Our Services

Most of our services can be booked as either semi-private or private charters. Semi-private boats are shared with other passengers traveling to the same destination and private charters are reserved specifically for your party. We are also easily able to accommodate large numbers of guests, such as for a wedding, with advanced reservations.

Locations and Services


Airport Transfers from St. Maarten to Anguilla and Day Trips 

When you arrive at Princess Juliana International Airport (SXM), our transfer guests are greeted right in the arrivals hall of the airport by a professional team prepared to escort you to our dock. Calypso will make your arrival and transfer process easy and enjoyable — learn how. We offer a broad array of services, whether it’s an individual traveling or a large number of guests for an event. Unless otherwise noted, advanced reservations are required.

Airport Shuttles (reservations recommended)

Our scheduled airport shuttles are $65 per adult (ages 12+) one way, $35 for children ages 5-11. Children under 1 year old are free. See our daily schedule below.

Daily Schedule for Airport Shuttles, Subject to Minor Changes Depending on Post-Hurricane Flight Schedules 

From Anguilla (AXA)

  • 7:45 am* Reservations only, required via phone
  • 9:15 am
  • 10:30 am
  • 12:00 pm
  • 1:30 pm
  • 3:00 pm
  • 4:30 pm

From St. Maarten (SXM)

  • 8:30 am* – Reservations only, required via phone
  • 10:00 am
  • 11:15 am
  • 12:45 pm
  • 2:15 pm
  • 3:45 pm
  • 5:30 pm

Private Airport Transfer

$400 for the first 4 passengers and $50 for each additional person. Private airport charters depart at whatever time is reserved by the passengers

Weekly St. Barth’s Shuttle

Spend the day in beautiful St. Barth’s doing whatever your heart desires. This shared shuttle runs on Tuesdays, departs Anguilla at 9:00am and St. Barth’s at 5:00pm. Average trip is 45 mins.

  • Semi-private: $200/person
  • Private Boats: Choice of day; $1800 round trip for 4 passengers, $50/additional passenger.

Sunset Cruises

A relaxing end to the day, our two-hour sunset cruise includes hors d’oeuvres, cold beverages and Calypso rum punch.

  • Semi-private: Leaves from Cove Bay every Tuesday & Thursday, $95 per person
  • Private: Choice of day; $350 for the first 4 passengers and $50 for each additional passenger.

Deep Sea Fishing (Private only)

Our knowledgeable captains can suggest fishing locations or bring you to your favorite spots. This excursion includes cold beverages and use of fishing gear.

  • $170 per hour (4-hour minimum) for the first 4 passengers and $50 for each additional passenger.

Snorkeling Excursions

There are over 30 beaches and many coves to explore in and around Anguilla. Our four-hour snorkeling excursions are a convenient way to explore the ocean and provide a unique perspective of the island from the water. Snorkeling excursions include cold beverages and use of snorkeling equipment if requested. Popular destinations include Dog Island, Prickly Pear, Sandy Island/Little Bay or Scilly Cay.

  • Semi-private: Every Wednesday, $95 per person
  • Private: Choice of day, $170 per hour (4-hour minimum) for the first 4 passengers and $50 for each additional passenger.

Customized Trips

Because we can tailor any trip to suit your interests, please contact us for prices on the following excursions or any others you do not see listed.

  • Shopping trips or day/evening trips to St. Maarten/Martin, St. Barth’s
  • Sightseeing tours around Anguilla, St. Maarten/Martin, St. Barth’s
  • Extended day excursions to Dog Island, Prickly Pear Island, Sandy Island — anywhere!

Weddings & Special Events

Let Calypso Charters help take some of the stress out of planning an island event.

With our advanced event reservation services, we can provide easy, direct booking for event guests, advanced information packages containing a description of the arrival process, the travel documents required to enter Anguilla to save transit time and a menu of excursions for guests to enjoy while they’re in Anguilla. We also have a network of local businesses we can recommend should you be seeking assistance with any part of the event planning process.