Islamorada Local Guide: Where to Eat, Play and Explore

Local Keys Guide put this Islamorada guide together straight from our own Islamorada listings, so every address, hour and price below comes from the business itself. It covers where to eat, what to do on the water, where to explore outdoors, and where to shop and get taken care of. Jump to the section you need.

Where to Eat

Islamorada Shrimp Shack has been family-owned since December 2011 and it was on Diners, Drive-Ins and Dives in 2016. Order the shrimp fritters with remoulade or the shrimp and grits; local fish comes "Senator" or "Continental" style. It sits at mile marker 81.9 at 81901 Overseas Hwy, open 11:30 am to 9 pm and closed Wednesdays.

Bad Boy Burrito is inside the Village Square at the Trading Post at 81868 Overseas Hwy, serving handmade burritos, tacos and sushi made fresh with organic, locally-sourced ingredients, including Key West pink shrimp, Kobe ground beef and grilled tofu. Try the signature "Hot, Salty, Sweet" Kobe burrito or the Cayo Hueso fish tacos.

ReelCatch is the restaurant at Amara Cay Resort, oceanfront at mile marker 80 at 80001 Overseas Hwy, with Alligator Reef Lighthouse on the horizon. It does breakfast daily 7 am to 11 am and dinner 5 pm to 10 pm, with happy hour from 4 to 6 and live music Thursday through Saturday.

Kindler at Three Waters Resort opened in January 2025 at 84001 Overseas Hwy, mile marker 84. The open kitchen is built around a wood-fired hearth, and nearly everything comes off it: wild-caught local seafood and free-range, grass-fed meats. Dinner runs Wednesday through Sunday 5 pm to 10 pm, with brunch Saturday and Sunday 10 am to 2 pm. Closed Monday and Tuesday.

Trading Post of Islamorada is a family-owned grocery at 81868 Overseas Hwy that has served the Keys since 1966, open 24 hours a day, 365 days a year. The full-service deli is known for its fried chicken and key lime pie.

On the Water

Robbie's of Islamorada is a working marina at 77522 Overseas Hwy, mile marker 77.5, open 7 am to 8 pm. Buy a bucket of bait at the tarpon feeding dock and the "Silver Kings," some over 100 lbs, come up off the pier to grab it. Rent a kayak or paddleboard for the mangrove tunnels, or browse the open-air vendor village.

Transparensea Glass Bottom Boat Tours leave from the World Wide Sportsman bayside marina at 81576 Overseas Hwy, mile marker 81.5. The 46-foot boat has 16 underwater viewing windows, so you watch the reef go by without getting wet. Day reef tours to Cheeca Rocks, Alligator Reef or Caloosa Rocks depart at 9:30 am, 12 pm and 3 pm, $75 for adults, $60 for ages 5 to 17, free under 5. The night tour leaves 15 to 30 minutes before sunset, when underwater lights bring out moray eels, octopus and lobster. The bayside sunset cruise is $50 for ages 5 and up. All trips run about two hours.

DirtyBoat Charters runs fishing trips out of Robbie's Marina at mile marker 77.5 on a 42-foot air-conditioned sportfisher, with Captain Kit Carson at the helm. The boat built its reputation on split charters, where two to four anglers who didn't arrive together share the boat and pay for their seat: $525 all in for the 6-hour split, $625 for the 8-hour. Private trips run from $1,400 for a 4-hour half day to $3,200 for the 10-hour daytime swordfish hunt. Hours are 6 am to 6 pm daily, with online booking and text available 24/7.

Outdoors

Anne's Beach sits at mile marker 73.5 on the Overseas Highway (73141 US-1) and is open daily from sunrise to sunset. The shallow water is good for wading and kayaking, and a 1,300-foot boardwalk winds through the mangroves. There are covered picnic pavilions, tables and restrooms, plus two parking lots along US-1. No lifeguards, dogs must stay leashed, and motorized boats and personal watercraft aren't allowed. The consistent winds also make it a popular kiteboarding spot.

Windley Key Fossil Reef Geological State Park is at 84900 FL-5, on land once quarried for the limestone used in Henry Flagler's Overseas Railroad. Walk the trails between walls of fossilized coral, then catch the visitor center exhibits on the railroad and the fossil reef.

Shops and Services

Rain Barrel Village at 86700 Overseas Hwy, mile marker 86.7, is a pet-friendly collection of artisan shops, galleries and eateries among tropical gardens. It's home to Betsy the Lobster, a 30-foot-tall, 40-foot-long sculpture of a Florida Keys spiny lobster, crafted in the 1980s by artist Richard Blaze and brought to the village in 2009.

Sway Islamorada is a boutique at 81585 Old Hwy, mile marker 81.5 oceanside, with coastal-inspired women's fashion, beachwear, jewelry, sunglasses, hats and handbags. It's open Monday through Saturday 10 am to 6 pm and Sunday 10 am to 4 pm.

Tackle Center of Islamorada at 82661 Overseas Hwy is a fishing tackle store stocked with rods, reels, lures, hooks, bait, tools and apparel for men, women and children. It also offers charter services.

Ciao Bella Salon and Day Spa of Islamorada at 82913 Overseas Hwy is a salon, day spa, wellness center, boutique and yoga studio, offering personalized treatments, yoga practices and a curated selection of beauty and wellness products.

Plan Your Day

Start at Robbie's when it opens at 7 am and feed the tarpon before the day fills up. Then head up the road for the 9:30 am Transparensea reef tour at mile marker 81.5 and have lunch down the street at Islamorada Shrimp Shack (closed Wednesdays). Spend the afternoon wading or picnicking at Anne's Beach at mile marker 73.5, then return to the marina for the night glass bottom tour or the bayside sunset cruise. Finish with dinner at ReelCatch, which opens at 5 pm with the lighthouse on the horizon, or at Kindler Wednesday through Sunday.