Your Guide to the Key Largo Destination Where Family, Food, and Sunsets Meet

The following is sponsored content by Key Largo Restaurants.

In the heart of downtown Key Largo, nestled off the Overseas Highway, sits a 2.5-acre property with a fabulous view of Florida Bay where patrons can enjoy free sunsets and experience three dining rooms, three bars, three happy hours and a weekly vacation rental property at one location.

The combination has made this spot into a Key Largo destination for many years. Visitors can pull in, park their car or boat, then decide which location to visit — or visit all three. With breathtaking views of South Florida sunsets, it’s a destination where locals and visitors can dine on a variety of specialties, with numerous options to choose from. Among the three locations, menus offer everything from fresh seafood and Certified Angus steaks to burgers, pasta, pizza, and lighter bites, accompanied by tropical spirits and cocktails.

Sandy Feet Key Largo

For more than a quarter of a century, entrepreneur Robert DiGiorgio and his family have welcomed travelers and regulars alike to this one-of-a-kind location in Key Largo. Visitors can stay at the property’s Sandy Feet Key Largo, a sprawling 10-bedroom vacation rental that shares the same slice of paradise along Florida Bay.

“It’s extremely exclusive, hidden off the highway,” Robert says, describing the property with the quiet pride of someone who knows he’s landed on something rare. “Since you’re directly on Florida Bay, looking at the Everglades, you get to take in the sunset.” 

But the site is also centrally located, making it convenient for guests to walk to many places.

The property centers around a pair of massive stilted houses big enough to host weddings, milestone birthdays, or entire families who’ve scattered across the country and want a week together without losing privacy. Ten bedrooms sleep up to 20 guests, and the porch views roll out across still bay waters that turn golden at dusk. A 120-foot dock stretches into the calm shallows, where guests can tie up boats or sip drinks as seabirds glide overhead.

“People come and get treated to a resort-like atmosphere,” Robert notes. 

And that’s part of the draw. The compound feels curated but unfussy — a throwback to the kind of Keys hospitality that’s welcoming without being over-commercialized. The DiGiorgios offer the charm of a family-run business layered with the amenities of a resort in a place that feels removed from the hustle and bustle of Miami.

Restaurants Rooted in Key Largo Lore

If you’ve eaten in the Upper Keys, chances are you’ve come across the DiGiorgio name. The family has been an integral component of Key Largo’s dining scene for decades with its beloved spots. There’s Cafe Largo, an Italian-inspired space closer to the highway that leans on family recipes. And nearby, patrons can stroll to Bayside Grille and Bayside Sunset Bar, a breezy pairing perched above the bay with wall-to-wall water views.

While each restaurant has its own identity, all three share a common DNA: They’re unfussy, local, and built around delicious fresh food and warm service. And the DiGiorgios’ vacation rental brings the same ethos to overnight guests, offering the chance to fold into the family’s small waterfront world for a week at a time.

Guests often start their days over coffee on the deck before migrating to Bayside for lunch or sunset drinks. Others walk a few steps farther inland to Cafe Largo for homemade pasta and wine under the palms. “They tie it all together,” Robert explains. “It’s the kind of setup where everything just flows.”

It’s a formula that works for multi-generational families — grandparents, siblings, and kids — who crave connection without the crush of a large resort. One group might plan day trips to snorkel at John Pennekamp State Park; another might lounge dockside until dinner. 

Key Largo, the northernmost of the Florida Keys, has always been the gateway island. It’s a quick drive from Miami, yet far enough to reset your internal clock. Palm trees replace billboards as time slows to the pace of the tide.

The DiGiorgio property amplifies that feeling. It’s positioned directly on Florida Bay, looking west toward the low silhouette of the Everglades. From there, the sunset unfolds in wide strokes — burnt orange bleeding into purples and soft pinks. 

“Since you’re right on the bay, you get those same sunsets dining at Bayside Grille,” Robert says. “People will literally just walk out on the dock with a drink and take it all in.”

It’s a scene that repeats itself nightly. The bay goes still, the last boats idle back in, and conversation flows across both the restaurant deck and the private porch of the house next door. In those moments, you realize why people keep finding their way back.

Bungalows Key Largo

Twice a year, the quiet view turns electric. Just down the shoreline, Key Largo’s Bungalows Resort stages full-scale fireworks displays every Fourth of July and New Year’s Eve — twenty minutes of choreographed color lighting up the sky. The DiGiorgio property happens to sit in the perfect viewing lane.

“Guests are so pleasantly surprised that they can step out in the backyard and just take in a full fireworks display without having to drive anywhere,” Robert says.

The DiGiorgio family’s hands-on approach augments the experience. Robert and his relatives have long balanced the dual worlds of hospitality and local life, weathering the Keys’ ups and downs while keeping their identity intact.

Over time, the restaurants have become landmarks in the social fabric of Key Largo life. The vacation property extends that same sense of community to overnight guests — not a corporate resort, but a living, breathing family endeavor.

That personal touch shows up in small ways: welcome notes left for guests, the way that Bayside’s staff remembers birthdays, or how Robert can often be found checking on diners and tenants. It’s the kind of operation where repeat visitors feel like part of the extended family.

“People end up celebrating here year after year,” Robert notes. “They tie it all together — the restaurants, the rental, the sunsets, the holidays. It has become their tradition.”

Despite its tucked-away setting, the property is still close to Key Largo’s dive charters, eco-tours, paddleboard rentals, and grocery stores. Miami International Airport is only about 90 minutes north, making arrivals surprisingly easy for family groups converging from different places.

That accessibility, paired with the privacy of a full house on the bay, makes the spot equally appealing to Floridians looking for a staycation and out-of-towners craving immersion in authentic Keys life.

“It’s close enough to everything, but once you’re there, you feel like you’ve escaped,” Robert says.

A Family Legacy

On most evenings, Robert can be found between the two restaurants, watching as the bay trades daylight for twilight’s glow. It’s a view he never tires of, and one he still pauses to appreciate. Upon his arrival in Key Largo, he learned from locals that no sunset is ever the same.

“That’s really what it’s all about,” he says. “You come down here, you slow down, and everything connects — the people, the food, the water, the sky.”

For anyone seeking that sweet spot between retreat and togetherness, the DiGiorgio family’s hidden corner of Key Largo offers the Keys as they’re meant to be experienced — one long, unforgettable sunset at a time.

Robert’s father, Pasquale “Pat” DiGiorgio, who at 90 years old remains a fixture at Cafe Largo and Bayside Grille, brought his children to Key Largo in the 1970s and 1980s on weekend trips to the family’s second home. “By the time I was 14, I was fishing, diving and snorkeling,” Robert recalls. “We’ve always loved Key Largo.” 

Robert is a Miami native born into the restaurant business. When he was just two years old, his father and mother owned the famed Mary’s Italian Restaurant in North Miami. From there, they ventured over to Hialeah, where they developed a commercial property and opened Pasquale’s Italian Restaurant. They had a loyal following from Hialeah, Miami Lakes, and Miami Springs for many years, eventually relocating to the Florida Keys. 

In 1991, the family bought a building with a rich history. Built in 1960, the property had been the original Key Largo Moose Lodge, the Key Largo Shopper, and then the city’s only Goodyear store, where locals got their cars serviced. The DiGiorgios transformed the property into Cafe Largo, a full-service Italian restaurant with 165 seats. As they were building out the space, Hurricane Andrew hit South Florida. While the storm spared the Keys from catastrophic damage, the family had to work with no electricity, even relying on help from a crew of National Guardsmen to install a Caesarstone bar. 

“This was really a labor of love,” Robert says. “That bar is still there, and we still remember the guardsmen that helped us carry it inside.” 

In response to a demand for waterfront dining, the DiGiorgios expanded four years later, opening Bayside Grille, which offers a distinctly Keys energy. The outdoor restaurant has an open-air bar, live music drifting over the water, and plates built around fresh, locally caught fish. The upstairs features an air-conditioned space with an incomparable view of Florida Bay. Bayside has even become the spot for the most photographed sunset in Key Largo. People from all over the world bring their photography and video equipment. The property is also the port of call for Caribbean Watersports’ Carolina Moon, a 37-foot catamaran available for charters.

For guests staying in the vacation rental next door, it’s more than convenience — it’s continuity. “Guests have this rhythm where they’ll spend the day relaxing, come over for cocktails, and then walk back home under the string lights,” Robert says.

And when they want a shift in atmosphere, they can walk to Cafe Largo. It’s an entirely different mood — cozy, candlelit, and rooted in the DiGiorgio family heritage. Home-style Italian dishes like veal Marsala and linguine with clams offer a taste of tradition that contrasts perfectly with Bayside’s island fare. Together, the two spots — which were featured on Guy Fieri’s Diners, Drive-Ins and Dives a few years back — give guests every option without diluting the laid-back authenticity that defines Key Largo dining.

A Destination Built for Gathering

Step inside one of the vacation homes, and it’s easy to see how it functions as a hub for large groups. The main floor opens into a bright shared space framed by panoramic windows, leading to oversized decks that invite gatherings at every hour. Bedrooms are split across three levels — enough space for privacy, but close enough to still feel connected.

Kitchens are large enough for group cooking, though most guests skip that for the DiGiorgios’ kitchens next door. With restaurants just steps away, many opt to let the professionals handle the meals so they can focus on family time instead.

“There’s really nothing else like it in Key Largo,” Robert says. “You can have 20 people staying at one location, but you don’t need to figure out the catering or where to eat. It’s all right there.”

Outside, the dock becomes the daytime social hub. Boats pull in after a day of fishing or cruising the bay’s hidden coves. Kids fish from the pier while adults open a bottle and start the grill. As the sun drops, the colors over the water intensify, and dinner plans shift naturally to whichever restaurant feels right that night.

As the Keys continue to evolve — with new hotels rising and short-term rentals reshaping neighborhoods — small family operations like the DiGiorgios’ compound stand as reminders of the region’s more personal past. They capture what longtime residents call “Old Key Largo.” It’s a world of open doors, easy laughter, and sunsets shared among friends and family. 

Plan your visit at keylargorestaurants.com and sandyfeetkeylargo.com.