boat trips | The Villa View

Want to experience one of the most serene and enjoyable boat trips in the Caribbean? The Chocolat is calling your name! The 35’ catamaran, equipped with the funny, informative Captain Rollins and his first-mate Deon, will take you to tropical escapes off of Anguilla such as Prickly Pear, Sandy Island, and on sunset cruises.

First-Mate Deon

I have gone a total of seven times, and have had absolutely nothing but unforgettable moments and many laughs. There is something everyone can do, ranging from snorkeling to sunbathing and relaxing. The trip began at 9:30AM when Captain Rollins picked us up on his dingy at Sandy Ground on the island of Anguilla. Once we reached Chocolat, Deon kindly helped us onto the catamaran, which is in pristine condition. We lathered up with sun-block and started talking to fellow boat-trippers from Florida and Boston. Who would’ve thought that these strangers would soon become close friends! Captain Rollins returned from transferring everyone to the catamaran and started giving his “safety-speech”. At first, Rollins seemed intimidating and tough, but this is only because he truly cares about the safety of his customers and his boat. As minutes passed, we realized he might be one of the most interesting Anguillans, full of exciting stories and hysterical jokes. Deon kept the rum punches, water, and beer flowing as we all made our way to Prickly Pear. My sister and I lounged on the front trampoline soaking up the sun rays as the water splashed onto the boat, cooling us off. It was absolute perfection.

Prickly Pear Island

We dropped anchor at our first stop: the shrubby island of Prickly Pear. Captain Rollins and Deon took our lunch orders and gave us the option of swimming/snorkeling to the island (which was about 150 feet from shore) or taking the dingy. Being too relaxed to swim, we decided that taking the dingy was a definite. We arrived on the island, grabbed some chairs and headed to the small hut to grab a drink and meet the infamous Alan. Laughing and talking to Rollins, Deon, Elvis, and Alan for about an hour straight was without a doubt the best time of the trip. Deon then rang the bell and we strolled up to the picnic tables and enjoyed a delicious indigenous meal including ribs, chicken, rice, and potatoes. Once we were finished satisfying our stomachs, we set sail for our next destination: Sandy Island. We got to the second island and snorkeled our way to the shore noticing a variety of absolutely gorgeous, colorful fish below us. After about an hour here, we headed back to Anguilla. It was about 4:30PM and the lighting was indescribable. The sea breeze blowing through our hair, the smell of fresh salt water, and the sound of laughter and great stories surrounded us. We docked at Sandy Ground and stayed on the boat for a little longer before we had to leave. It didn’t end there! Once our feet hit Anguillan land, we headed over to Elvis’ beach bar with everyone (including Captain Rollins and Deon). Great music, exciting people, and a fabulous atmosphere; what a way to end an amazing day!

Captain Rollins

Meeting the local Anguillans and fellow vacationers was the perfect mix that made this day trip one we will never forget. We became close friends with one family on the boat, who we see every year and enjoy even more memorable moments each time.

Want to learn more about Anguillan adventures? Chat with us at WIMCO.