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Rugged Monhegan, aka the Artists’ Island, lies about a dozen miles out to sea, and is reachable only by passenger ferries. About 60 hardy souls live here year-round, most making a living from the sea. If you get a sense of déjà vu when visiting Monhegan, it’s likely because so many of the island’s icons and vistas have been painted by American masters, including Robert Henri, Rockwell Kent, Jamie Wyeth, George Bellows, Edward Hopper, James Fitzgerald, Andrew Wyeth, Alice Kent Stoddard, Reuben Tam, and William Kienbusch. Artists and art lovers come in summer; bird-watchers flock here in spring and fall. Hiking trails access remote rocky beaches and craggy headlands. Go for the experience, the art, and the hiking, and don’t miss the museum at the lighthouse.

The 34,400-square-foot Squamish Lil’wat Cultural Centre engages visitors on many levels. Socially, it is the first joint cultural project between two separate native nations in North America. The center is also a stunning architectural addition to the community. The design of the concrete, cedar, and fir structure melds the longhouse of the coastal Squamish people with the traditional Lil’wat pit house. Permanent displays of carvings, dugouts, and implements used by the coastal fishermen and hunters are supplemented by temporary exhibitions, including a presentation about Canada’s infamous residential schools. The SLCC also anchors one of Whistler’s most exciting new projects, the Cultural Connector—a path that links six local arts institutions—which is another indication of Whistler’s rising status as a fine arts destination.

Anyone visiting Philadelphia who plans to include the Museum of Art and/or the Fairmount Water Works in their itinerary should consider taking a little extra time to stroll along nearby Boathouse Row. The adventurous who have a bit more time can consider renting bikes and riding the recreational path that runs alongside the banks of the Schuylkill River. Many of the historic boathouses date back to 1860, and the last house on the row at #15, Sedgeley Club, is Philadelphia’s only operating lighthouse, built in 1887. The Schuylkill River and rowing are inextricably linked and the first recorded regatta on the Schuylkill took place in 1835. There is a regatta scheduled nearly every weekend from March through November, and to view the races you’ll need to venture a little further north on Kelly Drive, past the Girard and Columbia Bridges. For anyone who’d like to view or photograph the iconic illuminated boathouses after dark, the closest viewpoints would be either of the elevated gazebos behind the Art Museum, or the riverfront gazebo adjacent to the Water Works complex.

Art isn’t the first thing that comes to mind when you think of Vegas unless you’re familiar with the term kitsch. However, Sin City has always looked to please almost every palate and many impressive art exhibitions and theatre are proving to be a worthy alternative to the neon lights of the slots. You may head to old Vegas for a cheap dinner and a show but have you ever thought of dinner and a Picasso? At Picasso in the Bellagio Hotel & Casino, you can dine beneath the original paintings by Picasso himself. It’ll certainly cost you at Julian Serrano’s restaurant and you may even feel as though you end up paying for one of the masterpieces upon the wall but the food and service are memorable. Try to get a table near the windows or outside on the patio for a view of the fountains. Can’t afford an entire meal but love Picasso? Head to the bar for a drink.

While traveling through Italy, my art history professor booked us students into religious colleges and convents. Wether it was to save money or because she thought osmosis would occur and our knowledge of Venetian Religious Art would be enhanced, I am not sure. However, as a non-religious person I really didn’t mind staying in a space dedicated to Christianity. The rooms were clean and the breakfast conversation was as interesting as the breakfast itself. But there is Wi-Fi, serene areas to write, relax and take in the sounds of the connecting church and the location is ideal for any traveler looking to explore a part of Venice that many tourists don’t see. The view from your room won’t disappoint either, and unlike hostels, for some reason I just felt like my stuff was safer with the prying eyes of Mother Mary, the crucifix adorned in every room and paintings of Don Orione looking over you.

Among the neighborhood’s art-minded hotels, the Gladstone is the most interactive, with shows, classes, and ongoing events. The 37 rooms, all designed by local artists, have breathed new life into the 128-year-old icon, which filmmaker Christina Zeidler took over in 2003 and revitalized in 2005. The Victorian landmark, named for its avenue (in turn named after four-time Canadian Prime Minister William Gladstone), has been a gathering spot for over a century. And it was home to legendary Toronto characters like cowboy Hank Young, who became a fixture at the hotel as a country singer in 1961 and manned the hand-operated elevator from 2005 to 2009, and Peter Styles, former host of Karaoke Night, with applause sign in hand. The legend of Hank lives on in a framed photo in the stairwell en route to the second floor.

The Gladstone continues to push the boundaries of community and culture with creative events like its educational workshop series, Get School’d, and its annual alternative design event, Come Up to My Room (CUTMR), which runs alongside the city’s Interior Design Show. Begin your stay in this architectural gem with a drink at the Café or Melody Bar (that is, if you’re not first thrust into Fameless Karaoke Night).

The central hub of downtown Amsterdam is Dam Square, and it’s been at the heart of the city’s history since the 13th century. Today, the open-air public space is ringed by shops and restaurants and packed with people, including street performers and tourists en route to nearby attractions like the Royal Palace, the National Monument, and the Nieuwe Kerk (New Church), where you can catch a horse-drawn-carriage tour of the city.

The real voyage of discovery consists not in seeking new landscapes, but in having new eyes. ~ Marcel Proust. For my inaugural highlight on AFAR, I am starting with my wife’s favorite quote, and a local sight in Chicago. Sometimes people feel they must jet off to some far off exotic place in order to ‘travel.’ However, if you gaze anew at your immediate surroundings with fresh eyes, you will discover an entire host of wonderful surprises. Here we have Cloud Gate, located down in Millennium Park, back before they buffed out the seams. The contrast between the organic form of ‘the bean’ and the structured grid lines, along with the warped fun house mirror quality of the city, makes this a truly unique destination.

The Place Bonaventure is widely recognized as one of the most important buildings constructed in Canada in the 1960s, though that’s not to say it’s universally loved. It’s a regular contender for the title of Montreal’s ugliest building. For the student of architecture, however, whether armchair or otherwise, it’s worth a visit to see an outstanding example of brutalist architecture. Architect Raymond Affleck’s vision was to turn the city inside-out in a building appropriate for its location in a cold climate. The Place Bonaventure was designed to include a conference center, hotel, and several floors of retail space, all along internal streets while the building presents a foreboding exterior of ribbed concrete (echoing the design of the seminal Architecture School at Yale University by Paul Rudolph) to the street. The entire complex included 3.1 million square feet of floor space, making it the largest building in the world when it was completed (in 1967). Much of the retail space was converted to offices in later renovations, though the conference center and the hotel (now the Hôtel Bonaventure Montréal) remain. The photo here was taken inside the hotel—a walk around their common spaces will give you a taste of Affleck’s vision for a new urban architecture.

St Stephen’s Green is a welcome spot of calm and green set in a Georgian square in the centre of Dublin. At around 20 acres, it’s large enough to feel you have escaped the bustle, but not so large that you can’t easily return to the fray once you are ready. There are formal manicured lawns and gardens in the middle, a large lake to the north - good for swan-watching - a bandstand and play area, and plenty of benches and other picnic spots. St Stephen’s is probably not the sort of place you’d deliberately set out to visit, but chances are good you’ll end up there anyway: it’s just off Grafton Street (one of the main shopping streets), and near other attractions dotted around what is known as Georgian Dublin, such as Merrion Square and Leinster House (the seat of Irish parliament).

On first glance, it would be easy to dismiss the 101 Hotel as merely a functional option. Stepping inside the austere five-story concrete building on Hverfisgata, however, guests discover an ultra-modern boutique lodging with minimal black-and-white decor—the work of owner-designer Ingibjörg S. Pálmadóttir—that gives it the feel of a chic downtown gallery. Contemporary paintings, photography, and sculptures by local artists appear througout the property, complementing the oak floors and wood-heavy Nordic furniture in the 38 rooms. Queen and king-size beds (there are no twin rooms) come topped with fine Italian linens, entertainment systems are state of the art, and open-plan bathrooms make extensive use of glass and offer Aveda bath products; deluxe rooms and suites up the ante with with claw-foot tubs. The hotel also has a moody restaurant and bar, a gym and spa, and a comfortable lounge area where you can put your feet up by the fire.

WOMB Gallery, located in Oklahoma City’s Automobile Alley district, is the work of The Flaming Lips front man Wayne Coyne. This place likes to call itself am “experience” and not a gallery as some displays are interactive and if you’re lucky you may even get to add your own piece of art in the collaborative 3-D room.

Even if you don’t have anything specific in mind to buy, go to browse Tamarindo’s main avenue for well-priced souvenirs. Here you’ll find traditional coffee and chocolate next to art and wood crafts. There are also supermarkets, drugstores, and jewelry and boutique stores. Whether it’s a valuable artwork or lovable trinket, it will remind you of your visit to this beautiful country.

This treasure trove of curiosities by Susanne Schmid and Simon Wirth in Kreis 4 sells all sorts of vintage objects and upcycled items, including Indian Mrinmaya statues, a mango- and teakwood art deco locker from a colonial hotel in Sri Lanka, and stuffed animals made in Chile from classic men’s handkerchiefs. You’ll also find Fiona Caulfield’s exquisite fabric-covered Love Travel Guides.

If rare antiques, exclusive ceramics, unique interior décor, and unusual souvenirs for home shelf display are your thing, and you have hundreds (or thousands) of dollars to spend, Stockholm’s antique scene certainly won’t disappoint. Modernity serves up pricey handmade jewelry, textiles, art, ceramics, lighting, and glassware.