October in the Keys: Taste the Keys, Best of the Upper Keys, and a Glass Bottom Boat That Moved

By Local Keys Guide

#Florida Keys#Events#October#Key Largo#Islamorada#Key West

October is when the Keys wake back up. The water drops a degree or two, the first cold front makes everybody pull out a hoodie they don't need, the September "Gone Fishing" signs come down, and by the third week the Overseas Highway has traffic again. Before that happens, there's a stretch of the month that belongs to the people who live here. This year the Upper Keys get most of it.

1. Taste the Keys runs all month (Oct 1 to 31)

The Key Largo Chamber of Commerce's Taste the Keys is a month of prix-fixe menus at 22 Upper Keys restaurants, $17 to $75 a person plus tax and tip. It's the cheapest way to eat at a place you've been meaning to try.

The list runs from Key Largo staples like Mrs. Mac's Kitchen, The Catch and Zaika Indian Cuisine to the bayside sunset spots, down to a couple of Islamorada places. Vicky Bakery is on it too, if your idea of a prix fixe is pastelitos. Here's the whole lineup, with a listing for every one:

Key Largo

Tavernier

Islamorada

There's also a Signature Dish Showdown, where diners vote for the best plate of the month. Order the dish the restaurant is entering. That's the one the kitchen is trying hardest on.

The trolley tours. Two nights, 5 to 9:30pm, a tasting and a drink at four stops each. $150 a person ($125 for Chamber members), 21 and up.

Thursday, Oct 15: Snook's Bayside, Sol by the Sea, Lido 73 and Mrs. Mac's.
Thursday, Oct 29: The Catch, Sundowners, Buttonwood Grill and Zaika.
Local Tip: Book the trolley. Nobody has to be the designated driver on US 1, and you'll hit four places in one night that would take you a month of Tuesdays on your own.

2. Best of the Upper Keys: get your votes in

Keys Weekly's Best of the Upper Keys is the one local award that people up here actually argue about. Nominations run once a day through Sunday, Oct 4, at 11:59pm, so if you're reading this on the 4th, you still have tonight. Go nominate the bartender who remembers your order, the mechanic who didn't overcharge you, and the breakfast spot you'd rather tourists didn't find.

Winners get announced in Keys Weekly once the votes are counted. Watch for it. It's the closest thing the Upper Keys have to a locals' cheat sheet. Until then, here's ours: the Upper Keys guide.

3. The glass bottom boat moved to Bass Pro

If you've been to Islamorada any time in the last few years, you may remember the Transparensea glass bottom boat running out of Robbie's Marina. It doesn't leave from there anymore. The boat now runs out of the World Wide Sportsman marina at mile marker 81.5, bayside, the big Bass Pro Shops property about 4 miles north of Robbie's.

This matters because a lot of older listings, reviews and travel sites still say Robbie's, and it's an easy way to end up at the wrong marina ten minutes before departure. Park at World Wide Sportsman and walk to the bayside marina out back. Their directions page has the details.

The boat itself is the same: 46 feet, 16 underwater viewing windows, and a Seakeeper stabilizer that takes most of the roll out of the ride. Day trips go out to Cheeca Rocks, Alligator Reef or Caloosa Rocks. The night glass bottom boat tour leaves just before sunset and uses underwater lights to bring up moray eels, octopus and lobster, which is the reef most people never see. In October the water is still clear and the sunsets get early enough that the night trip doesn't keep the kids up too late.

We added them to the guide this week: here's our Transparensea glass bottom boat tours listing, with tour times, prices and a booking calendar right on the page. Or start from their own site for glass bottom boat tours in Islamorada.

Local Tip: Take the 3pm day tour on Thursday, Oct 15, then walk over to the Morada Way Art Walk (6 to 9pm, between mile markers 81 and 82). The boat is back by about 5, and the art walk is right next door.

4. Stone crab season opens Oct 15

Claws are legal from Oct 15 to May 1 and have to measure 2 7/8 inches. Every fish house in the Keys has a line that first week. It's worth standing in. Get them cold, cracked, with mustard sauce, and don't let anybody talk you into heating them up.

5. REEF Fest, Key Largo (Oct 15 to 18)

Four days of dives and conservation talks, run out of REEF's Ocean Exploration Center at 98380 Overseas Hwy. Divers, this is your week in Key Largo. Everyone else: go to the evening happy hours anyway. That's where you meet the people who know where the fish are.

6. Fantasy Fest, Key West (Oct 16 to 25)

Ten days of costume parties and street fairs. This year's theme is "Musical Icons and Iconic Musicals." The parade is Saturday, Oct 24, on Duval. Old Town rooms for parade weekend are close to gone. If you're not into it, this is the week to stay in the Upper Keys and let Key West have its fun.

The October Short List

Thursday, Oct 15 is the day. Stone crabs open, the first trolley tour rolls, REEF Fest starts and the Islamorada art walk is that night. Pick two.
Eat one Taste the Keys menu a week. Four weeks, four restaurants, nobody has to cook.
Take somebody who doesn't snorkel to the reef. That's what the glass bottom boat is for.
Watch the weather. Hurricane season runs through Nov 30. October is usually quiet, but usually isn't always.

Enjoy it. By Thanksgiving we'll all be complaining about traffic again.

Slow down... you are on island time, baby! 🌴