Day Trip to Islamorada

Islamorada sits at the top of the middle Keys — roughly 75 miles and 90 minutes from Key West along the Overseas Highway. It's quieter than Key West, more established than Marathon, and has a claim to being the sportfishing capital of the world that nobody seriously disputes. For a day trip, it's the right combination of accessible and authentic — you'll see fishing boats in the harbor, eat well, and find snorkeling that's better than what the Key West tour boats offer.

Robbie's Marina — Feed Tarpon from the Dock

Robbie's at mile marker 77.5 is the most iconic stop on the drive up the Keys. The marina basin is full of tarpon — 50, 80, sometimes 100+ pound fish that gather at the dock waiting to be fed. You buy a bucket of bait (roughly $5) and hand-feed them from the dock. It's a genuinely unusual experience — these are large, powerful fish, and they're used to being hand-fed by tourists, which makes it both more and less impressive than it sounds.

The marina also has a full-service restaurant, kayak and paddleboard rentals, and is the departure point for several snorkeling tours. If you're driving up from Key West, stop here for 45 minutes before heading further north.

Sportfishing Charters

Islamorada's charter fleet is the main event if you're serious about fishing. Options range from shared half-day reef trips ($300–$500 for up to 4 people) to full-day offshore charters ($800–$1,500+ depending on the target species and boat).

Key species by season:

• Tarpon: March–June (peak: April–May). The signature Islamorada experience — catch-and-release for these fish is the norm.
• Bonefish: Year-round, best October–May. Shallow water, sight-fishing, technically demanding.
• Permit: November–April. Challenging catch; guides usually target them with live crab bait.
• Mahi-mahi: May–September. Offshore, fast action, good eating.
• Sailfish: December–March. Offshore, exciting hookups.

Book through Islamorada fishing charters on Viator →

Snorkeling Off Islamorada

The reef system off Islamorada is extensive and less visited than the Key West sites. Operators out of Robbie's Marina and other Islamorada harbors run trips to sites that the Key West fleet doesn't use:

The Patch Reefs — The backcountry patch reefs between Islamorada and the reef line are smaller and more intimate than the main reef. Good for kids and beginners, and the visibility is usually excellent.

Alligator Reef — A well-established site with good coral and fish density. Accessible from Islamorada-based boats.

The advantage of snorkeling from Islamorada: smaller boats, less crowded, and the captains know sites that the Key West operators don't. Book Islamorada snorkeling tours on Viator →

The History — Hurricane Monument and the Old Lighthouse

Islamorada's history is tied to the 1935 Labor Day hurricane — the most intense hurricane to make landfall in US history, which destroyed the Islamorada Key and killed hundreds of WWI veterans working on the Overseas Highway. The Hurricane Monument at Mile Marker 81.5 is a memorial to those who died. It's a stark, simple monument worth a five-minute stop.

The old Indian Key and Lignumvitae Key state botanical sites are accessible by kayak or boat tour — Lignumvitae Key has the old Chemist's house ruins. If you have a half-day and you're into history, this is a good half-day.

Where to Eat

Lorelei Restaurant (Hadley Marine) — Home of the best key lime pie in the Florida Keys. Get a slice, get a piece of pie to go, have it with Cuban coffee. The restaurant itself is waterfront with good sunset views; the menu is seafood-and-Keys casual. Bring cash for the tarpon feed.

The Longboard at Mile Marker 80 — The consistently excellent dinner option in Islamorada. Order the catch of the day. The cocktail menu is good, the service is professional, and the setting is waterfront without being touristy. Reserve for dinner.

Morovin Cafe — Good breakfast if you're making the drive up in the morning. The breakfast burrito is the move; strong Cuban coffee. Less scenic than the waterfront spots but the food is reliable.

Robbie's Marina Restaurant — Casual waterfront dining. The fish sandwich is good; the sunset from the dock tables is the main event. Good for a lunch stop between activities.

Getting There

Drive north from Key West on US-1 (Overseas Highway). It's 75 miles to Islamorada — roughly 90 minutes with normal traffic. The highway is two lanes most of the way; pull off at the scenic overlooks and the Robbie's Marina stop at mile marker 77.5 to break up the drive.

The most scenic section is the bridge between Lower and Middle Keys — if you see a large bridge to the right with an old bridge running alongside it, that's the Seven Mile Bridge area (heading north from Marathon). Worth a stop for photos from the old bridge's pedestrian walkway.

Full day trip itinerary, fishing charter booking links, and restaurant guide — keywestondemand.com →