The Trip: A bike tour customized by Gray & Co. in Portugal’s southern Alentejo region offers a glimpse into another era: Medieval castles atop rolling hills, herds of sheep in green pastures, and tiny cobblestoned villages. From $1,800.
The Retreat: It took José António Uva 15 years to regain ownership of his family’s farm after it had been taken over by the government during Portugal’s nationalization wave in the 1980s. It took him another 14 years to painstakingly build São Lourenço do Barrocal (pictured above) into a resort that showcases the region’s heritage. “Above all, what we are trying to portray is a sense of pride in our culture,” says Uva, the farm’s eighth-generation owner. “We revived traditional crafts for some of the materials we used, like the terra-cotta roof tiles.” Set on 2,000 acres, São Lourenço is a labor of love for Uva and his wife, an architect who helped him renovate the property and convert the whitewashed farm buildings into 24 guest rooms and 16 cottages. The Uvas want the place to feel like home, as it is for their family when they’re not in Lisbon. You might find them swimming with their two young boys in the outdoor pool or riding horses to nearby Monsaraz Castle.
The Trip: An eight-night, 106- to 154-mile cycling and hiking trip through Rajasthan with Backroads explores Brahmin temples, centuries-old forts and citadels, the indigo-washed city of Jodhpur, and ancient caravan routes through the dramatic Thar Desert. From $6,800.
The Retreat: Here’s your chance to play maharajah for a couple of nights. RAAS Devigarh, an 18th-century palace, is now a haven for travelers about 15 miles north of the city of Udaipur. Originally named Delwara Palace after the village where it’s situated, the property was built on land that was a gift from one royal family to another. Two Indian architects led a restoration effort that took 750 people close to 15 years to complete. The result is nothing short of cinematic, whether you’re taking a walk through the manicured gardens filled with the scent of frangipani or stepping out of your marble-floored suite onto your jharokha, a carved enclosed balcony, to face the rolling Aravalli hills. The equally majestic, light-filled spa focuses on ancient Ayurvedic treatments. Book a private dinner inside Sheesh Mahal, an intimate space adorned with hand-decorated mirrors, where past kings of Devigarh once supped with their queens and entertained guests.
The Trip: Food- and wine-focused bicycle tour company DuVine offers a five-night, 64-mile itinerary near Cape Town that focuses on sampling the region’s outstanding wines and traditional braai (barbecue). From $5,895.
The Retreat: To arrive at Tintswalo Atlantic, cyclists pedal a sun-kissed coastal stretch of the Cape Peninsula to a rocky beach just 15 miles south of Cape Town. From the ocean-facing verandas of all 11 guest rooms, it’s not uncommon to see breaching humpback whales during calving season between June and November. Tintswalo Atlantic is a passion project for the South African owners, who rebuilt the lodge from the ground up in 2015 after a devastating wildfire. Some of the furniture was carved from the wood of milkwood trees that burned. Each of the rooms is designed to evoke a different island from around the world: The Robben Island suite—named after the former prison island where Nelson Mandela was held—features textiles made by local tribes, while the Zanzibar Suite has an elaborate carved door from Tanzania. The restaurant’s menu focuses on sustainable local seafood.
The Trip: The craggy shorelines and quiet, persimmon tree–lined villages of Japan’s Noto Peninsula, an hour’s flight west of Tokyo, are the focus of a seven-night, 193-mile cycling itinerary with Butterfield & Robinson. From $9,495 per person.
The Retreat: The smell of cedar from your soaking tub. The feel of tatami mats on the soles of your feet. The sight of a sun-dappled interior garden. Such sensual pleasures are a constant presence at the 10-room Kayotei ryokan (traditional Japanese inn) in the hot springs town of Yamanaka. The ryokan’s onsen (communal bath) draws water from nearby hot springs, as do the three rooms with their own soaking tubs. Every ingredient of the nightly multicourse dinner, or kaiseki, has a story: The organic rice comes from a local farmer who uses ducks, not chemicals, to control pests and weeds, and the seaweed is harvested along the coast by hand. After dinner, you’ll return to your shoji screen–lined room to find your tatami bed set out for you—with heated sheets on colder nights—waiting to usher you into blissful, uninterrupted sleep.