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Latitudes is the acclaimed restaurant at the Sunset Key Cottages, on Sunset Key, a small private island accessible only by boat. Take the ferry across the Key West Harbor—your scheduled ferry time is your reservation time. The dreamy ride across the gulf waters sets the tone for the rest of the evening. While most restaurants in Key West have flexible dress codes, if any, Latitudes is a place you should break out the nice clothes. If the weather’s nice, ask to eat on the patio, which is decorated with twinkling lights wrapped around the green palms that surround the courtyard, and features tables set with white cloths and candles.

Since 1970, owner and Virginia native Joel Cohen and his family have been offering trendy business, casual, and evening clothing to women of various ages and sizes as well as jewelry, handbags, purses, belts, and other accessories. Popular brands include Angel, Crystal Boutique, Finley, Zelda, Stizzoli, and Joseph Ribkoff. To define your colors and style, staff act as your personal shoppers allowing for a comfortable shopping experience.

It was Christmas Day, and the fastest route from Bakersfield to Morro Bay. The route that didn’t involve freeways. {We like that.} So we headed west on Highway 58, through the otherworldly power stations and desolate cotton fields of Rosedale and then up and up and up til we could gaze out over the cold green hills. The winter-dry grass waved in a bitter wind, snow dusted across distant mountain tops. We danced in place, to keep from freezing. A remote and winding road, this one reminds you that even central California has hidden pockets, little spaces where you might, maybe, just vanish.

Philadelphia locals who love the outdoors are particularly fond of walking, jogging or biking the scenic 8.5-mile riverfront “Loop”. The Loop is what we call the recreational path that runs from near the Art Museum to the west side of the Schuylkill River on Martin Luther King Drive, then crosses the Falls Bridge in East Falls, and continues along Kelly Drive back to Boathouse Row, Lloyd Hall and the Art Museum. (Or it can be done in the reverse.) One of the best things about this route for cycling or jogging is that Martin Luther King Drive is closed to vehicular traffic from 6 am to 5 pm on Saturdays and Sundays from April through October. (A small portion of the road from Eakins Oval to Sweetbriar Drive re-opens to traffic at 12 noon.) Bike rentals are available from Wheel Fun at Lloyd Hall. The view of Boathouse Row above is just one of many scenic views from Martin Luther King, Jr. Drive (formerly known as West River Drive) on the west banks of the Schuylkill.

Zurich West’s answer to Bahnhofstrasse is lined with boutiques of its own, the most popular of which are Einzigart for design-minded goods like Kristian Vedel’s handcrafted birds and Little Black Dress for chic, edgy takes on the style classic. The restaurant Josef has long served as the neighborhood’s unofficial canteen with its imaginative tapas-sized dishes and buzzing bar scene. Photo © Gian Marco Castelberg/The Brander

When you’re ready to call it a day on the slopes, take Park City Mountain Resort’s Quittin’ Time run down to High West, the world’s only ski-in gastro-distillery. Tour the space, then try the 36th Vote Barreled Manhattan, made from a pre-Prohibition cocktail recipe that calls for aging the drink for 90 days in white oak barrels. The food goes down pretty easily, too: A bowl of elk chili will warm you right down to the toes of your ski socks. For lighter fare, the popcorn tossed with bacon, caramel, and cashews is sweet, salty, and a nice counterpoint to a glass of double rye.

Hudson Trail Outfitters is a local chain that caters to outdoor enthusiasts in the Washington, D.C. area. The first store opened in 1971 with the goal of selling the highest-quality specialized gear and apparel and providing top-notch customer service. The strategy worked: The shop became a huge success, and four more have since opened in Maryland, Virginia, and D.C. Part of what makes the company special is its focus on the community. It holds weekly events that include yoga, hiking, biking, paddling, and boot camp meet-ups. This is a must-stop for information on the area’s best trails and natural highlights.

The city’s most famous snowbird, architect Frank Lloyd Wright, spent winters at his home and architecture school in the Sonoran Desert. Taliesin West brings the horizontal lines and organic materials of Prairie School design to the desert landscape in low, skylighted buildings. Behind-the-scenes tours visit the pop-up structures that students have designed as living spaces amid the barrel cactus and paloverde trees.

Right on Key West’s famous Sunset Pier and next to Mallory Square, Ocean Key is at the center of the action, proven by the flocks of tourists who descend on the pier every evening at sundown. Inside the resort, the contemporary rooms are decorated in tropical colors like bright lime and turquoise, and have bathrooms with rainfall showers and whirlpool tubs and private balconies with views of the Gulf of Mexico or buzzy Duval Street. The angular pool is surrounded by cabanas and day beds; grab a ringside seat for the daily fashion show at Liquid, the kicking poolside bar. Prefer a quieter experience? The spa has a full range of treatments and packages that lean heavily on Asian traditions and ingredients, from Balinese massage to a Javanese rice-and-turmeric body scrub.

IndexG B&B was an art gallery before the owners renovated the second floor into a four-bedroom bed and breakfast. Housed on a sleepier stretch of Gladstone Avenue but close to the action of both the West Queen West and Parkdale neighborhoods, this family-run B&B offers affordable rooms and minimal amenities. Art is displayed throughout the hotel, and it is all available for purchase. With much to do in the area, this is a well-located hub from which to discover the best of Toronto.

Telluride’s literary mecca, this beloved store is stacked with more than 10,000 books at any given time. The expertly curated regional books section is a fount of the Wild West’s writing prowess, with illustrative tomes on the town’s lurid backstory (you’ll want to peruse Tomboy Bride: A Woman’s Personal Account of Life in Mining Camps of the West). When your eyelids get heavy, head to the tiny coffee bar—squirreled away at the back of the shop—for a caffeine jolt to bolster an afternoon of reading.

Dining at one of Negril’s excellent cliffside restaurants is highly recommended, and the gorgeous setting of Ivan’s Bar & Restaurant at Catcha Falling Star makes it a very nice option. The longtime favorite has one of the best views along the coast and serves lobster dinners and classic Jamaican cuisine with a bit of a modern twist. Guests are seated under an open-sided thatched roof or out under the stars at private tables on a patio near the cliff’s edge. Another favorite choice for romantic cliffside dining is the restaurant at Rockhouse Hotel. (If you want more cocktails post-dinner, walk down to LTU Pub and mingle with the locals. Casual eateries and cliff bars along West End Road include 3 Dives and Sips & Bites.)

The Iris Inn, a luxury Shenandoah bed and breakfast, is the perfect base to explore Virginia’s Blue Ridge mountains. Located 30 minutes from Charlottesville, the Inn is close to nearly 30 wineries and is within a few minutes drive to the southern entrance of Shenandoah National Park. Owners Dave and Heidi Lanford warmly welcome visitors to their cozy mountainside inn with gourmet breakfasts and a complimentary nightly happy hour. The eco-friendly B&B also offers an electric vehicle charging station.

The 25hours brand is known for its playful take on the hotel experience, and this Zurich establishment follows suit. With an interior concocted by local designer Alfredo Häberli, the space features the usual mix of colorful, offbeat furnishings, slick design, and casual friendliness, as well as the cute touch of Häberli’s personal city tips scrawled on various surfaces.

The rooms and suites are separated into categories of silver, gold, and platinum to reflect the city’s banking-capital status. That’s as corporate as it gets, however, since the interiors are decidedly funky, with bold colors, quirky carpets and artwork, and angular work desks. The hotel also offers a restaurant, living room and business lounge (with iMac workstation and free Wi-Fi), plus an in-house kiosk that stocks everything from necessities (shampoo and toothpaste) to accessories (Freitag bags).

The Southernmost Point buoy, at the corner of Whitehead Street and South Street, marks not only the spot for the southernmost point of the continental United States but also the distance (90 miles) to the next country, Cuba. The buoy, installed by the city in 1983, is visited by thousands of people each day. (Before the buoy, a small sign stood at the spot alongside a line of seashells for purchase.) Taking a photo in front of the buoy is imperative for a first visit to Key West, so bring a tripod, or ask a stranger to snap a few shots. Buskers play music, and street vendors sell food and goofy souvenirs and slash open coconuts to drink.