This first-of-its-kind European offering is the ultimate two-wheeled fantasy: On this nine-day trip, there'll be seven days of personalized training in Aigle, at the International Cycling Union's new ultramodern World Cycling Center (WCC), and in surrounding alpine terrain. With your coach, seven-time world track champion and Frenchman Frederic Magne, you'll train on the WCC's state-of-the-art 200-meter wooden track and on daily rides ranging from 25 to 75 miles. Base camp is a Victorian-style four-star hotel on Lake Geneva's eastern shore. From there, ride along Rhone Valley roads and into the Vaud Alps, with views of the Matterhorn and Mont Blanc providing inspiration as you grind up legendary mountain passes. Out-of-the-saddle luxuries include thermal spas, private wine tastings, a trip masseur, and regional specialties like saucisson Vaudois (local sausage).
High Point: Cranking up the famous hairpin turns of the Grimsel and Furka passes before hopping the cable car to the top of 9,603-foot Eggishorn Mountain for a view of Europe's largest glacier, the Aletsch.
Low Point: Trying to avoid too much pinot noir at the farewell dinner, knowing there's a timed 91-mile race in Bulle—the Pascal Richard Cyclosportif—still to come.
Travel Advisory: High-altitude climbs combined with August heat can mean easy dehydration, so keep the fluids coming.
Outfitter: Velo Classic Tours, 212-779-9599, www.veloclassic.com
When to Go: August
Kayaking the Douro River
On this 11-day flatwater float on the Douro River from Quinta das Aveleiras to Peso da Régua, through northern Portugal's fertile port-wine region, you'll paddle three to five hours daily, stretching out with afternoon hikes across golden-terraced hillsides. In the fall, glide through the grape harvest, feasting on feijoada (bean-and-meat stew) and the ruby-hued regional wines (you can pick tinta amarela grapes off the vine from the seat of your kayak), staying at manor houses and 18th-century blue-tiled quintas (wine estates).
Outfitter: Explorers' Corner, 510-559-8099, www.explorerscorner.com
When to Go: June, September
Sicily and the Aeolian Islands by Sea
Price: $8,950 and up
The intimate 32-passenger Callisto is your luxurious floating hideaway on this nine-day sail through Italy's southern islands. Begin with an architectural tour of Palermo's 11th-century splendors, then set sail for the sun-blasted Aeolian Islands, seven volcanic spurs north of Sicily. When you're not scuba-diving, snorkeling, and swimming in tucked-away coves or hiking up a live volcano, lounge at Lipari Island's San Calogero, the oldest-known spa in the Mediterranean, or take a siesta deckside, grappa in hand.
Outfitter: Butterfield & Robinson, 888-596-6377, www.butterfieldandrobinson.com
When to Go: July
Hiking Hadrian's Wall
Price: $3,495 and up
Follow the winding route of Hadrian's Wall on Britain's newest long-distance trail. The Roman-era engineering feat stretches for 70 miles along the Scottish border, connecting two coasts. Start in Bowness-on-Solway, where the wall meets the sea on the west coast, and hike eight to ten miles a day through a magical landscape little changed in 2,000 years: lush hills, heather-covered moors, and rolling dales pocked with deep forests. En route, explore Roman forts, archaeological sites, and the bird-rich tidal estuary of Budle Bay. Your guide, Peter Goddard, has hiked the area for more than 30 years and is a local-history buff, as you'll learn over family-style dinners at country B&Bs.
Outfitter: Wilderness Travel, 800-368-2794, www.wildernesstravel.com
When to Go: July