Review Author

Joey Skladany

Contributing Writer

After spending a day in my hometown of Naples, Fla., it’s easy to see why the oceanside locale has often been labeled as the “happiest city in America.” After all, there’s not much to complain about when the sun is shinin, and the seagulls are chirping, luring you to the Gulf’s turquoise waters like a siren song. 

But what was once considered a primarily retirement and vacation community is now brimming with world-class shopping, attractions, nature preserves, and dining, along with the tourists to explore everything the ever-evolving city has to offer. 

Through this very apparent, though somewhat jarring burst in popularity, historic hotels like the Inn on Fifth have remained a constant. The property, which sits above Naples’ lifeblood of bustling Fifth Avenue, welcomes guests in a long yet unassuming lobby fitted with a boutique gift shop. Not much, other than necessary renovations to mask wear and tear and keep up with contemporary style trends, has changed in its over 30-year history. 

Rooms in the main building are modern yet unstuffy with a black and white motif and bold pops of red — a departure from the cool blue tones often found in beachy destinations, yet the perfect backdrop to the main street’s ostentatious displays of wealth through sleek and shiny sports cars, oversized Chanel sunglasses, and diamond tennis bracelets. 

Those who book a stay at the Inn’s Club Level suites across the street enjoy larger rooms, free daily breakfast, happy hours, and 24/7 access to snacks and refreshments. Most of these accommodations also include balconies for the winding banyans and sky-high palm trees that line two rows of seemingly always-active sidewalks. 

The Inn’s prime location is, arguably, its biggest draw, as Naples’ downtown district is not only chock-full of one-of-a-kind art galleries, clothing stores, jewelry shops, restaurants, and ice cream parlors, but it also leads directly to the ocean where the city’s iconic pier (still under construction post-Hurricane Ian damage) makes the perfect backdrop for a sunset photo. If you choose not to venture off its grounds, the Inn offers a decent-sized gym, as well as a spa with treatments that range from salt scrubs and body wraps to facials and therapeutic massages. Its pool, surrounded by ample seating, a fire pit, and a bar, is also the place to unwind and completely disconnect from the trials and tribulations of everyday life. 

But perhaps the most surprising standout for the hotel is its exceptional housekeeping services. Every return to the room brought a sense of calm and relaxation, with items meticulously cleaned, folded, and organized, so you have no choice but to throw on a robe and enjoy the living space. Sometimes, it’s the little things that make the biggest impressions, much like Naples’ untampered beauty, that keep its residents and visitors content year-round. 

Fast Facts

Location: Naples, Florida

Address: 699 Fifth Avenue South, Naples, Florida 34102

Rating: Four-Star 

The Vibe: As the only hotel offering on Naples’ famed Fifth Avenue, the Inn has become as renowned as the street itself. It is also a must-visit for any prospective visitor who wants to ditch the oceanfront views of Vanderbilt Beach in favor of cosmopolitan life. 

Food + Drink: The property houses Ocean Prime and Truluck’s on its ground floor, though I highly recommend the latter for some of the best steaks and seafood that Southwest Florida has to offer. It touts a robust menu with standout dishes like prime meatballs, miso-glazed sea bass, lumina lamb chops, and ribeye, as well as Naples’ largest inventory of fresh stone crab claws. And don’t skip dessert — though key lime pie is a Sunshine State staple, the carrot cake with spicy pecans and warm butterscotch is a showstopper. 

Amenities: Outdoor pool with bar and restaurant; gym; spa; private ballroom and boardroom; cruiser bike rentals; complimentary shuttle service; dog-friendly 

Our Favorite Thing About the Hotel: Though Fifth Avenue is a place to see and be seen in affluent Naples, the Inn’s luxurious vibes also feel cozy, welcoming, and unpretentious. A recent staycation allowed me to completely detach from my surroundings, despite the area’s familiarity. And as someone who suffers from chronic anxiety, I can assure you that this is no easy feat. 

5 Nearby Attractions: Tin City Waterfront Shops, Naples Botanical Garden, Sugden Community Theatre, Cambier Park, Naples Zoo at Caribbean Gardens

Any Personal Neighborhood Recs?: Allow yourself to get lost among Fifth Avenue’s rows of unique businesses like Naples Soap Company and Silver Eagle Gallery, but don’t forget to appreciate Naples’ natural gems by venturing towards the beach, parks, or mangroves for outdoor exploration. 

Rooms: 119 rooms and suites

Pricing: Deluxe rooms start at $226/night

Closest Airport: Southwest Florida International Airport in Fort Myers (RSW)