Pool time in Tuscany

Dinner at Le Sirenuse overlooking Positano

Hiking in the Dolomites

Costa Esmeralda in Sardinia

Cycling through Puglia

Sailing on the Amalfi Coast


The boot-shaped country offers up so many diverse regions. With so much potential for custom luxury travel, there’s no end to the possibilities of Gray & Co.’s private active trips in Italy.

Starting in the north, jet to the Dolomites, a dramatic mountain range characterized by rock walls, pinnacles and pillars, where the luxury Rosa Alpina Hotel & Spa serves as our base. With your expert Gray & Co. guides, enjoy customized hikes to spot wildflowers, chamois, mountain pheasants, eagles and marmots. There’s great biking to be had here, too, both casual pedaling and more serious spinning, as well as rock climbing, zip lining and, for the especially hearty, via ferrata. Built by WWI soldiers, these rigorous trails — whose name translates to “iron road” — incorporate metal ladders to help navigate the steep, but almost impossibly beautiful, terrain.

Southwest of the Dolomites lies the Veneto region. Set near the foothills of the Alps and along the shores of Lake Garda and the Adriatic Sea, this is one of the mostly culturally rich, wealthy and industrialized parts of Italy. It’s also home to stylish countryside villas and picturesque vineyards, which makes it one of our favorite Italian spots for biking. The Hotel Villa Abbazia, a charming family run 18th-century mansion, and the Cipriani in Asolo are top places to stay.

Heading west, Piemonte’s famous truffles, chocolate, and barolo wines are best enjoyed after daily bike rides — some of the country’s most scenic — past centuries-old castles, Medieval villages, and distant mountain peaks. Though most come to bike for the barolos, many convert to the barberas and barbarescos—with barolo and barbaresco being a mere 10 miles apart.

Everyone knows Tuscany, whose rolling hills, cypress trees and medieval hilltop towns are the definition of bellissima. The best luxe hotels for bikers and hikers, thanks to their proximity to vineyards and smooth pavement, include Belmond’s Castello di Casole and Rosewood’s Castiglion del Bosco. Next door, the lesser-known Umbria region offers up the city gems of Perugia and Assisi, as well as quieter roads for cycling.

South of Naples, on the famous Amalfi Coast, hike the Path of the Gods, a trail dotted by lemon groves and olive trees, with cliffs that drop dramatically down to the Mediterranean. Charter a yacht — or take your own — to cruise over to the island of Capri for more trails, Roman ruins and endless style. Or base yourself from one of our favorite hotels on the mainland, such as Le Sirenuse, in Positano, or the family-friendly Santa Catarina in Amalfi, where owners Antonio and Carla Sersale and Crescenzo Gargano, respectively, have crafted perfection in paradise.

All the way down in Puglia, the heel of the Italian boot, explore lands of ancient olive trees, whitewashed villages, Adriatic and Ionian beaches, wheat fields, vineyards and trulli — the region’s iconic conically shaped stone buildings. The extensive tertiary road system here — and the perpetually sunny weather — make for great biking. You’ll also love the local cuisine featuring sweet tomatoes, fresh burrata and fresh seafood.

Even further south lies Sicily, where travelers explore hilltop towns, including Taormina, famous for its ancient Greek amphitheater, winding streets and Mount Etna views — most enjoyably viewed with cocktail in hand from the terrace of the Belmond Grand Hotel Timeo. The best biking in Sicily is around the Baroque city of Ragusa and near the Roman ruins of Agrigento. Not to be missed culinary delights include eggplant caponata, grilled sardines and gelato. (Sicily is purportedly the birthplace of this frozen delight.) Off Sicily’s northern coast are the Aeolian Islands, much loved by the private-yachting crowd.

Off Italy’s southeast coast, on the island of Sardinia, the Emerald Coast or Costa Esmeralda has long been the playground of the wealthy, who often take advantage of private yachts to connect the best beaches, bike rides and trailheads. We love the chef-owned Petra Segreta Resort & Spa, where great island cuisine meets luxe lodging. The authentic Su Gologone hotel, located inland, is another treasure — part museum, part gallery, part restaurant.