You’re looking at a map of Florida’s Gulf Coast, and your eyes probably drift straight to the big names. Tampa. Sarasota. Maybe Siesta Key because you’ve heard about the "world’s best sand." But then there’s this skinny, 12-mile sliver of land sitting right between the Gulf of Mexico and Sarasota Bay.
That’s Longboat Key.
Honestly, it’s easy to overlook if you aren't paying attention. It looks like a thin needle threading the needle between Anna Maria Island to the north and St. Armands Circle to the south. But if you actually zoom in on Longboat Key Florida on map, you’ll realize this isn't just another beach town. It’s a highly specific, somewhat quirky, and definitely expensive piece of geography that splits itself across two different counties.
The Weird Geography of a Split Island
Most people don't realize that Longboat Key is a bit of a geopolitical headache—in a fun way.
The island is almost perfectly bisected. The northern half sits in Manatee County. The southern half belongs to Sarasota County. Why does this matter? Well, if you’re living there or even just visiting, your zip code might be the same (34228), but your property taxes, school zones, and even which sheriff’s deputy shows up can change depending on which side of a literal line in the sand you’re standing on.
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The "main street" isn't a downtown strip with shops and cafes. It’s Gulf of Mexico Drive. Basically, it’s the spine of the island. It runs the entire 12 miles from the Longboat Pass Bridge in the north to the New Pass Bridge in the south.
If you’re driving it, you’ve got the Gulf on your right (if you're heading north) and the Bay on your left. But don't expect to see the water the whole time. Huge hedges and massive Mediterranean-style estates act like a wall. It’s a very private place. You sort of have to know where the public access points are, or you'll just be staring at expensive landscaping for twenty minutes.
Where Exactly Is It?
To find it, look for latitude 27.38° N and longitude 82.63° W.
If you’re flying in, you’re likely landing at SRQ (Sarasota-Bradenton International). From there, it’s a 25-minute crawl through traffic, depending on the season. In the winter? Good luck. The population swells from about 7,500 year-round residents to double that when the "snowbirds" arrive.
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- To the North: You’ve got Anna Maria Island. It’s more "Old Florida"—think flip-flops, colorful wooden cottages, and ice cream shops.
- To the South: You hit St. Armands Circle and Lido Key. This is the high-end shopping and dining hub.
- To the East: Sarasota Bay. It’s a playground for dolphins, manatees, and people who own boats that cost more than most people's houses.
- To the West: The Gulf. Just pure, turquoise water.
The Real Estate Reality Check
Let’s talk money for a second. If you’re looking at Longboat Key Florida on map because you want to buy a slice of it, you should know the market is in a weird spot right now.
As of late 2025 and moving into early 2026, the median home price has been hovering around $1.25 million. But here's the kicker: prices actually dropped about 11% to 12% over the last year. It’s a "buyer’s market" technically, but when the entry-point for a decent condo is still $600,000, "affordable" is a relative term.
I saw a listing just the other day—a 2-bedroom unit in the Longboat Harbour area—selling for about $590,000. On the flip side, some guy just bought a Gulf-front estate for $30.3 million. That’s the record for the island. It’s a land of extremes. You’re either in a sleek, glass-walled condo like the ones at the new St. Regis, or you’re in a quiet, older neighborhood on the north end like "The Village."
A Quick History Lesson (No, Seriously)
Before the luxury resorts and the $30 million mansions, Longboat Key was basically a giant seafood buffet for the Timucuan and Calusa tribes.
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Spanish explorer Hernando de Soto’s scout, Juan Anasco, reportedly rowed a "longboat" through the north pass in 1539. That’s where the name comes from. It wasn’t really "settled" by Europeans until 1891 when Thomas Mann (a Civil War vet) grabbed a homestead grant.
During World War II, the island was used as a target range for B-21 and B-26 bombers. They literally had gates across Gulf of Mexico Drive to stop the few cars that existed so planes could fly over and fire 50-caliber bullets into the sand. Imagine trying to explain that to a tourist today who’s just trying to find a parking spot at Whitney Beach.
Navigating the Island: Practical Tips
If you're planning to visit or explore, here is how you actually handle the island.
- Beer Can Island (Greer Island): This is at the very northern tip. It’s not a real island anymore—it’s more of a peninsula. It’s famous for the "driftwood" trees that have fallen into the water. Great for photos, but the current in the pass is dangerous. Don't try to swim across to Anna Maria. You won't make it.
- Public Access: Unlike Siesta Key, which has a massive public parking lot, Longboat is stingy. Look for the small blue "Public Beach Access" signs. Most have maybe 5 or 10 parking spots. If you aren't there by 9:00 AM, you’re walking a mile.
- The Food: Everyone goes to the Dry Dock Waterfront Grill. It’s almost a cliché at this point, but the grouper sandwich is actually worth the wait. For something quieter, head to Shore on the north end.
- The Environment: 90% of the properties here are at extreme risk of flooding. If you’re looking at a map and seeing how thin the island is, you’ll realize why. It’s basically a sandbar with fancy plumbing.
Actionable Next Steps
If you're serious about visiting or moving here, start by checking the tides. Because the island is so low-lying, "sunny day flooding" happens.
Check the local Town of Longboat Key website for beach nourishment updates. They spend millions of dollars every few years pumping sand back onto the beaches because the Gulf likes to take it away.
Download a dedicated parking app or use a GPS that shows real-time traffic for the Ringling Bridge. If that bridge is backed up, you aren't getting onto the island for at least 45 minutes. Plan your entry and exit times around the "rush hour" of people leaving the beach at sunset.