Islamorada—the "Village of Islands"—spans six keys in the Upper Florida Keys and bills itself as the Sport Fishing Capital of the World. For reunions of 15-30, this laid-back stretch of US-1 offers world-class marine encounters, legendary fishing, and that unmistakable Keys vibe where flip-flops are formal wear. The challenge is that everything is linear (spread along one highway), parking is limited, and popular spots fill fast. This guide solves those problems.
Already chosen Florida? Read the Florida Planning Guide.
Theater of the Sea
The world's second-oldest marine mammal park (opened 1946), Theater of the Sea offers intimate animal encounters in a natural lagoon setting carved from an old quarry. Unlike mega-parks, the small scale means you're feet away from dolphins, sea lions, stingrays, and sea turtles. Swim-with-dolphin programs, sea lion shows, and guided lagoon tours make this a highlight for all ages.
SCOUT LOGISTICS
General admission is $35/adult with group rates for 15+ at $28/person. Dolphin swim programs ($215/person) are limited to 6 participants per session—book multiple sessions for your group at least 2 weeks ahead. The park is compact (2-3 hours covers everything) and fully walkable. Shows run on a schedule; grab a show times sheet at entry and plan your route. Free parking with space for 50+ cars. The on-site restaurant handles groups of 20+ with advance notice. Bring swimsuits for the bottomless boat ride and wading lagoon.
Website: theaterofthesea.com
Robbie's Marina (Tarpon Feeding)
A quintessential Keys experience, Robbie's Marina is famous for the massive tarpon (some over 100 pounds) that congregate at the dock waiting to be hand-fed. Beyond the tarpon, Robbie's is a full-service marina offering kayak rentals, boat tours to Indian Key and Lignumvitae Key, snorkeling trips, and a funky outdoor market with local art and food vendors.
SCOUT LOGISTICS
Dock access is $2.25/person; fish buckets are $4 each. No reservation needed—this is a walk-up activity perfect for groups of any size. The tarpon are most active in the morning. For groups, the real value is combining tarpon feeding with a boat rental or guided tour. Kayak rentals ($40/hour single, $55/hour tandem) and boat tours to Indian Key ($40/person) depart from the same dock. The Hungry Tarpon restaurant on-site has outdoor seating for 40+ but expect 30-minute waits at lunch. Parking is free but the lot fills by 11 AM on weekends.
Website: robbies.com
Anne's Beach
Named after local environmentalist Anne Eaton, this bayside beach offers shallow, calm waters perfect for wading and a long boardwalk through mangroves. Unlike ocean-side beaches, Anne's Beach has a sandy bottom that stays knee-deep for hundreds of feet—ideal for young children and non-swimmers. The elevated boardwalk provides shaded walking and bird-watching opportunities.
SCOUT LOGISTICS
Anne's Beach is free with no admission fee, but parking is the major constraint—only 20 roadside spaces that fill by 10 AM on weekends. There's an overflow lot 0.25 miles south. For groups, arrive early or bike from nearby accommodations. The beach has no facilities (no restrooms, no food vendors, no lifeguards)—pack everything you need. The shallow water and lack of waves make it the safest Keys beach for toddlers. Bring water shoes; the bottom can be rocky in spots.
Website: islamorada.fl.us
Indian Key Historic State Park
This 11-acre island, accessible only by boat or kayak, was once a thriving settlement and the original county seat of Dade County before being destroyed in an 1840 Seminole raid. Today, visitors explore ruins overgrown with tropical vegetation, an observation tower with panoramic views, and excellent snorkeling in the surrounding shallow waters. It's a hidden gem that most tourists miss.
SCOUT LOGISTICS
The island is free to visit but requires boat access. Robbie's Marina (0.75 miles away) offers guided boat tours ($40/person) and kayak rentals ($40/hour) to reach the island. For groups of 15+, book a private boat charter from Robbie's that can shuttle your entire group. The island has a dock, walking trails, and an observation tower but no restrooms, water, or shade structures—bring sun protection and water. Allow 2-3 hours including transit. Best visited in morning before afternoon heat.
Website: floridastateparks.org
Islamorada Sandbar
The Islamorada Sandbar (also called the "Island Party Sandbar") is a shallow sandbar in Florida Bay that emerges at low tide, creating a natural gathering spot where boaters anchor and wade in knee-deep turquoise water. On weekends, it transforms into a floating party with dozens of boats, music, and a festive atmosphere—think tailgating on the water.
SCOUT LOGISTICS
The sandbar is only accessible by boat—rent from Robbie's Marina or local outfitters ($250-$450/day for pontoon boats holding 10-12 people). For a group of 15-30, rent 2-3 boats and raft up together at the sandbar. Check tide charts—the sandbar is best at low tide when you can stand and walk. Bring coolers, sunscreen, an anchor, and a Bluetooth speaker. There are no facilities whatsoever. The sandbar is located at approximately Mile Marker 80 on the bayside—ask your boat rental for exact GPS coordinates. Weekdays are much less crowded than weekends.
Website: islamorada.fl.us
Ken O.
Founder of AmazingReunion and veteran reunion organizer who has coordinated 50+ family gatherings across the US. I built this platform to handle the unique logistics of Florida Keys island destinations.