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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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!





Just off Duval on Petronia Street, Red Shoe Island Bistro is one of Key West’s best-kept secrets. There are only two din...
05/18/2026

Just off Duval on Petronia Street, Red Shoe Island Bistro is one of Key West’s best-kept secrets. There are only two dinner seatings a night. It's a pretty unique vibe!

I love the yellowtail snapper, seared scallops, and the lavender cheesecake everyone talks about. It's one of the few places where you definitely need to make the reservation! 🍋🍰

If you haven’t been to Harpoon Harry’s, I think you’re missing out on a true Key West staple. This cash-only, old-school...
05/10/2026

If you haven’t been to Harpoon Harry’s, I think you’re missing out on a true Key West staple. This cash-only, old-school diner across from the Seaport serves up hearty comfort food all day long — from massive breakfasts to late-night plates that hit spot on.

The vibe is a bit quirky yet cozy, but certainly nothing fancy or touristy, which is exactly the point. The staff, many of whom have been there for years, treat you like a regular from the moment you walk in.

It’s busy for a reason: great food, great people, and the kind of local charm that makes you feel like you’ve found the “real” Key West.

Louie’s Backyard is a must-stop for any Jimmy Buffett fan in Key West! 🌴🎶Tucked away at 700 Waddell Avenue, this oceansi...
05/08/2026

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

Hank’s Hair of the Dog Saloon on Caroline Street is one of my go-to spots. It’s dog-friendly, always lively, and there’s...
05/08/2026

Hank’s Hair of the Dog Saloon on Caroline Street is one of my go-to spots. It’s dog-friendly, always lively, and there’s almost always live music thanks to a steady mix of local favorites and touring acts playing daily, year-round.

Garbo’s Food Truck is right there too—yes, the one from Diners, Drive-Ins & Dives. Everything’s good, but the Cayo shrimp tacos are my absolute favorite and the reason I never leave hungry.
Music usually starts around 1:00 p.m., happy hour runs 4:00–6:00 p.m., and the food truck stays open late—perfect for when a quick stop turns into the whole night.

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 ...
05/08/2026

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, bring a travel hammock and grab a shady table! Hold on to your receipt and come back for the sunset. Or just stay all afternoon into the evening. The best day ever.
🌴 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 very Key West.
🌴 Thursday Farmer’s Market on the Truman Waterfront — local deliciousness and products by artisans.
🌴 Exploring the side streets — the real charm hides off Duval. This is exactly where you will find unique charming homes like this!
🌴 Monday night bingo at the Green Parrot — laughter and Jell-O shots. All proceeds go to charity.
🌴 Sunset at the Truman Waterfront — less crowd, more peace. 🌅
🌴 Morning harbor walks with a café con leche and a breakfast sandwich from 5 Brothers — my favorite little ritual. ☕
🌴 Kayaking in the mangroves — just you, the water, and a whole lot of calm.



📷 DatGuy in Paradise

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620 Thomas Street #199 Shipyard
Key West, FL
33040

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