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In the Napa Valley—and in Yountville, in particular—most hotels err on the side of sophisticated luxury. Which makes the North Block Hotel’s quirky style such a breath of fresh air. With the look of a Mediterranean town’s cobbled street, complete with lemon trees and hand-painted tiles, one of Napa’s few modern boutique hotels also displays quirky pieces like The Big Book of Boobs in its lobby. It’s hard to pass through the lobby without having a friendly concierge hand you a glass of bubbly, and the umbrella-shaded “sidewalk” tables seem like places you’d actually while away the hours over bottles of good wine with good friends. The trendy restaurant channels a midcentury Italian cool that’s more Fellini than Michelangelo, unlike most Napa wineries’ inclinations, and the fact that it doesn’t have a Michelin star is actually a vote in its favor in sometimes stuffy, star-saturated Yountville. Of course, the spa is still as luxuriously pampering as any in wine country, and the understated rooms are as decked out with designer amenities as they ought to be—and you might actually be having enough fun to enjoy them.

Chef Tory McPhail was recently named James Beard’s Best Chef South and his forward-looking take on Creole classics keeps this New Orleans institution, which has launched the careers of the likes of Paul Prudhomme and Emeril Lagasse, current. Still, you can’t go wrong with classics like the turtle soup, gumbo, and bread pudding souffle. On Saturday and Sundays, there’s more pomp than usual, including a jazz trio that makes its way from table to table, but weekday lunches are nearly as iconic and, thanks to 25-cent martinis, a good reason to have a midday cocktail.

Frank Altamura took his time renovating the old Italian grocery store — where he remembers shopping as a child — at the north end of Yountville. His dream was to turn the partly dilapidated building into a casual restaurant with great pizza and Napa Valley wine where locals would love to eat. His dream came to fruition when Ciccio opened its doors in 2013. The menu is simple, straightforward and ever-changing based on what Altamura is bringing in from his Napa ranch, where he also grows Cabernet Sauvignon, Nebbiolo, Sangiovese and Negroamaro for his eponymous wine. Chef Polly Lappetito (former Executive Chef at The Culinary Institute of America) traveled far and wide in search of the perfect pizza crust, but her’s is in a category all its own — prepared in a hand-tiled, wood-burning pizza oven imported from Italy.

Not just a wonderfully large bookstore—although it is that—the University Bookstore is also a café and a fantastic gift shop. The two-level bookstore has a textbook section for students and general fiction and nonfiction for the public, as well as a good selection of art supplies and kids’ crafts and toys downstairs. The large front room is devoted to all things fun: journals and stationery, makeup counters, bags and silver jewelry, candy and novelty items, soaps and housewares. If you’re a Husky fan, they have plenty of team merchandise, too. The Seattle bookstore has frequent author reading events (shown above: a cupcake-loving dragon sketched by illustrator Jackie Morris during a Robin Hobb reading), so check their calendar and see what’s going on while you’re in town.

Located along M Street in the heart of Georgetown’s hustle and bustle is the oldest extant home in DC. Built by a Pennsylvania cabinetmaker/carpenter in 1765 using locally sourced rock, timber, and earth, the Old Stone House still retains its rugged stone appearance even after being threatened with demolition in the 1950’s. It was the urban legend that President Washington and city designer Pierre L’Enfant met here to plan the layout of DC that saved the building. Today, guests can tour the three-story structure to learn about its history and late 18th century colonial living in the DC area.

The Seattle Great Wheel, completed in June of 2012, is located at the Seattle Waterfront. It is a little expensive, and nerve-wracking on the way up, but it’s worth it. The Ferris wheel is one of the biggest in the U.S., and provides a spectacular view of Elliot Bay, Downtown, and much more. In addition, at one point during the ride, it actually goes over the water!

Everyone in these parts eagerly awaits the Florida stone crab season, which runs from October through May. As soon as it starts, they flock to Joe’s Stone Crab, a South Beach institution that’s been cracking the sweet crustaceans for more than 100 years. Tuxedo-clad waiters serve claws ranging from medium to colossal, best eaten with a side of mustard sauce (while wearing a bib). Joe’s tangy Key lime pie is the way to end your meal. While the crab, sold at market price, never comes cheap, the fried chicken is a steal at $6.95.

Why we love it: A pedigreed stay that perfectly marries fin de siècle charm with modern luxury

The Highlights:
- A French Renaissance–style building designed by America’s first female professional architect
- Fireplaces and deep-soaking tubs in some rooms
- An in-house craft brewery that serves pints in a “bar-cade” with pinball machines

The Review:
When The Lafayette opened in 1904, it was immediately hailed as one of the country’s finest hotels. America’s first female professional architect, Louise Blanchard Bethune designed the seven-story, redbrick-and-white-terra-cotta property to blend “the best that science, art, and experience can offer for the traveling public,” which at the time meant telephones and hot water in every room. Renovations in the late 1940s introduced several Art Deco elements that still remain, while a 2012 restoration helped bring the hotel into the modern era.

Today, The Lafayette is part of the Wyndham Hotel Group’s Trademark Hotel Collection and features 13,500 square feet of meeting space. It’s also home to a 15-barrel craft brewery, where guests can enjoy beers and pub fare while playing arcade games; a small-batch coffee roastery with freshly baked pastries; and an outpost of Groom Service Beauty & Dry Bar for blow-outs, professional makeup, manicures, and more. The 57 rooms and suites feature wall murals of vintage photos, designed to complement a palette of plum, brown, and dusty gold. Some have fireplaces, deep-soaking tubs, and full kitchens, too. If you’re looking to indulge, book the Lafayette Suite, which includes a Juliet balcony, double-sided hearth, and dining table suitable for large gatherings.

Located in a former home built more than 100 years ago, this intimate restaurant excels in ambience and Caribbean specialties. Outdoor tables sit next to a pool and pretty tropical gardens, while the dining room boasts an array of European antiques. A son of the restaurant’s original owners, the current chef specializes in such dishes as bouillabaisse, crunchy okra, and cinnamon-and-brown-sugar sweet potato mash. Also on offer is seafood prepared with local spices and coconut milk. Whatever you choose, don’t miss the wine cellar, which once functioned as the home’s cheese room and now features nearly 2,000 bottles by 120 labels.

With killer views of the waves crashing onto Ocean Beach, the Beach Chalet Brewery & Restaurant is one of the best places to grab a bite and watch the sunset in San Francisco. Before its current incarnation, the 1925 Spanish revival building served as a beach changing room, an Army outpost during WWII, and a VFW hall. The disused building was shuttered in 1970, but spared for its landmark WPA murals and mosaics. Come to see the murals, and stay for the food and Ocean Beach views. Upstairs, above the visitor center, the Beach Chalet Restaurant serves fresh fish and steaks. Downstairs, opening out to Golden Gate Park, the sunny and more casual Park Chalet offers burgers or fish and chips, and live music on weekends.

Referred to by locals as Bustani ya Mungu—literally, “the Garden of God"—this national park is a botanist’s delight, bursting with the colorful orchids, lobelias, and lilies that thrive in the fertile volcanic soil. This veritable Serengeti of flowers is also a bird- or butterfly-watcher’s paradise, with many endemic species swooping and fluttering amid the open and fertile grasslands. The plateau is accessible by 4x4 from Mbeya. Follow one of the hiking trails along the impossibly beautiful rolling plains or attempt a hill climb in the shadow of the looming peaks of the Kipengere, Poroto, and Livingstone mountains. The best time to visit is during the blooming season between October and April.

In a city that takes itself so seriously—running the United States is an intense business, after all—the Hotel Madera is a breath of fresh air. Just a couple of leafy blocks from always-lively Dupont Circle, the Kimpton-run boutique hotel looks like a 1960s apartment building on the outside, belying interiors adorned in colorful, batik-inspired fabrics and perks like in-room yoga mats and an evening wine hour. In other words, the Madera is the kind of place where you relax. The laid-back and trendy restaurant takes its design cues from a fairy-tale forest, and pets are as catered to as children and bachelorette groups. It’s hard to beat the Dupont Circle location, too, which puts the White House, the Kennedy Center, and trendy neighborhoods like Logan Circle and U Street all within throwing distance. No, it’s not the fanciest stay in town, but D.C. doesn’t need another fussy hotel to attract visiting dignitaries—and you’ll have more fun at the Madera, anyway.

At Helen’s, it’s all about the pie. Sure, there’s more on the menu, but the wild-Maine-blueberry pie at the restaurant has earned fame far beyond the state’s borders. For starters, it’s an authentic taste of down east Maine. To be truly down east, you should be here, in Washington County, Maine’s wild-blueberry country, with a landscape defined by blueberry barrens studded with glacial erratics. Machias, the county’s biggest town and one of the few with a traffic light, is home to the Wild Blueberry Festival in August—and to Helen’s, which has been dishing out slabs of freshly baked wild-blueberry pie since 1950. One bite, and you’ll understand the love.

Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel plates with no visible seams, the polished surfaces of this 33-foot-tall sculpture reflect infinite variations of the Chicago skyline. The work’s design was chosen from among more than 30 others commissioned by the city, and it was inspired by liquid mercury.

Why we love it: A historic property full of local details that make guests feel at home in Minneapolis

The Highlights:
- Prime location in the trendy North Loop
- Site of one of Minneapolis’s best restaurants, Tullibee
- Local literature, artwork, and spirits in every room

The Review:
A former farm implement warehouse, the Hewing Hotel has a rustic yet refined sensibility. Located in the heart of the North Loop, just a short walk from some of Minneapolis’s best restaurants and shops, the property mixes exposed timber and brick, tall ceilings, and original industrial elements with high-end finishes, creating an environment that’s at once local and luxurious. Available in five different layouts, the 124 rooms, including 14 suites, are individually designed with exposed wood, metal, and brick accents, plus local details like books, artwork, minibars, and Faribault Woolen Mills throws that speak to Minneapolis. Should you be traveling with your pet, simply pay a $75 fee and you’ll find their name written on a chalkboard alongside those of other furry guests, all under the heading “V.I.Pets,” as well as a treat-stocked bowl in your room.

Although Hewing guests are surrounded by one of the city’s most vibrant neighborhoods, they’ll want to save at least one night for dining at the hotel’s renowned restaurant, Tullibee, which serves rustic Nordic cuisine alongside craft cocktails, local beers, and house-made sodas. For something more casual, head to the Rooftop Bar & Lounge for drinks and city views. Also on the roof is a pool and Nordic-inspired sauna, though guests may be more inclined to visit the Hewing Spa, where they can enjoy a range of massages, plus add-on services like wraps, scrubs, and face masks. When you want something more active, head to the 24-hour fitness facility, stocked with treadmills, stationary bikes, and elliptical trainers; the yoga studio, which offers weekly classes through Gem Life Yoga; or the front desk, where you can rent a custom Handsome bicycle to explore the city.