Naples, Florida

Situated on Florida’s southwest coast, Naples manages to feel both refined and relaxed. Its wide, sugar-sand beaches and calm Gulf waters set the tone for an easygoing escape. The buzzy downtown, anchored by Fifth Avenue South, is lined with open-air restaurants, eclectic shops, and art galleries, its shaded sidewalks staying lively well past sunset. Travelers can also tee off at one of nearly 100 local golf courses or head to protected areas like Clam Pass Park and Delnor-Wiggins Pass State Park, which preserve stretches of coastlines that still feel untouched.

Where to Stay

The Naples Grande Beach Resort bridges Naples’ urban polish and coastal calm, offering the best of both worlds. A mangrove boardwalk leads directly to Clam Pass Beach, while three pools, five bars and restaurants, and a full-service spa make it easy to stay put once you arrive. Many rooms open onto balconies — several with Gulf views — for al fresco hangs.

Scottsdale, Arizona

Set in the Sonoran Desert, Scottsdale's mix of outdoor access and distinctive modern design makes it one of the most versatile winter destinations in the country. Camelback Mountain and the McDowell Sonoran Preserve offer some of Arizona’s best hiking, while Taliesin West, Frank Lloyd Wright’s desert home and studio, anchors the region’s architectural pedigree. In Old Town, midcentury buildings now house galleries, cocktail bars, and design-forward restaurants, including FnB and Olive & Ivy.

Where to Stay

Opened in 1956 and fully restored in recent years, the Hotel Valley Ho is a midcentury landmark in the heart of Scottsdale. Rooms are bright and geometric, with vintage furnishings and pool-facing patios. Additional highlights include ZuZu, the hotel’s restaurant and bar, and two pools — one lively, one serene. Across town, the Mountain Shadows Resort Scottsdale offers a serene counterpoint in Paradise Valley. Its glass-and-stone architecture frames the views of Camelback Mountain, while a compact golf course, tranquil spa, and the Hearth ’61 restaurant create a refined, low-key ambiance.

Honolulu, Hawaii

One-part glimmering metropolis, one-part surf town, Honolulu balances skyline and shoreline in a way that feels uniquely its own. Waikiki Beach remains the city’s centerpiece, its world-famous stretch of sand drawing swimmers, surfers, and sunbathers year-round. Just beyond, trails climb Diamond Head Crater, while Pearl Harbor offers a sobering look at history. The neighborhoods of Kaka‘ako and Chinatown have evolved into creative hubs, filled with galleries, murals, and independent restaurants such as Moku Kitchen and The Pig and the Lady.

Where to Stay

A few blocks off bustling Kalākaua Avenue, the Wayfinder Waikiki offers a design-forward take on the classic Waikiki stay and feels more neighborhood hangout than resort. Its bold interiors — a mix of local art, tropical prints, and warm wood tones — feel distinctly of the place. The on-site drinking and dining offerings (which include a poke bar, coffee shop, and poolside cocktail bar) keep the energy high and the vibes laid-back.

Grand Cayman, Cayman Islands

Grand Cayman has long been a Caribbean standby, but its clarity — in water, pace, and mood — sets it apart. Seven Mile Beach, often ranked among the best in the world for its stunningly clear turquoise waters and soft white sand, is its main draw. Offshore, Stingray City remains a signature experience, while the Cayman Turtle Centre and Queen Elizabeth II Botanic Park highlight the island’s connection to its native landscape. We'd also be remiss not to highlight Grand Cayman's surprisingly sophisticated food scene, shaped by a strong farm-to-table culture. Favorites include The Brasserie, which offers a daily changing menu, and Calypso Grill, a British-Caribbean institution overlooking the harbor.

Where to Stay

Across from Seven Mile Beach, Sunshine Suites Resort offers a central home base for exploring this idyllic island paradise. Spacious all-suite accommodations feature kitchenettes and dining areas, perfect for cozy nights in. Property amenities include manicured gardens, a restaurant, and a pool and sundeck.

St. Pete Beach, Florida

On a barrier island west of St. Petersburg, St. Pete Beach balances Gulf Coast ease with a hint of nostalgia. Its stretch of serene shoreline is flanked by low-slung motels and weathered beach bars reminiscent of a bygone era. When you need a change of pace, Downtown St. Pete offers a cultural counterpoint complete with the acclaimed Dalí Museum, contemporary galleries, and a food scene that spotlights local seafood — don’t miss Wild Child for international fare and craft cocktails or OLIVIA for classic Italian cuisine.

Where to Stay

The Beachcomber sits directly on the sand, with a low-rise layout and tropical courtyards that capture the area’s low-key, laid-back feel. Two pools and shaded patios offer spaces to unwind, while the resort’s iconic Jimmy B’s Beach Bar - recognized as one of the best beach bars in Florida by Southern Living - keeps a steady rhythm with live music from day to night.

Explore more destinations across the Benchmark Resorts & Hotels portfolio, a collection of distinct, independent properties by Pyramid Global Hospitality. Located in diverse destinations across the globe, Benchmark’s resorts and hotels reimagine immersive travel, inspiring guests to create memories born from meaningful exploration, authentic moments, and innovative experiences – no matter the occasion. Benchmark guests can earn complimentary gift cards, on-property perks, and destination experiences through the collection’s signature Mosaic Rewards program.