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On a quiet residential street one block from the popular vintage shops, bars, and restaurants of Milwaukee Avenue, the Wicker Park Inn is one of the best values in Chicago, attracting an eclectic clientele of older couples, families who book the whole place for weddings and other special occasions, and young travelers eager to live like a local amid the vibrant culture of the Wicker Park and Bucktown neighborhoods.

The Carrington’s long and rich history spans nearly 125 years since her opening by Sydney hotelier Harry Rowell. Originally named The Great Western, this Grand Old Lady soon became a popular retreat for international guests, Sydney’s elite, and adventurers eager to explore the Blue Mountains’ natural wonders. The hotel is steeped in history, tales of adventures and royalty, and perhaps even a ghost tale or two. The walls are covered with vintage photographs and the place looks like it was sealed in a time capsule (and yet still boasts modern amenities like wifi). The hotel bar is vintage, perfect for a glass of wine or local pint after a long day of adventures in the Blues. There are function rooms, a pool table, an elegant dining room (plus a more casual dining establishment, which used to be the town bank, on the property, as well as a stand-alone pub), as well as a 100-year old regulation snooker table. An onsite bottle shop is available, offering a wide variety of gourmet foods and excellent beers and wines, and a brewpub is even in the works.

One of my favorite places in the whole world—Vieques! I’m actually a little apprehensive to share, because I’d love to keep it the semi-secret it is. If you time it well, you can have this beach all to yourself.

Hyde Park is happening. Catering to the University of Chicago crowd and its visiting dignitaries, the five-year-old Sophy takes inspiration from hometown literary and musical heroes, whose artworks ornament the walls in the popular and always convivial Mesler restaurant. Taking the title of the first boutique hotel on Chicago’s South Side when it opened in 2018, the property occupies a prime spot on 53rd Street—a vibrant commercial hub lined with shops and restaurants owned and frequented by a diverse population that range from academics to local politicians to the city’s cultural influencers. Former UofC professor Barack Obama’s home (and his under-construction presidential library) are nearby.

A recent makeover of the Four Seasons Hotel Chicago from Houston-based Rottet Studio did away with the dark and clubby vibe common in older Chicago hotels in favor of a brighter natural palette. Today, the lobby is open and bedecked in oversize floral arrangements; the open-plan lounge there, with its modern glass chandelier, has become a high-end local watering hole known as the Social Bar. The new Adorn restaurant is now a big-night-out dining destination courtesy of chef Richie Farina’s creations that range from a perfectly prepared filet mignon to caviar and eggs. Upstairs, the 345 guest rooms—more than half are suites—feature understated grays and pale greens and come with deep soaking tubs and (if you ask) unimpeded views of Lake Michigan.

Set high above the St. Lawrence on Cap Diamant, overlooking Old Québec, this imposing yet inviting landmark is as much a lodging as it is a tourist attraction, borne out of its reputation as the most photographed hotel in the world. Opened in 1893 by the Canadian Pacific Railway to drum up luxury riders for its trains, the castle-like Fairmont Le Château Frontenac feels every bit as grand today as it must have when Roosevelt and Churchill secretly hatched plans for the invasion of Normandy here in 1943—and it continues to be the hotel of choice for A-list celebrities and other notables. A $75 million renovation in 2014 updated the 611 rooms with a more contemporary feel, draping spaces in chic furnishings and soothing shades of gray and cream, plus butter-yellow or soft turquoise accents. The spa features seven treatment rooms adjacent to an indoor pool, whirlpool, steam rooms, and a gym, but the hotel has become a destination for its food: Champlain restaurant is helmed by acclaimed young chef Stéphane Modat and offers a modern take on Québécois cuisine alongside magnificent views, while 1608 Wine & Cheese Bar highlights local wines, cheeses, and charcuteries.

One of the most luxurious Western guest ranches, opened in 2005, Paws Up Montana, in Greenough, sprawls over 37,000 acres of classic Montana landscape: elk-filled meadows, rocky peaks, and ponderosa pines in the Blackfoot Valley, with the river of the same name running through it all. The most sought-after accommodations are the “glamping” tents on the banks of the Blackfoot or along Elk Creek that are available May through October and organized into five separate camps, taking just six guests each. The camps combine a Western lifestyle with an African safari formula: canvas suites with private baths, a communal dining pavilion with fireplace and fire pit, private camp chef, and butlers to help organize guest activities. Families and friends who prefer four walls between themselves and nature stay in enormous wood-and-stone villas with heated hardwood floors, fireplaces, leather furniture, huge flat-screen TVs, and panoramic windows; some of these homes come with outdoor hot tubs and tented bedrooms for kids.

All guests have the opportunity to hike, rappel, canoe, play paintball, take cooking classes, and more, but the main action is on-site fly-fishing and horseback riding for all levels on 100 miles of private trails or in a 23,000-square-foot equestrian arena; adults and kids 12 and up can help move small herds of Black Angus cattle on sample stock drives. If parents want private adventure time, kid wranglers entertain young’uns. In the evening, communal entertainment takes place in a renovated barn that serves as stock sales venue, dance floor, and movie theater. Despite the busy activity menu and flow of golf carts transporting guests to and fro, the ranch is large enough, and accommodation so widely spaced that guests can survey the landscape and not see anyone.

Running along the side of Diocletian’s Palace is the Riva, a seafront promenade lined with tall palm trees, bustling cafés, and shaded benches. Stretching from the bronze map of Split to the popular Marmontova shopping strip, it’s one of the busier places in town. Join the fashion-conscious locals gossiping over coffee at sunny cafés, or simply hang out here while you wait for your ferry to the islands.

In the heart of SoHo, the colorful Crosby Street Hotel is a boutique from the Firmdale Hotels group out of London. In 2009, owner and design director Kit Kemp opened this fresh, whimsical property, full of art, bold patterns, and a feminine touch that is frequently missing from the more common masculine-themed hotels of New York. Rooms feature floor-to-ceiling warehouse-style windows, with gorgeous views over SoHo and lower Manhattan. The ground-floor bar is a popular gathering place for New Yorkers, but many common spaces at this hotel are reserved just for guests. The Sculpture Garden and vibrant Drawing Room with deep, plush couches provide space to relax after a day of shopping in SoHo’s boutiques. There is also a 99-seat cinema where films are screened weekly.

An anchor in CityCentre (the 37-acre, mixed-use development unveiled in west Houston in 2009), Hotel Sorella has an intimate, boutique feel with graphic interior touches and contemporary furnishings. Guest rooms have floor-to-ceiling windows, walk-in showers, and custom beds with Egyptian cotton linens and non-allergenic goose down and foam pillows. Amid 22 upscale shops (Lululemon, Kendra Scott, Anthropologie, Free People, Paper Source, and H&M) and an eight-screen Studio Movie Grill, the hotel’s back door is an outdoor plaza with green space where kids can run around. Musicians play Wednesday through Saturday. The open-air, European-style development caters to pedestrians and alfresco dining.

Marché d’Aligre is a very special place: Commerces de bouche (mouth businesses!) line up to sell their goods, an orchestra of voices calls out daily specials, and cheesemongers offer free samples. The market’s selection changes with the seasons. In summer, apricots from the Roussillon, figs from Toulouse, and bouquets of herbs from Provence spill from cases and perfume the air. As fall arrives, the butcher will display fresh game from the hunt, and there’s usually at least one stand where someone is shucking fresh oysters. After your visit here, your appetite will surely be piqued; happily the neighborhood is rich in restaurants that base their menus on what’s fresh at the market.

Imagine sitting in your own private jacuzzi sipping Greek wine, while the shops, restaurants, and homes in the village of Oia are bustling with people and lit with their warm glows. It is from the balcony of the Endless Blue Suite at Aspaki Hotel that you can experience this magic. While there are an abundance of accommodations at your fingertips in the stunningly beautiful, white-washed village, the traditional Aspaki Hotel is unique and truly luxury with a personal and friendly touch. Set on one of the most-photographed private pathways in Oia, the Endless Blue Suite is gorgeous with its peach and light blue colored exterior, and can be seen throughout the town and spotted from the water below. The suite has a loft-style bedroom, spacious living area and kitchen with windows throughout, but it’s the outdoor balcony with jacuzzi that sets it apart from the rest. With an uninterrupted panoramic view of the Caldera and village, it feels as if you’re hanging on the cliff’s edge overlooking the Aegean Sea. It doesn’t seem quite real and is like your own Greek island home that you don’t want to leave. I highly recommend the Endless Blue Suite for a couple on their honeymoon or celebrating a special occasion, and Aspaki Hotel also offers other suites perfect for any stay.

If you’d like the space and privacy of a vacation apartment but still want the service and amenities of a hotel, the Cottages & Lofts at the Nantucket Boat Basin are ideal. You’ll be whisked away from the Hy-Line ferry and taken to the wharves of Nantucket’s harbor, about as close you can get to the water without staying on a boat. Cottages and loft rooms range from studio-size to three bedrooms, all with full kitchens and private patios. A complimentary shuttle bus can take you to the beach, and bicycles can take you wherever you can’t walk from the cottages. There’s no restaurant on-site, but plenty of options are at the marina, and guests get a discount at the White Elephant’s Brant Point Grill. Children and pets are VIP guests as well: Kids get fishing and beach gear to use during their Nantucket stay, and a pet concierge will assist with stays at the “Woof Cottages.”

The California Academy of Sciences is an unfortunately stuffy name for an institution that is anything but staid. The country’s largest natural-history museum includes an aquarium, a planetarium, an enormous rain-forest exhibit under a 27-meter-tall (90-foot-tall) dome, and a living roof that looks like a science-fiction fantasy. A visit here can feel like a trip to an amusement park, with a series of attractions to check out, but all of them are educational. The building itself is part of the appeal of the Academy. (Like the nearby de Young, the old home of the California Academy of Sciences was damaged in the 1989 Loma Prieta earthquake, and starchitect Renzo Piano designed its very environmentally friendly replacement.) It would be easy to spend an entire day or more seeing all of the Academy’s exhibits, so be prepared to pick and choose among them.

Bright and early, just before the sun comes up over Mount Bromo, Mount Semeru and Mount Batok, with ample rolling fog and an epic eruption for good measure. We climbed Mount Penanjakan in our Toyota 4x4 pre-dawn in the headlights of some 1,200 other vehicles. Once at the viewpoint my travel partner and I decided against the same shooting vantage as everyone else - all 3,000 tourists, gah - and climbed down the hill for a better look (and a few square feet to dig in our tripods). As soon as the sun started to shine and illuminate the volcanoes in the distance, all the nuisance and discomfort of the day, all the pain and suffering associated with actually making the trip to Bromo, it vanished. We spent the next hour shooting one of the most incredible sunrises I have ever witnessed. Getting here is a bit of a package-tour nightmare, but so very much worth it in the end.