Islamorada Dining Guide

Lifestyle
August 26, 2025
Islamorada Dining Guide

If you’re planning a trip to the Florida Keys — or you’re lucky enough to live here full-time — chances are, you’re wondering where to eat in Islamorada. From upscale seafood and steakhouses to casual spots with long-time local followings, Islamorada has quietly become one of the best food destinations in South Florida.

As lifelong locals (our family has been here since the 1950s), we’ve watched Islamorada evolve—and the restaurants with it. Here’s your local-approved guide to what’s new, what’s classic, and what not to miss next time you’re hungry in the Upper Keys.

New Restaurants in Islamorada (2025 Hot List)

Kindler at Three Waters Resort

(MM84)

Formerly the iconic Postcard Inn, the reimagined Three Waters Resort has officially reopened — and with it comes one of the best new restaurants in the Upper Keys: Kindler.

Their philosophy? Quality, sustainability, and local sourcing. Think wild-caught seafood, grass-fed meats, and ingredients you can feel good about. The vibe is elevated coastal — and the plates reflect that balance of craft and creativity.

Local Tip / Our Favs:
Tuna Crudo, Banana Leaf-Wrapped Mahi-Mahi, and the Yes, Please cocktail. Trust us, you want a reservation.

Flagler Station at Whale Harbor

(MM83)

This new waterfront steakhouse is a standout addition to Islamorada's dining scene. Flagler Station combines Prime steakhouse classics with the added bonus of the laid-back rooftop cocktail lounge that overlooks the Atlantic — and one of the best sunset views in town.

Expect a menu stacked with center-cut ribeyes, 22 oz Chateaubriand, Colorado lamb, and a full seafood spread that includes a 16 oz Australian lobster tail.

Local Tip / Our Favs:
Start with a drink upstairs during golden hour. Then order the  Colossal Crab Cocktail, Ribeye Center Cut 16 oz, and finish with an Espresso Martini.

Drift on the Beach at Islander Resort (MM82)

Romantic, scenic, and full of flavor — Drift on the Beach delivers a high-end experience rooted in simple, flame-cooked dishes. Located beachfront at the Islander Resort, this new restaurant blends coastal tradition with elevated technique, highlighting the ingredients themselves.

Local Tip / Our Favs:
Grouper, Lamb Chops, and the Gluten-Free Key Lime Pie. This is a perfect date-night spot — especially if you time it with sunset.

Tried & True: Islamorada Dining Favorites

Some restaurants just stick around—and these staples are proof that when the food (and vibe) are good, you don’t mess with a good thing.

Square Grouper Islamorada

Stylish, consistent, and fresh. Great seafood, strong cocktails, and both indoor/outdoor seating. We love the coconut shrimp and seafood stew—but the upstairs bar is our sleeper favorite for apps and views.

Green Turtle Inn

A piece of Islamorada history since the 1940s. The Green Turtle is known for hearty breakfasts, brunches, and comfort food with a Keys twist. Shrimp & grits, sticky buns, and bloody marys are staples.

Chef Michael’s

Elegant and inventive, Chef Michael’s is known for ultra-fresh local seafood, steaks, and creative specials like lionfish and hogfish. It’s upscale but welcoming — and consistently one of the best dining experiences in town.

Old Tavernier Restaurant & Lounge

Ask any local where they eat, and this name comes up. A casual spot with serious flavor—expect Greek and Italian family recipes, fresh seafood, and house olive oil straight from their grove in Southern Greece.

Whether You're Visiting or Moving Here — Come Hungry

The Islamorada dining scene continues to evolve, offering visitors and locals alike more variety than ever before. From sunset steakhouses and elevated island cuisine to classic Keys institutions, there’s something here for every palate.

And if you’re thinking about making Islamorada your full-time home (or finding your dream getaway), we’d love to help.

About Us – The Lindback Team

Our family has been part of the Islamorada community for generations. We raised our kids here, built businesses here, and know these waters, roads, and restaurants better than anyone. From helping clients buy their first island home to selling multi-million-dollar waterfront estates, we bring local knowledge, experience, and heart to every relationship.

With over $700 million in closed sales and a full-service, client-first approach, we’re here to guide you home — whether you're buying, selling, or just beginning to dream about island life.

📍 Want to talk Keys real estate?
➡️ Contact The Lindback Team
➡️ Browse Islamorada Homes for Sale