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Imagine the lightning-like stripe down the side of a yellowtail snapper or the marbled, almost serpentine pattern on a black grouper. The waters off the Florida Keys teem with such visually stunning marine life, and the crews of Gulfstream Fishing, Inc. know how to catch them. The Gulfstream IV, a 58-foot party boat that’s inspected twice a year by the US Coast Guard, motors approximately 60 passengers swiftly out to deep-sea fishing spots thanks to twin Detroit 8v92 turbo engines. Once anchored, the ship’s amenities—which range from men’s and women’s restrooms to a galley serving snacks—keep anglers comfortable between casts.

In addition to daily party outings, Gulfstream’s crews charter small-group trips that include evening shark fishing, offshore and inshore outings for trophies such as sailfish and tarpon, and trips onto coastal flats for catches such as bonefish and barracuda. They also organize private fishing charters to celebrate special occasions, such as a bachelor party or buying your first boat. An FAQ page answers many questions before guests head out.

1801 N Roosevelt Blvd
Key West,
FL
US

Amidst the sparkling waters of the Florida Keys, Key Largo Fisheries has furnished kitchens and kebabs with fresh seafood fetched from local fishermen and exotic locales since 1972. Succulent shellfish including lobster ($10.99/lb.), stone crab ($12.99–$29.99/lb.), and shrimp ($9.99–$15.99/lb.) newly plucked from nearby waters unbutton their hard-shell exteriors to reveal butter-ready meat. Grouper ($15.99/lb.), yellowtail snapper ($12.99/lb.), and other finned fare make enticing grilled or fried main dishes, and an array of premade items including crab cakes ($7.99 for two) and smoked fish dip ($15.99/qt.) supplies gatherings with quick, convenient eats. To sate seafood cravings or cede to mermaids begging for scraps, the Take Away Cafe populates its menu with a range of oceanic ambrosia.

1313 Ocean Bay Drive
Key Largo,
FL
US

Paired up with a Professional Association of Diving Instructors Divemaster, adventure-hungry divers and snorkelers board the Looe Key Reef Resort and Dive Center’s 45-foot catamaran boat to explore the sandy bottom abundant with sea creatures. Consisting of coral fingers and sand channels, the Looe Key Reef spans 5 square miles and carries a protected status thanks to its partially endangered sea dwellers. After a brief 5-mile boat ride, patrons can dive or snorkel up to 30 feet into the depths to witness angelfish, turtles, parrotfish, and nonbiting sharks go about their daily lives performing mundane chores and routine errands. Clear, 80-degree waters provide a comforting, almost-otherworldly experience as swimmers glide past ocean flora and extraterrestrial interlopers. Click here to check out pictures from past expeditions.

27340 Overseas Highway
Summerland Key,
FL
US

Lifelong diver Captain Slate is very popular with an unusual demographic: fish. For more than 35 years, he's been cuddling with nurse sharks, petting moray eels, and feeding barracuda by holding bait in his teeth. These animals—who have been featured with him on many television programs, including Ripley's Believe It or Not—have grown so accustomed to people that they report in regularly for Captain Slate's Creature Feature excursion, a dive that allows groups to touch the tamer beasts instead of just sketching them in waterproof notebooks.

Captain Slate labels the Creature Feature as his favorite dive, but it must have been hard to choose from so many different sites. On any given day, he might take clients through coral kingdoms or the hull of a shipwreck, such as The Eagle. (Look out for the two goliath groupers that live there—they're the size of cars.) New divers can earn their flippers beforehand at one of many diver certification classes. And, if you meet someone special during a trip, Captain Slate can even conduct your underwater wedding.

51 Garden Cove Dr
Key Largo,
FL
US

Florida Keys Kiteboarding promotes board-based enjoyment of the sparkling ocean tides around the island of Marathon through kiteboarding and standup paddleboarding (SUP) lessons and rentals. Before strapping into a parachute, novice kiteboarders can start out with a beginner lesson or work on fundamentals with a trainer kite to help build muscle memory. SUP presents ocean-goers with a more easygoing activity, allowing them to paddle their boards across the placid ocean surface at their own pace. The team also runs SUP yoga classes, during which participants move into yoga poses while balancing atop their floating boards.

11201 Overseas Hwy
Marathon,
FL
US

Aside from living deliverables, Marco Island Florist also sends nonbreathing day brighteners in the form of rainbow latex balloons ($29.95), air-freshening Poo Pourri spray ($14.95 for 4 oz.), and brownie dozens ($34.95), perfect for neighboring Partridge families. Groupon holders can opt to pick out a gift in-store or use today’s deal for easy online ordering, where the charitably minded can use the growing together pull-down menu to contribute 2% of their order to an organization of their choice.

178 S Barfield Dr
Marco Island,
FL
US