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Straw Hat, on quiet Meads Bay, is an established favorite with over 20 years to its name. Its creative menu of Caribbean cuisine with a twist will have you returning to this beautiful indoor-outdoor beachfront restaurant. It’s the perfect spot for a meal and an afternoon on the sand, or for watching sports. Try the ceviche of red snapper, the bigeye tuna flatbread, or the grilled crayfish with Anguillan rice and peas, among many other picks.

The beloved Dar Ahlam resort has taken its show on the road with Route du Sud, a six-night driving tour to five destinations with three private retreats that showcase the shape-shifting landscapes of isolated southern Morocco, one property at a time. The first stop is the hillside Maison des Arganiers, two and a half hours from Marrakech, in a rocky landscape facing miles of argan groves; next comes La Maison de l’Oasis, nestled in an oasis of palms; and the final private destination is the dramatic La Maison Rouge, which sits at the edge of a red canyon. Along the way you have beach picnics, nomadic campouts, and scenic drives through dramatic desert dunes.

Fly fishing may not be top of mind while walking through San Francisco’s Financial District, but fantasies of casting in crystal clear rivers and commencing the day around a campfire are sure to materialize once you step inside Lost Coast Outfitters. The upscale sporting goods store specializes in top-of-the-line fly fishing gear, but shop owner George Revel has an eye for provisions that tug at the inner outdoorsman in all of us, such as indestructible Yeti coolers, leather-trimmed duffle bags from Filson, and classic Simms flannels in timeless red-and-black check. The grand historic Beaux Arts building only adds to the appeal, as does the 300-plus-bottle whiskey collection hidden behind a wall of waders and waterproof booties. Pro tip: Inquire about joining the exclusive Tin Cup Society to gain access to speakers, casting clinics, expeditions, and curated gear packages.

Among California’s 21 Spanish missions, the late-18th-century national landmark Mission Santa Barbara is considered the “queen of the missions.” Those interested in early California history will also want to stop by the whitewashed, red tile–roofed El Presidio de Santa Bárbara, a late-18th-century Spanish military outpost that was built by local Chumash Indian laborers. The park’s nearby adobe homes have exhibits of historic objects found in the area. The legacy of this period lives on at the Santa Barbara County Courthouse, a masterpiece of Spanish colonial revival architecture built in 1929 and just five minutes on foot from the Presidio.

The owners of Sidework hit on the idea for their cozy little eatery after listening to locals grumble about how hard it was to find a low-key place to have a drink and casual bite during the summer and winter tourist seasons. They already owned the brewpub around the corner, so they turned the adjacent space—which they used for “sidework” like filling water pitches and rolling silverware into napkins—into the spot everyone was craving. Today the narrow, intimate bar serves self-described “American-American comfort food,” which includes small plates like blue claw crab soup, fig flatbreads, and charcuterie boards, and larger dishes such as olive-oil-poached branzino and beef short ribs in red wine reduction. For the perfect start to your night, drop by during the daily happy hour for discounts on select wine, beer, cocktails, and mini filet mignon sliders.

The red-gravel paths that wind among 6,000 plant species, past a babbling stream, and into deeply shaded areas may make you forget you’re in the center of a loud, bustling city. That said, many visitors don’t know that the Botanical Garden includes a small butterfly garden. It’s closed during the week, but you can still peek over a low wall to watch some 50 butterfly species flit about their business. And for one glorious hour, from noon to 1 p.m. on Saturdays, the gate is thrown open and the public is free to walk sunny paths among shoulder-high flowering hedges as colorful, flirtatious butterflies alight on amused visitors’ heads, shoulders, and arms.

The Four Seasons earns its five stars for everything from its location—smack in the middle of Seoul’s most-visited palaces and landmarks—to its detailed amenities, such as customizable mattresses. Rooms overlook Gyeongbokgung Palace, the largest and arguably most beautiful of the royal residences, or Cheonggyecheon stream, each a few minutes’ walk from the hotel. Its seven restaurants and lounges include a two-level sushi and sake bar, a Michelin-starred Cantonese restaurant, and an exotic cocktail bar hidden speakeasy-style in the basement. The massive wellness center combines traditional Korean spa rituals with personalized beauty treatments and a 24-hour gym with panoramic views. An indoor pool and saunas, a virtual golf simulator, and a Lego kids’ lounge provide something for every guest.

Put on your comfortable shoes and head to the many trails of Cayman Brac to see wildlife, as well as scenic and geological sights. There is a path for all skill sets. Listen to the mating calls of the parrots flying above at the National Trust Parrot Reserve Hiking Loop, or descend carefully into Peter’s Cave and move through the various layers to discover a truly breathtaking natural wonder. Most hotels have a brochure of all the hiking trails; this includes images, difficulty, and a brief description of each trail.

A Greek Revival family mansion built at the turn of the 20th century, Hotel Ella owes both its name and its grandeur to its very first lady of the house, Ella Wooten. Known for her impeccable style and grand tastes, Ella was a fixture of Austin high society who hired the stone carver responsible for the Biltmore Estate to craft her house’s columns and verandas and worked with Neiman Marcus’ Stanly Marcus to redecorate the interiors in 1925.

Nowadays, Hotel Ella pays homage to her good taste with fashionably understated decor, a locally sourced restaurant, and an art collection that the original proprietress would have coveted. Works include original Ansel Adams photographs and Wooten family portraits and jewelry. The owners pride themselves on making guests feel just as pampered as Ella might have, with perks like a free town car service—even though the hotel is within walking distance of downtown—and a concierge team for whom no request is too much.

Key West’s most famous literary resident, Ernest Hemingway, lived in this two-story Spanish-colonial villa for nearly a decade and composed several of his best-known works here. His second wife, Pauline, insisted they add a pool to the spacious grounds—the first inground pool in Key West. The cost ballooned to around $20,000, a fortune in the 1930s, and was said to have contributed to the breakup of their marriage. It’s just one of the fascinating stories guides will share on the half-hour tour of the home and gardens (included in the price of admission). And yes, you’re guaranteed to see plenty of six-toed cats, descendants of Hemingway’s original six-toed cat, Snow White.

This little private church is probably the most photographed stop in Oia. Our rented house was right next to it but lower on the steps so we could see lots of people getting lots of photos. Married couples would take their photos next to it, photographers were offering workshops that included this spot. I woke up at 5.30AM to wonder when nobody else was around. Best time of day to walk around this very busy tourist destination.

The cobalt-blue-and-brick-red residence where now-legendary Mexican visual artist Frida Kahlo grew up—and at times lived with husband Diego Rivera—is one of the city’s most consistently packed attractions; buying tickets in advance is strongly recommended. That said, the visit is essentially (and justifiably) mandatory and offers fascinating glimpses into this extraordinary woman’s life and work. In addition to holding some of her paintings, the house also functions as a showcase for her library, astounding wardrobe, and collection of pre-Columbian artifacts; it additionally bears witness to her close association with left-wing politics. What’s more, the museum portrays the artist’s struggles with depression, marital infidelities, disability, and illness. The house’s garden—home to a modest café and mostly bashful felines—makes for a great breather before more strolling in the Coyoacán neighborhood.

Although this popular Prenzlauer Berg café only opened in 2005, it feels as if it has been part of the neighborhood forever. Lines from the 1919 poem by Kurt Schwitters that provided the café’s name adorn the walls alongside a reproduction of an Alphonse Mucha mural, and the interior has a classic art deco look (red leather banquettes, marble-topped tables, and red curtains) that perfectly matches the traditional German menu of breakfasts and lunches. It’s most famous for the former, including muesli and egg and crepe dishes, as well as elegant, bountiful tiered platters that brim with meats, cheeses, and fruits. Come early on weekends to beat the local families to a table, especially on the outdoor patio, which is perfectly positioned for people-watching.

The Castelo de São Jorge, is one of the Alfama neighborhood’s most historically significant monuments. Plan a visit late in the afternoon so that you can explore every nook and cranny and learn about the castle’s abundant history. Stay for golden hour so that you can capture the light as it dances on the castle walls, and later to watch the sunset dip below the horizon.

Its massive size, centrality to daily life in the capital, and easy accessibility (a Metro station opens up right onto the plaza) makes the Zócalo an ideal place for large-scale temporary exhibits. The government hosts occasional exhibits and makes entry free for residents and visitors alike. Past exhibits have included Gregory Colbert’s “Ashes and Snow,” a show of large-format photos of animals and people, and Willy Souza’s “Mexico en tus sentidos” (“Mexico in your senses”), lush, vivid photos of people and places around Mexico. To see if a show is planned during the time you’ll be visiting, check the website of the Secretary of Tourism.