An Insider's Guide To Islamorada, FL
Islamorada is a fisherman’s paradise. Situated between Florida Bay and the Atlantic, the waters of the Florida Straits stretch and creep into the mangroves, creating hidden pools and secluded flats perfect for casting for bonefish, snook, tarpon and redfish. About 10 to 20 miles offshore, the waters deepen and take on the azure hue of the Gulf Stream, and depending on the season, teems with sailfish and marlin, kingfish and wahoo. There’s a good reason it’s known as the sport fishing capital of the world.
We’ve been coming to Islamorada for as long as we can remember. When we started vineyard vines, this is where we took our crew for our first company outings. The people are salty, the sunsets are great, the fish never stop biting and the drinks are cold—what else could you want? Check out our insider’s guide before you plan your next trip.
Islamorada 101: What To Do

Go Fishing

There’s a reason why Islamorada is called the ​​Sport Fishing Capital of the World; virtually every type of fish worth catching swims in the surrounding waters. Whether you’re looking for an in-shore flats experience or an offshore, deep-sea adventure, there are plenty of guides, charters and shops worth checking out. We’re big fans of gearing up at Florida Keys Outfitters.

Kick Back And Relax

For a stretch of land that’s less than 7 square miles, there’s still plenty to discover around Islamorada. Anne’s Beach is renowned for its boardwalk and picturesque mangroves. Founders Park is home to a public pool, picnic areas and plenty of family friendly activities. And a boat trip out to Lignumvitae Key Botanical State Park makes for a great day trip.

Get On The Water

The Florida Keys are a paradise for people who love the water. Sailing, kayaking, scuba diving and swimming with dolphins at the Theater of the Sea are just a few of the must-try attractions during your visit. Or venture offshore about a mile to the famous Islamorada Sandbar for a family-friendly party scene unlike any other, on land or at sea.
Dining & Drinks

Green Turtle Inn

Part of the local scene since 1947, the Green Turtle still offers the same great casual vibe and local cuisine that has made it a mainstay for all these years. Learn more.

Morada Bay

Tucked away on a palm tree-spotted beach, Morada Bay is one of our favorite places to catch the sunset. Grab an Adirondack chair, some fish tacos and a cold beverage and watch the sky transform into a breathtaking show of color. Learn more. Learn more.

Islamorada Beer Company

Started by our friends Chris and Whitney Trentine, this is a great place to catch up with locals and enjoy a cold beverage. Learn more.

Lorelei Restaurant

We first discovered the Lorelei during Shep’s bachelor party back in 1999. And while most of that trip was (and still is) a little blurry, we knew that this was a place we’d keep coming back to. Even after all these years, it’s still our favorite spot to go after a day on the water to catch up with friends, enjoy a cocktail and some live music while taking in the sunset as locals and tourists congregate around a high-top table known as “Town Hall.” The drink of choice is always a frozen rum runner (for us, at least). And if aloe vera isn’t cutting it, a 151 floater will definitely take the sting out of your sun-kissed skin. Learn more.

Our Fishing Friends

Nate Weinbaum

Our friend Nate spent most of his life working hard, running his own construction business. Then one day, he started thinking: Every day is a gift, might as well spend it doing what you love. So, he started fishing full-time and never looked back. Read more.

Gary Skrobeck, Jr.

There’s an old saying in the fishing world—a guide gets to give somebody the best day of their life, and they get to do it every day. This idea is not lost on Gary Skrobeck Jr., an Islamorada native and son of a longtime Keys guide. Read more.

Connor Flamm

We met Connor a few years back when we needed a flats guide who knew where to find the fish. His affable demeanor and laid-back approach made for a great day on the water—it didn’t hurt that we caught a bunch, too. Read more.

Sandy Moret

Within the fly fishing community, Sandy is held with a reverence typically reserved for the likes of Tiger Woods or Tom Brady—and for good reason: he’s been throwing flies in the Keys, and around the world, for more than 40 years. We’ve known Sandy since we first started coming to Islamorada years ago, and no trip to Islamorada is complete without a visit to his shop, Florida Keys Outfitters. Whenever we get out on the water with him, we end up learning as much about life as we do throwing flies. Read more.

Key Destinations

Robbie's of Islamorada

Hand-feed massive tarpon, stock up on local wares or just feast on fresh seafood, you can do it all at this one-stop-spot for all the best of what Islamorada has to offer. Learn More.

Alligator Reef Lighthouse

Located about 3 miles offshore, this iconic lighthouse sits atop a stretch of water that bridges the shallow reefs of the Upper Keys with the deeper reefs of the Middle Keys, making it a prime spot for snorkeling and fishing.

Mooring's Village

Upscale accommodations, modern amenities and unbeatable ocean views are just part of the allure of this outstanding beach resort. Learn more.

Daily Activities

Work On Your Stand-Up

Stand-up paddleboarding is one of our favorite ways to explore the waters around Islamorada. It’s eco-friendly, a great workout and offers a unique perspective you can’t find anywhere else. We definitely recommend heading out for an adventure among the mangroves atop a board.

Two Wheel Tours

Whether you’re heading into town or along the Overseas Heritage Trail, going by bike allows you to enjoy the scenic beauty of Islamorada at a slower pace. The stretch between mile marker 80 and 90 along the Old Road offers ocean views and a pleasant woodsy residential landscape.

Relax & Refresh

Sometimes the best thing to do is grab a cold drink and do absolutely nothing at all. Islamorada’s beaches, resorts and wellness spas are must-visit destinations. Pack a book, fill a cooler, slather on the SPF and find serenity on your terms—our go-to is usually a simple beachside hammock.

Dive Right In

Anne’s Beach is probably the best spot for a dip with the family, as the water is shallow and the waves are minimal. But with beaches stretching along almost the entirety of the Atlantic side of Islamorada, finding a place to cool off in the waves shouldn’t present any challenges

What To Pack
Everything you need to bring when you’re bound for Islamorada.