no…..I’ll have another rum punch, please! So, we spent the next couple of hours just chatting with our new friends and having an all-around great time.

Back to Sandy Ground. With all the work out of the way, the crew is finally able to enjoy a cold beer with us. Cheers, ya’ll!

BooZoo(excerpt from TripAdvisor.com)TripAdvisor.com
4994MM

Eleven of us took the lunch trip to Prickly Pear island on “Tradition”. She is a West Indian wooden sloop kept in the most impeccable condition by her -justifiably- proud owner. From the moment we set foot on board until the moment we got back on shore at the end of the trip we were completely spoiled – freshly squeezed orange juice in the mimosas, home baked muffins, fresh fruit skewers. When we arrived on Prickly Pear we enjoyed an excellent lunch, snorkeling and basking in the sun. Part of our group had never been sailing and a couple of our number were experienced sailors with experience of traditional boats. Everyone had a great time. Sailing weather was glorious and while the captain certainly didn’t ‘dumb down’ the sailing experience, even the newbies we’re completely comfortable. It was a memorable day and an unforgettable experience.

Visited April 2014

4994MMfrom TripAdvisor.comTripAdvisor.com
Ann_2014948
“Highlight of Our Anguilla Visit!”
5 of 5 starsReviewed April 7, 2014

After reading other reviews about Tradition being a must-do in Anguilla, my significant other and I booked a trip and were so glad we did so! It was our first trip to Anguilla and out first full day on the island–a great way to start our trip. We did the day sail to Prickly Pear with the lobster lunch. Another family had booked the same trip as us, but their son came down with the flu and they cancelled, so it turned into a private sail! Laurie, Deb and Brennon crew Tradition and made the experience really special. We had a great time learning about Tradition, hearing stories about Anguilla, spotting sea turtles glide by and relaxing on deck on our sail to Prickly Pear. On arriving at Prickly Pear, we snorkeled for an hour or so. My boyfriend and I thought Prickly Pear was the best snorkeling on Anguilla with Little Bay being the second best (we only snorkeled a few times, so we may have missed good snorkeling elsewhere during our week stay). We had a delicious lobster lunch at the Prickly Pear restaurant beach hut. If you like lobster, this is a must. We found some great shells after lunch on the beach and fed yellow finches sugar right out of our palms. The wind died on our way back to Anguilla so we had to use the motor. In order to not get us back too early since motoring was quicker, Laurie and Deb suggested we go to Little Bay on the way back. We snorkeled here as well and saw huge sea urchins as well as a sea turtle swim ahead of us! Tradition was the highlight of our trip and a truly unique experience. I highly recommend Tradition to all!

Visited April 2014
Ann_2014948from TripAdvisor.comMax Mobilcom
Jim R

“A ‘Must Do’ when visiting Anguilla”
5 of 5 starsReviewed March 23, 2014
We’ve been visiting Anguilla for 15 years and we always try to experience something new each trip. I have to say that this is one of the best experiences yet. Laurie, Deb and Brennon were great hosts (and sailors) and truly added to the great experience with their superb hospitality while providing interesting stories about the island and sailing. My 2 sons (aged 6 and 9) thoroughly enjoyed the day trip out to Prickly Pear. My 9 year has still not stopped talking about having the opportunity to ‘take over the helm’! We’re looking forward to another adventure on Tradition when we return to Anguilla next year.

Visited March 2014

Jim Rfrom TripAdvisor.comTripAdvisor.com

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Tradition Sailing Charters
Facebook IconAugust 29, 2016 at 5:00 pm

BREAKING NEWS: Who wants to spend tomorrow here? We had a last minute booking for our Half Day sail tomorrow, August 30 and still have space available! 1-264-476-7245 before 7pm tonight if you'd like to join in the fun!
#Anguilla #Sail #TraditionSailingCharters
http://www.tradition-sailing.com
#Repost: @anivillas

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Tradition Sailing Charters
Facebook IconAugust 26, 2016 at 9:56 pm

Captain Laurie always has the hot girls wrapped around him! Meet the gorgeous @carazavaleta, host of #TravelShow @privateislandtv. Looking forward to watching this on AWE TV when it airs.

http://www.tradition-sailing.com

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Tradition Sailing Charters
Facebook IconAugust 25, 2016 at 10:52 am

We're pretty excited about being featured on @destweddingmag. Pick up your copy of the September/October 2016 edition and see why #Anguilla is THE place to plan your #DestinationWedding!

http://www.tradition-sailing.com

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Tradition Sailing Charters
Facebook IconAugust 24, 2016 at 1:07 pm

It's #WeddingWednesday and guess which island is featured in the September/October 2016 issue of @destweddingmag

#Anguilla #Wedding #SecretParadise

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Tradition Sailing Charters
Facebook IconAugust 23, 2016 at 8:24 pm

Today's Sunset Inspiration: Golden Goose . #AnguillaSunset #Inspiration #flyhigh #GoldenEgg
http://www.tradition-sailing.com
📷: Deborah Vos

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Tradition Sailing Charters
Facebook IconAugust 22, 2016 at 9:59 am

NEWSFLASH: Tonight could be your last chance of the season to hear Captain Laurie's stories of the Caribbean! With the weather bearing down on us later this week, we might be finished for the season.

Join us tonight for what could be our last amazing Sunset and Starlit Sail for this season!

Call us at 1.264.476.7245 or go to http://www.tradition-sailing.com before NOON today to sign up!

#Repost @rasheedshakur with @repostapp
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Captain. Drinking Buddy. Story teller. Belonger. Friend. I love this picture of Lawry telling the story of active volcanos in the Caribbean. This was the last trip I took on @traditionsailinganguilla a couple weeks ago. That boat and I have so much in common. We both took 9 months to make. We were both born in 1978. We both moved to the Caribbean to semi retire. 😁 Thanks for all the sunsets guys. See you in two months! #sailing #sail #sailboats #saillife #caribbean #caribbeansea #caribbeanlife #anguilla #anguilla2016 #anguillalife #expat #expatlife #ocean #mast #tack

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Tradition Sailing Charters
Facebook IconAugust 19, 2016 at 11:18 am

If @destweddingmag recommends that you book #traditionsailinganguilla for your Wedding or "Trash the Dress" party, you know it's going to be unforgettable!
#Anguilla #weddingideas #destinationwedding

http://www.tradition-sailing.com

#Repost @destweddingmag with @repostapp
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#LittleBay on the north coast of Anguilla isn't just a pristine little beach cove + crystal clear snorkeling spot filled with sea turtles, spotted rays + colorful parrot fish. It's also a perfect #trashthedress shoot locale! You can only get there by boat so charter the gorgeous red-hulled 'Tradition' for an unforgettable day trip. (📷: Art Director: Vicky Hodges) #dwh #dwhmag #surroundmewithwater

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Facebook IconAugust 18, 2016 at 8:27 pm

Hello, Beautiful! #Anguilla #FullMoon #Paradise

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Facebook IconAugust 18, 2016 at 5:34 pm

Cooling off and hanging out after a delicious Lobster Lunch on deck. How has your Thursday been? #HalfDaySail #Anguilla #BestLunchSpot

http://www.tradition-sailing.com

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Tradition Sailing Charters
Facebook IconAugust 17, 2016 at 9:35 am

We're going to be having one of those nights tonight! Sunset and Starlit Sail anyone?
#Anguilla #SunsetSail
http://www.tradition-sailing.com
#Repost @erikafrantzve with @repostapp
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...the type of nights where morning comes too soon.

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Tradition Sailing Charters
Facebook IconAugust 16, 2016 at 10:39 pm

Tradition Sailing Charters with Deborah Vos and 6 others.

Amazing day of filming with @carazavaleta for the Travel Show #PrivateIslands which airs on #AweTV. This lady was a blast to work with: Funny, Intelligent, Adventurous and absolutely beautiful inside and out! #TravelShow #Anguilla

http://www.tradition-sailing.com

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Tradition Sailing Charters
Facebook IconAugust 15, 2016 at 5:57 pm

On our days off, I like to get high. #viewfromthetop #traditionsailinganguilla #Mondays

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Facebook IconAugust 13, 2016 at 9:11 am

This is absolutely fantastic! #MarineLife #SavingNemo #Anguilla

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A Small Caribbean Island Inspires a Global Innovation

finance.yahoo.com

A globally significant innovation is quietly taking place on the island of Anguilla, British Caribbean. Perhaps best-known for her beautiful beaches, celebrity sightings and as the stunning backdrop for ...

Tradition Sailing Charters
Facebook IconAugust 11, 2016 at 12:50 pm

Spaces are filling up fast! Tonight we have a full boat, but we have a few spots left on Friday and Saturday nights sail. What are you waiting for? Call now for a magic night of stargazing on the deck of Tradition! #ShootingStars #nightsky #Anguilla

http://www.tradition-sailing.com

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Facebook IconAugust 11, 2016 at 6:57 am

We're ready to take in the show! Space still available!

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This Year's Perseid Meteor Shower Is Going To Be Quite A Show — Here's How To Watch

http://www.npr.org

Stargazers, get ready for something spectacular on Thursday. The annual Perseid meteor shower, already one of the most reliably impressive celestial events, promises to be especially good this year.

Tradition Sailing Charters
Facebook IconAugust 10, 2016 at 12:30 pm

If you love sailing under the night sky, you won't want to miss these sailing events! Three very special sunset and stargazing excursions during the peak of the Perseids Meteor Shower. Reserve your evening of pure magic now! #ShootingStars #nightsky #Anguilla

http://www.tradition-sailing.com

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Facebook IconAugust 9, 2016 at 4:16 pm

Tradition Sailing Charters updated their cover photo.

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Tradition Sailing Charters's cover photo
Tradition Sailing Charters
Facebook IconAugust 9, 2016 at 2:24 pm

We're shooting for the stars! The Perseids Meteor Shower will be peaking this Thursday, Friday and Saturday. There is no better place to watch this stunning phenomenon of shooting stars than on the deck of Tradition!
Who's joining us for the star-gazing sail?
#PerseidsMeteorShower #Anguilla #StarGazing

http://www.tradition-sailing.com

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Tradition Sailing Charters
Facebook IconAugust 8, 2016 at 7:39 am

We love providing unforgettable memories for our guests!

#Repost @ashbjett with @repostapp
・・・
Had the most amazing experience yesterday, spent with some of the coolest people we have ever met! Deb and Laurie took us on an adventure on their old sail boat, Tradition! Some of the best stories, views, mimosas, rum punch and definitely the best lunch we've had on the island! Kyle and I's first sailing experience- a day we will remember forever! Thank you!! #traditionsailingcharters

http://www.tradition-sailing.com

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Facebook IconAugust 6, 2016 at 10:08 am

When we stretch our boundaries and get out of our comfort zone, magic happens. #paradeoftroupes2016 #bestfriends #anguillasummerfestival

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Facebook IconAugust 5, 2016 at 10:11 pm

Today, we interrupt our regularly scheduled program of sailing to bring you this extra special feature: Parade of Troupes' #anguillasummerfestival #ParadeofTroupes2016

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Facebook IconAugust 4, 2016 at 10:48 am

Love the beach bags our guests brought with them for today's Half Day Sail! I want!!#beachbags #Anguilla #TraditionSailingAnguilla

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Facebook IconAugust 2, 2016 at 7:04 pm

Real Deal, Winner of the Anguilla Tuesday Race to Island Harbor sailing back to Sandy Ground at Sunset. #SunsetSail #RealDeal #Anguilla

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Tradition Sailing Charters
Facebook IconAugust 2, 2016 at 11:27 am

Have you met Thomas yet? Thomas first started sailing at the Anguilla Youth Sailing Club, eventually becoming one of the instructors. He now works with us as well as the AYSC. This young man is a great sailor, hardworking, attentive, and incredibly polite.
We love that he's part of the Tradition team!
#anguillayouthsailingschool #AnguillaYouth

📷: Cindy McDavid Photography

http://www.tradition-sailing.com

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Tradition Sailing Charters
Facebook IconAugust 1, 2016 at 9:26 pm

Happy August Monday everyone! We took the day off and spent time with friends and family @roysbaysidegrill My "sister"and I kayaked through the mass of boats anchored on the beach in Sandy Ground, finding friends and played "pirate", refusing to leave until we got some treasure. Carib and wine were produced and we paddled on. A fantastic day on Sandy Ground! How did you spend your August Monday?

#anguillaaugustmonday2016 #anguillasummerfestival

http://www.tradition-sailing.com

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