Boston hotelier buys Naples resort for $41M


  • By Louis Llovio
  • | 1:55 p.m. July 16, 2026
  • | 2 Free Articles Remaining!
Boston hotelier the Pyramid Global Hospitality has bought the Naples Bay Resort & Marina.
Boston hotelier the Pyramid Global Hospitality has bought the Naples Bay Resort & Marina.
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  • Charlotte–Lee–Collier
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The Naples Bay Resort & Marina has sold to a Boston hospitality investment firm for $41.25 million.

The property, which according to Collier County records sold in a pair of transactions, was bought as part of a joint venture between Pyramid Global Hospitality and Western & Southern Financial Group.

According to a statement from Pyramid, it will oversee the day-to-day operations and the resort will be part of its independent Benchmark Resorts & Hotels collection.

Naples Bay sits on the city’s upscale Fifth Avenue South. It has 85 guest rooms and suites, as well as residential-style cottages. There is a 97-slip full-service marina, 31,000 square feet of retail space, three bars and restaurants and nearly 15,000 square feet of indoor and outdoor meeting and event space.

There also is the private Naples Bay Club. It has three pools, a lazy river, an adult-only swim and relaxation area, a full-service spa and a 2,500 square-foot fitness center, as well as a TopGolf Swing Suite and a six-court tennis center.

Benchmark, according to its website, currently operates 44 properties across the continental U.S. as well as Grand Cayman, Bermuda and Hawaii.

In Florida, it operates eight properties including the Naples Grande Beach Resort and the Saddlebrook Resort in Wesley Chapel.

In a LinkedIn post, Pyramid’s CEO Warren Fields wrote that the company will “work hand-in-hand with the resort associates to build on all the amazing work they are already doing.”

 

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Louis Llovio

Louis Llovio is the deputy managing editor at the Business Observer. Before going to work at the Observer, the longtime business writer worked at the Richmond Times-Dispatch, Maryland Daily Record and for the Baltimore Sun Media Group. He lives in Tampa.

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