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Courtesy Nautical Miles

The Yacht Charter That Changed How I See Naples

With chilled wine, breezy playlists and all logistics handled, Gulfshore Life’s Natasha Gonzalez sets sail with Nautical Miles for a luxury escape that redefines what it means to play tourist in your own town.

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BEST EXCURSION 

“Growing up in Naples, I’d frequently go boating with my best friend’s family. I was your typical Florida girl—zooming across the Gulf on Jet Skis and coasting along through channels gave me an unbound sense of freedom. Some things never change. In my adulthood, I’ve chartered plenty of cruises in search of that feeling of escape on the water,  but none have captured the effortless comfort of my first venture with Nautical Miles’ luxury fleet.

Last September, the sales team and I set out from Downtown Naples for a three-hour private yacht cruise through our local waters with Nautical Miles founder Justin Perun. While the entrepreneur admits he’s no sea dog (captains cover the nautical expertise), his role—and the heart of the brand—is crafting the experience around it. The fleet’s vessels range from 40 to 120 feet and includes everything from low-key day trips to over-the-top themed charters, like a recent Wine of the Sea excursion with Naples Sailing & Yacht Club featuring bottles aged underwater. This month, a tight guest list boarded a yacht docked steps from the track at the Formula 1 Miami Grand Prix for a VIP racing celebration that featured a catered menu and open bar—no jostling crowds required. 

Before we stepped aboard, the tone was set. A detailed preference sheet let us plan the day to a T—curating our food and drink setup and opting among sightseeing, dolphin-spotting and sunset routes. We chose a slower cruise through the shallows to catch sight of Port Royal and Aqualane Shores’ grand estates. 

Justin greeted us with Champagne in hand at a Naples launch site—a departure spot for Nautical Miles’ 19-vessel fleet, which also operates in Marco Island, Tampa and along the East Coast, with private dock pick-up available. The wine fridge was already stocked, he assured us, and since we’d passed on the private chef service, the crew tucked our sandwiches and charcuterie into the galley. That handoff turned out to be the heaviest lift of the day. 

We spent most of the afternoon on the aft deck, retreating into the cabin when we needed a blast of AC, the sliding doors open to the breeze and the Gulf views beyond. Our playlist drifted from a Bluetooth speaker we didn’t have to ask for. Those quiet conveniences—the chilled wine fridge, the music control, the ease of doing nothing—added up to something more refined than your typical sandbar Sunday. Curated but never fussy. 

Our Prestige 550 yacht comfortably fit our nine-person team. At one point, a few of us climbed up to the cockpit lounge to bask in the sun while I nestled into the aft deck’s L-shaped bench by the teak table for a quieter moment. The alfresco setup gave front-row views of the coastal mansions and cerulean water.

Justin told us he likes to surprise guests with small, personal gestures that leave an impression. When one couple was celebrating their wedding anniversary, he discovered their first dance song and played the tune as guests arrived and boarded the yacht. While we didn’t have anything specific to toast, the day felt like a celebration. From the water, my hometown all looked more vivid—the architecture, the town’s growing scale, the way it opened up to the sky. And swapping a sandy beach towel for cushy seating and a gently rocking yacht? Hard to top.  

Even for seasoned boat owners, there’s something indulgent about surrendering the wheel. No logistics, no cleanup—just a new perspective on familiar waters and the rare opportunity to simply kick back and enjoy the ride.”