Throughout the Keys, I sleep with my hotel balcony door pushed wide open whenever the temperatures allow, making the most of tropical nighttime symphonies I never hear back home. At Oceans Edge Resort & Marina on Stock Island— Key West’s less polished but still charming neighboring isle—my dive alarm comes in the form of crowing roosters and mysterious splashing from the surrounding mangroves, the outlines of which are just beginning to materialize in the dawn light.

A quick in-room coffee and drive-through breakfast sandwich and we’re on our way to one of the most famed wrecks in the Keys with Captain Hooks/Dive Key West, which runs regular trips to the USNS General Hoyt S. Vandenberg. Dive instructor Henry Rose tells us endangered sawfish have been spotted a few times of late on Western Sambo Reef, as well as hundreds of barracuda hanging around the kingpost of the Vandy. A former Air Force missile-tracking ship sunk in 2009 as an artificial reef, the 524-foot-long behemoth has quickly become one of the crown jewels of the Florida Keys Wreck Trek.

“Diving here is a box of chocolates,” says Rose as we deflate our BCs for a negative entry in the current. “You never know what you’re going to get.” Our bottom time is shorter than usual on this particular day, with the current ripping, but we spend our time ogling the barracuda hovering in formation above the bow and follow a huge tilefish through the rusting rails before calling the dive due to waning air.

Dreaming of the sawfish, we motor to Cannonball Cut for our second dive. One of the least visited sites along Western Sambo, it’s raining fish everywhere as we fin past coral heads and dip under ledges. Bar jacks, yellowtail snappers, purple damsels and parrotfish swirl. I catch sight of a sizable reef shark in the distance, but he’s gone in a flash on the current. I’m lollygagging near a ledge when I surprise both myself and the resident 500-pound grouper, Gilsen (a riff on Wilson from the Tom Hanks movie Cast Away), who flees with a dramatic flourish of his fins. Mallory Square is the default spot for Key West’s Sunset Celebration and a must-visit at least once, with its cast of dexterous humans, souvenir-hawking artists and impromptu salsa dancers who try to steal the spotlight from the setting sun. But I have a favorite, quieter spot for sunset at Fort Zachary Taylor State Park, where the gently sloping beach is shaded by Australian pines.

It’s a privilege just to breathe in and out while admiring those deep-blue Florida Keys waters that shimmer with the promise of everything we know is alive and swimming beneath.

MUST STAY: Oceans Edge Resort & Marina on Stock Island fronts a marina and has paddleboards and kayaks for exploring the surrounding mangroves.

MUST EAT: Breakfast at Blue Heaven is a must for banana pancakes at outdoor tables where roosters peck and preen. On Stock Island, anything hogfish is a winner at Hogfish Bar & Grill.

MUST DIVE, WRECK: In roughly 150 feet of water, the General Hoyt S. Vandenberg has a storied military past and bustles with pelagics and vibrant macro life.

MUST DIVE, REEF: In the spur-and-groove maze of Western Sambo Reef, you’re just as likely to see sea turtles and 500-pound grouper as reef sharks and schooling reef fish.

Explore all stops on the Ultimate Scuba Road Trip through the Florida Keys:
Key Largo | Islamorada | Marathon | Big Pine Key