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Anguilla Day Trip – Tradition Sailing Trip to Prickly Pear, Lobster Lunch and Snorkeling

Jun 10, 2020

Hi!  It's Karen from Karen Vincent Solutions.

Since I grew up sailing all summer, I am always looking for a good boating adventure when visiting warm, tropical places.  Our day trip on the sailboat Tradition to Prickly Pear Cay, one of Anguilla’s protected offshore cays, did not disappoint!  Prickly Pear Cay is a pair of uninhabited islands divided by a narrow boat channel. 

The Western cay is mostly rocky coral reefs without easy access, while the Eastern cay has a large white sand beach with beautiful blue/green, clear water for both swimming and snorkeling.  Our sailing trip on Tradition took us the to the Eastern cay where we enjoyed snorkeling, time on the beach and a delicious lunch at the Prickly Pear Bar and Restaurant. 

We started our adventure at Sandy Ground on Anguilla, which is where most, if not all, boating trips depart from on the island.  We were met by Captain Lauri who arrived at the dock with a huge smile and welcomed us in his motorized raft to be shuttled out to Tradition, a historic, handmade sailboat.

When we pulled up to Tradition, we were greeted by Deb, who, from the moment we stepped on the boat, took care of our every need.  While we waited for the other guests to be transported out to the boat, Deb poured mimosas and helped us get acclimated to the boat.  We quickly got to know other guests on the boat and truly enjoyed every one of them.  We were all there to relax, enjoy the ocean and snorkeling and have a fun day…and that is exactly what we did!

After a safety briefing and an overview of what the day would look like (and maybe another mimosa), we were off.  As we were leaving Sandy Ground, Deb asked for some of the guests to help her raise the sails which, it turns out, is quite a big job.  The heavy wooden boom and sail took quite a bit of effort to raise up the wooden mast.  My husband volunteered to help Deb which I found entertaining to watch! 

Once the sails were up, Lauri dropped his fishing line in the water off the stern of the boat and we were on our way. We learned about the history of Tradition, how it was built by hand, how it was used in rum smuggling and how they upkeep it today which was all very interesting.  It was a gorgeous, warm day and the sailing conditions were perfect. 

We continued to get to know our new sailing friends, and even found some who live only an hour away from us, all while taking in the beautiful scene on the comfortable and spacious deck of the boat.  We even saw some dolphins swimming right in front of the boat! 

We passed by Sandy Island, which is a small, yet amazing island my husband and I spent the day on a couple days prior.  To learn a little more about Sandy Island and why it is so special, check out my blog post Anguilla – Sandy Island Day Trip

Deb continued to attentively check in to see if anyone needed anything and provided us with some interesting information about the area as well as how she found her passion for boating and for doing what she is doing today. 

Upon arriving at Prickly Pear, we were given complimentary snorkels and fins and jumped in the water to snorkel along the reef.  The water was so clear, and we enjoyed seeing bright colored fish and interesting coral.

The boat crew brought all our needed belongings to shore where they were waiting for us along with water or other drinks upon finishing our snorkeling.  There were beach chairs and umbrellas for us to use while waiting for lunch.

When lunch was ready, we went into the Prickly Pear Bar and Restaurant and enjoyed a delicious lunch, while sitting at picnic tables, with our new friends, in the open-air restaurant.  I had the Caribbean lobster and my husband had the chicken and ribs and both came with salad, rice and potatoes.  Both dishes were excellent. The lobster practically melted in my mouth!

My husband is very well versed in all things barbecue and could not say enough about how delicious his food was.  After digesting for a bit, we swam back to the boat (there were rides available for those preferring not to swim) and headed on back to Anguilla. 


On the way back, Deb continued to be the hostess with the mostest and made sure anyone wanting rum punch, beer, wine, water, or soda had what they wanted.  She also passed around big slices of juicy watermelon and freshly baked jumbo Tradition chocolate chip cookies. 

With Lauri at the helm, the sail back was just as enjoyable as the sail out to Prickly Pear Island.  I highly recommend this trip for anyone visiting Anguilla.  On a scale from one to ten, it was a ten plus! Lauri and Deb should be proud of the amazing experience they create for their guests. 

Live your best Boss Lady life!

~ Karen

Karen Vincent Solutions


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