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Plan Your Own Puglian (or Biking) Adventure

Writer Paul Greenberg and his friend David Gold bicycled across the untouched Italian region of Puglia in his latest feature for AFAR. He left with a great story, as well as some great tips on how to do your own version of the trip through untouched Italian hillsides.

Find Your Bicycle Tour Outfitter:

Gray & Co.
Paul Greenberg’s bicycle trip was organized by Gray & Co. “When you bike, the countryside becomes your museum,” says company founder and AFAR Travel Advisory Council member Cari Gray. “On more traditional trips, you don’t meet the farmer, and you don’t hang out with the fisherman. And you can’t smell olive trees from the back of a car.”

Gray exclusively organizes custom trips. “We emphasize choice and flexibility,” she says. “It’s not just the same formula with different people.” During a tour in Chile, for example, you might cycle around the conical volcanoes in northern Patagonia, bike to vineyards for wine tastings, and sample grilled lamb at a traditional asado. From $1,200 per person, per day. 416-998-4082. – Lara Takenaga 

Corsica—one of the company’s most challenging destinations—beckons with its panoramic seaside views and pink granite cliffs. During a six-day trip, participants cycle to artist enclaves, jet ski in the Mediterranean, and try local specialties like wild boar charcuterie and goat cheese. From $4,698. 888-883-7948.

Southern Visions
But if you need to keep rolling, Southern Visions specializes in tailor-made cycling trips (guided and self-guided), food hunting, hands-on cooking classes, and historical experiences in Puglia. Founded by a former professional cyclist, the outfitter stocks a comprehensive selection of carbon road bikes and premium hybrid bikes, and can provide local guides deeply immersed in the area’s culture and history.

A 10-day itinerary in Vietnam and Cambodia combines cycling and riverboat cruising as you travel along the Mekong River. Between visits to Angkor Wat and artisans’ workshops, you’ll pedal through an ecological reserve and past rice fields and mangrove forests. From $6,398. 800-462-2848. – Lara Takenaga 

Trek Travel
A new Portugal itinerary is part of One, a tour series that lets you unwind at a single high-end property for the entire trip to avoid the pack-schlep- unpack cycle. As you bike through the Alentejo region, you’ll explore an ancient Roman temple, visit a local pottery museum, and sample aged Portuguese cheeses. From $3,299. 866-464-8735. – Lara Takenaga 

DuVine Cycling & Adventure Co.
Active cyclists should consider DuVine’s van-supported California Coast tour from Santa Barbara to San Francisco. Tick everything off your West Coast wish list after biking the 17-Mile Drive and Pacific Coast Highway, wandering through Hearst Castle, and hiking among giant redwoods in Big Sur. From $4,995. 888- 396-5383. – Lara Takenaga

Where to Stay:

Masseria Montelauro 
A luxury masseria (manor farm) near the southern town of Otranto, Montelauro was originally built in 1878. Its 29 rooms, many with vaulted stone ceilings, look out onto a central garden and swimming pool or command views of the countryside. Although it has become a favorite among Italian celebrities, Montelaiuro retains an intimate family feeling, especially in the terrace restaurant.

La Sommita Hotel
Located in the hilltop town of Ostuni, this small boutique hotel has stunning views of the valley and coast below and a wonderful aperitif-tasting menu. From $173. 

Masseria Torre Maizza, Masseria Torre Coccaro
The sister resorts near Monopoli feature lovely spas, broad terraces for a sunset aperitif, fortified towers from the 15th century surrounded by olive groves, and restaurants on the beach. From $321.

Masseria Fumarola 
Not far from the historical town of Martina Franca, Fumarola’s 14 suites, each with unique interior designs, are built from trulli, traditional Apulian drystone huts with conical roofs. The property is owned and managed by an aristocratic family from Lecce. Meals here are a beautiful experience; the kitchen is run not by a professional chef but by a genuine Pugliese home cook, a mother who makes everything from scratch.

What to Eat:

L’Altro Baffo, Otranto
Try the sea urchin carbonara and squid in primitivo sauce in an elegant, quiet, romantic setting. If you’re lucky, the waiter will offer you the laurel and fennel digestivi at the end of your meal.

Pescheria 2 Mari, Savelletri
Be sure to order a bottle of white Sale wine to accompany the seafood crudo in this little glass box of a restaurant right by the sea.

L’ Angolo Blu, Gallipoli
The modern preparations of daily caught fish and such local specialties as purple prawns are gorgeous to look at on the plate and even better to eat. Make a reservation in advance.

Doppiozero, Lecce
Have a long, relaxed lunch of salad, pizza, or sandwiches—featuring excellent cured meats and cheeses—in a beautiful outdoor seating area right next to the Cathedral of Lecce. With dessert have a traditional iced coffee with almond milk.

What to Do Off Your Bicycle:

Museo Faggiano, Lecce
In his small private archaeological museum, Luciano Faggiano displays artifacts from multiple layers of Lecce’s history— Messapian, Roman, medieval, Byzantine—that he discovered digging beneath the floor of what he once hoped would become his restaurant.

Terme di Santa Cesarea
In the small coastal town of Santa Cesarea Terme, partake of the thermal sulfuric waters and various other wellness treatments, such as massage and respiratory therapy, in an updated classic 19th-century spa. For something more brisk, plunge into the crystalline ocean waters just outside.