Sun and Fun-Seeking Guide to Islamorada

Any Keys trip starts in either Miami or Key West. Regardless of where you begin your Keys adventure, you’re taking the earliest possible flight.

Miami: If you’re flying into Miami, you’ll pick up your rental and get the heck out of dodge. You’ll need a reward for your bravery, so your first stop is Key Largo. To really set the tone for the trip, I’ll stop at the famed Caribbean Club for a smash burger, Snooks for their incredible smoked fish dip, or Alabama Jacks for their conch fritter.

Key West: If you’re flying into Key West, be sure to explore after picking up your rental car. Pop by Cuban Coffee Queen for breakfast and a cortadito and then take a walk. You’re officially in the Keys! Pro tip: grab lunch at Keys Fisheries in Marathon for a freshly caught meal.

After you’ve checked in to your accommodations, get acclimated and find a spot to watch the sunset before dinner.

After breakfast, take advantage of any complimentary activities your resort offers: beach yoga, paddleboarding, kayaking, snorkeling, and of course, being poolside or at the beach. After a full day of R&R, we’re heading to happy hour. For me, a Keys trip isn’t complete without at least one happy hour at Lazy Days. They have one of the best happy hours on the island with 2-for-1 peel ‘n’ eat shrimp and wings and a number of drink specials.

Pro tip: Skip the overcrowded trip to Robbie’s and get better tarpon views at the dock at Lazy Days.

You cannot go to the Florida Keys without getting on some type of watercraft.

Option 1: Go fishing. Islamorada is the self-proclaimed fishing capital of the world! Charter a boat, catch some fish.

Pro tip: Take advantage of a local hook’n’cook! Take your freshly caught fish to Chef Michael’s for lunch and for under $30, they will prepare your fish and provide you with salads and sides family style. Don’t forget to call ahead.

Option 2: Hit the famous sandbar.

If walking in the middle of the ocean is on your bucket list, there is no place better. This sandbar is a favorite pastime for locals and visitors alike. While your charter will likely have water floats for you to use, you’ll only be in about knee-deep water, so standing or sitting is completely normal. There are so many great charter companies to choose from, but for the best of the best, you’re booking small group charters with Captain Carly at Islamorada Private Charters, large group boat charters with Islander Girls, and everything in between with Spray Watersports. Whether you arrive by big boat, small boat, jet ski, or kayak, bring the vibe with your favorite boat drinks, beach snacks, and vacation-forward playlist. And don’t forget your reef-safe sunscreen!

Pro tip: Get on the water early with a bayside mangrove tour to see everything from manatees, dolphins, nesting birds, and of course, toilet seat cut (#IYKYK) before cruising over to the sandbar. Unless it’s a windless, no-cloud-in-the-sky kind of day. Then you start at Alligator Reef Lighthouse for the best snorkeling in the Keys. I’ve seen everything from black tip reef sharks, to sea turtles, dolphins, and even pink meanie jellyfish.

After you return to dry land, freshen up and keep the party going by heading to a bayside establishment for dinner and live music.

If it’s a quick weekend trip and you’re heading home, grab a coffee at Midway Cafe and soak up your Islamorada morning before heading home.

Extending your stay? There’s so much more Islamorada and the Florida Keys has to offer, so trust me when I say, there’s more where this itinerary came from!

Here are some of my top dining recommendations to visit during your stay.

Breakfast

Midway Cafe: This is the only place to get breakfast in my book, and if I could eat here every day, I would. Get there before 10 a.m. to avoid the out the door lines. Dare I say the best Key Lime Pie in the Keys?

Good food, great drinks, unforgettable time

Lazy Days: Most tourists will drive right past Lazy Days without a second glance, but for locals, it’s a top choice, especially for their daily happy hour specials. Show up early, grab a seat, and let the evening unfold.

Lorelei: Don’t leave without trying the Key Lime Colada! It’s as iconic as the stunning sunsets and live music that make this spot a true island staple. Equal parts lively and breezy, it’s the full Florida Keys experience in one place.

Tiki Bar at Three Waters: A vibey, can’t-miss tiki bar where the food and drinks are both firing on all cylinders. The kind of place that’s easy to stumble into and impossible to leave early.

Top-notch dining

Square Grouper: Another cheeky, local favorite where there is truly something for everyone. Pro tip: go at 4:20 p.m. and head upstairs to Sunset Lounge for happy hour then at 4:55 p.m., head downstairs and put your name in for a table. This place is first-come, first-served

Kindler: She is the newest star on Islamorada. New dining concepts in the Keys are hard to come by, and Kindler is truly impressive. Almost everything on the menu is wood-fired, adding depth of flavor to every bite. The staff and service are absolutely exceptional.

Dive of dives

Looking for a no-frills, late night with a host of different characters? Head to Hog Heaven for an oceanfront bar with cold drinks, good company, and zero pretense—exactly what a Keys dive bar should be. Want something indoors with AC? Check out Whistle Stop. Pool tables, darts, and my personal favorite, a smart digital jukebox where you pick the jams.