Capri Town to Belvedere Tragara, Capri, Italy
The Stroll: This one-mile foray begins in bustling Piazza Umberto I and continues along Via Vittorio Emanuele and Via Camerelle to Via Tragara (follow the hand-painted signs). Stunning vistas of the Southern Coast, dotted with umbrella pines, culminate in a sweeping view of the Faraglioni, three massive rocks rising from the cobalt sea. It’s no wonder Caesar Augustus chose to build Europe’s first villa here in 29 B.C. If you’re feeling energetic, follow the signs to the Arco Naturale (Natural Arch), an additional 30 minutes’ walk up a series of steps.
When to Go: Spring and fall offer mild temperatures and fewer crowds (although you’ll always find crowds).
Cliff Walk, Newport, RI
The Stroll: Breezy and salt-kissed, this 3.5-mile circuit starts at Memorial Boulevard, where rugged cliffs meet Easton’s Beach, and ends at Bailey’s Beach. Anyone can manage the first third, which is paved and relatively flat; it takes you past Gilded Age mansions to the 70-room Italian Renaissance–style palazzo The Breakers. Only the sure-footed should venture farther, where it’s necessary to hike over boulders alongside 70-foot drop-offs to the Atlantic.
When to Go: May or September, when the weather is warm, but the seasonal crowds haven’t arrived or have already dispersed.
The Hong Kong Trail, Victoria Peak, Hong Kong
The Stroll: This vertiginous 60-minute loop around the summit of 1,811-foot Victoria Peak delivers a bird’s-eye view of one of Asia’s most striking skylines. You’ll see architectural masterpieces by the likes of I. M. Pei, Norman Foster, and César Pelli, lapped by a teal-hued harbor. After a steep ascent via a legendary funicular tram (first opened in 1888), walkers venture through pine and bamboo groves to discover a city vista full of colonial and modern gems.
When to Go: The mildest, driest months are mid-September to late February; visit during the Mid-Autumn Festival (late September/early October), when street vendors sell tasty moon cakes on almost every corner and the river fills with floating paper lanterns.
Paseo de la Princesa, Old San Juan, Puerto Rico
The Stroll: Best done in mid-morning or late afternoon, this sultry seaside promenade hugs the massive 17th-century walls along the southern end of Old San Juan. It begins on a leafy, circa-1853 esplanade lined with sculpture and vendors selling piragua (shaved ice drenched in sweet syrup) and leads to the bronze Raíces Fountain. If you turn right, past the San Juan Gate, you’ll come face to face with the Bay and the massive San Felipe del Morro fortress.
When to Go: With its year-round temperatures of 83–85 degrees, anytime is great.
The Seawall, Vancouver, British Columbia
The Stroll: This 13.7-mile pathway is the perfect place to appreciate the city’s natural beauty and cultural gems. It winds along the shore from Coal Harbor through the 1,000-acre Stanley Park to False Creek and Kitsilano Beach. The best part? The tranquil, 5.5-mile Stanley Park lap with groves of cedars, hemlocks, and fire on one side and Vancouver’s spectacular mountain-ringed downtown on the other.
When to Go: The climate is mild almost year-round, but May through September is the best time to enjoy the outdoors.
Montreux to Chateau de Chillon, Switzerland
The Stroll: Follow in the footsteps of romantic scribe Lord Byron—who after a visit here penned his poem “The Prisoner of Chillon.” You’ll amble along the shores of Lake Geneva for approximately 2.5 miles, starting in the charming Montreux village and ending at the 800-year-old Chillon fortress. The path, lined with a kaleidoscope of flowers, has heavenly views of the Alps, while the turreted castle makes its own wine, Clos de Chillon.
When to Go: May and September are particularly lovely.
Across the Golden Gate Bridge, San Francisco
The Stroll: Forget your fear of heights and enjoy one of the world’s best thrill walks: a 3.4-mile round-trip jaunt along the east sidewalk (accessed via the newly remodeled visitor plaza). Conditions above the bay can be breezy, foggy, or brilliantly blue, so make sure to check the weather beforehand.
When to Go: March through May and September through November are your best bets for warm temperatures and clear skies.
Old Town Walls, Dubrovnik, Croatia
The Stroll: The medieval walls date back to the 14th and 15th centuries and encircle Dubrovnik’s golden-beige Old Town (nicknamed the Pearl of the Adriatic). Despite being only 1.3 miles, the circuit can take an hour or more to walk due to a number of steps and views so magnificent you’ll want to snap a picture every 100 feet. Also, be sure to stroll the Old Town’s Stradun, a promenade lined with stylish boutiques, ice cream shops, and art galleries.
When to Go: Summers here can be scorchers, so aim for April through May or September through October.
Tidal Basin, Washington, D.C.
The Stroll: Our nation’s capital has countless monuments, but few have as serene a setting as those dedicated to presidents Thomas Jefferson and Franklin D. Roosevelt. That’s because they flank the Tidal Basin, ringed by a pathway planted with 1,800 cherry trees (a gift from Japan in 1912). Enter the 1.5-mile loop from the National Mall and walk to your left toward the gleaming white Jefferson Memorial, then head east to the FDR monument.
When to Go: Skip the summer, when D.C.’s humidity soars; early April is best—the cherry trees burst with pale pink blossoms.
Bondi to Bronte, Sydney, Australia
The Stroll: Beach-hopping takes a seriously scenic turn on this 1.5-mile walk between two of Sydney’s loveliest strands. Along the way you’ll pass dramatic sandstone cliffs, Tamarama Beach (nicknamed Glamarama for its beautiful sun-worshippers), and the Bondi Icebergs’ impressive oceanfront pool. If the fresh air and views aren’t reward enough, a string of glitzy cafés along Bronte Road serve up tasty down-under dishes.
When to Go: Aussie summer—January through March—when the weather is just right and locals flock to the beach.
Wales Coast Path, Wales
At approximately 870 miles, the Wales Coast Path traces the country’s complete coastline. But you don’t have to endure the entire trek to glimpse its highlights: the misty mountains of Snowdonia, the Dee Estuary’s cockle- strewn beaches, or Breezy Cardigan Bay.
California Coastal Trail, Bay Area, California
The Devil’s Slide, a new, 1.3-mile expansion of the California Coastal Trail, ends at dramatic Pacifica State Beach, where wet-suit-clad surfers scout the waves and wildlife spotters observe migrating peregrine falcons, gray whales, and common murres nesting offshore.
Waitukubuli National Park, Dominica
The 115-mile Waitukubuli National Trail—the Caribbean’s first long-distance path—puts the island’s exotic terrain on full display: you’ll pass banana plantations, waterfalls, and surreal Boiling Lake (which really bubbles) before emerging onto the coast with views of Guadeloupe.
Rota Vicentina, Portugal
The best way to explore Portugal’s wild, windswept southwest? Rota Vicentina’s 75-mile Fisherman’s Trail, which hugs the Alentejo shoreline and its undulating dunes, prime nesting grounds for white storks and the rare blue magpie.
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