Jump to the third day of Hawks Cay’s Learn to Sail Program, when you cruise away from the Florida Keys and into the Atlantic Ocean on your own. No instructor on board. With a 15- or 20-knot breeze filling your sails, you tack and jibe over open water in your custom-designed 26-foot keelboat, dolphins arcing in your bow wave as you spew salty jargon with the ease of Jean Lafitte. The intensive three-day program, which delivers a U.S. Sailing basic keelboat certificate (your ticket to rent and captain a 26-footer pretty much anywhere), emphasizes focused instruction on the water. "It’s a wide-open ocean playground here," says head sailor Craig Yakel, "once you get past the $7 million homes along the waterway." Your digs aren’t too shabby either: a private island resort on Duck Key with an upscale, though barefoot-casual, West Indies feel (sailing course, certificate, and three nights’ stay, $1,545; hawkscay.com).
During the off-season, the Jersey shore reveals its better half. The little town of Stone Harbor lies near the south end of Seven Mile Island surrounded by salt marsh, protected bay, and the Atlantic Ocean. Hole up in the Golden Inn right on the beach and pay off-season rates (doubles from $99; goldeninn.com). If you bring a kayak, put in at Nummy’s Island at the ancient Lenape Indian shell pile—the highest spot on the horizon—and paddle a string of marshes, small islets, and dead-end creeks amid scores of surf scoters, black skimmers, terns, and oystercatchers. No boat? Just walk around. You’ll have little company on the shore or at Quahog’s in Stone Harbor, which specializes in "sustainable seafood." Spend the next day two-wheeling 15 miles down Ocean Drive to Cape May (Harbor Bike has cruisers for $12 a day; harborbike.com), passing surf fishermen tossing lines for stripers. At Cape May Bird Observatory you can learn the names of all the birds you couldn’t ID yesterday (njaudubon.org). When you return, grab a seat at Fred’s Tavern. Like the rest of the shore, it’s locals-only.
Hemmed by the Chesapeake Bay and the Potomac and Rappahannock Rivers, Virginia’s Northern Neck is a paddlers’ promised land. "It’s just two hours southeast of the cacophony that is the D.C. metro area," says local kayaker Dave Clarke. "Dropping a kayak into its hundreds of creeks, rivers, and inlets is divine." Clarke suggests launching in Belle Isle State Park at the end of State Route 354. Keep an eye out for blue crabs, bald eagles, red foxes, the occasional river otter, and—most of all—"a 40-foot-tall lighthouse near the end of the road," says Clarke. "That’s Captain Tom’s Seafood. Head to the crab shack out back. He’ll sell you a fresh bushel of the best lump backfin crab you’ve ever had." Nearby Tides Inn puts you in the midst of it all, and solitude is guaranteed (doubles from $285; tidesinn.com).
Fall colors linger through November in northern Georgia, but if you’re not careful, leaf peeping in Fort Yargo State Park can turn into a contact sport (camping, $23; gastateparks.org/info/ftyargo). That’s because if you’re in Fort Yargo, a 1,814-acre woodland between Atlanta and Athens, you’re mountain biking the 11.4-mile singletrack Outer Loop, which features some technical rock and root garden sections. And brace yourself for the roller-coaster Horseshoe Drop: 18 feet down, 80 percent up—a major whoop-de-doo. For a lazy Sunday ride, opt for the flat, winding 7.2-mile Inner Loop, which skirts Marbury Creek Reservoir. To focus on the scenery, don your plaid pants and tee off on the park’s 18-hole disc golf course, one of the most scenic and challenging anywhere—lots of trees, a 260-acre water hazard (the reservoir), and the odd deer. The park office sells discs.