Leave a Message

Thank you for your message. I will be in touch with you shortly.

Browse Properties
Sunlit pale coastal home with a silver metal roof, covered entry, shell-aggregate path and sculptural tropical planting.

Cheeca and the Islander Now Share an Operator. Here's What That Stretch of Islamorada Holds for Locals This Fall

Johnny Morris grew up in the Missouri Ozarks, fly-fishing streams for perch and smallmouth bass. At 16 he caught his first tarpon on a fly, fishing Buchanan Bank out of Bud N' Mary's Marina with his best buddy, his father and Capt. Sonny Eslinger. He told that story in June, when Bass Pro Shops, the company he founded, announced it had bought Cheeca Lodge & Spa, as Keys Weekly reported. On October 14, the company announced a partnership with Schulte Hospitality Group to acquire the Islander Resort next door at oceanside mile marker 82, with the two companies operating both resorts.

With World Wide Sportsman already part of the Bass Pro family, Bass Pro and its partner now run a continuous stretch of Upper Matecumbe Key. Most of that beachfront is built for overnight guests. For people who live in Islamorada, the most open door in the whole deal is a 7,500-square-foot nonprofit museum at the north end of the Islander, and the deal just committed $500,000 to it.

What changed hands, and when

The Cheeca purchase was announced June 16. The price was not disclosed. Keys Weekly noted that Northwood Investors had been seeking as much as $300 million, citing an April Bloomberg report, but that was an asking figure and not a confirmed sale price. The resort has 254 rooms, a nine-hole, par-3 course designed by Jack Nicklaus and a 525-foot fishing pier.

The Islander deal followed four months later. Bass Pro's nature-based resorts division is partnering with Schulte Hospitality Group to acquire it, and Keys Weekly reported on October 15 that financial terms were not disclosed. The Islander dates to 1951. It covers 24 acres, with 114 bungalows and suites plus 25 bayside villas. Its last reported sale was in January 2021, for $73 million.

Here is how Bass Pro's announcement describes the combined property:

"Together, Cheeca Lodge and The Islander will offer guests almost a mile of pristine private beachfront, nearly 400 accommodations, a world-class spa, five breathtaking pools, six unique dining experiences, Jack Nicklaus Signature par-3 golf and world-renowned fishing opportunities."

The third piece sits on the bay side. The same release names World Wide Sportsman Store & Marina as the "launch point" for anglers staying at either resort. The store is at 81576 Overseas Highway. George Hommell Jr. and Billy Pate founded it in 1967, and it later became part of Bass Pro.

Day to day, both resorts will be run by Joy Michelle Boyd, the Islander's current manager and president of the Florida Keys Resort & Lodging Association Chapter. She reports to Debbie Bennett, who leads Bass Pro's Nature-Based Hospitality Division and Big Cedar Lodge.

Where the gate closes

"Private beachfront" is the operative phrase. Here is what each venue on the stretch says about access, based on the resorts' own pages:

Venue Property Access, per the resort
Nicklaus par-3 golf course Cheeca Resort guests only; included in the daily resort fee
525-foot fishing pier Cheeca Described as a guest activity, with rods and licenses through Guest Adventures
Atlantic's Edge, Mia Cucina, Nikai Sushi Bar & Restaurant, Tiki Bar, 25 South Cheeca Listed with hours; Atlantic's Edge takes table reservations; no stated non-guest policy
Coccoloba Islander Described as serving guests, families and locals
Tides Beachside Bar & Grill Islander Open daily; kitchen 11 a.m. to 10 p.m. Tuesday through Saturday, 11 a.m. to 5 p.m. Sunday and Monday
Drift on the Beach Islander Part of the current dining lineup
Sandy's Bar Islander Poolside, seasonal hours through Guest Services

Coccoloba is the one restaurant on the stretch whose own description names locals. Its schedule is unclear, though. The Islander's main dining page lists it as open daily, while Coccoloba's own page shows lunch Friday and Saturday only, 11 a.m. to 4 p.m. Call before you drive over.

Cheeca's grounds also hold Pioneer Cemetery, where members of Islamorada's homesteading families are buried: the Russells, Parkers and Pinders, who farmed limes and pineapples here in the late 1800s. Travel coverage has described visitors reaching the cemetery through the lodge's welcome gate, with the caveat that access is sometimes restricted. Check with the front gate before planning a visit.

The museum outside the resort fee

The Florida Keys History & Discovery Center sits on Islander property, but it is run as a separate organization. A registered 501(c)(3), the Florida Keys History and Discovery Foundation, operates it. The center opened in 2013. Longtime local coach Rich Russell has chaired the foundation's board since it began.

Its 7,500 square feet hold permanent displays on Upper Keys history and coral reefs, rotating exhibits, a research library and a 35-seat documentary theater. It is open Tuesday through Sunday, 10 a.m. to 5 p.m. General admission is $15. Visitors 55 and older pay $12.50, students pay $6 and military visitors get in free. Islander guests get 50% off general admission, and the door is open to anyone who buys a ticket.

The center is the one place on this stretch where the new operators put money in on day one. Bass Pro, Johnny Morris, Darryl Schulte and other donors committed $500,000 to it as part of the Islander announcement. The release ties that gift to Islamorada's fishing heritage and to promoting the area's "captains, marinas, resorts, restaurants and other destinations" through Bass Pro's national and international customer base.

The center's fall lecture series is its most regular draw for the public. Each evening opens with a social hour at 5 p.m., and the talk starts at 6. Tickets are free for members and $10 for everyone else, according to Keys Weekly. The local chefs panel ran October 14, and the South Florida ghost stories night is set for October 28. After that, two talks remain this year. To reserve a seat, contact [email protected] or 305-922-2237.

The calendar on that mile, November through January

Between the museum talks and the fishing tournaments, the next three months on this stretch look like this:

  1. November 11: "The 14th Colony: the American Revolution's best kept secret," a lecture at the Discovery Center.
  2. November 12 to 14: Cheeca's 14th Annual All American Backcountry Tournament.
  3. December 4 to 6: the 63rd Annual Islamorada Sailfish Tournament. Festivities begin Friday, December 4, and fishing runs December 5 and 6.
  4. December 9: "The Florida sponge war: conflict between Key West and the Gulf towns," the last Discovery Center lecture of the year.
  5. January 22 to 24, 2027: Cheeca's 37th Annual Presidential Sailfish Tournament. The tournament series lists January 23 and 24 as the fishing days.

The Presidential tournament goes back to Cheeca's years as host of President George H.W. Bush's bonefish tournament, which the resort held for a decade. The sailfish event has continued since. It will be the first January edition under the new owners.

What "unite" commits to so far

The October announcement says both resorts "will continue normal operations through the transition while plans are being developed to enhance and unite The Islander and Cheeca resort properties." It adds that "every effort will be made to retain much of the charm and character" of both. KeysNews coverage describes plans to connect guest amenities across the two properties. Neither company has published a site plan, a construction proposal or a timeline.

So the pieces with firm dates and published prices are the ones listed above. The museum is open six days a week at $15. Two lectures remain at $10 each. Coccoloba's page names locals. The sailfish season runs from early December into late January. Anything beyond that depends on plans the new operators have not yet released.

If you own property along this part of Upper Matecumbe, or you're weighing a home near MM 82 as the two resorts become one, I'm glad to talk through how the changes around Cheeca, the Islander and World Wide Sportsman might fit into your plans. Request a private consultation with Ally Kelley, and we'll start from what is confirmed today.

Follow Us On Instagram