Restaurant suggestions

Question

Visiting Islamorada for a long weekend in January. 3 couples in our 50s, 60s, staying at the Chesapeake Bay Resort. Looking for dining suggestions on Islamorada. We don’t need ‘fine dining’ but wouldn’t mind it. Priorities are good fresh local food, tasty cocktails, views. We’ll have cars so willing to travel to neighbouring keys if an easy (short) drive. Thanks for any input!

Answer

Islamorada is a fantastic spot for a long weekend, especially for couples who appreciate fresh seafood, scenic views, and relaxed yet high-quality dining. Being based at the Chesapeake Bay Resort gives you easy access to several excellent local restaurants along the Overseas Highway and nearby keys.

Here are some dining suggestions that combine fresh local food, tasty cocktails, and great ambiance:

Morada Bay Beach Café: Famous for its waterfront setting, sunset views, and Caribbean-inspired cuisine. The seafood is fresh, and their cocktails are inventive. Outdoor seating right on the sand makes it a perfect spot for a relaxed evening.
Lazy Days Restaurant: Located right on the water, Lazy Days is known for fresh fish, Key lime pie, and a friendly, laid-back atmosphere. Their cocktails are strong and well-crafted, and the views of the bay are excellent.
Chef Michael’s: A slightly more upscale option with excellent seafood and a focus on local ingredients. Perfect if you want a “special dinner” feel without being overly formal.

Other options worth considering if you’re willing to drive a short distance along the keys:

Green Turtle Inn (Islamorada): Historic spot with a charming ambiance, serving both seafood and American cuisine. Great for dinner with cocktails and a cozy vibe.
Robbie’s of Islamorada: More casual, famous for its dockside dining and tarpon feeding experience. Offers fresh seafood and casual drinks; fun if you want a lighter, more interactive experience.
Key Largo options (about 25–30 mins away): Places like Snook’s Bayside or The Fish House offer excellent seafood with waterfront views, making a short drive well worth it.

Tips for your dining experience:

Make reservations when possible, especially at popular spots like Morada Bay, as January weekends can be busy.
Consider outdoor seating to fully enjoy the bay views and the tropical weather.
Check daily specials or catch-of-the-day menus for the freshest seafood offerings.

Overall, Islamorada has a wonderful mix of casual and slightly upscale dining, with the majority of restaurants focusing on fresh, local seafood and vibrant cocktails. With your cars, you can easily explore neighboring keys for additional dining experiences without feeling rushed.