The Cayman Islands are widely hailed as a prime action-packed destination for all types of sportfishing, from casting in the flats for the wily, surprisingly strong "gray ghost" bonefish to trolling for giant, equally combative blue marlin. Conditions are ideal for big game fish: The water temperature varies only 8 to 10 degrees annually, so the bait and their pelagic predators hang out all year. The big lure for anglers is the big game-fish run near the coast, as close as a quarter-mile offshore.
Experienced, knowledgeable local captains charter boats with top-of-the-line equipment, bait, ice, and often lunch included in the price (usually $550–$750 per half day, $900–$1,500 for a full day). Options include deep-sea, reef, bone, tarpon, light-tackle, and fly-fishing. June and July are particularly good all-around months for reeling in blue marlin, yellow- and blackfin tuna, dolphinfish (dorado), and bonefish. Bonefish have a second season in the winter months, along with wahoo and skipjack tuna. Marine Park laws prohibit fishing or taking any type of marine life in protected areas. Local captains promote conservation and sportsmanship through catch-and-release of both reef and pelagic fish not intended for eating and all billfish, unless they are local records or potential tournament winners.
Bayside Watersports. Longtime fisherman Captain Eugene Ebanks established Bayside Watersports in 1974. The family-run West Bay–based company operates two first-class fishing boats, ranging from 31 feet (Lil Hooker) to 53 feet (the Happy Hooker, which sleeps six for overnight charters farther afield). The tradition began with the original Hooker, named after the Moldcraft Hooker lure and whose team, led by son Al Ebanks, caught a 189.4-pound yellowfin tuna in 1989 that still stands as the island record. They do reef-, tarpon-, and bonefishing trips, but their real specialty is deep-water fishing, such as at 12-Mile Bank, a 3-mile (5-km) strip 90 minutes west of Grand Cayman, where leviathan fighters congregate around the submerged peak of an underwater mountain. Morgan's Harbour, West Bay, Grand Cayman. 345/949–3200; www.baysidewatersports.com.
Black Princess Charters. Captain Chuckie Ebanks leads deep-sea and reef fishing as well as snorkel trips on his fully equipped and supplied eponymous 40-foot Sea Ray. Rates are reasonable, and he can arrange clean, inexpensive accommodations. Grand Cayman. 345/916–6319; 345/949–0400; www.fishgrandcayman.com.
Captain Asley's Watersports. This family-run operation prides itself on personable, flexible, and customized charter services for deep-sea, light-tackle, and bonefishing. A privately chartered fishing vessel can run from $500 (small boat, half day) to $1,200 (big boat, full day). Captain Asley has plied these waters since the 1960s; now his affable, patient kids and extended family (usually Derrin, Dwight, and Kevin) captain the five boats. They're all expert coaches, coaxing a confident approach even from first-timers, though they'll take experts to troll the lesser-known depths; ESPN's Bass Pros selected them as a "preferred outfitter guide." Like many other operators, they also run snorkeling, diving, and sunset and dinner cruises. Grand Cayman, KY1-1110. 345/949–3054; 345/926–2525; www.caymanfishinguide.com.
Oh Boy Charters. Charters include a 60-foot yacht with complete amenities (for day and overnight trips, sunset and dinner cruises) and a 34-foot Crusader. Charles and Alvin Ebanks—sons of Caymanian marine royalty, the indomitable Captain Marvin Ebanks—jokingly claim they've been playing in and plying the waters for a century and tell tales (tall and otherwise) of their father reeling them in for fishing expeditions. No more than eight passengers on the deep-sea boats ensures the personal touch (snorkeling on the 60-footer accommodates more people). Guests always receive a good selection of their catch; if you prefer others to do the cooking, go night fishing (including catch-and-release shark safaris), which includes dinner. Grand Cayman, KY1-1302. 345/949–6341; 345/926–0898; www.ohboycharters.com.
R&M Fly Shop and Charters. Captain Ronald Ebanks is arguably the island's most knowledgeable fly-fishing guide, with more than 10 years' experience in Cayman and Scotland. He also runs light-tackle trips on a 24-foot Robalo. Everyone from beginners—even children—to experienced casters enjoy and learn, whether wading or poling from a 17-foot Stratos Flats boat. Free transfers are included. Captain Ronald even ties his own flies (he'll show you how). Grand Cayman. 345/947–3146; 345/946–0214; www.flyfishgrandcayman.com.
Sea Star Charters. Friendly Caymanian Clinton Ebanks does what it takes to ensure a wonderful time on his 27- and 28-foot cabin cruisers and a 35-foot trimaran used primarily for snorkeling cruises. A good choice for beginners, he leads light-tackle, bone-, and bottom-fishing and offers a nice cultural experience as well as sailing charters and snorkeling with complimentary transportation and equipment. Aka Captain Clinton's Watersports, the company accepts only cash and traveler's checks. Grand Cayman, KY1-1206. 345/949–1016; 345/916–5234.