Stride and Seek

Now, being a very good walker myself (translate that: incompetent at tennis, uninterested in golf, and terrified of downhill speed), I’m delighted to help him out. Walking, I explain, is as exhilarating or as Zen-ful as one chooses to make it. If I don’t want to listen to this usually cheerful gentleman whine for the next six weeks, imagine how many others out there will thank me for this.

So, my cranky friend, here are some walks that will tempt and delight even you.

You’re welcome.

That fat, emerald-fringed crescent of shimmery white sand floating just off the western shore of Marco Island once was a sandbar, but shifting sands finally earned it official designation as Sand Dollar Island. Pushing semantics, yes, but still an idyllic start for your first walk. Park at the county-run Tigertail Beach recreational area and stroll the boardwalk over the dunes to the beach.

Warm up those calf muscles with a wade or swim the 150-or-so yards through the lagoon to the Gulf side of the island. It’s all virgin beach, dunes, salt scrub and one of North America’s most important nesting areas for the endangered piping plover. Around the bend, it feels like a desert island. Afterward, wade back to the mainland and walk briskly south along the graceful curve of beach toward the high-rise resorts in the distance. Pause at the newly renovated Marco Island Marriott for a Caribbean seafood lunch alfresco at Quinn’s on the Beach—no shirt, no shoes, no problem—before the return stroll.

If it’s a romantic walk you have in mind, start at the Marriott and walk north to Tigertail and Sand Dollar Island, then return for sunset and cocktails under the stars at Quinn’s to the tropical sounds of live island music.

Five miles

What? You’ve lived here (pick one: six months/six years/your whole life) and you never knew that the DuPont daughters built a high stone wall around their Old Naples home after the Lindbergh baby kidnaping? And that the wall is drenched in 75-year-old passionflower vines spilling into the crushed-shell alley out back? Then I sincerely doubt you’re even aware of the dozens of secret little alleys tucked between the avenues behind Old Naples’ most historic homes.

Even back in the 1880s, Neapolitans had style: They considered it crass to have mail delivery, garbage pickup or fish deliveries at the front door. But I digress. Take this walk I’ve outlined for you and you’ll get a respectable cardio workout and the chance to do the kind of close-up gawking that just isn’t possible through a car window. You’ll see (not in order of appearance): Old Florida beach houses and Mediterranean mansions. The first Seminole market that’s now a trendy bistro. Avenues of royal palms and bougainvillea-draped walls. Castles and turrets and gingerbread and tin roofs. Courtyards and fountains. Six-figure sculptures and funky folk art. The hottest pink hot-pink house in the universe. Lush, lush tropical gardens. Hidden beach paths and 3,000 or so coconut palms. (True factoid: Old Naples has the largest stand of coconut palms in Florida.)

And along with it, you’ll get tales of mystery and intrigue from the highbrow to the lowbrow that will make you a hit at the next cocktail party.

Rise early to start your walk at the Naples Pier (12th Avenue South). Besides exquisite cool air and new morning light, you’ll meet the great blue herons, snowy egrets and dedicated humans catching their breakfasts/baitfish as the case may be. Walk briskly south for 2.6 miles to the end of the earth at Gordon Pass. This stretch of beach parallels glamorous Gordon Drive, so you can pick up some useful ideas for your next beachfront estate. Pause at the pass to watch the big yachts and deep-sea fishing charters heading into the Gulf. Now turn back, and just before reaching the colorful beach cabanas of the private Port Royal Club, take the pathway off the beach at either 32nd or 34th Avenue South. Turn left onto Gordon Drive and follow the bike path north.

Cross Gordon Drive at Galleon Drive and stroll down the royal palm-lined avenue, across the tiny Lantern Lake bridge to the beautiful Trinity-by-the-Cove Episcopal Church. You may turn back here, or if you’re not finished gawking at the mansions, go another half-mile to the cul de sac.

Back at Gordon Drive, go right and walk one mile on the bike path to 12th Avenue South. Turn left to the Palm Cottage, where you have pre-booked a private 90-minute insider’s stroll along Old Naples’ avenues and alleys with historian John Mayer. $15 gets you a tour of Palm Cottage—Naples’ oldest house—and a head full of lore, characters, ghostly happenings and juicy skeletons-in-closets. Afterward, stroll over to Third Street South for a well-earned lunch.

Seven miles

A particularly nice all-day hike is in the 7,000-acre San Felasco Hammock State Preserve a few miles north of Gainesville. Early morning walkers are rewarded with close-up sightings of white tail deer and wild turkeys; a sharp eye may catch a gray fox or bobcat. My last excursion netted some fascinating armadillo encounters. Don’t laugh. I learned that the funny-looking creatures hop like bunnies and stand on their hind legs to impersonate kangaroos. Oh, and those who think of Florida as flat should pop over to the giant limestone-walled sinkhole called Devil’s Millhopper. Its 232 steep wooden steps to the bottom are guaranteed to accelerate your heart rate, Mister Cranky Athlete. The name has something to do with bones that early explorers found at the bottom—supposedly the remains of those on the way to meet the devil.

Now that you have your walking legs, it’s time to get serious. Pack your bags for Nova Scotia and its easternmost island, Cape Breton. You want misty mountains, startling cliffs and raging oceans; saltwater estuaries, weathered fishing villages and grand old maritime lodges with lawns sprinkled with colorful Adirondack chairs? Cape Breton is your place. Your destination is the 185-mile Cabot Trail, consistently named among the most spectacular scenic drives in the world.

The top loop of the trail encircles the Cape Breton Highlands National Park. Choose any well-marked trail along the parkway and set off into the land of moose and whales, waterfalls and soaring eagles. Follow country roads through farmlands and golden salt marshes. Take the coastal route from art colonies to seafaring villages. My favorite is Neil’s Harbor, where those silvery-white towels flapping gently on the clotheslines aren’t towels at all, but big sheets of salted codfish, drying in the sun. Most of the wooden fishermen’s cottages were floated in from Newfoundland about a century back, and the little seaside hamlet has barely changed since. (Well actually, the lighthouse is an ice cream concession in summertime, and the locals think it’s amusing that tourists will pay actual money for their broken-down lobster traps, but that’s about it.)

Nearly every house in Neil’s Harbor is white. Apparently they reserve the colored paint for their jellybean-hued fishing boats.

Besides being one of the world’s largest exporter of blueberries and Christmas trees, this wild and unspoiled land is the purest seat of Celtic music and culture outside of Scotland. Every autumn, world-renowned Celtic musicians gather for the island-wide Celtic Colours Festival. It’s a magnificent time to plan your walking vacation, but you must book lodgings months in advance. Even if you miss the festival, the greatest treat after a day’s walking is to encounter an impromptu Ceilidh (pronounced Kay-lee, it’s Celtic for "gathering"), ensuring lively music, storytelling, eating and drinking till the wee hours.

Cape Breton’s trails are rated from 1A (baby stroller level) to 5C (so rugged that five miles is plenty for one day).

If you’ve followed my instructions, you could now possibly be in the best shape of your life. So, as your reward I present to you a glorious seven-day walk across Tuscany. You’ll be walking a good 10 miles a day, but except for the climb to the medieval villages, they’re gentle miles. And when you factor in generous amounts of Brunello di Montalcino wine, locally pressed extra virgin olive oils and oven-fragrant breads; plus farm cheeses and pasta made by the gods themselves, you’ll barely notice the miles.

Your walk will take you to ancient walled and gated cities with narrow cobbled lanes; through centuries-old vineyards and orchards of gnarled olive trees; along forgotten country paths and through vast expanses of swaying grasses (green in spring; golden in summer); to Etruscan tombs and the cave of St. Francis of Assisi. You may be invited to a private estate drenched in wisteria vines, perhaps to dine with the resident count or countess.

You carry only a small pack—everything else is being transported from last night’s stay to this one, while you’re indulging in some Tuscan feast at an olive refinery or picturesque organic farm. And the moment you find yourself a bit hungry along the way, by magic a tailgate repast has been all set up just around the next bend.

Sounds like a lot of work, doesn’t it—planning such a week. It is, but not for you. Because you’re "walking with the Wayfarers," the crème de la crème of walking tours. Not the most expensive, but unsurpassed in the art of immersion for an authentic experience. I had previously walked with the Wayfarers through Provence, and I was certain nothing could live up to that experience. I tried it, and trust me, it can.

You may not dine with the same counts and winemakers, or be guests of the same estate-holders on your Wayfarers walk, for each year there are little surprises. You won’t see the inside of a vehicle unless you decide to retire early for a foot massage or a nap on your Tuscan balcony. In a week you’ll walk 50 to 60 miles, but you won’t notice it.

In fact, my cranky athletic friend, you will conclude that walking is not half bad. In fact, you might be just a bit depressed when your six weeks of doctor-imposed probation are up, and all you have to look forward to is a game of tennis.