Biking the Southern Hills
An east-to-west odyssey across the sole of Italy's boot, from Bari to Lamezia Terme, weaves through untrammeled Puglia, Basilicata, Campania, and Calabria—regions as beautiful as Tuscany and the Amalfi Coast, minus the tourists. You'll start the 12-day trip in Puglia, with its ancient beehive-domed limestone dwellings, or trulli, and cycle about 50 miles a day over rolling countryside to the cave city of Matera, a World Heritage Site. After visiting Greek, Roman, Byzantine, and Norman ruins, hit the wilds of Pollino National Park, and wander the beaches of Cilento Peninsula, which juts into the Tyrrhenian Sea. You'll also check out archaeological digs at ancient sites, see fresh mozzarella di bufala stretched by hand, and end the days with bacchanalian feasts and luxe rooms in cliff-perched palaces.
High Point: The ten-mile descent to Cittadella del Capo and your swanky digs for the night: the Palazzo del Capo, a five-star seaside resort.
Low Point: A fiery tongue from an irresistible pepperoncini, the Calabrese hot pepper.
Travel Advisory: Take it easy on the Cirò; wine or you might find the roadside donkeys keeping pace with you the next day.
Outfitter: Ciclismo Classico (800-866-7314, www.ciclismoclassico.com)
When to Go: June
Price: From $3,795
Inn-to-Inn Sea Kayaking, Hiking, and Yoga on Crete
During eight days on Crete's southern coast, perfect your morning sun salutation in an ancient Venetian fortress overlooking the Mediterranean, paddle through Gaudiesque caves, and hike the Samaria Gorge, Europe's version of the Grand Canyon. You'll sleep seaside at quiet family-run inns and lounge on white-pebble Sweetwater Beach, where clear springs flow from the rocks and bathing suits usually get left on the shore.
Outfitter: The Northwest Passage (800-732-7328, www.nwpassage.com)
When to Go: May and October
Hiking from Mont Blanc to the Mediterranean
On this 15-day north-south traverse of the French Alps, hike more than 80 miles on sections of the GR5 trail, from Mont Blanc to the Côte d'Azur. Traveling up to ten miles per day, traipse through Vanoise and Mercantour national parks—home to ibex and golden eagles—and over 9,000-foot mountain passes to snooze in snug inns and mountain refuges. Eventually, the glacial valleys and granite spires give way to sunny Mediterranean villages.
Outfitter: Wilderness Travel (800-368-2794, www.wildernesstravel.com)
When to Go: June to September
Price: From $3,795
Highlands Off-Road Coast to Coast
This eight-day bike ramble winds 230 miles—from Loch Hourn, on the west coast, to Montrose, on the east. With plenty of climbs and bangin' descents, you'll pedal 35 miles a day along drovers' roads and forested singletrack, skirting the Cairngorm and Grampian mountains and crossing the River Dee before hitting the North Sea. Your toughest day: climbing 2,507-foot Corrieyairack Pass. At night, luxuriate at charming inns, sampling Scotch whisky.
Outfitter: Saddle Skedaddle (011-44-191-265-1110, www.skedaddle.co.uk)
when to go: June and August
Price: From $915