Istanbul

While the city's major sites offer a heavy dose of its native history—ie: they can't be missed—experiencing Istanbul's more contemporary persona is revealed by heading directly to the bustling Beyoglu district, where cutting-edge boutiques and design shops line narrow, cobblestoned pedestrian-only side streets and main drag, Istiklal Caddesi. English may not be widely spoken here, but the warmth of the local shopkeepers and proprietors make the journey more than manageable, not to mention, ripe with offbeat surprises.

• Antijen Yenicarsi Caddesi 7/b, +90 212 249 47 09
The first things you'll notice in this cool, quirky boutique are the horror movie-inspired mannequins with werewolf heads donning the shop's latest looks. Not something you see everyday, but it's perfectly emblematic of the slightly offbeat, totally unique items you'll find here. Shop owner Nïlufer Karaca designs the shop's in-house line, which includes plastic-covered Glen plaid coats and sturdy, brightly colored leather handbags. There's also a vast assortment of indie Euro-based denim brands for guys and girls by Produkt, Oscar Jacobson, and Jack & Jones, among others.

• Bis Wear Hayriye Caddesi 20/3, +90 212 244 77 35
Designer Reyhan Erturk's shop would be at home in any style-conscious 'hood, from Nolita to Hoxton. As it happens, this petite but chic space is located on the little cobble-stoned street of Hayriye Caddesi and features gorgeous embroidered sheath dresses, handcrafted jewelry, and knit accessories like gloves and scarves perfect to stash away for next season.

• Chic Yenicarsi Caddesi 9/a, +90 212 252 30 55
On the fashion-forward Yenicarsi Caddesi, the eclectic outpost Chic beckons with its brightly lit interior and vibrant array of—wait for it—chic items from the likes of Japanese designer Tsumori Chisato, Scandinavian labels Bik Bok and Gestuz, as well as from fashion mainstays like Anna Sui, Marni and Chloé. A wide array of fun, whimsical accessories and unexpected jewels are also on hand.

• D Art and Design Faikpasa Yokusu 6/1a, +90 212 249 8091
You've probably never seen paper put to such inventive—and beautiful—use as in the works displayed in this tiny gallery in the heart of the antiques and design district. Six Turkish artists are represented, showing geometric jewelry, ceramic-like paper sculptures, lithographs, and papier-mache. The stark alabaster tone of the artwork and walls give the space a striking, ethereal quality, which makes for a perfect momentary escape from nonstop activity out on the streets.

• Ara Café Tosbag Sokak 8/a, +90 212 245 4105
Owner Ara Guler is perhaps Turkey's most prolific photographer, and his eponymous café buzzes with energy at all hours of the day and night. A favorite brunch spot for Istanbul's young trend-setters and local bohemians, Ara serves delicious grilled kebabs and koftes—minced meat mixed with spices, onions, and various other ingredients. Located in an alley right off the Istiklal Caddesi, Ara is perfect for refueling between shopping sprints.

• House Café Gecidi Ishani 9/1 Sumbul Sokak, +90 212 245 9575
Tucked discreetly on a side street off the Istiklal Caddesi, the House Café feels virtually miles from the buzzing shopping district just a block away. The vibe is best at night when the soft, candlelit rooms reflect off the large antique mirrors hanging on the exposed-brick walls. The super-strong Turkish coffee and expertly made Mediterranean-inspired pizzas and fresh salads are especially good.

• Pia Bekar Sokak 6, +90 212 252 7100
Part bar, part café, Pia is an established Beyoglu hangout, serving a satisfying oeuvre of comfort foods (like the excellent pesto linguine) in a snug, two-level spot with warm lighting and a jovial crowd. Do as the locals do and order a cup of koyu cay (strong Turkish tea) to sip while you plot the remaining afternoon's itinerary.

• 45'lik Yenicarsi Caddesi, 60, +90 212 249 9727
Discover Istanbul's version of the urban hipster at this low-key, stylishly grungy dive bar, where the drinks are cheap and the fellow imbibers plenty. A back patio comes in handy on warm nights, where you can sip Efes (Turkish beer) and listen to a selection of mainstream and underground sounds.

•Istanbul Modern Meclis-I Megusan Caddesi, Liman Isletmeleri Sahas, 4 Antrepo, +90 212 334 7300,
It's not in Beyoglu, but for art and design lovers, a quick tram ride to the Tophane neighborhood for a visit to Istanbul's epicenter of contemporary art is a must. The collection isn't as extensive as those you'd find at the Tate Modern or the Pompidou, but it does offer a fascinating and diverse survey of Turkish artists, displaying video installations, photography, and painting. The pristine galleries offer a special perspective on the history of modern art in the country, and the unobstructed view of the Bosphorus from the top floor is a must-see.

Heading off the beaten path in the city's Beyoglu district.