There was much local breast-beating when off-the-beaten-track sushi place Ambrosia decamped from its longtime home (now the site of the Good Life) for the Miami Modern porte cochere of the redeveloped Santa Maria Suites Resort. Fortunately, it proved a smart move. The new space is much larger—though reservations are still recommended—and the decor whiffs of mid-century with round wicker chairs, black lacquer, and a soothing jazz soundtrack. But most important, the menu of rolls like lobster tempura has been maintained. Any doubters as to the place's authenticity will be silenced by the condiments. They use the real stuff, so the pickled ginger isn't Day-Glo pink and the wasabi is nice and powdery.

Open Mondays through Saturdays 10 am to 2 pm and daily from 6 to 10 pm.

This popular brunch spot, on the quieter end of Duval Street, specializes in nearly 20 varieties of crepes, with fillings that include bacon, mushrooms, and béchamel; goat cheese and walnuts; and sea scallops in white wine and cream. Grab a table on the porch to eat.

Caribbean-themed American and veggie fare draws tourists and locals to this legendary eatery, which served its first meal in September 1992. The menu is heavy on the local seafood, with staples like barbecued shrimp or seared scallops Provençale. The building that houses Blue Heaven has been through many iterations—most of the tables are situated in the outdoor courtyard, where Hemingway refereed boxing matches and customers watched cockfights (there are still chickens pecking about). The patio surface is paved with slate pool-table tops from the restaurant's days as a billiard hall and ice-cream parlor. Diners with more risqué tastes should request a seat in the second-floor gallery, formerly a dance hall and bordello (you can still peek through peepholes into tiny rooms). Reservations are not accepted for breakfast or lunch and there's usually a line, especially for Sunday brunch. It's worth the wait for fragrant house-made banana bread.

Open Mondays through Saturdays 8 am to 3 pm and 5 to 10:30 pm, Sundays 8 am to 2 pm and 5 to 10:30 pm.

This local institution is another only–in–Key West landmark. It doesn't look like much (if you can say that a building that looks like it was cobbled together precariously from wrecked trucks isn't much), but the sandwiches of fresh-caught fried fish are legendary. The best time to stop by is Friday night, when you can enjoy your sandwich and a cheap beer while listening to an impromptu jam session by local musicians.

Open daily 11 am to 9 pm.

With its white tablecloths and hushed ambience, this is one of the poshest places on the island. The intimate, 50-seat restaurant adjoins the Marquesa Hotel, and the food is vaguely Floribbean or fusion. Dishes include a macadamia-crusted yellowtail snapper or conch and blue crab cakes. In addition to the extensive wine list, there's a fun, full martini menu, from Gibsons to dirty to blue cheese–olive versions. Come here if you're craving something a bit more serious than the anything-goes, no-worries-man vibe of most down-home joints nearby.

Open daily 6 to 9:30 pm.

There's a never-to-be-settled debate as to who makes Key West's best Cuban coffee, a sugary shot of espresso called buchi. Inexplicably, the two top rivals for the crown are in a grocery store and a laundromat. Five Brothers is a café and food market crammed with provisions and pots dangling from the ceiling (930 Southard St.; 305-296-5205). Besides buchi and café con leche, they also offer daily specials like ropa vieja (Cuban shredded beef) that go fast—get there before 2. At Sandy's Café inside the M&M laundry, you can linger at one of the outdoor stools and sip a buchi along with one of the killer Cuban sandwiches (1026 White St.; 305-295-0159).

El Siboney has been the island's premier Cuban joint since 1984. Located in a low-slung building on a residential corner, the restaurant was taken over by new owners in 2004. Thankfully they haven't changed a thing. The menu still includes staples like ropa vieja (shredded flank steak with a tomato-based sauce) and a fragrant picadillo (ground beef), as well as a perfect Cuban sandwich. Daily specials like avocado salad or grilled snapper are posted on the whiteboard outside by the front door. No matter what you order, you will get a red plastic basket of crisp-toasted Cuban bread oozing with melted butter. The best time to come is lunchtime, when El Siboney doubles as a local gathering place-cum–gossip hub.

Open daily 11 am to 9:30 pm.

Co-owners Tasha Cole and Morgan Kosut opened this sparkling new restaurant in 2008. Once home to Ambrosia, the space is now very Mad Men meets Florida tropical: white walls dotted with swirling decals, flickering tea lights all over the bar, mod furniture that is brightly colored and artfully mismatched (try to get one of the two tables with velvet armchairs instead of traditional seats). The food is modern American with a twist. Try the gooey mozzarella sandwich served with thick curry-accented tomato soup for dipping, or the fish tacos piled high with diced mango and charred chunks of mahi mahi. Be sure to save room for the banana-bread French toast, served with homemade vanilla ice cream.

Open Tuesdays through Sundays 6 to 10 pm.

Stock your minibar or condo kitchenette with gourmet groceries from Fausto's Food Palace. There are two branches, but the Fleming Street location will deliver as long as your purchase is over $25 (522 Fleming St.; 305-296-5663 and 1105 White St.; 305-294-5221; www.faustos.com). The Waterfront Market is a good place to pick up picnic items like deli meat, cheese, and fresh produce before setting sail for the day. If you buy delicious mangrove snapper—or catch it yourself—the Schooner Wharf Bar will grill, broil, or fry it up for you.

An oldie but goodie, this Key West institution frequented by Jimmy Buffett—and just about every upscale tourist who comes to Key West—is housed in a historic oceanfront home. Norman Van Aken got his start here along with Susan Ferry of Café Marquesa, but these days, its executive chef Doug Shook who whips up steaks, chops, and seafood with a Caribbean flair; lobster braised in truffle butter is a popular appetizer. It's expensive; lunch is the best buy. Channel your inner Buffett and order a margarita at the romantic outdoor Afterdeck bar, which serves until 2 a.m. Reservations for dinner are essential.

This always packed eatery is all about location, location, location; diners regularly compete for patio tables to watch the human carnival on Duval Street. The fruit-infused Floribbean cuisine (standouts include shrimp in a mango barbecue sauce, filet mignon with chimichurri, and jerk pork) is a bit overpriced but worth it.

This neighborhood café would be easy to overlook, with its plastic garden chairs, posters on the walls, and wipe-clean floral plastic tablecloths. But the lure isn't the decor, it's the food. Paradise is known for its gut-busting Monster sandwiches, made to order and stacked with fistfuls of deli meats, mustard, fresh-cut onions, and tomatoes and served on still-warm Cuban bread. Prices are reasonable (around $7) and you can save a buck by ordering the "lite" version, which means less meat. But what's the fun in that? Make sure you're not in a rush, though—sandwiches are constructed at a pace that's casual even for Key West.

Open daily 6 am to 4 pm.

Funky Caribbean and veggie fare draws tourists and locals to this legendary eatery. The decor is Key West scrappy—most tables are situated in the outdoor courtyard, where Hemingway refereed boxing matches and customers watched cockfights. A curiosity: The patio surface is paved with slate pool-table tops from the restaurant's days as a billiard hall and ice-cream parlor. Diners with more risqué tastes should request a seat in the first-floor gallery, formerly a dance hall and bordello. You can still peek through peepholes into tiny rooms. Reservations are not accepted and there's usually a line (especially for brunch), but it's worth the wait.

This little bistro, housed in a former luncheonette on a quiet street in Old Town, is easy to miss. But the Asian fusion menu, ranging from meat loaf to mahimahi, is worth seeking out. Try the Asian-style yellowtail snapper, banana chicken, and shrimp salsa with chile lime chips. Reservations are recommended.