George Town

Blue Wave and Waterman surf and clothing shops have same owners (Waterman is in Seven Mile Beach). At the George Town shop you'll find brands like Billabong, Quicksilver, and Olukai, plus essentials like sandals, sunglasses, and surfboards.

Owner Tony Crescente and younger brother, maitre d' Carlo, offer a simpatico dining experience, practically exhorting you to mangia and sending you off with a chorus of ciaos. There's some decorative formaggio (cheese): murals of grape clusters and cavorting cherubs, paintings of the Amalfi Coast, and una finestra sul mare ("window to the sea") stenciled redundantly over arches opening onto the harbor. The kitsch doesn't extend to the kitchen. Sterling Italian favorites include lemony veal piccata; gnocchetti in velvety four-cheese sauce with a blush of tomato; and seafood grill in parsley-garlic-lemon sauce. Enjoy grappa at the marble bar of Il Bacio lounge amid its wooden wine racks (the impressive selection isn't overly Italian-centric). The patio juts over the harbor, and moonlight, abetted by a sound track of Bocelli to Bennett, can transform an amorous coward into a Casanova.

Ads trumpet that this restaurant overlooking a garden with a cheery tropical motif is "where the islanders dine"; indeed they have since the Robinson family started selling takeout from its kitchen in 1965. The West Indies breakfast, themed lunch, and Taste of Cayman dinner buffets are legendary spreads. Local food (curried goat, oxtail with broad beans, turtle soup, and heavy cake) is authentic, hearty, and cheap. Pricier global dishes range from chop suey to enchiladas to fine Indian vegetarian options like samosas and masala dal (lentils simmered with green chiles).

On the surprisingly large, eclectic Asian-tinged menu using ultrafresh ingredients, standouts include homemade carrot cake, mango smoothies, cranberry-Brie-pecan salad, and rosemary-roasted portobello and pesto chicken panini. The espresso martini will perk up anyone wanting a pick-me-up. A feast for weary eyes as well, with rotating artwork (much of it for sale) and stylish mosaic mirrors contrasting with faux-brick walls and vintage hardwood tables.

This classic clapboard seaside shanty couldn't be homier: constructed from an old fishing vessel, the structure is an authentic representation of original Caymanian architecture. The deck is perfectly placed to savor the breezes and water views, and the chill Caribbean vibe makes it feel as if you're having the freshest seafood at a friend's home. The owners source fresh, local ingredients wherever possible and developed relationships with Caymanian fishermen, who often cruise up to the dock with their catch. Savor jerk fish tacos, saltfish fritters, coconut shrimp with pineapple tomato salsa, and golden crunchy breadfruit fries. Landlubber selections run from pork chops with pineapple butter to baby back ribs braised in Jack Daniels. Free Wi-Fi and occasional DJs are bonuses.

Built in 1908 as the Petra Plantation House and transformed into the island's first upscale establishment decades ago, this grande dame evokes bygone grandeur sans pretension. The interior rooms, awash in crystal, recall its plantation-house origins. Outside, hundreds of sparkling lights adorning the gazebos compete with the starry sky. Live nightly music and rumors of a charming blond ghost trailing white chiffon complete the picture. Expertly executed classics include panfried foie gras with black currant and green apple purees, salted mango chutney, and microgreens; roasted lobster in creamy Chardonnay sauce; and chicken cordon bleu. The subtle yet complex flavor interactions, stellar service, and encyclopedic if stratospherically priced wine list ensure legendary status. Nightly happy hours with discounted tapas at its On the Rocks bar are a substantial bargain.

This stylish upstairs bistro has mahogany furnishings, ship's lanterns, porthole windows, fishing rods, and Harvey's action-packed marine art. Seasonally changing dishes are peppered with Caribbean influences and the seafood is carefully chosen to exclude overexploited and threatened species. Silken lobster bisque is served with puff pastry, there's scallops Rockefeller with spinach and béarnaise sauce, and the mahimahi-crab supreme has a champagne sauce. Many specialties are cheaper at lunch; there are often prix-fixe dinner specials. The downstairs section, Bar Crudo, offers sensational drinks specials and tasty tapas.

The nondescript building belies the lovely marine-motif decor and luscious seafood at this second-story restaurant overlooking the harbor. Enjoy lobster prepared several ways (all à la sticker shock) along with reasonably priced wine, which you can sample by the glass in the cozy bar. The two musts are the Cayman Trio (lobster tail, grilled mahimahi, and garlic shrimp) and the Pot (lobster, giant prawns, and crab). The wildly popular Friday lunch special is the decadent CI$19 lobster burger, a hefty heifer topped with a perfectly cooked 3-ounce lobster tail, bacon, cheddar, shrimp, jalapeño, and onion rings (add the day's special wine for CI$9/bottle). The kitchen happily provides reduced-oil and -fat alternatives to most dishes; vegetarians love the flavorful chile-lime polenta with grilled artichoke in mango cream, and tofu, zucchini, and yellow-squash spaghetti. The balcony offers a breathtaking view of the sunset tarpon feeding.

One of the locals' favorite burger joints—not a fast-food outlet—MacDonald's does a brisk lunch business in stick-to-your ribs basics like rotisserie chicken and escoveitch fish. The decor features yellows and pinks, with appetizing posters of food and a large cartoon chicken mounted on the wall—all an afterthought, really, to the politicos, housewives in curlers, and gossipmongers.

Actuaries, bankers, and CEOs frequent this contemporary throwback to a colonial country club for lunch and "attitude adjustment" happy hours for creative cocktails and complimentary canapés. Inviting fusion farm/sea-to-table cuisine, emphasizing local ingredients whenever possible (the restaurant has its own boat and garden), includes terrific bar tapas. Several evenings, you can get a five-course market-driven Random Acts of Cooking blind tasting. Dishes deftly balance flavors and textures without sensory overload: this is serious food with a sense of playfulness. Save room for dessert, from an artisanal cheese plate to an ice cream and sorbet tasting menu to elaborate architectural confections. Lunch is more reasonably priced but equally creative; the adjacent Market excels at takeout, and the wine list is well considered.

On the George Town waterfront, Artifacts sells Spanish pieces of eight, doubloons, and Halcyon Days enamels (hand-painted collectible pillboxes made in England), as well as antique maps and other collectibles.

Optimally located downtown and one of the leading shopaholics' targets (you can't miss the cotton-candy colors), this mall contains a Kirk Freeport department-store branch (Tag Heuer to Herend porcelain, Mikimoto to Mont Blanc), swank Lalique and Lladró boutiques, La Parfumerie (which often offers makeovers and carries 450 beauty brands), and other usual luxury culprits.

The store has a collection of the acclaimed underwater shutterbug's spectacular color and limited-edition black-and-white underwater photos as well as the latest marine camera equipment. Cathy will autograph her latest coffee-table book, talk about her globe-trotting adventures, and schedule private underwater photography instruction on her dive boat, with graphics-oriented computers to critique your work. She also does wedding photography, above and underwater.

The popular restaurant and bar (formerly Hammerheads), adorned with wild murals, fab old-timer photos, and surfboards doubling as signs, offers a classic Cayman sight: fishers anchor their boats right offshore and display their catch right outside (condo and villa renters, head here if you're in the market for fresh fish). The capable kitchen specializes in classic Caymanian cuisine; farm-to-table Thursdays are justifiably popular. This is also a prime pyrotechnic sunset- and cruise ship-watching spot, where locals laze in locally carved chairs, sipping house microbrews on the vast thatch-shaded, tiered deck. Stop by the Swanky Shack by the entrance for souvenir T-shirts and island gossip.

In this brewery occupying the former Stingray facility, tour guides explain the iconic imagery of bottle and label as well as the nearly three-week brewing process: 7 days' fermentation, 10 days' lagering (storage), and 1 day in the bottling tank. The brewery's ecofriendly features are also championed: local farmers receive the spent grains to feed their cattle at no charge, while waste liquid is channeled into one of the Caribbean's most advanced water-treatment systems. Then, enjoy your complimentary tasting knowing that you're helping the local environment and economy. The little shop also offers cute merchandise and a happening happy hour that lures locals for liming (as a sign prominently chides: "No working during drinking hours").

Built in 1833, the historically significant clapboard home of the national museum has had several different incarnations over the years, serving as courthouse, jail, post office, and dance hall. It features an ongoing archaeological excavation of the Old Gaol and excellent 3-D bathymetric displays, murals, dioramas, and videos that illustrate local geology, flora and fauna, and island history. The first floor focuses on natural history, including a microcosm of Cayman ecosystems, from beaches to dry woodlands and swamps, and offers such interactive elements as a simulated sub. Upstairs, the cultural exhibit features renovated murals, video history reenactments, and 3-D back panels in display cases holding thousands of artifacts ranging from a 14-foot catboat with animatronic captain to old coins and rare documents. These paint a portrait of daily life and past industries, such as shipbuilding and turtling, and stress Caymanians' resilience when they had little contact with the outside world. There are also temporary exhibits focusing on aspects of Caymanian culture, a local art collection, and interactive displays for kids.

Surprisingly, this growing company, established in 2008, is Cayman's first distillery. It's already garnered medals in prestigious international competitions for its artisanal small-batch rums (and is now making a splash with its smooth Gun Bay vodka as well). You can stop by for a tasting and self-guided tour (a more intensive, extensive guided tour costs $15) to learn how the rum is aged at 7 fathoms (42 feet) deep; supposedly the natural motion of the currents maximizes the rum's contact with the oak, extracting its rich flavors and enhancing complexity.

This small courtyard shopping center is noted for its specialty jewelers and antiques dealers.

A cigar-store Indian points the way into this tobacco emporium, which sells the island's largest selection of authentic Cubanos (and other imports), including such names as Upmann, Romeo y Julieta, and Cohiba, displayed in the dark, clubby surroundings. The enthusiastic staff will advise on drink pairings (bold older rum for a Montecristo No. 2, cognac for smaller Partagas Shorts, a single-malt scotch such as Glenmorangie for the Bolivar Belicoso Fino). There's a small airport branch and one at the Kimpton Seafire Resort + Spa as well.

This mall caters to more casual shoppers with the T-shirt Factory, Island Treasures, Havana Cigars, Blackbeard's Rumcake Bakery, and the Surf Shop. It also contains a kid-pleasing 12,000-gallon saltwater aquarium with sharks, eels, and stingrays.

World-renowned marine biologist, conservationist, and artist Guy Harvey showcases his aquatic-inspired, action-packed art in every conceivable medium, from tableware to sportswear (even logo soccer balls and Zippos). The soaring, two-story 4,000-square-foot space is almost more theme park than store, with monitors playing sport-fishing videos, wood floors inlaid with tile duplicating rippling water, dangling catboats "attacked" by shark models, and life-size murals honoring such classics as Hemingway's The Old Man and the Sea. Original paintings, sculpture, and drawings are expensive, but there's something (tile art, prints, lithographs, and photos) in most price ranges.

Grand Cayman's Hard Rock replicates its 137-odd brethren around the world, especially on the weekends, only with more specialty drinks (try the Orangelicious margarita with Monin pomegranate and blood-orange juices) to complement its extensive burger selection. A 1960 pink Cadillac, a Madonna bullet bra, and rotating memorabilia (gold records, costumes, guitars, and autographed photos from Elton John, Korn, John Lennon, U2, and *NSYNC) are the decor.

This state-of-the-art facility seats 330 for theatrical performances, concerts, dance recitals, fashion shows, beauty pageants, art exhibits, and poetry readings sponsored by the Cayman National Cultural Foundation.

Hurley's is open Monday–Saturday 7 am–11 pm. It's well-known for its hot take-out dinner specials.

Locals appreciate Island Jewellers for its affordable line of watches, especially top-notch Swiss brands, from Movado to Marvin to Maurice Lacroix, and selection of stunning diamonds and jewelry There's another branch with similar inventory in the Flagship Building.

Here you'll find 15 duty- and tax-free stores, including Swarovski Boutique, Island Jewellers, and Churchill's Cigars (with bars like Margaritaville to de-stress in after binge shopping).

This downtown shopping center, home to the Kirk Freeport flagship department store, is ground zero for couture; it's also known for its boutiques selling fine watches and jewelry, china, crystal, leather, perfumes, and cosmetics, from Baccarat to Bulgari, Raymond Weil to Waterford and Wedgwood (the last two share their own autonomous boutique). Just keep walking—there's plenty of eye-catching, mind-boggling consumerism in all directions: Boucheron, Cartier (with its own miniboutique), Chanel, Clinique, Christian Dior, Clarins, Estée Lauder, Fendi, Guerlain, Lancôme, Yves Saint Laurent, Issey Miyake, Jean Paul Gaultier, Nina Ricci, Rolex, Rosenthal and Royal Doulton china, and more.

This store is open Monday–Thursday 7 am–10 pm (11 pm Friday and Saturday) and is a particularly good source for traditional Caymanian fast food (oxtail, curried goat) and beverages at the juice bar. It also carries the largest selection of organic and special dietary products; the pharmacy (Monday–Saturday 8 am–9 pm) stocks homeopathic and herbal remedies.

Stores in the Landmark sell perfumes, treasure coins, and upscale beachwear; Breezes Bistro restaurant is upstairs.

The center hosts events throughout the year: Battle of the Bands competitions, concerts by top names on the Caribbean and international music scene such as Maxi Priest, stage productions, pageants, and sporting events.

Befitting its name, Magnum Jewelers traffics in high-caliber pieces by the elite likes of Girard-Perregeaux and Harry Winston for a high-powered clientele. A talented team source distinctive contemporary watches and bijoux (especially increasingly rare colored diamonds) for their equally glittery celebrity clientele, who appreciate a bargain like the rest of us. Smaller spenders might appreciate whimsical items such as pendants with hand-painted enamel sandals or crystal-encrusted purses.

Grand Cayman's Margaritaville is a vast upstairs space that usually bustles with life (especially down its Green Monster waterslide or by its rooftop pool); the Friday evening happy hour is especially popular, with an overgrown frat-party atmosphere, and though drinks may be a bit pricier than at other waterfront locations, the jollity, 25 TVs, surprisingly tasty tacos, and free Wi-Fi definitely compensate. It closes early except on Friday night.

Perched on the water's edge, this bar has great sunset views. The leviathan open-sided cabana is drenched in Rasta colors and crowned by an intricate South Seas–style thatched roof with about 36,000 palm fronds. Christmas lights and the occasional customer dangle from the rafters. They offer great grub, and the crowd is a mischievous mix of locals, expats, and tourists.

This office provides a map of historic and natural attractions, books and guides to Cayman, and information on its website about everything from iguanas to schoolhouses. The expanded gift shop provides one-stop souvenir shopping, from hair clips to logwood carvings to coconut soaps, all made on the island. Regularly scheduled activities range from boat tours through the forests of the Central Mangrove Wetlands, to cooking classes with local chefs, to morning walking tours of historic George Town. The office is walkable from George Town, but be aware that it's a 20-minute hike from downtown, often in the heat.

About 1½ miles (2½ km) south of George Town, Pure Art purveys wit, warmth, and whimsy from the wildly colored front steps. Its warren of rooms resembles a garage sale run amok or a quirky grandmother's attic spilling over with unexpected finds, from foodstuffs to functional and wearable art.

Both fishermen and financiers savor sensational sunsets and joyous happy hours, then watch tarpon feeding at this open-air, marine-theme bar on a jetty. Boaters and snorkelers, before and after checking out the wreck of The Cali, cruise up the ladder for drinks, while anglers leave their catch on ice. There's complimentary snacks on Friday and pub fare at fair prices until midnight.

South of the Grand Old House, this tiny but popular protected swimming and snorkeling spot makes a wonderful beach wedding location. The bottom drops off quickly enough to allow you to swim and play close to shore. Although slightly rocky (its pitted limestone boulders resemble Moore sculptures), there's little debris and few coral heads, plenty of shade, picnic tables, restrooms, and parking. Surfers will find decent swells just to the south. Note the curious obelisk cenotaph "In memory of James Samuel Webster and his wife Arabella Antoinette (née Eden)," with assorted quotes from Confucius to John Donne. Amenities: parking (no fee); toilets. Best for: snorkeling; sunset; swimming.

This is indeed a preferred hangout for the diverse after-work crowd, which packs both the cozy club space (adorned with customers' ties) and breezy patio, absorbing the high-octane cocktails and nightly musical mix (from country to salsa, karaoke to live bands). Happy hours are joyous indeed with CI$5 martini specials. It's invariably lively—a favorite spot for birthday, office, and bachelor and bachelorette parties and a prime place to eavesdrop on local gossip.

Dance near the water to mellow music on Saturday evening; when there's a wedding reception in the pavilion, the crashing surf and twinkling candles bathe the proceedings in an almost Gatsby-esque glow. For something less sedate, try salsa lessons and dancing on Tuesday after dinner; most Fridays morph into a wild 1970s disco night (after the free hors d'oeuvres served during happy hour). The legendary Barefoot Man (think a Jimmy Buffett–style expat) performs Saturday. The stunning seaside setting on tiered decks compensates for often undistinguished food and service. The Ports of Call bar is a splendid place for sunset, and tarpon feeding off the deck happens nightly at 7 and 9.

This company bakes, then vacuum-seals more than 10,000 of its world-famous rum cakes daily, adhering to the original, "secret" century-old recipe. There are eight flavors, from banana to Blue Mountain coffee, as well as several varieties of candy, from taffy to truffles. The 12-year-old rum, blended from private stock though actually distilled in Guyana, is a connoisseur's delight for after-dinner sipping. You can buy a fresh rum cake at the airport on the way home at the same prices as at the factory store.