See Italy On Two Wheels
Tuscany
To heck with a tour bus—the best way to experience Tuscany is by bike. Pedal through the countryside by day, stopping to sample wines and gelato, then stroll around the picturesque towns come evening, ducking into trattorias for the best pasta you'll ever have. Forgo the hassle of organizing your own itinerary and book with a tour operator, like Ciclismo Classico, which specializes in biking and hiking excursions in Italy. Its six-day Assaggio Toscana trip includes one organized wine tasting (you can do others on your own), a cooking demonstration with a local chef, and an olive oil tasting at one of the region's famed presses.

The biking kicks off 25 miles south of Florence in San Donato. The route winds 150 miles through terraced hillsides, hugging the river Arno, to the Renaissance town of Arezzo before ending in the village of Cortona. The terrain is moderate, with plenty of rest stops, but plan to be on your bike for about 30 to 40 miles each day (you can opt for longer routes if you want more time in the saddle).

After an intense day on the road, it's nice to know you won’t be roughing it come nightfall. Instead you'll rest up in unique villas, like Fattoria degli Usignoli ("Farm of the Nightingales"), built by friars in the 1400s and perched 1,300 feet above sea level near San Donato. You'll spend another night at the trendy Vogue Hotel in Arezzo and two final nights in the Villa Marsili, within the town walls of Cortona.

Details The Assaggio Toscana trip starts at $3,195; ciclismoclassico.com.

Surf Down Under
New Zealand
With mountain ranges, volcanoes, lush rain forests, and sandy beaches, New Zealand is a fantasy playground. And with nearly 10,000 miles of coastline, you know the surf will always be up. Find all the good spots by registering for New Zealand Surf Tours' five-day surf safari. It's tailored to beginners, but the outfitter can direct advanced surfers to off-the-beaten-path locations to catch perfect swells.

You'll meet your guides in Auckland, New Zealand’s cosmopolitan center, then head north to the peninsula fittingly known as Northland. Whitesand beaches and cozy harbors dot the east side, while wilder dunes are found on the west. Your base will be in Shipwreck Bay at the northern tip of the country, where you'll stay at the school’s beachfront Ahipara Surf Lodge, which has six bedrooms and a pool. Days start as early as 6 a.m. with two-hour surfing sessions at different beaches within an hour's drive. You'll return to the lodge to eat, then swim, bike, or relax before heading back out for an afternoon session.

While the lure of the ocean is strong, set aside time to check out the city scene too. Auckland is urban, but you still get the feeling of being close to nature. Thrill seekers won't want to miss the Sky Jump—a 630-foot controlled leap (you're guided down by cables)—off the Sky Tower, the tallest tower in the southern hemisphere ($186; skyjump.co.nz). Too much adrenaline for you? From downtown, take the 10-minute Fullers Passenger Ferry ($9 round-trip; fullers.co.nz) to the village of Devonport, which is packed with cafés, boutiques, and art galleries.

Details New Zealand Surf Tours' five-day trips start at $530 (newzealandsurftours.com). In Auckland, stay in the heart of downtown at the SkyCity Grand Hotel. It has luxurious rooms, a day spa, and a heated lap pool (from $225; skycity auckland.co.nz).