How many people who stop at mile marker 17 for dinner, bait or a sunset drink have actually slept in one of Sugarloaf Lodge's 31 rooms? The listing that went public this spring leads with those rooms. Since 2005, though, the hotel has been the smallest part of what happens on this 10.6-acre stretch of gulfside Sugarloaf Key. The parts that keep people coming are a chef's restaurant, a working marina and an airstrip full of parachutes. All of them depend on the land changing hands carefully.
Where the Listing Stands in October
In April 2026, Ted Lund's Above the Fold reported that Sugarloaf Lodge was listed for $45 million. The package covers a 31-room waterfront hotel, a restaurant and bar, a tiki bar, a 5COP liquor license, commercial retail space and a three-bedroom residential unit. It also comes with 24 vested hotel development rights, enough to take the property to 55 rooms in a county where new hotel rooms are hard to come by.
A Florida Keys Free Press brief filled in the rest. It lists marinas, tennis courts, a tiki bar and events venue, office space leased to local businesses, and a 5,300-square-foot restaurant leased to South of the Seven.
Neither report names a buyer or a contract, and both present the lodge as a property on the market. Above the Fold said the property could go several ways: renovate what's there, build out the vested rooms, or reposition it entirely as a boutique waterfront resort.
Thirty-One Rooms, and Everything Around Them
The best way to see why the sale matters to people who never book a room is to list who's actually working on the property right now.
| On the property | What it offers | Posted schedule |
|---|---|---|
| South of the Seven | Chef-driven dinner, bar with light snacks | Dinner Tuesday to Saturday, 5 to 9 p.m.; bar from 4:30 p.m. |
| Sugarloaf Marina, 17015 Overseas Highway | Bait, tackle, fuel, boat and kayak launches, rentals, eco tours, fishing guides | Daily, 7:30 a.m. to 6 p.m. |
| The tiki | Sunset seats, drinks from the marina or restaurant | No posted hours |
| Skydive Key West | Tandem jumps that land on the airport property | About 350 jump days a year |
Each of these runs on its own schedule, and only the hotel depends on overnight guests. The marina sells fuel and bait to anyone with a trailer. Skydive Key West takes reservations online and fills the sky over Upper Sugarloaf most days of the year. The lodge's own website calls the tiki a place to watch the sunset with a drink from either the marina or the restaurant.
The Kitchen That Was Invited In
South of the Seven's backstory explains what the property has turned into. Chef Paul Kapsalis and his wife, Kris Kubik, own and run the restaurant inside the 1950s-era lodge. According to a Florida Keys tourism profile, the couple were part-time Lower Keys residents known for cleaning up and feeding neighbors after Hurricane Irma in 2017. They were then asked to come up with a restaurant concept for Sugarloaf Lodge and opened South of the Seven in April 2019.
Kapsalis trained at the Culinary Institute of America and has cooked at the James Beard House in New York and at the Inn at Blackberry Farm in Tennessee. He and Kubik ran Green Springs Bistro on Tampa Bay for nearly two decades before the Keys. The menu shows it. The tourism profile names whole-fried local rosefish with Thai chile sauce, tomahawk steaks, and drunken rum cake topped with toasted coconut and fresh cream as house favorites. It also singles out whole-fried soft lobster and fish collars as dishes regulars ask for. On a night when the boats bring in several kinds of grouper or snapper, Kapsalis serves them side by side as a flight. The restaurant's own site promotes the Tomahawk Club, a bone-in steak of 60 to 65 ounces.
"Find the best and freshest ingredients. Treat them with love and respect." Chef Paul Kapsalis's motto, as quoted by the Florida Keys tourism council
A practical note: the South of the Seven homepage lists dinner from 5 to 9 p.m. in one place and 5:30 to 9:30 p.m. in its footer. The menu and contact pages say 5 to 9 and suggest calling ahead, so a call before driving over is the safe bet. Day-to-day specials are posted on the restaurant's Facebook page.
Before the Restaurant, a Dolphin
The lodge has always been more than a motel. A Pennsylvania strip-mining company built it in the late 1950s, the same company that dredged and developed much of Sugarloaf Key. Its modern identity dates to 1973, when Lloyd and Miriam Goode moved down from Philadelphia, bought the property and raised their family there. Under the Goodes it became part marina, part motel and part gathering place.
The roadside draw was Sugar, an Atlantic bottlenose dolphin who lived in a lagoon on the property and performed every day. A 1997 report says Sugar lived at the lodge from 1968 until her death in 1997. She was blind in one eye and was not considered a candidate for release. Above the Fold writes that she's said to have inspired Carl Hiaasen's 1991 novel Native Tongue, the book that introduced Skink.
The guest list is a local legend of its own. Hunter S. Thompson was a frequent guest. He set off fireworks in the plumbing, drove Lloyd Goode to distraction, and ran his "Gonzo Tours" into the Sugarloaf backcountry from the property before he moved on to Boog Powell's Marina on Stock Island. The lodge and its airstrip appear in the 1989 James Bond film Licence to Kill. Curt Gowdy, Ted Williams, Paul Newman, Jonathan Winters, Mel Fisher and Jimmy Buffett all spent time there.
The airstrip in that Bond film is the same one Skydive Key West lands on today, and the anglers the Goodes served are the same customers the marina sells bait to every morning. The draws have changed, but the land still carries more of the property's traffic than the hotel does.
Wilma and the Twenty-Four Rooms
The turning point came in 2005. Hurricane Wilma's surge swept across the Lower Keys, and the lodge lost 24 rooms. According to Above the Fold, it never fully recovered and slowly fell into disrepair, even as its land and entitlements grew more valuable.
The listing's 24 vested development rights match the number of rooms Wilma took 20 years ago. Whoever buys the property will be deciding, in effect, whether to rebuild the hotel the storm cut down or put the whole site to a different use. Above the Fold notes that with so few new hotel opportunities left in Monroe County, properties with existing density rights, waterfront access and highway visibility have become especially attractive to investors.
For a dinner regular, a backcountry guide or a family that launches kayaks at the ramp, the hotel's long decline is part of why the tenants grew so important. Over the last 20 years, the best reasons to pull off U.S. 1 at mile marker 17 have been a restaurant brought in after Irma, a marina that's open every day, and a sky full of tandem jumpers. Lund closed his piece by noting that the next owner may keep parts of that history or reimagine the site entirely.
November on the Flats
Sitting on U.S. 1 between Key West and Marathon, the lodge has long drawn drive-to visitors and boaters looking for the nearby backcountry and reef fisheries. Next month brings the event that best fits that long history.
The 13th annual Sugarloaf Showdown runs Nov. 12 to 14. It opens Thursday with bag pickup, a mandatory rules meeting and the start of the silent auction, followed by two days of fishing and an awards celebration on Saturday. The Lower Keys Guides Association hosts it as a catch-and-release tournament for bonefish, permit and barracuda, with fly and spin divisions and a youth division. Keys Weekly reported that the 2025 field filled in under 48 hours. Entry is $350 per boat, and online auction proceeds go to the Guides Trust Foundation, which helps Keys fishing guides and their families through crises.
The tournament began as a small, homegrown way to bring anglers to the Lower Keys in the quiet fall season. "It's a chance for our community to come together, spend time on the water with family and friends and celebrate the incredible fishery that makes the Lower Keys so special," tournament director Jessyca LaBadie told Keys Weekly. Tournament week also falls on nights South of the Seven serves dinner, Thursday through Saturday, so a table after the weigh-ins is one phone call away.
If you'd like a closer look at how sales of legacy properties like Sugarloaf Lodge have played out in the Lower Keys, Ally Kelley would be glad to talk it through with you. Request a private consultation, and we can cover what entitlements, vested rights and waterfront parcels mean for your own corner of Sugarloaf Key.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
