Islamorada's New Dining and Art Scene: A Local's Guide to Morada Way and Beyond

The stretch of Old Highway between mile markers 81 and 82 has always been the quiet heart of Islamorada. On the third Thursday of every month, that quiet turns into something else. Galleries prop open their doors past sunset, the beer garden behind Florida Keys Brewing Company fills up, and the line at the Green Turtle Inn stops being a line and starts being a conversation.

If you have lived here a while, you already know the map. What you might not have clocked is how much of it has changed in the last two years.

The thesis, before the roundup

Islamorada's food and gallery scene has quietly reorganized itself around one walkable half-mile. Between the reopening of the former Postcard Inn as Three Waters Resort, the reimagining of Papa Joe's on its original 1938 footprint, and the steady programming of the Morada Way Arts & Cultural District, a resident can now put together an entire evening, drinks through dessert through a new piece of art on the wall, without touching the Overseas Highway between courses. That is a genuinely new fact about living here, and it is worth planning around.

What's actually new on the plate

Kindler at Three Waters Resort. The old Postcard Inn is gone. In its place, the reimagined resort brought Kindler, a wood-fired kitchen leaning on wild-caught seafood and grass-fed meats. If you are ordering for the table, the tuna crudo and the banana leaf-wrapped mahi are the plates that keep coming up. Reservations are not optional on a Friday.

Drift on the Beach at the Islander Resort. Beachfront, flame-cooked, and timed to sunset if you plan the reservation right. Grouper and lamb chops anchor the menu, and there is a gluten-free key lime pie that has become its own quiet local recommendation.

Papa Joe's Waterfront. The original Papa Joe's stood for almost 75 years before its 2010 demolition, and the reimagined Papa Joe's Waterfront reopened in 2024 on the same footprint. Tiki bar for adults, a lawn for families, dining room for the sunset. It is one of the only spots in the Upper Keys where the same address sees both the Atlantic and Florida Bay sunsets from the property.

Lido 73. The Wrights, who already own Italian Food Company locations in Islamorada, Tavernier and Key Largo, opened their fourth concept at 90451 Old Highway. The building used to be a dive center, and they kept the underwater photography by Stephen Frink on the walls. Menu skews grilled seafood, focaccia sandwiches, Cacio e Pepe arancini. Boat access from the water. Six days a week, lunch and dinner.

A quick reference for planning a week:

The galleries most residents still skip

The Art Walk has been running since 2011, and the galleries are open every day, not only on the third Thursday. Most residents cycle through the same two or three. The district is bookended by the Hurricane Monument at MM 82 to the north and the Green Turtle Inn at MM 81.2 to the south, and inside that span there is more than the drive-by suggests.

• Tayler Hale's studio. Tucked behind the beer garden at Florida Keys Brewing Company. Hale is a Key Largo native whose work reads as a study of the way light behaves on Keys water. If he is there, he is usually working.
• Jessica Ann Art. Owner-artist Jessica Ann Hessing sells tropical and marine paintings, photography, wearable art, and a sustainably produced line of candles with Keys-inspired scents. She was also commissioned to create the current version of the mermaid that stands outside the Lorelei.
• Morada Way Clay. A working ceramics studio and gallery featuring local potters. Good place to buy something that will not end up on a coffee table in a rental unit.
• Gallery Morada. The corner gallery at Morada Way and the Old Highway. American craft, nationally shown artists, and the visual cue that tells you where the district starts.

The Morada Way Art Walk runs the third Thursday of every month, 6 to 9 p.m., along Morada Way between MM 81 and 82. It has been a monthly institution since 2011, and it is one of the few nights when the food, drink, live music, and gallery hours line up on the same block at the same time.

How to actually do a Third Thursday

If you have driven past the crowd for the last five years and never actually parked, this is the practical version.

1. 6:00 p.m. — Start at Florida Keys Brewing Company. Grab something from the taps and take it into the beer garden. The custom hats and koozies are the honest tourist purchase your out-of-town guests will actually use.
2. 6:30 p.m. — Cross to Tayler Hale's studio. It is a two-minute walk from the beer garden. Even if you are not buying, the work-in-progress view is worth ten minutes.
3. 7:00 p.m. — Walk the galleries north toward the Hurricane Monument. Jessica Ann Art, Morada Way Clay, Gallery Morada. Fish printing at Gyotaku by Lisa Lee if you have never seen the process.
4. 8:00 p.m. — Dinner. Green Turtle Inn if you want the historic table. Kaiyo Grill if you want sushi. Chef Michael's if you want the tasting menu. Ma's Fish Camp if the kids are with you.
5. 9:30 p.m. — Sunset already passed, but the Lorelei's cabana bar runs late. Live music seven nights a week, and the mermaid out front is the one Jessica Ann Hessing built.

That is a full evening inside roughly one mile of highway. No one needs to drive between stops.

The old guard still worth the reservation

New openings are only interesting because of what they are added to. The places that have been anchoring Islamorada for decades are still doing the work.

The Lorelei Restaurant and Cabana Bar at MM 82 bayside is still the sunset the postcards were built around. Breakfast, lunch, dinner, live entertainment nightly, daily happy hour from 4 to 6. The Green Turtle Inn has been on the highway since the 1940s, and its breakfasts and brunches are the reason locals still book weekend tables there rather than treating it as a tourist stop. Florida Keys Brewing Company remains the most-celebrated micro-brewery in the island chain, and it still does the practical work of anchoring the Art Walk crowd.

Chef Michael's, Ma's Fish Camp, Kaiyo Grill, Morada Bay Beach Café, Pierre's, and the Islamorada Fish Company are all within walking distance of the district. Seven of Islamorada's most-referenced restaurants sit inside a corridor most residents can cross in ten minutes on foot. That density is the actual story.

One last calendar note

The 34th Annual Island Fest ran on March 28 and 29, 2026, at Founders Park (MM 87 bayside), organized by the Islamorada Chamber of Commerce. The 35th edition is already on the books for April 10 and 11, 2027. A juried art show with more than 100 artists, the Taste of Islamorada cook-off, the classic car show, and the "What Floats Your Boat?" homemade boat race are the anchors. If you have children in the house, the Island Nights Car Show at Founders Park and the I.CARE Trash Derby Festival, sponsored by the National Marine Sanctuary, are the two dates locals actually put on the fridge.

For a village of roughly 6,000 full-time residents, the density of what is actually happening inside a mile-long stretch of Old Highway is unusual. Most weeks it is easy to miss. On the third Thursday of the month, it is impossible to.

If your interest in Islamorada eventually turns from where to eat this Thursday to where you might live full-time, the boutique team at Sally Stribling Luxury Group has been watching this stretch of the Keys for decades. Let's Connect when you are ready.