A number of boating options are available for airport transfers, day trips to offshore cays or neighboring islands, night trips to St. Martin, or just whipping through the waves en route to a picnic spot.
Calypso Charters. Book a private or semiprivate charter with Calypso on one of their five powerboats for a trip around Anguilla, a fishing trip, or a sea excursion to St. Barth, St. Maarten, or the surrounding islands. They offer a lovely two-hour sunset cruise leaving from Cole Bay every Tuesday and Thursday. They also provide airport transfers. Sandy Ground Village, n/a Anguilla. 264/584--8504; www.calypsochartersanguilla.com.
Funtime Charters. With five powerboats from 32 to 38 feet, this charter and shuttle service arranges private and scheduled boat transport to the airport, including luggage services ($70 per person); day trips to St. Barth; and other powerboat excursions. The air-conditioned 42-seat Sunshine Express runs to SXM in the late night and early morning, as well as interisland excursions. Cove Bay, n/a Anguilla, AI2640. 264/497–6511; 866/334–0047; www.funtime-charters.com.
Junior's Glass Bottom Boat. For an underwater peek at sea turtles and stingrays without getting wet, catch a ride ($20 per person) on this boat. Guided snorkeling trips and instruction are available, too. Junior is great with kids and very knowledgeable. Best to book in advance, especially during holidays. Hotel transport is available. Shoal Bay Village, n/a Anguilla, AI2640. 264/497–4456; www.junior.ai.
No Fear Sea Tours. In addition to private airport transportation, day snorkeling trips, sunset cruises, and fishing trips on three 32-foot speedboats and a 19-foot ski boat, this charter service offers water-sports rentals (tubing, skiing, knee-boarding). Cove Bay, n/a Anguilla, AI2640. 264/235–8406; www.nofearcharters.com/.
Sail Chocolat. This 35-foot EDEL catamaran, with four private cabins, is available for private charter or scheduled excursions to nearby cays. Captain Rollins is a knowledgeable, affable, safety-conscious guide. Trips visit Prickly Pear Cay for snorkeling, then on to Sandy Island for lunch. Sandy Ground Village, n/a Anguilla, AI2640. 264/497–3394; www.sailinganguilla.com.
Sandy Island Enterprises. Picnic, swimming, and diving excursions to Prickly Pear Cay, Sandy Island, and Scilly Cay are available through this outfit, which also rents Sunfish and windsurfers and arranges fishing charters. The Sandy Island sea shuttle Happiness leaves from the small pier in Sandy Ground daily November–August and by reservation September and October. Sandy Ground Village, n/a Anguilla, AI 2640. 264/476–6534; www.mysandyisland.com.
Sea Pro Boat Charters. Whether it's kayaking, windsurfing, stand-up paddleboarding, or waterskiing, head to Sea Pro's center at Sandy Ground. They also run a sunset cruise, a sightseeing tour around the island, a shopping trip to St. Barth, a night in St, Maarten, or a chance to snorkel at some of the less accessible reefs and shoals. They have a beach bar in Sandy Ground with a water trampoline and live music on Sundays, too. Sandy Ground Village, n/a Anguilla. 264/584--0074; www.seaprocharters.com.
Surf AXA. Surf AXA offers everything for beginner or experienced surfers and paddleboarders, including instruction and rentals. They offer guided surf tours, too. South Hill Village, n/a Anguilla. 264/582--7425; surfaxa.com. $60 half-day surfboard rental.