If you enjoy action fishing, Cayman waters have plenty to offer. Experienced, knowledgeable local captains charter boats with top-of-the-line equipment, bait, ice, and often lunch included in the price (usually $550 to $750 per half day, $900 to $1,500 for a full day). Options include deep-sea, reef, bone, tarpon, light-tackle, and fly-fishing. June and July are good all-around months for fishing for blue marlin, yellow- and blackfin tuna, dolphinfish, and bonefish. Bonefish have a second season in the winter months, along with wahoo and skipjack tuna.
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, the "Hooker" fleet, 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, 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 as well, but their real specialty is deep-water fishing, such as at 12-Mile Bank, a 3-mi (5-km) strip just 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. Black Princess Charters, owned by Captain Chuckie Ebanks, is fully equipped for deep-sea and reef fishing as well as snorkel trips on his fully equipped and supplied eponymous 40-foot Sea Ray. His rates are comparatively reasonable, and he can arrange clean, inexpensive local accommodations. Grand Cayman. 345/916–6319 or 345/949–0400. www.fishgrandcayman.com.
Captain Asley's Watersports. Captain Asley's Watersports prides itself on personable, flexible, and customized charter services for deep-sea, light-tackle, and bonefishing. The cost for a privately chartered fishing vessel can run from $500 (small boat, half day) to $1,200 (big boat, full day). The owner of this family-run operation, Captain Asley has plied these waters since the 1960s; now his affable, patient kids and extended family (usually Darrin, 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 all 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. email@example.com.
Oh Boy Charters. Oh Boy Charters charters a 60-foot yacht with complete amenities for day (and overnight) trips, as well as sunset and dinner cruises, plus a 34-foot Crusader. Alvin Ebanks—son of Caymanian marine royalty, the indomitable Captain Marvin Ebanks—jokingly claims he's been playing in and plying the waters for a century and tells tales (tall and otherwise) of his father reeling him 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 or 345/926–0898. www.ohboycharters.com.
R&M Fly Shop and Charters. Captain Ronald Ebanks of R&M Fly Shop and Charters 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 will enjoy and learn from the trip (whether wading or poling from a 17' Stratos Flats boat); free transfers are included. Captain Ronald even ties his own flies (he'll show you how). Grand Cayman. 345/947–3146 or 345/946–0214. www.flyfishgrandcayman.com.
Sea Star Charters. Sea Star Charters, aka Captain Clinton's Watersports, is run by Clinton Ebanks, a fine and very friendly Caymanian who will do whatever it takes to make sure that you have a wonderful time on his two 27- and 28-foot cabin cruisers (and from the 35-foot trimaran used primarily for snorkeling cruises), enjoying light-tackle, bone-, and bottom-fishing. He's a good choice for beginners and offers a nice cultural experience as well as sailing charters and snorkeling with complimentary transportation and equipment. Only cash and traveler's checks are accepted. Grand Cayman. 345/949–1016 evenings; 345/916–5234.