Unforgettable Experiences in Islamorada

Islamorada offers a vibrant mix of water adventures, cultural experiences, and laid-back leisure activities that capture the essence, history, and everyday vibes of island life in the Upper Keys.

Located between Key Largo and Marathon, this group of islands supports access to offshore excursions, quiet land-based exploration, and public venues that shape how locals and visitors spend their time. Understanding the complete list of things to do in Islamorada means going beyond water sports and fishing to include the local businesses, museums, and preserved areas that define its identity.

The following sections break down specific experiences that distinguish Islamorada from other locations in the Florida Keys.

Located on the grounds of the Islander Resort, the Florida Keys History & Discovery Center is a two-story museum with permanent and rotating exhibits focused on the natural and cultural history of the Upper Keys. Exhibits include topics such as shipwrecks, hurricanes, early settlers, and the Flagler railway. The center also has a theater that hosts lectures and community programming throughout the year.

Each exhibit includes detailed text, photographs, and objects that allow you to engage with Islamorada’s local past and its connection to the broader region.The second floor also includes fine art displays from local and regional artists.

Morada Way Arts & Cultural District spans several blocks off the Old Highway and includes galleries, studios, and performance spaces that showcase local residents' visual and creative work. The district’s monthly Third Thursday Art Walk is one of Islamorada's main public events, including open studios, outdoor vendors, and live music.

The district features small businesses and galleries such as the Jessica Ann Art Gallery and the Limelight Studio + Gallery, along with printmakers, photographers, ceramicists, and artists who have their art displayed in galleries or maintain working studios. The walkable layout makes it easy to move between venues. The art events often include food trucks and pop-up shops, giving it a social structure that encourages participation. It's one of the most dependable year-round cultural activities in the Upper Keys.

Fishing remains one of the most popular things to do in Islamorada, and there are dozens of charter services based out of marinas on both the Atlantic and Florida Bay sides. Offshore charters target mahi-mahi, sailfish, and tuna, while backcountry charters operate in the shallower waters around the Everglades and the Gulf of Mexico, often focused on tarpon, bonefish, and snook.

Onsite services offer full-day and half-day charters with licensed captains. Trips are customizable based on target species and group size. The availability of skilled guides, well-maintained boats, and short access to deep water and flats make Islamorada a practical destination for first-time and experienced anglers.

Ecotours and sunset cruises also provide an excellent opportunity to get on the water, discover wildlife, and enjoy the stunning natural beauty of the Florida Keys.To book your adventure, visit local tour operators' websites or call them directly for availability and reservations.

Islamorada provides access to offshore islands like Indian Key and Lignumvitae Key, which are only reachable by kayak or shallow-draft boat. Launch points are near the Islamorada Fish Company and along the Old Highway near the kayak ramps. Rentals are available through outfitters such as Backcountry Cowboy and others in the area.

Indian Key includes trails and ruins from a 19th-century settlement, while Lignumvitae Key supports a preserved hardwood hammock and a ranger station. The paddle to each island typically takes less than an hour, and the protected water allows for steady movement even in moderate weather.

The Islamorada Brewery and Distillery is a must-visit destination for craft beers and spirit connoisseurs. This establishment offers locally crafted beers, house-distilled spirits, and a lively, family-friendly atmosphere. Not only does the Islamorada Brewery and Distillery offer crafted beers and distilled spirits, they also offer a vibrant outdoor beer garden and food truck. The outdoor beer garden offers a very relaxed setting with shaded seating, fans that mist, and yard games, making thi the ultimate spot for relaxation. The food truck offers Keys style pub appetizers, handhelds, and more. The brewery also offers.

Located in Islamorada’s Pioneer Cemetery, the Florida Keys Memorial is also known as the Hurricane Monument. It honors the over 400 people who lost their lives in the Labor Day Hurricane of 1935, one of the most intense hurricanes to make landfall in the United States. The monument includes a simple obelisk and a marker listing the names of those known to have died.

The site sits just off U.S. 1 near mile marker 82 and is accessible on foot. Visitors often stop briefly to read the historical signage and view the structure, which includes a time capsule sealed in the base. It’s one of the most concentrated places to learn about a single event that significantly shaped the development of Islamorada.

Theater of the Sea is a marine park located just north of the main section of Islamorada that offers educational programs, guided tours, and animal interaction experiences. It features dolphins, sea lions, stingrays, and tropical birds, and includes walking paths through landscaped gardens and aquatic exhibits.

Visitors can join scheduled programs, walk the grounds, or book swimming sessions with marine mammals. The site includes a small beach area, boat tours through the lagoon, and daily shows. Theater of the Sea operates year-round, allowing guests to see animals up close while learning about marine conservation in a structured setting.

Stopping at Robbie’s of Islamorada is a great way to experience the Florida Keys with a blend of adventure, wildlife, and local culture in a laid-back setting. It is a place where visitors can create many memories. Visitors can purchase a bucket of fish to enjoy feeding the large tarpon that gather near the docks, providing an exciting experience. At Robbie's of Islamorada, visitors can embark on jet ski adventures, fishing charters, glass bottom boat tours, kayaking and paddle board tours, and so much more. Robbie's also offers an open-air shopping experience with many talented artists and vendors. After a day full of activities, guests can relax at the beautiful waterfront restaurant, which serves fresh, locally sourced cuisine and signature cocktails in a relaxed atmosphere. Whether you are looking for adventure, relaxation, or a taste of local culture, Robbie's of Islamorada has something to offer everyone.

Alligator Reef Lighthouse, located approximately four nautical miles offshore of Islamorada, is a Florida Keys gem. This serene spot, known for its crystal-clear blue waters and protected reef full of abundant wildlife, is a perfect place to snorkel. The lighthouse itself is 136 feet tall and was built in 1873 with a unique underwater structure where schools of fish gather. Depths of the water near the lighthouse range from 5-15 feet, making it a go-to spot for snorkelers. The reef is home to over 500 species of wildlife. This spot is an excellent place to make unforgettable memories and experience natural beauty.

Visit the Islamorada sandbar and enjoy crystal-clear blue waters, a unique social scene, and natural beauty. The Islamorada sandbar sits just offshore located near mile marker 84 on the Atlantic ocean side, off the coast of Overseas highway. Whether you decide to rent a boat, join a tour, or go with locals, getting to the sandbar is relatively easy. Many rental companies or charters are available nearby in Islamorada. The beautiful turquoise waters are the perfect place for snorkeling, lounging, and floating. During weekends and holidays, the sandbar becomes a popular spot for visitors and locals making it a floating party where people gather, socialize, play music, and enjoy food and beverages.

When you're ready to take the next step toward buying, selling, or investing in Islamorada, Coastal Realty of the Florida Keys offers the experience and attention to detail you need. Since 2016, this locally owned boutique has built a strong reputation for delivering personalized service, local insight, and hands-on support throughout every transaction. If you're exploring real estate opportunities in Islamorada, you can count on Coastal Realty of the Florida Keys to guide you with professionalism, care, and a full range of resources tailored to your goals.

Connect with the team today and view available real estate here.