A Week of Dream Dining in Southwest Florida

Our food editor takes you through seven days of her favorite dining spots.

The No. 1 question I get asked because of my job is, “What is your favorite restaurant?”

It’s kind of like making me pick between Sissy and Buddy (I’m kidding—but thankfully I have only one super-adorable kiddo so far). That said, I do have a short list of ones I keep in my back pocket for when people ask the inevitable.

This is my ultimate itinerary for a fairy-tale week of Southwest Florida dining. Pixie dust is factored in, as no one’s going to zip between even Fort Myers Beach and Cape Coral every day, let alone Naples and Sanibel. It’s also worth noting that most people other than yours truly (and perhaps truck drivers), can’t eat as much as or go as hard—so adjust accordingly and please be safe. Uber, Lyft, shuttles and taxis are thriving here for a reason.

MONDAY/Naples

Let’s start the week with a bang.

Third Street South is always a road to deliciousness, and rolling into a table aside the koi fountain at Jane’s on 3rd Garden Café will not disappoint. With people-watching between sips of a bellini, I’m hoping to see one of the stuffed challah French toast specials (the raspberry-peach is make-your-eyeballs-roll-up-to-the-sky good), but I’m equally happy with a goat cheese, spinach and ham omelet.

Window shopping will work up an appetite for round two: lunch overlooking the pristine canals radiating from The Village Shops on Venetian Bay. I like to be outdoors along the glass rail at M Waterfront Grille, with only my bento box of an apple-fontina grilled cheese with the day’s soup, salad and fruit obstructing my view of the turquoise beyond. (If at The Village for dinner, I prefer to cross the plaza for Tony Ridgway’s Bayside Seafood Grill & Bar; he’s one of Naples’ legendary chefs, and the sunsets from both the buttoned-up upstairs dining room and the open-air upper deck are nothing short of sublime.)

Rounding out the day, I can’t recommend any place more highly than USS Nemo for a consistently on-point taste of the Gulf. The French-Canadian chef-owner has been satisfying my cravings for his funky fusion of Japanese, Indian, French and Italian influences ever since I moved to town seven years ago. I would go just for the miso-glazed sea bass (which is my annual birthday request)—but because it somehow manages to get increasingly crowded, random weeknights are usually my jam.

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TUESDAY/Naples and Bonita Springs

Awash in red-checkered glory, Joe’s Diner has definite retro appeal. What keeps me coming back is its chef-owner’s more-is-more approach. Everything I fantasize about before 7 a.m. makes an appearance in “Joey’s Ultimate Challenge,” a goopy stack of eggs over-easy, home fries, sausage gravy, biscuits, bacon and cheese. Should I be in the mood for a little sugar, however, I gravitate to one of the three branches of Poached. Also owned by a classically trained chef, the otherwise nondescript cafés shine with seasonal specials like caramel apple pancakes and staples like banana bread French toast.

A little midday run with Fernández the Bull is always exciting—whether it’s the house Cuban sandwich, fried stuffed yucca or the lechon asado I use as a yardstick for all others. (Another Latin love, El Gaucho Inca, does exceptional Argentine and Peruvian comfort food for another mood, another day.)

In an effort to save myself for dinner, at maximum I’d grab a cup of locally roasted coffee from Kunjani Craft Coffee & Gallery right about now, or an organic juice from Food & Thought’s café (a week without one is not a week).

For a relatively small town, Bonita Springs has an outsized number of exceptional independent eateries like Wyld’s Café, Petar’s Restaurant, C Level Bistro and The Other Side Bistro. But it’s worth the planning required to secure a dinner reservation for one of the booths surrounding the 5,000-bottle wine tower at Angelina’s Ristorante. There’s something extra-special about sitting in a private chandelier-illuminated nook that amplifies the hallmarks of fine dining (valet parking, complimentary digestivi, waiters lavishing attention). And I’m grateful the agrodolce ravioli di zucca, stuffed with butternut squash and capped with candied walnuts and arugula, is there for my indulgence.

WEDNESDAY/Fort Myers Beach, Sanibel, Fort Myers, Cape Coral

Harnessing teleportation powers, I’ll skip around Lee County today, beginning with the Heavenly Biscuit. The technicolor cottage in Fort Myers Beach is home to arguably the best cinnamon rolls and namesake flaky discs of butter and flour. (Although I prefer Fort Myers Beach for breakfasts and fried shrimp platters, if I were to be there at sunset, it’s hard to top Jack’s Farm to Fork, which transforms vegetables into art with every bite.)

Because I love food almost more than life itself, I become giddy crossing the Sanibel Causeway. The barrier island is a fixed-in-time paradise with pastel structures sporting wraparound porches—with winsome eateries that have withstood the test of time by continuing to innovate, such as Sweet Melissa’s. Perhaps the only place I can think of that has a lamb neck sugo on the dinner menu, it puts forth unique sammies, like the smoked New York strip with onions and blue cheese on ciabatta, by day.

Seeing as I live in Naples, I’d probably soak up all the Sanibel dining I could while there, with a beachfront dinner at The Mad Hatter (a trip down this rabbit hole yields wonders like phyllo pockets of goat cheese in a strawberry-Port reduction). But if I spent more time in the area, I’d probably head over to Azure in Fort Myers. One of the most talented chefs in our region, Joe Pittman, entertains diners who line the bar for a front-row seat to his open kitchen. I love his take on escargots (sans shells), as well as when his Southern upbringing seeps into classics like grenouille, giving it a Low Country accent.

Nights out have become synonymous with Cape Coral. Hipper, edgier and just plain cooler as a whole, the southern stretch of the Cape is a must. The best restaurant to open there over the past year, Point 57 Kitchen & Cocktails, has a killer drink list and bar that feels like what you’d get if you glamorized a Hemingway Key West haunt. Big Blue Brewing, while shorter than average on the volume of house microbrews, makes it up with character, scheduling bands Wednesday through Saturday. Jumping around, I also return to the pioneering Nevermind, a gritty bar with super-stiff mixed drinks from Shannon Yates, a kingpin behind the area’s renaissance. When my focus shifts to food, I hop across the street to late-night pizza lounge Nice Guys. The Truffle Shuffle with provolone, Parmesan, crisped sage, portobellos and requisite truffle oil is an antidote to an impending hangover.

THURSDAY/Fort Myers, Cape Coral

On another day in Lee County, depending on my mood, I’d spring for either Crave in Fort Myers (from-scratch everything down to the deli meat)—or Cape Coral’s Hart & Soul Café (homey but heavy) or Café YOU (the menu is decorated with “GF” and “V” icons). Daily specials at Hart can run from Belgian waffles with wild berry compote to a prosciutto-leek omelet to a crab cake Benedict. At Café YOU, its Australian owner places a premium on carefully crafted espressos and brekkies like shakshuka with organic eggs and toast schmeared with a lemon-spiked avocado-feta mash. (P.S. They have not one but three in-house chefs who put on wine dinners and other special events each month.)

If I want to stay put in the Cape throughout the morning, I’d hit up Fish Tale Grill by Merrick Seafood. The family owning it runs the market next door that pretty much supplies every Cape restaurant with their catches. Going straight to the source for a navy blue mug of liquid-gold lobster bisque and coconut shrimp with mango coulis can’t be beat.

Dinner is a definite at Gloria Jordan d’Cabral’s La Trattoria Café Napoli. She’s got an incredibly loyal following in Fort Myers for a reason—a night there and you feel like you’ve stepped into an extension of her Spanish-Cuban home. The stuffed plums, paella and tapas galore can make it hard to leave without feeling full.

A beeline up U.S. 41, and I’m happy to float around the River District. After a round or two in the industrial-chic taproom of the just-opened Millennial Brewing Company, I spill into the beer garden at the new Downtown Social House a few blocks away. I’ve been loving its Edison-lightbulb bistro lights, young (but not too-young) professional patrons and nuanced drinks, like a spicy watermelon-tequila number. Because Skybar is next door, I climb three flights of stairs to watch the river twinkling in the moonlight—exactly what I’m imbibing at this point barely matters as warm breezes flirt with my hair.

FRIDAY/Bonita Springs, Naples

One place I routinely trek to in the northern reach of Bonita is the mostly outdoor-seating Garden Café. A local caterer owns and runs it. His specialty? Rib-sticking comfort food, like pork belly Benedict with béarnaise on sourdough crostini. The café’s rainbow-hued umbrellas are adorable, but since you most want to go when it’s nice outside, two other Bonita breakfast spots are solid fill-ins: Survey Café, for a mean egg wrap with sharp cheddar and spicy mayo, and Bonita Brunch, which has an even mix of indulgences and waistline-friendly options.

A quick lunch from the original Jimmy P’s in Naples yields melt-in-your-mouth ground beef that’s on the short list of the best burgers in town (the Pepper family also now has outposts in Bonita and on Immokalee Road).

In observance of TGIF, I hit Barbatella. Nothing makes an hour happier than an incredible array of Italian wines by the glass and haute nibbles including crisped Neapolitan-style pizza. The cherry on top of the gelato is the restaurant’s eye candy: a stunning casual-chic motif dripping in crystals and intricate moldings. (FYI, its sister restaurant a few doors down, Sea Salt, has an impressive wine dinner program with visiting vintners, and the chefs do exceptional experiments in molecular gastronomy to pair with the meals.)

A toss-up for dinner would be between Bha! Bha! Persian Bistro and the progressive Indian fare of 21 Spices by Chef Asif, with the former narrowly prevailing. It’s a tough call, for both fine dining establishments strike a balance between modern and traditional dishes that is still novel in this neck of the woods. But each time I return to Bha! Bha!, I marvel at the flavors, whether savory (haleem bademjune, an eggplant and lentil puree with caramelized onions and toasted walnuts) or sweet (plum lamb braised in pomegranate sauce with big chunks of stone fruit).

Mirroring the demographic shift northward, nights out north of Pine Ridge Road have become du jour. I’d probably stop by any of the following: Paradise Wine (for live music), Bone Hook Brewery (to chill), Public House (ditto) or Burn (to dance).

SATURDAY/Naples

My latest obsession is the new duo of Timeless – an MHK Eatery and La Colmar Bakery & Bistro just north of Central Avenue downtown. While La Colmar is open every morning for pastries made from imported 00 French flour, Timeless does weekend brunch right with a crazy short rib hash employing roasted beets, sweet potatoes, frizzled leeks and burst yolks for a colorful and tasty tableau. On my way out, I’ll stop in the bakery for several days’ worth of croissants and baguettes to go.

Next, I can’t help but revisit Third Street South. It doesn’t have the most restaurants, but it handily has the highest concentration of exceptional restaurants in Southwest Florida. The outdoor patios must have pheromones, and I’m pulled toward two that are owned by the local D’Amico family, Campiello and The Continental. The latter, a bougainvillea-lined steakhouse, is one of Naples’ priciest tickets at night, so the midday deals prove irresistible.

Every now and again, I indulge in some day-drinking, and for this I fall squarely in line with my younger self—cold suds, best procured at picnic tables. Ever since the Naples Beach Brewery unveiled a new taproom a few years ago, it has been a go-to.

Post-showering and some dolling up, I head back downtown. Fifth Avenue South’s The French and Osteria Tulia vie for my attention. Both are owned by the same chef, Vincenzo Betulia, and his approach that puts unique spins on rustic dishes within each canon is perpetually fruitful. The French gets my business tonight, if only because I still get a kick exploring the menu (it opened in January 2017), and I’m somewhat powerless to resist the recipes Julia Child helped popularize. (By the way, the other nearby Gallic temple I frequent is Bleu Provence, for a serene South-of-France vibe and a wine list that could be mistaken for an encyclopedia—it’s routinely honored with Wine Spectator’s Grand Award.)

The appropriate nightcap choice is to cocktail it for another hour or two, first at Bar Tulia (the best spirits program anywhere, period) and then at The Bevy (a newbie that takes crafting mixed drinks seriously).

SUNDAY/Naples, Bonita Springs

Of course, I saved the best for last.

My husband’s and my Cheers/Central Perk/Sur is The Bay House (I’m loosely defining our “neighborhood” as a 10-minute radius around our home). We go for casual dinners in the tavern side when we want to hear local bands and have a cheeseburger with house-made pimento oozing into every bite. We take out-of-towners to the formal dining room for a genteel evening overlooking the tranquil mangrove inlet and starring superior Southern-inflected seafood (think: Gulf-caught coastal pan roasts with Carolina Gold rice). But we’ve come to love our Sunday morning ritual of shrimp and grits with poached eggs, corn muffins and coffee—and an Irish folk band’s jigs in the background. (Because I could never tire of Southern comforts—grits, biscuits and waffles, hallelujah!—we start Sunday with a stop at 7th Avenue Social when we’re in downtown Naples.)

Continuing the day of decadence, an afternoon pick-me-up at the original Royal Scoop in Bonita Springs tides me over with a taste of Americana in every lick of the ice cream churned there.

And our regular cure to the Sunday night blues is “linner,” an early dinner at 4:30ish. To cap off a perfect 10 of a week, we need to see the sun set in style, which means either a trip to Gumbo Limbo or Baleen. I elect the former at The Ritz-Carlton, Naples when we want piña coladas and mango-macadamia nut salads in an appropriately tiki-esque setting. I go for the latter, the freshly polished gem at LaPlaya (the restaurant and resort underwent a renovation in the fall), for a splurge with more panache. Since both are in hotels, exceptional service is par for the course, and the menus always manage to pique our interest and make us fall in love with the Gulfshore all over again.

Still hungry? Check out our Restaurant Guide.