Dave Portnoy, the founder of Barstool Sports, has paid a record $27.7 million for a waterfront home in Islamorada, Florida, ...

In an era where beach parking can cost more than a decent lunch, Anne’s Beach offers a refreshing financial reprieve – it’s completely free, a concept almost as rare in Florida tourism as snow. The ...

Between Miami’s glitz and Key West’s revelry sits a slice of old Florida so delightfully odd that it stops traffic—literally—along the Overseas Highway in Islamorada, where a massive lobster sculpture ...

Coral Keys Adventures recently announced the official launch of its new tour boat service out of Whale Harbor Marina, MM 83.4, in the Florida Keys. With the grand opening held on Aug. 13, the company ...

Driving up and down the Florida Keys, millions of people have traveled through Islamorada and over the series of bridges and fills that link Upper Matecumbe to Lower Matecumbe Key. While moving ...

The Sunshine State is a great all-year-round destination with many unique things to do. With 2172 km (1350 miles) of gorgeous ...

If you're near Miami or traveling along the Florida Keys, you don't want to miss out on the chance to see some aquatic shows ...

The Islands of Islamorada in the Florida Keys has the views, the amenities and the vibe of a five-star resort – without much ...

The Florida Keys compound is Portnoy's second Florida home; he also purchased a house in Miami for almost $14 million in 2021 ...

The property had been listed for $31.2 million in June 2025, the Wall Street Journal reported, and Portnoy, a Massachusetts ...

Sen. Ana Maria Rodriguez (R-Doral) filed a bill this week in the legislature to make the American flamingo the official state bird and desig ...

Dave Portnoy is expanding his real estate presence with a new Florida Keys residence, and breaking records while doing it.