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Downtown Denver’s most playful hotel, The Curtis offers whimsy in spades. Guests are encouraged to unleash their inner child with board games, toys, and old-fashioned candy in the lobby, while each level riffs on a different pop-culture genre, from “Sci Fi” adventure to “Dun Dun Dunnnnn!” horror (fittingly on the 13th floor). Standard rooms are filled with pops of color; unexpected elements in themed rooms include green ectoplasm-inspired floors in the Ghostbusters room and a wall-mounted sailfish in the Jimmy Buffett room (perhaps you’ll finally find that lost shaker of salt). The Corner Office restaurant and martini bar is retro-cool, with plaid upholstery and ‘60s-mod light fixtures, and the menu highlights street and comfort food favorites from all over the globe alongside inventive housemade cocktails and Colorado craft beer. There are also 24-hour business and fitness centers, but nothing about the hotel takes itself too seriously—except, of course, when it comes to showing guests a good time.

Wilensky’s is sort of an institution in the Mile End. Family-owned since its opening in 1932, the place is famous for its extremely cheap snacks, no-nonsense approach, and retro decor. Pressed tin ceiling, Kik Cola clock, ring-up cash register, old-fashioned soda fountain—this place sometimes feels like a time warp or, at the very least, a museum. Perhaps what makes Wilensky’s so special is, incidentally, the Special ($3.90): “All-beef salami with all-beef baloney grilled to mouth-watering perfection on a tasty roll with a hint of mustard.” But don’t try to change anything in it—the owner, Ruth, will not have it. The Special is what it is, and no amount of money will make Ruth change it. Hell, she even wrote a poem about it: When ordering a Special, you should know a thing or two. It is always served with mustard; it is never cut in two. Don’t ask us why; just understand that this is nothing new. This is the way that it’s been done since 1932. Amen to that.

Recalling Saigon’s past, Cuc Gach Quan offers fine Vietnamese fare in a cozy setting that re-creates the home of the owner’s grandmother—a French-colonial house with worn, wood-plank floors; retro furnishings; warm lighting; and a floating staircase to connect the two levels. It’s grown in popularity ever since Brad and Angelina ate here in 2011, but the menu continues to focus on Vietnamese dishes while following the approach summarized in its motto: “Eat green, live healthy.” Expect menu items such as fresh spring rolls with shrimp, crispy sea bass, and fantastic homemade tofu fried with chili and lemongrass.

Located a few blocks from Courthouse Square and Whiskey Row in downtown Prescott, about 100 miles north of Phoenix, the Motor Lodge is ideal for a retro road trip. The 13-room lodge began life around 1910 as summer cabins. After a century of serving as all manner of accommodation, it was purchased in 2008 by Joe Livingston and Brian Spear, who set out to prove it had at least one more life as a modern boutique hotel, complete with comfy beds, tastefully eclectic decor, flat-screen TVs, and free Wi-Fi. One of the few hints that this is no longer an old-fashioned motor court is the bright yellow exterior doors and other splashes of color that suggest a more modern era. Still, there are throwbacks—some delightful (the room porches which are close enough together, and few enough in number, that chats with people who might otherwise remain strangers seem the neighborly thing to do) and some not so much (the tiny bathrooms in most of the rooms that would have passed without comment in earlier decades). Mostly, though, the two hosts seem to be striving for, and achieving, a hospitality that often becomes a guest’s strongest memory.

Why we love it: A classic St. Pete stay with a beachfront location and retro vibe

The Highlights:
- Cabana rooms with private patios by the pool
- The largest heated pool on St. Pete Beach
- A beach bar with frozen cocktails and live music

The Review:
Nicknamed “the Santorini of St. Pete Beach” for its white-and-blue color scheme, the Postcard Inn on the Beach strikes a balance between playful and sophisticated, attracting families and young couples alike. Set right on the beach, the property boasts a large heated pool, fitness center, and beachwear boutique, plus extras like a fire pit, beach cabanas, bicycles, and fun games like ping-pong and beach volleyball. The 196 bright, breezy guestrooms feature local artwork that pays homage to St. Pete’s surfers and sun worshippers of yesteryear, plus lime, teal, and sea foam accents for a funky vibe. Those looking for a little something extra should book one of the cabana options, which come with private patios right by the pool.

In the morning, guests can fuel up with locally roasted Kahwa coffee and freshly baked donuts at on-site cafe, P.S. Grind. Later in the day, head to the Beach Bar & Snack Shack for sandwiches, frozen cocktails, and live music, or Stamps Lobby Bar and Restaurant for blackened mahi tacos, barbecue dry-rubbed burgers, and other classic American dishes.

If Southern California had ever been annexed by La Serenissima Repubblica di Venezia, the Fairmont Grand Del Mar would be the governor’s palace—all marble columns, gold-leafed staircases, and hand-stenciled ceilings. Even the 400-acre grounds, with their classical fountains, garden rotundas, and neatly arranged cypresses, are true to the retro Italianate vibe. The luxuries, however, are modern—namely, the 18-hole Tom Fazio–designed golf course and the critically acclaimed restaurant Addison. There, Relais & Châteaux grand chef William Bradley lures locals and travelers with his contemporary French cuisine, a seasonal tasting menu, and a wine list of more than 3,500 selections. (There are a few other drinking and dining options, too, including a casual all-day option, a clubby grill room, and a nightclub for live music and weekend DJs.)

The hotel’s 249 guest rooms and suites feature European-style soaking tubs, and views over the gardens, golf club, or Los Peñasquitos Canyon Preserve. Two opulent villas—ranging in size from 4,500 to 5,000 square feet—are tailor-made for families and larger groups. The spa here is also one of San Diego’s best: Book a signature Renaissance spa therapy, and follow the scent of eucalyptus-infused mist all the way down a grand staircase to your Moor mud wrap.

Sure, the Hotel Vintage is classic (it was built in 1894 as the Hotel Imperial, one of Portland’s most iconic grande dames, and is listed on the National Register of Historic Places), but its name references another kind of vintage: the many renowned wines of the surrounding Willamette Valley. When the hotel reopened in 2015 after an extensive renovation, it announced partnerships with 117 local wineries (one for each guestroom), each of which sends a representative at least once a quarter to pour at the guest-only wine hour held every evening. Rooms feature original artwork made from recycled corks, and the trendy lobby bar (named for Bacchus, the god of wine) and local landmark of a restaurant offer an impressive list of some of the best local and Italian wines.

Even those who don’t share the hotel’s passion for vino will find plenty to love, from the famously superlative Kimpton service to the private outdoor hot tubs and custom Public bicycles available to borrow. Also on-site is a game room—an extension of the lobby bar where guests and in-the-know locals mingle over retro video game consoles (Atari, anyone?), shuffleboard, and pool. We’ll raise a glass to that.

Yes, New Mexico actually has an official “state question"--since 1996, referring to the ubiquitous chile sauce, it’s “red or green?” Fortunately you don’t have to choose just one; the local way to say ‘can I have both’ is just one word: “Christmas.” If you’re driving through New Mexico on the way to Arizona and points beyond, the only town of any size on I-40 between Albuquerque and Flagstaff is Gallup. For road-trip food here, get away from the Interstate and its humdrum chain restaurants. Seek out Jerry’s--a block off old Route 66. You can’t miss the retro neon sign, and there’s often a line out the door for its New Mexico-style fare. Gallup is surrounded by Navajo, Hopi, and Zuni lands--you might well be one of the few non-Native-Americans eating here at breakfast or lunch. The restaurant allows local vendors to come in and show their wares--usually jewelry and bracelets--while you eat. (You can request a ‘do not disturb’ sign for your booth if you want.) “Hole in the wall” gets overused, but Jerry’s definitely fits that description. Nothing pretentious here--but the flavor of the chile sauce is as good as you’ll find in Albuquerque or Santa Fe. A recommendation: the flat cheese-and-onion-enchiladas, topped “Christmas” style with a fried egg on top. And don’t forget to sop up the sauce with the sopaipillas, saving some of the frybread to top with honey as a dessert afterwards...

The Grand Central Oyster Bar celebrates its 100th anniversary this year as a New York institution. Located in the lower concourse of Grand Central, it serves over 25 varieties of oysters daily. There is a huge menu of American seafood—chowder, fried clams, lobster rolls, clams casino—whatever you are looking for, they will have it. The Oyster Bar is also famous for its architecture—the beautiful arched tile ceilings are the hallmark of famed Spanish architect Rafael Guastavino, who left his unique stamp across NYC. Take your pick from three different seating areas: a series of old-fashioned, U-shaped counters which seem to be popular with tourists and locals; the oyster bar, which would be perfect for singles or those dining in pairs; and the saloon-type restaurant in the back, popular with the business crowd. Wherever you are sitting, it will be bustling with activity. While there are several other oyster bars in the city, the Grand Central Oyster Bar offers a piece of New York history. It’s like stepping back in time, a retro celebration of old Americana that generations of locals, tourists and travelers have visited over the years. My suggestion is to stop in for fresh oysters and cold beer at the bar.

West Randolph Street in Chicago’s West Loop has become a new home to the city’s culinary talents. Stephanie Izard first drew crowds cooking dishes like roasted pig face at Girl & the Goat (the restaurant pictured above). She then opened Little Goat, a retro diner, across the street. Graham Elliot Bowles keeps it simple at his casual g.e.b, where each dish has no more than three ingredients. On a more elegant note, the prix-fixe menu at Grace, from chef Curtis Duffy, features dishes such as kampachi with coconut, lime, basil, golden trout roe, and pomelo presented in a cylinder of frozen ginger water.

With its fourth U.S. location, the Hoxton brings its signature coolness to the old Los Angeles Railway Building in the center of downtown. The 1922 structure is now home to 174 hotel rooms, three bars and restaurants, and The Apartment—the Hoxton’s signature meeting and event space, complete with stylish conference rooms and a communal kitchen filled with tasty snacks. The F&B outlets come courtesy of the team behind New York’s popular Sunday in Brooklyn, and range from Sibling Rivalry (an all-day lobby spot with seasonal comfort food and its own soft-serve bar) and Pilot (a Mediterranean-inspired rooftop bar and restaurant by the pool) to an as-yet-unnamed bar set to open in early 2020.

Why we love it: A reimagined motel with quirky design, mineral pools, and a spa straight out of a Wes Anderson movie

The Highlights:
- Three different mineral pools for soaking in the sun
- A laidback spa with a twist on Calistoga’s classic mud baths
- Fun amenities like bikes, lawn games, and Polaroid cameras

The Review:
Inspired by classic roadside motels, Calistoga Motor Lodge sits at the end of the Silverado Trail, offering guests a casual, quirky stay in Napa’s northernmost town. The boutique property features a design by New York-based firm AvroKo, with lots of midcentury-modern furniture, bright pops of color, and retro details to transport visitors back in time. Simple yet cozy, rooms feature bold carpets, vintage-inspired fabrics, and cheeky art (think needlepoint signs reading “No selfies in the bathroom” and fabric animal heads mounted on the walls), plus tiled bathrooms with rainfall showers and signature bath products from on-site MoonAcre Spa. In addition to custom-designed hoodie bathrobes and freshly ground pour-over coffee, guests can look forward to unconventional extras like hula hoops, Mad Lib books, and Etch A Sketches for passing time between activities. If you bring along your pet, the hotel will even provide a dog bed, water and food bowls, and treats to make your four-legged friend feel at home.

Committed to local culture, Motor Lodge often hosts community events like group hikes, outdoor movie nights, and festivals. On Maker Mondays, local artisans even pop up at the hotel to host lessons in print making and more. When it comes time to relax, guests can repair to the three on-site mineral pools, all fed by natural geothermal hot springs and surrounded by loungers and cabana beds, or the whimsical spa, which offers everything from massages and body scrubs to less-traditional mud baths and salt soaks in clawfoot tubs. Afterward, soak up the sun in the spa garden, play a round of cornhole on the lawn, gather around the firepit, or grab a complimentary bike and make the short ride into town. Just be sure to borrow a Polaroid camera from the lobby so you can document your adventures at the surrounding wineries, boutiques, and galleries.

Why we love it: A hipster hotspot that’s as stylish as it is affordable

Highlights:
- A range of room types for all travelers
- Local hangouts like the on-site diner and pool bar
- A prime location in one of Austin’s coolest neighborhoods

The Review:
While locals are committed to keeping Austin weird, there’s nothing strange about the new East Austin Hotel, a soon-to-be hipster haunt where millennial pink accents and midcentury chic mix with details that embody the city’s independent spirit. Here, guests find a variety of accommodations to suit all types of travelers, from cabin rooms with shared bathrooms to poolside suites with private balconies, but all feature Scandi-inspired furnishings and quirky touches like turtle-shaped ottomans, Moroccan pillows, and retro Victrola radios.

Vintage pendants hang over the bar at on-site restaurant Sixth & Waller, a self-described “global diner” that serves international comfort food like family-style latkes, chicken-fried steak, and mango cream pie. Equally stylish is The Upside, a rooftop bar with cocktails inspired by the Caribbean and Central and South America, and Pool Bar, which welcomes both guests and locals with frozen drinks and Instagram-friendly dishes like gochujang queso and jackfruit bánh mi. The hotel also boasts a stylish gift shop with local gifts like handcrafted ceramics and leather goods, but if you’d rather venture out, stop by the concierge desk and grab a curated map that highlights neighborhood hotspots with live music, authentic food, and more.

Why we love it: A roadside motel reborn as a stylish wine-country hideaway

The Highlights:
- Fun revived-retro style
- Wine country views for days
- Flavor-packed seasonal menus

The Review:
Mid-century roots meet rustic chic at this boutique property set on five acres overlooking the winelands of North Santa Barbara County. Originally built in the 1950s as a motel—it’s conveniently located just off the 101 freeway—the Skyview emerged from a multi-million-dollar renovation with a style that pays homage to its history, but also includes all the needed modern conveniences. Ranging from Cozy and Classic to Deluxe and Junior Suite options, the 33 rooms offer comfort in the form of mid-century-inspired furnishings, warm hardwood flooring and accents, high-speed Wi-Fi, leather club chairs, down duvets, and locally made bath products. Higher categories feature etxras like fireplaces, private patios, outdoor showers, or firepits.

The restored 1950s-era pool is now heated, ringed with striped loungers, and served by attendants (a menu of snacks and drinks is available), while the stylish lobby is the place for complimentary breakfast backed by wine-country views. The lively Norman restaurant culls produce—and wine—from the surrounding region for its fresh, flavorful menus; brunch on the terrace is particularly popular. Unlike in the past, when the motel’s guests were probably just looking for a clean roadside stop, Skylark is now a destination of its own—a hub for exploring wineries, borrowing a bike to visit the galleries and restaurants of historic Los Alamos, or just sipping a drink around the outdoor firepits.

The first true boutique hotel on L.A.’s east side, the Hotel Covell fits into its trendy Los Feliz neighborhood so well that it feels like it should have been there for years. Created by a veteran of the Los Angeles bar and restaurant scene, the nine-room hotel takes its inspiration from a fictional character’s life: George Covell, an imaginary writer, started out in Oklahoma in the 1930s and ’40s before dividing his time between New York and Paris, where his daughter Isabel grew up. Each distinctively (and painstakingly) decorated suite is based on a place George or Isabel lived, from a rustic-chic Oklahoma house to a 1970s Parisian apartment.