Islamorda day trip itinerary stops

Islamorada, in the Florida Keys (mile maker 90-72), is our favorite village of islands. It's the sport fishing capital of the world, and we love all the locally owned restaurants, breweries, and beachfront hangouts.

When family and friends visit, we take them to our favorite spots, sure to please any first-time visitor. Today, we’re sharing our must stop Islamorada Itinerary for the ultimate day trip.

trailer trash bloody mary

First Stop: Robbies

Feed the Tarpon at this famous marina that gets thousands of visitors yearly. With that said, make sure you get there early. Grab a Trailer Trash Bloody Mary when you arrive, accompanied by its beef jerky straw, shrimp, and traditional fixings.

Islamorda day trip itinerary stops

upstairs bar with a great view-Post Card Inn

Second Stop: Post Card Inn

The Post Card Inn is our favorite spot to grab a lite bite with the best water view in town. We go to the adults-only raw bar, but they have family seating downstairs. We've had many items from the menu, including sushi, oysters, and fish dip. The menu changes regularly from what we've seen. We've sat for countless hours staring out into the picturesque Atlantic ocean. (updated 2024-currently closed for rennovations)

Islamorada Shopping

Third Stop: The Rain Barrel

If you want to do a little shopping, grab a lobster roll and score some complimentary Sangria, the Rain Barrel is your next stop. Take a picture with Betsy the lobster out front and enjoy the local art, jewelry, boutiques, and souvenirs the Keys offers. They even have a bar inside and offer free sangria with your purchase.

Islamorada brewing co

Fourth Stop: Islamorada Brewing Company

Islamorada Brewing Company is our favorite place to grab local brews, wine, spirits, and their homemade seltzers. They have a pet-friendly tropical beer garden on the back porch, and inside, they have board games to play at your table. They have some light food items, and sometimes a food truck is on-site. There's something for everyone here.

our favorite places to eat in Islamorada

Beyond its natural allure, Islamorada is renowned for its culinary offerings. From fresh seafood shacks to gourmet dining experiences, the village's restaurants serve delectable cuisine influenced by the area's coastal location. Here are our top recommended dining spots in Islamorada.

#1 Lazy Days Islamorada offers excellent views, tarpon feeding, and a unique experience of cooking your catch. If you're planning a fishing trip, check out our post, Cook Your Catch in the Florida Keys, for a memorable dining experience.

#2 Italian Food Company - I know what you're thinking: why am I telling you about an Italian restaurant in a region where fresh fish is on every menu and is some of the best in the nation? Well, this place is just that good. The owners are from Italy and specialize in hand-made pizzas and pasta dishes. My husband loves the Spaghetti Cacio e Pepe that, on special occasions, can be served and presented tableside straight out of a giant block of parmesan. Remember to save room for dessert - the Torta Ricotta E Pera is one of the best desserts I've ever had. It's a Ricotta cream and pear pie with a hazelnut crust; I get it every time I visit.

#3 Best Sunset View at Papa Joe's Waterfront-We had dinner and drinks here, and the food was pretty good; it was an opening week, and they didn't have a full menu yet, but the view here was truly captivating here at this amazing water-front restaurant in Islamorada. It now gets our vote for the best sunset view in Islamorada over other popular spots. You can check out the live webcam here and see for yourself. https://papajoeswaterfront.com/live-webcam/

#4 What the Fish Rolls: Located in the neighboring town of Tavernier, this restaurant with a canal view is one of our favorite lunch spots. It offers a delicious selection of locally caught specialties. Enjoy seasonal favorites such as crab cakes or lobster rolls and a wide variety of seafood buns and ready-to-eat entrées. Check out our Instagram to watch a short video detailing our recent visit-Exploring Islamorada Lunch Stops

Join our Florida Keys Happenings Facebook page. The group is dedicated to the many wonderful food offerings and activities in the Florida Keys. We’re sharing the best happy hours, water views, events, and love for Island Life.

Click here to join: Florida Keys Happy Hour and Happenings

Islamorada public beaches

There are a few public beaches in Islamorada. Anne's Beach is a famous public beach that offers a beautiful stretch of sand, clear waters, and the opportunity to relax and enjoy the tropical surroundings.

Another option is Founders Park, which features a man-made beach, swimming area, and various amenities such as picnic pavilions, sports facilities, and a dog park. Both locations are great options for enjoying the sun, sand, and sea in Islamorada.

Florida Beaches

We hope you enjoyed our islamorada itinerary

Please travel responsibly. The city of Islamorada does offer a free ride share.