Testimonials

Here’s what people are saying about Calypso!

We overheard a Calypso Charters captain & his crew speaking with other tourists about visiting Anguilla’s other nearby islands. They connected us with their booking office and we chartered a boat for a day trip to St Barths. When locals learned about plans, they reassured us that Calypso was stellar and that we were in great hands. They were right! From the reservation to the pickup at our hotel, the customs paperwork… everything was effortless. We felt like their personal guests.

The ride to St Barts was short and smooth. The boat was impeccable & the crew provided refreshments, safety tips for being in another country and took the time to guide us to several spots around the island via boat. They allowed us free time at each destination and allowed us choices about where to anchor. They introduced us to the kayak and paddleboard operator at one of the beaches. Captain & crew kept us thoroughly entertained through the whole trip. We also enjoyed the night lights and music on our trip home!

The folks at Calypso Charters created a magical, once in a lifetime experience. We highly recommend Calypso Charters so they can make your Anguilla holiday just as memorable as ours.

— Will & friends


Calypso Charters is a true Caribbean gem that enhanced my vacation experience.  The chartered boat we took from Anguilla to St. Barth’s was clean and well-maintained with whichever amenities you may need.  What made the day tour so pleasurable was -highly recommend them for any transportation needs by boat and will definitely use them the next time I visit Anguilla.

— Patricia Perez, Los Angeles, CA


I worked as a concierge specialist on Anguilla for over two years and consistently booked my guests with Calypso Charters because they offer excellent, personable service with great value for the money.

One of my favorite stories is when I was asked to book an excursion for four guests, including one who was especially nervous about boats & the ocean because she couldn’t swim. Knowing how great the crew is, I explained the circumstances to them & was reassured that they could help her be comfortable and enjoy the journey.

The three hour charter I booked for them turned into a FIVE hour charter! The afternoon became the highlight of her trip & her thank you letter to me said ‘The boat crew made it easy for me to enjoy being on the ocean & allowed me a chance to see Anguilla from a very special perspective.

Don’t hesitate to book with Calypso. These guys love their jobs & it shows!

— Catalina Hawley, Anguilla BWI