[The Local's Guide] Stock Island At Sunset: Your Hidden Harbor Route 🌅

After watching another stunning Keys sunset at Mallory Square last night...

I couldn't help but smile, thinking about what was happening just a bridge away.

Because while everyone knows our famous Key West celebrations...

There's this other kind of sunset magic happening on Stock Island.

A different kind of beautiful.

Where working boats glide home at dusk...

Fresh catch gets unloaded while pelicans dive...

And the whole harbor turns to liquid gold.

Welcome to Safe Harbor Marina.

Let me paint you a picture of your perfect evening:

You pull in around 5:30...

(Early bird gets the best views. And dinner reservations.)

Park in the marina lot.

Walk past the processing houses...

Where massive ice machines hum and shrimp boats tower above you...

Follow that old wooden dock all the way out.

About 200 feet.

And then...

Pure Keys magic unfolds.

The sun starts its descent...

Painting the whole harbor in warm golden light...

While fishermen unload their day's catch...

And pelicans dive between the masts.

This is another side of paradise.

Raw. Real. Beautiful.

And after that sun drops...

You've got some serious decisions to make.

All of them delicious.

[YOUR AFTER-SUNSET FEAST GUIDE]

THE CLASSIC MOVE:
🍹 Hogfish Bar & Grill (Casual & Laid-Back)

Location: 6810 Front St, Stock Island, FL
Website: hogfishbar.com

Must-Try: The legendary Hogfish Sandwich – fresh, flaky hogfish with Swiss cheese, mushrooms, and onions, served on Cuban bread. Pair it with a cold beer or a rum punch for the full island experience.

Why We Love It: Old Florida vibes, picnic tables right on the dock, and no touristy crowds—just locals, fresh seafood, and epic sunset views.

THE ELEGANT CHOICE:
🦞 Matt’s Stock Island Kitchen & Bar (Upscale with Stunning Views)

Location: 7001 Shrimp Rd, Key West, FL
Website: perrykeywest.com

Must-Try: The Stock Island Lobster Ravioli, packed with local lobster and rich, creamy sauce. Don’t skip the Sunset Rum Punch—it’s the perfect way to toast the evening.

Why We Love It: Waterfront fire pits, comfy lounge seating, and a relaxed-yet-refined atmosphere. You can even sip your cocktail while watching boats head out for night fishing.

THE DOCK-TO-DISH EXPERIENCE:
🐠 The Docks Restaurant + Raw Bar (Fresh Seafood with a Working Waterfront Feel)

Location: 6840 Front St, Stock Island, FL
Website: thedocksstockisland.com

Must-Try: Peel & Eat Key West Pink Shrimp—sweet, tender, and served with house-made cocktail sauce. Pair it with a frozen Key Lime Colada for the ultimate tropical treat.

Why We Love It: This is the real deal—you’re eating right next to where the fishing boats bring in their daily catch. Sunsets here feel like a true island experience.

THE SOUL OF THE KEYS:
🍽️ El Siboney Stock Island (Authentic Cuban Cuisine)

Location: 5501 5th Ave, Stock Island, FL
Website: elsiboneyrestaurant.com

Must-Try: The Ropa Vieja—tender shredded beef in a savory tomato sauce, served with rice, black beans, and sweet plantains.

Why We Love It: A local favorite for authentic Cuban flavors, generous portions, and a cozy, family-friendly atmosphere. It’s the perfect spot to savor a hearty meal after a serene sunset.

THE HIDDEN GEM:
🍤 Roostica Wood-Fire Pizzeria (Italian Comfort with an Island Twist)

Location: 5620 MacDonald Ave, Stock Island, FL
Website: roostica.com

Must-Try: Their famous Shrimp Scampi Pizza, featuring local shrimp, roasted garlic, and mozzarella on a wood-fired crust.

Why We Love It: If you want something different from seafood, Roostica serves some of the best pizza in the Keys. Plus, their cozy patio offers a warm, inviting spot to wind down after sunset.

[WHAT YOU NEED TO KNOW]

THE PERFECT TIMING:
• Arrive 5:30pm
• Sunset colors begin 6:00pm
• Peak magic 6:45pm
• Dinner reservations 7:30pm

THE ESSENTIALS:
• Marina parking
• Bring cash (some spots are old school)
• Camera for those golden hour shots
• Light jacket (evening breeze)
• Comfortable walking shoes

PRO TIPS:
• Make dinner reservations early
• Chat with locals for their favorites
• Respect the working boats
• Tip generously
• Make memories

[WHY YOU'LL LOVE IT]

Here's what makes Stock Island special...

It's where working boats still paint the horizon...

Where fish houses keep ancient traditions alive...

Where sunset isn't just a moment...

It's part of the rhythm of life.

This is your chance...

To sit on a dock at dusk...

Watch pelicans dance...

Breathe in that salt air...

Taste catch that was swimming this morning...

And discover another beautiful piece of Keys magic.

Next week:
That secret backyard BBQ spot...
(And yes, there really is a password...)

See you at sunset,
Brian

Florida Keys Road Trip Team

P.S. Those garlic knots at Roostica? They've started friendships and tested marriages. Worth every carb. 🌴