Day Two: Circumnavigating Key West
5 a.m.: "What do red, yellow and green stand for?" I asked Derek while shaking him awake. "Huh? What's happening? Apples?" he groaned.
"Nope, not apples," I said. "It stands for 40-mile-per-hour winds and rain." The weather outside was howling, and those colors on my iPhone's radar image meant another hour of listening to loud snores.
By 7:30, a heavy caffeine buzz mixed with the background noise from obnoxious TV ads was distressing enough to make a cat swim laps. So we ventured through the storm to the Lorelei (305-664-2692, www.loreleifloridakeys.com) for the outstanding biscuits and sausage gravy.
An hour later, a few sun rays peeked through the clouds. "Gotta love Florida weather," Chris said. "One minute, it looks like the reincarnation of Hurricane Andrew and the next, pure paradise."
9 a.m.: Skimming over liquid glass.
9:30 a.m.: We found a slack-high tide at the Channel Two Bridge. Looking into the clear depths below, Derek waggled his first two fingers in a peace sign - the scuba diver's universal indicator for lobster. "I've always wanted to catch a lobster," Tyler said. Ten minutes later, Tyler had his wish.
10 a.m.: The Long Key State Park flats, with its roving sharks and rays, looked too good to pass. Derek and Chris stood on the casting platforms armed with 8weight fly rods and small toad flies.
Sighting a dozen bonefish in a half-hour gave us heart murmurs, but the fish remained out of range. Derek plucked a jack crevalle off the back of a ray for some excitement.
11:30 a.m.: We interrupted 20 miles of smooth running past Duck and Grassy keys with a refueling stop at Captain Hook's on the south side of Vaca Cut (305-743-2444, www.captainhooks.com).
"You think we can make it to Key West today? It's not even noon, and according to the GPS we're 50 miles from Southernmost Point," Derek said.
"Not before we catch a permit at Pigeon Key," I replied. "Then we can forge ahead."
12:15 p.m.: Call me clairvoyant. Derek poled into a strong current exiting the Gulf side over Pigeon Key Bank. Among the many turquoise pot holes on the edge of the lush flat, a 15-pound permit fell victim to my crab.
2:30 p.m.: Derek and I were on cloud nine. The adrenaline from the catch, added to warmth from the tropical sun, put us in a Key West state of mind. "A two-hour run should put us there around 5 p.m., enough time to get settled before we hit Duval Street," Derek said.
4:30 p.m.: We stopped to pole a broad flats basin between Saddlebunch and Pelican keys. Small lemon sharks chasing mullet wrinkled the calm water around us, but we had no luck fishing the hot, low water.
6 p.m.: Approaching Key West's Southernmost Point from the water differs considerably from walking up to the land marker amid groups of shutter-happy tourists. We could also look back at the 160-mile run from Miami and know that the return trip was more achievable than we'd thought.
Tyler called his friend Bear Holeman, a Key West guide who had generously offered us local intel. He said that fishing had been quiet on the ocean side, and that if permit and tarpon were our game, then we'd better cancel our Duval plans and boogie up to Big Spanish Cay.
We took his advice, and with the help of the GPS, we headed around to Big Pine on the Gulf side. Along the way, Derek called his good friend and noted TV host Jose Wejebe, who lives in Summerland Key, for advice about hotels with waterside dockage. Jose suggested Palmer's Resort in Big Pine (305-872-2157, www.palmersresort.com), but when he unexpectedly offered for us to stay at his house, we jumped at the chance.