Boats Doing 150 Miles an Hour, Watched From a Bar Stool

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Florida Keys Road Trip | October 28, 2026

Hey Keys lovers! The glitter is swept up and the feathers are gone. Fantasy Fest ended Sunday.

And Key West, being Key West, is giving itself about five days off before the next thing arrives.

This Sunday the race boats parade into town, and by the middle of next week there will be forty-foot offshore powerboats running at better than 150 miles an hour a short distance off the Old Town waterfront.

Here is the part that should not work and somehow does.

You can watch the whole thing standing on land. For free. With a drink in your hand.

Almost nowhere else on earth can you say that about this sport, and the reason comes down to an accident of geography.

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❓ Keys Trivia

Offshore powerboat racing is normally a sport nobody watches in person, because it happens miles out at sea where spectators cannot follow.

In Key West you can see it from shore.

Why?

Answer at the bottom of the newsletter.

📣 The Mile Marker Roundup

November opens loud and then settles into the best stretch of weather the Keys get all year.

North to south.

🦞 The whole chain: Spiny lobster, still in season Florida spiny lobster runs through the end of March, so it is on good menus the length of US-1 right now. All the meat is in the tail, no big claws, and it is sweeter than the cold-water kind. Grilled, with butter and lime.

🦅 MM 56, Marathon: Last call on the hawk migration The fall raptor count at Curry Hammock winds down around the middle of November. Peregrines, kestrels and broad-wings funneling down the chain toward open water. A free show if you know to look up. Directions →

💀 Stock Island: Scarecrows and Skeletons in the Forest Still running at the Key West Tropical Forest and Botanical Garden. Scarecrows and skeletons built from recycled materials by local artists and students, placed along the trails through tropical hardwood. The Keys version of an autumn garden walk, and almost nobody outside the island knows it exists. Directions →

🚤 MM 0, Key West: The race boat parade Sunday, November 1. The boats come into town and get shown off before anybody races anything. Forty-foot hulls on trailers moving slowly through Old Town, which is a genuinely strange and wonderful thing to stand next to. Check the schedule -→ Race World Offshore 2026

🏁 MM 0, Key West: Race days Wednesday November 4, Friday November 6 and Sunday November 8. Racing off the waterfront, with testing and related events filling the days between. Check the schedule -→ Race World Offshore 2026

🎬 MM 0, Key West: Key West Film Festival November 18 through 22, centered on the Tropic Cinema on Eaton Street. Screenings and filmmaker programming in a town with a long creative streak of its own.

🌴 Partner Spotlight

Race Week, Then the Quiet Part

Two different Novembers are about to happen, and they are a week apart.

The first week belongs to the races. Key West fills up, the waterfront is busy, and the town has an engine noise running through it. If that sounds like your kind of week, go, and stay close enough to walk.

Then it goes quiet, and that is the part we keep telling you about. Average high around 81 degrees. Roughly two inches of rain for the entire month. Warm water, open restaurants, and the winter crowds still weeks away.

Mid and late November is the best combination of weather and value in the Keys calendar, and it is the stretch most people never think to book.

FloridaKeysResorts.com can help you compare places to stay from Key Largo to Key West, with nobody taking a commission out of the middle.

See Florida Keys resorts →

🧩 Deep Dive

The Sport You Normally Cannot See

Offshore powerboat racing has a problem that most sports do not.

It happens offshore.

That is not a joke, it is the entire difficulty. The boats are enormous, the speeds are absurd, the courses are long, and almost all of it takes place far enough out to sea that spectators standing on a beach see nothing at all. You can watch it on a screen. You can watch it from a boat, if you have a boat and you know where to put it. Mostly, you cannot watch it.

Which is why what happens in Key West is unusual.

To understand it you have to understand what is under the water around the island.

Most of the American coastline shelves out gently. You walk into the Atlantic off Florida's east coast or the Gulf side and the bottom falls away slowly, a foot at a time, for a very long way. Deep water is miles from shore, which is where the race course has to be, which is why you cannot see it.

The Keys do not work that way.

This island chain is the top edge of an old coral reef platform. The water around it is shallow and strange, cut through with channels, and in places the usable deep water comes in remarkably close to land. Key West has been a working deep-water port since the wrecking era precisely because of this. Big ships could get close. Navy ships could get close. The geography that made the island valuable in 1830 is the same geography that makes the race work now.

So the course can be laid out near enough to the waterfront that the boats are not specks.

You get engine noise you can feel in your chest. You get hulls coming out of the water. You get the thing offshore racing fans normally travel by boat to see, available to anybody standing on a seawall.

And because this is Key West, the seawall in question has bars behind it.

There is a version of this sport that costs a lot of money and involves a chartered spectator boat and a cooler. It is a good day. We are not talking anybody out of it.

But the free version is standing on land with a drink, watching something that in most of the world requires a helicopter.

👀 Where to Watch Without Paying Anybody

The VIP packages sell themselves. Here is the other list.

The Truman Waterfront and the harbor walk. Open, free, and oriented at the water. Get there early on a race day and bring something to sit on.

Mallory Square. You already know how to find it. On a race day it is doing a different job than at sunset.

The Hyatt and Ocean Key waterfronts and the bars along that stretch. Buy a drink, stand at the rail. This is the bar stool version and it is the most Key West way to do it.

A bicycle. Seriously. On race days traffic in Old Town is a problem and parking is worse. A bike turns the whole waterfront into one continuous viewing stand.

Two honest notes.

Conditions decide everything. Wind and sea state move race schedules, so check the day's plan before you commit a morning to it.

And the boats are loud in a way that surprises people. If you are bringing kids or anybody sensitive to noise, hearing protection is a real consideration, not a precaution.

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Big Event Week, Same Old Trick

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The shape is always the same. A place that is somehow still available, a price a little better than everything else you have seen, and an owner who needs the deposit today by Zelle because another family is asking about it.

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🍹 Four Things We'd Tell a Friend

Go to the parade, not just the racing.

Standing next to a forty-foot race hull on a trailer in a narrow Old Town street is a better photograph than anything you will get of a boat at speed from four hundred yards.

Park once and walk.

Or do not bring the car into Old Town at all on a race day. The island is two miles of walkable and the waterfront is the whole point.

Check the schedule the morning of.

Offshore racing runs on sea conditions. Plans move. A sixty second check saves a wasted morning.

Then come back three weeks later.

Late November has the best weather of the year and almost nothing competing for your attention. Different trip entirely, and the one we would book.

📖 One More Thing

Lost in the Keys: Mile Marker Thoughts is out.

It is about this drive. The bridges, the bars, the stops you mean to make and the ones you make by accident, and what goes through your head on a road that is mostly water.

If you have read it, a review helps more than you would think.

Get the book → Lost In The Keys

🕰️ Lore & Legends

Seventy Miles Past the End of the Road

Everybody thinks Key West is the end.

It is not. Keep going west another seventy miles, across open water with no land in between, and you arrive at a cluster of tiny islands called the Dry Tortugas.

Sitting on one of them is a fort.

Not a small one. Fort Jefferson is an enormous six-sided brick fortress covering most of Garden Key, built with something on the order of sixteen million bricks, hauled out there by ship in the middle of the 1800s because somebody decided the United States needed to control the shipping lane between the Gulf and the Atlantic.

They never finished it.

The foundations settled, the technology of warfare moved on faster than the masonry did, and the fort was obsolete before it was complete. It never fought a battle.

What it did instead was hold prisoners.

The most famous was Dr. Samuel Mudd, the physician who set John Wilkes Booth's broken leg after the Lincoln assassination. He was sent to the Tortugas, and when yellow fever swept the fort and killed the post surgeon, Mudd took over treating the sick. He was pardoned a few years later, in part because of it.

Today it is a national park. No roads, obviously. You get there by boat or seaplane, it takes most of a day, and the water around it is some of the clearest in North America.

Which is the detail that gets us.

The biggest brick building for hundreds of miles, built for a war that never came, sitting on a sandbar in the middle of the ocean, with a coral reef growing around it.

November is the right month to go see it.

✅ Trivia Answer

The deep water comes in close.

Most coastlines shelve out gradually, so offshore racing has to happen miles from shore where nobody on land can see it. The Florida Keys sit on an old coral reef platform where usable deep water runs in near the island, which is the same reason Key West became a serious port in the first place.

So the race course can be set close enough that you can watch it from the seawall.

A sport that is normally invisible, made visible by a reef.

If you are going to be down there for race week, hit reply and tell us where you plan to watch from. We will pass the good answers along to everybody else.

And if you are not, here is the one to put on the calendar.

Three weeks from now the engines will be gone, the island will be quiet, the average high will be eighty-one, and it will rain about twice all month.

That is the Florida Keys at their absolute best.

Almost nobody books it.

Until next week, keep your windows down and your watch off.

The Florida Keys Road Trip Team

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