Bing Crosby, Ted Williams, Jane Woodward and President George H.W. Bush are some of the names who’ve visited Cheeca Lodge in Islamorada through the years.
And before Cheeca Lodge, the former Olney Inn’s first guest was President Harry S. Truman.
The storied resort — now a luxurious place with 243 rooms — in the heart of Islamorada could soon be in the hands of new ownership. That’s according to a recent Bloomberg report that Northwood Investors is seeking a buyer. And they’re hoping to reel in a buyer for $300 million, according to the report.
The resort was acquired by Northwood in 2011 for an undisclosed amount. The registered investment adviser is run by John Kukral, former president and CEO of Blackstore Real Estate Advisors.
Cheeca Lodge as many know it began in 1946, when the first hotel and restaurant opened for business on the property. Its history, however, goes back to the late 1800s, when the first homesteaders settled in Islamorada. Members of these pioneer families, the Russells, Parkers and Pinders are buried and memorialized at the cemetery. They farmed limes and pineapples, and built the Pioneer Cemetery that still stands.
The Richardson family, founders of Vick’s Chemical Company and the ones partly behind the Matecumbe Club, eventually took ownership of the property. They built a private residence on the grounds. The property was eventually sold to the Mills family, who opened the first hotel and restaurant on the island, known as Casa Islamorado.
In 1946, Clara May Downey from Olney, Maryland purchased the property and renamed it Islamorada Olney Inn. The 22-bungalow Olney Inn was destroyed by a hurricane, leading the property to change hands to Cynthia Twitchell, heir to the A&P Grocery fortune. She built the main lobby, oceanfront villas, tennis courts, a golf course designed by Jack Nicklaus and the world famous fishing pier.
Twitchell combined her nickname, Chee, and her husband’s name, Carl, to create the moniker Cheeca. The Twitchell’s then relinquished ownership to Carl Navarre, a Coca Cola executive, in 1976.
Cheeca Lodge welcomed famous guests who appeared on Curt Gowdy’s outdoor show “The American Sportsman,” which took place in Islamorada and ran from the 1960s to the ’80s. Islamorada’s reputation as the “Sportfishing Capital of the World” is often attributed to Gowdy.
The resort also served as home to President George H.W. Bush’s bonefish tournament for a decade. The Presidential Sailfish Tournament continues to this day.
In 2024, Cheeca Lodge unveiled 43 oceanfront suites to the property. The recent addition featured a new conference center and two ballrooms.
Nightly stays at the resort for late April range from $724 to upwards of $900 depending on the type of room.
