The Best Boats in Anguilla

General Questions

How far in advance should I book?
We recommend booking as soon as you know you are traveling since there are several times of year that we will sell out. We have very reasonable change policies should something unexpected happen and you need to adjust your plans.

How do I book?
Book your airport transfers between Anguilla and St. Maarten online here. If you’re interested in booking an excursion, please contact us directly at 264-462-8504 or

What if my arrival flight is delayed?
Good question! First, please contact us asap at or 264-462-8504 or 264-584-8504. Because the ports on both St. Maarten close at 6:00 p.m. and Anguilla closes at 5:00 p.m., we are required to pay overtime to operate after these times.

What if my flight is canceled?
It’s not uncommon for this to occur, particularly during the winter months. In the event your flight is canceled, please contact us asap at or 264-584-8504 to let us know. We can either reschedule you for a different boat or will issue you a credit toward future travel if you need to change your travel plans entirely. Click to read the entirety of our Terms and Conditions here.

What forms of payment do you accept?
We accept Mastercard, Visa, and American Express. Cash is also accepted.

Should I be tipping anyone?
For transfers between islands – The dock porters are staffed by each island’s dock management and rely heavily on tips for income. While it is not required, we recommend tipping each dock’s porters $1 per bag at the beginning and end of each boat ride when you are arriving and departing from St. Maarten and Anguilla. For example, have cash ready to tip $1/bag upon departure from St. Maarten, $1/bag on arrival in Anguilla and the same in the opposite direction when returning to go home. For excursions – Tipping is solely at your discretion. If you’re happy with your captain and crew, they will always appreciate a tip!

It looks like my group is too big for your boats… Now what?
No problem! We have extra boats that can be used to bring over many passengers at once. Please call our office to make arrangements for large groups.

Do you offer group rates?
Yes! For groups of 20+, we offer group rates. Please call or email us to make arrangements.

Do you go to St. Barth?
We do! We have a Tuesday St. Barth Shuttle, perfect for a day trip. We leave Blowing Point at 9 a.m. and leave Gustavia, St. Barth at 5 p.m. The trip takes approximately 45 minutes. We also offer private boat charters to St. Barth. For more details on pricing, please contact us.

Airport Transfers from St. Maarten to Anguilla Questions

Do you include taxi between the airport and the dock?
We include ground transportation between the Princess Juliana International Airport and our dock in St. Maarten on arrival and departure. We don’t include ground transportation on Anguilla. However, taxis are always available at the Blowing Point Ferry Terminal in Anguilla. We can also pre-arrange a driver for you, for your arrival, departure, or even for your entire trip.

What do we do when we get off the plane in St. Maarten … How do we find you?
You’ll see our agent at the arrivals area at the Princess Juliana International Airport, holding a Calypso Charters sign.

Where is the dock in St. Maarten?
We operate from the Anguilla-St. Maarten dock located literally a couple of minutes from the Princess Juliana International Airport.

Where is the dock in Anguilla?
For transportation to and from St. Maarten, we operate from Blowing Point Ferry Terminal.

How long is the trip between Anguilla and St. Maarten?
It is approximately 25 minutes, depending on wind and sea conditions.

Which boat time should we book when arriving at St. Maarten?
Our schedule is based on popular flight arrival times. We find that for most passengers, booking a boat which departs 45-60 minutes after your scheduled arrival time is a good estimate because you’ll need to collect your luggage and go through immigration at the airport, then travel to the dock with our driver.

Which boat time should we book when leaving Anguilla?
Most major airlines require passengers to check in 3 hours prior to the scheduled departure time. We recommend booking a boat no less than 3 hours before your flight departure time. It takes time to get through immigration at the dock in St. Maarten, to get to the airport, to check-in, then go through immigration and security at the airport, plus, “island time” is a real thing and we want you to have plenty of time to get home as stress-free as possible.

What if we fly through the airport on the French side, St. Martin?
We operate from the Dutch side, St. Maarten, but we can arrange for our drivers to pick you up. Please call or email our reservations office to make these arrangements.

Excursions Questions

Which excursion is best for us?
Most of the time, our excursions are appropriate for most everyone. However, we recommend taking into consideration the length of the excursions and the fact that it’s usually very sunny and often hot and windy. A long day on the water may not be suitable for everyone!

Where will we go?
If you’re booking a private charter, we go wherever you’d like to go! Our agents can assist with planning your trip, and our captains are very knowledgeable guides and can suggest stops along the way.

What’s included in the price of the excursion?
For day trips, we have complimentary snorkeling gear on board. Please be sure to provide your reservations agent with the shoe size of every snorkeling so we can have fins that will fit you!

What time do excursions begin?
It all depends on the type of excursion you book. Private charters leave at whatever time you would like. Shared charters leave at set times depending on which one you choose.

What should we bring with us?
For daytime excursions, it’s a good idea to wear a swimsuit and to bring along a towel, sunscreen, hat, and a change of dry clothes (you might appreciate it while eating lunch). It’s also usually a smart plan to bring along a long sleeve shirt for added sun protection, particularly if you’re fishing. For sunset cruises, we recommend comfortable clothes, no heels or dress shoes, and a light sweater or long sleeve shirt in case you’re chilly. Of course, for all the trips, bring a camera or your phone for taking pictures!

Can we bring our own food or drinks on board?
Yes, but please let our reservations staff know in advance. We can also help to arrange catering if you’re interested.

What happens if the weather isn’t good?
If the weather is poor or the conditions are unsafe, we will cancel our excursions. What does “bad weather” mean? It typically means very rough water or high winds, but not clouds or passing showers.

Can we bring our kids along?
Yes! In fact, our captains and crew are great with children. We also have children’s life vests aboard all of our boats and kids’ snorkeling gear.

Where does the boat leave from & how do we get there?
While most of our excursions leave from the dock at Cove Bay or Sandy Ground, a few excursions leave from other areas. Your booking agent will provide you with complete details.

Didn’t see your question?
Email us at or call us at 264-584-8504.