Luxury Boating in Old Naples: Marinas, Charters, and Waterfront Dining

In Naples, Florida, the boating lifestyle is a refined pastime—as central to the coastal enclave's identity as its "Golf Capital of the World" pedigree. From Gulf-front estates to restaurants and docks along Naples Bay to days spent aboard elegantly appointed yachts, this is a town where maritime living meets sophisticated taste. Whether you're an experienced boater, a seasonal resident looking to charter for the day, or simply someone who appreciates waterfront dining, Naples delivers a world-class experience on and off the water.

In this guide, we explore the top marinas offering yacht access and services, the most exclusive charters available for private cruising, and a curated collection of upscale waterfront restaurants that invite you to dock, dine, and unwind—all with the elegance that defines the Old Naples lifestyle.

In addition to its popular and well-appointed daily and short-term public marinas and the expansive Naples Boat Club, the city boasts several high-end marinas and notable yacht clubs.

Perfectly positioned in the heart of downtown, Naples Bay Resort & Marina offers everything from overnight slip rentals to private boat access for residents and guests. Its direct connection to the Gulf through Naples Bay makes it a favorite Paradise Coast destination for heading out to Keewaydin Island or the Ten Thousand Islands. The resort also boasts a full-service spa and upscale boutiques—ideal for those seeking a seamless resort-to-sea lifestyle.

Situated adjacent to Rookery Bay, the ultra-private Hamilton Harbor Yacht Club is one of Naples' most exclusive destinations for serious boaters. Members enjoy world-class steel-reinforced concrete boat storage, concierge fueling, and a sophisticated waterfront clubhouse restaurant that rivals any fine dining establishment in town. With immediate Gulf access and a serene natural backdrop, it's a hidden gem for those who prize discretion and distinction.

Tucked into Crayton's Cove, Naples Yacht Club (NYC) is among the world's most distinguished boating organizations. In addition to being the city's first and oldest private club, dating back to 1947, NYC also ranks as the top yacht club in Florida, fifth in the US, and a top 50 club in the world. For those fortunate enough to receive an invite, membership offers access to an extraordinary clubhouse, first-class dining, and a private marina for members and reciprocity with the Florida Council of Yacht Clubs. 

For those without a personal vessel—or simply seeking a curated on-water experience—Naples is home to a selection of private charter operators that redefine what it means to cruise in style.

The 105-foot luxury yacht Naples Princess offers both public and private cruises along the shimmering waters of Port Royal, Gordon Pass, and the Gulf. Guests can book narrated lunch or sunset dinner cruises, or reserve the yacht privately for celebrations, corporate events, or sunset cocktail affairs. With two open-air decks, a full-service bar, and exceptional onboard dining, it's a favorite for entertaining in motion.

Operating a meticulously maintained Hinckley 40 classic yacht, Night & Day Charters offers one of the most intimate and elegant boating experiences in Southwest Florida. Perfect for private parties of up to six, this charter specializes in sunset cruises, intercoastal dining excursions, and tailored itineraries. Expect handcrafted cocktails, Gulf breezes, and the kind of service that mirrors a five-star resort.

For a more adventurous yet equally luxurious option, Pure Florida, operating out of the Tin City waterfront, offers upscale excursions from dolphin-watching tours to customizable private charters for groups large or small. Meanwhile, BRADventures Dining Destination Charters go a step further, offering full-day cruises that include stops at waterfront restaurants across Marco Island or Fort Myers, complete with gourmet dining and optional beach anchoring. Expect to pay premium rates—often upward of $3,000 per day—but the experience is nothing short of bespoke.

There's something inherently indulgent about dining with a view, particularly when the scenery is of South Florida's brilliant Gulf Coast or the stunning yachts traversing Naples Bay. In Naples, that experience is elevated by an impressive selection of restaurants that pair exceptional food with marina-front ambiance.

A long-time favorite for locals and visiting yachters, The Boathouse on Naples Bay offers panoramic waterfront views, dockside seating, and a menu that leans into fresh seafood, hearty burgers, center-cut steaks, and nautical-centric cocktails. With four distinctive seating areas overlooking Naples Bay—the Gangway Lounge, Lido Deck, The Bridge, Lower Promenade—the Boathouse is a lively, coastal-luxe setting. It's one of the most accessible and enjoyable places to dine after a day on the water.

In addition to serving as a jumping-off point for charters, Tin City Naples plays host to over 30 shops and boutiques, as well as a handful of other attractions. It has exceptional dining options. Among them are the waterfront establishments of Pincher's Crab Shack and Riverwalk. For one of Naples' best burgers and to cure an ice cream fix steps from the Bay, M&M's Café is a local treasure. 

If you're mooring at Naples Bay Resort, you'll find an array of options at your fingertips. From the refined American cuisine at Indulge to cocktails and small plates at BlueWater Bar & Grill, each venue provides a casually elegant atmosphere with views of the marina. For something more spirited, Nosh on Naples Bay offers globally inspired bites, as does Blackbird Modern Asian, both featuring lively dining and social scene overlooking the water.

For a brunch favorite, head just north of the Tin City Bridge to EJ's Bayfront Café at the Naples Bayfront. Sail into the seafood-centric Dock at Crayton Cove, which offers four first-come, first-served slips. (The Naples City Dock is next door, should you find the restaurant’s docks occupied.)

Whether you're launching a vessel from your private dock, chartering a luxury yacht for a milestone celebration, or simply savoring an exquisite meal at water's edge, Naples offers a boating and waterfront experience defined by elegance, ease, and impeccable taste.

If you're ready to explore luxury boating in Naples, or you're interested in a home or investment property in Old Naples—or considering listing one of the area's extraordinary waterfront residences for sale—contact Andrew Christopher today to start your Naples real estate journey. From oceanfront estates to historic properties, let Andrew's experience and decades of firsthand knowledge of Old Naples guide you through this extraordinary and highly sought-after luxury real estate market.