The Rooster's Retreat - Shipyard Key West

The Rooster's Retreat - Shipyard Key West Welcome to The Rooster's Retreat - A Key West Condo in the Truman Annex. Shipyard Unit #199
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Whoever said Mondays are boring has never spent one in Key West. 🌴🍸Kick off the night with Bingo at the Green Parrot (fr...
08/31/2026

Whoever said Mondays are boring has never spent one in Key West. 🌴🍸

Kick off the night with Bingo at the Green Parrot (free Jell-O shots + rowdy fun).

Then slip into the garden bar at Virgilio’s for $7 martinis—Espresso, Dirty, Cosmo, you name it.

Finally, stumble across the lane to Mary Ellen’s drunken spelling bee, where the laughs last all night.

In Key West, Mondays aren’t the start of the work week—they’re the start of the party.

The only thing missing from this photo is you and a cold beverage listening to the tunes coming from the stage!🍹🍹.... be...
08/30/2026

The only thing missing from this photo is you and a cold beverage listening to the tunes coming from the stage!
🍹🍹
.... because Sunset Pier is definitely THE place to be to watch Key West's world famous sunset!

🌅🌅
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One of my favorite Key West finds is The Roost, and the funny thing is, we found it completely by accident.We wandered i...
08/29/2026

One of my favorite Key West finds is The Roost, and the funny thing is, we found it completely by accident.
We wandered in one afternoon because we needed a little break from the nonstop Duval Street buzz. So we did. And then we kept coming back.

The Roost has a relaxed, slightly sophisticated vibe, comfy chairs and really good cold cocktails. And it's extra fun when Paul is behind the bar!

There are a few bar snacks, too, but my favorite part might be the happy hour. It runs all day until 6 p.m., which makes it an especially nice afternoon stop.

It’s one of those places that feels a little removed from the usual Key West hustle without actually being far from it.
🍸🌴

Cheers!


Louie’s Backyard is a must-stop for any Jimmy Buffett fan in Key West! 🌴🎶Located at 700 Waddell Avenue, this oceanside g...
08/29/2026

Louie’s Backyard is a must-stop for any Jimmy Buffett fan in Key West! 🌴🎶

Located at 700 Waddell Avenue, this oceanside gem is known for its incredible food, breezy cocktails, and legendary connection to Buffett himself.

👉 Head out back to The Afterdeck Bar for a drink and one of the best sunset views on the island—especially magical as the days grow shorter.

Fun fact: When Jimmy sang “I knew I could use a Bloody Mary, so I stumbled next door to the bar” in Trying to Reason with Hurricane Season, he was talking about Louie’s! Over the years, he often returned with his sisters, and this was the heartfelt spot chosen for his memorial celebration. 💛

It’s a little off the beaten path from much of Old Town and the port—walkable, but best enjoyed by bike or a quick Lyft. However you get there, it’s absolutely worth the trip.

Seats are waiting for you at Schooner Wharf Bar!This place is a Key West classic! It's located in the Historic seaport a...
06/23/2026

Seats are waiting for you at Schooner Wharf Bar!

This place is a Key West classic! It's located in the Historic seaport and my favorite place for peel and eat pink shrimp. They have live entertainment every day (including a fun magician) and it's also dog friendly. Another fun part: Morning Happy Hour!

If it's your first time down, definitely check it out!










This little list pretty much sums up my favorite things to do in Key West! What about you — what’s on your must-do list ...
06/01/2026

This little list pretty much sums up my favorite things to do in Key West! What about you — what’s on your must-do list when you’re here? 😎☀️

🌴 Fort Zachary Taylor Beach — best beach on the island, hands down. Pack a picnic and grab a shady table!
🌴 Captain Tony’s — watching people try to toss a quarter into the fish never gets old. Go ahead… take your shot! 🪙🐟
🌴 Happy hours + live music — it’s a full-time hobby down here. 🍹
🌴 Dessert to-go from Moondog Cafe — that pastry case is pure trouble (in the best way).
🌴 Wandering through the cemetery — quirky, historic, and so Key West.
🌴 Thursday Farmer’s Market on the Truman Waterfront — local goodies, live tunes, and perfect people-watching.
🌴 Exploring the side streets — the real charm hides off Duval.
🌴 Monday night bingo at the Green Parrot — laughter, locals, and Jell-O shots.
🌴 Sunset at the Truman Waterfront — less crowd, more peace. 🌅
🌴 Morning harbor walks with a café con leche from 5 Brothers — my favorite little ritual. ☕
🌴 Kayaking in the mangroves — just you, the water, and a whole lot of calm.

It’s not just a rumor anymore! One of the most exciting things happening on Duval St! This is going to be a crazy fun lo...
05/28/2026

It’s not just a rumor anymore! One of the most exciting things happening on Duval St! This is going to be a crazy fun location for The Tuna! 🐟🍹🌴

Seats are waiting for you at Schooner Wharf Bar!This place is a Key West classic! It's located in the Historic seaport a...
05/26/2026

Seats are waiting for you at Schooner Wharf Bar!

This place is a Key West classic! It's located in the Historic seaport and my favorite place for peel and eat pink shrimp. They have live entertainment every day (including a fun magician) and it's also dog friendly. Another fun part: Morning Happy Hour!

If it's your first time down, definitely check it out!








At the very top of the lower 48, Angle Inlet, Minnesota has its own Northernmost Point buoy!...but maybe the crowd there...
05/20/2026

At the very top of the lower 48, Angle Inlet, Minnesota has its own Northernmost Point buoy!...but maybe the crowd there is a bit more… spacious than the mostly-busy Southernmost Point in Key West.

Anyone pulled off both? That’s definitely good for a fun story— sunscreen to snowdrifts! 🏝️❄️

If you had to pick, where would you start first, HA !?!

This is simply 1.25 miles of awesomeness! But don't forget to take time and wander off to the side streets. Renting a bi...
05/18/2026

This is simply 1.25 miles of awesomeness! But don't forget to take time and wander off to the side streets. Renting a bike is the best way to do this!





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620 Thomas Street #199 Shipyard
Key West, FL
33040

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