- Local places
Theater of the Sea
Windley Key Fossil Reef Geological State Park
Formerly a quarry, Windley Key Fossil Reef Geological State Park is now a beautiful Florida State Park where you can explore history and see cross sections of ancient coral.
History of Diving Museum
The perfect place for both divers and ocean-lovers, the History of Diving Museum explores man's quest to discover, understand and venture beneath the sea.
Islamorada Tennis Club
For over 25 years, the Islamorada Tennis club has offered the only clay courts in the upper Florida Keys. It’s the ideal place for match play and tennis during your stay.
Lignumvitae Key Botanical State Park
Ranger-guided tours allow you to explore this scenic island featuring virgin tropical hardwood forest habitat showcasing the native flora and fauna of Florida's Upper Keys.
Long Key State Park
Explore an unspoiled island that was once the site of Henry Flagler’s Long Key Fishing Camp, a luxury destination for the rich and famous, along with many of the world's greatest salt water anglers.
John Pennekamp State Park
As the first underwater park in the United States, John Pennekamp State Park showcases the area’s best diving and spectacular natural beauty, all within a short distance of Chesapeake Beach Resort.
Wade out from our shore and reel in a tarpon or search for a marlin. Our onsite fishing charters provide both deep-water game and backwater sport fishing.
Angelika Clothing Company
The Florida Key's largest and most complete women's clothing store, Anthony’s always offers the complete line of Liz Claiborne women's wear.
Backcountry Cowboy Outfitters
Browse an impressive selection of outdoor wear from The North Face, Exofficio, Mountain Hardwear, and Horny Toad along with footwear from Keen, Chaco & Mion, and more.
Cover to Cover Books
This is a unique bookstore offering an Internet cafe, coffee bar, tutoring, books, and plenty of gifts for everyone on your list.
Key Ingredient Charters
Enjoy backwater and flats fishing with one of the best teaching captains in the area. Ideal for the new angler or seasoned pro, your fishing adventure is sure to be enjoyable.
Chesapeake Blue Water Charters
Choose the Danica Anne, a 42 foot post for offshore fishing, and go for the monster marlin or dolphin - or if you prefer, fish for the smaller varieties such as yellowtail snapper.
Whale Harbor Marina
Robbie's Party Boat
For a small fee, your child can feed tarpon at Robbie's Marina. Tarpon and sharks also hang out at many waterfront restaurants, such as the Islamorada Fish Company, where they sometimes put on free shows.
This small beach offers a scenic walkway and great views of the shallows surrounding Islamorada. It has bathrooms and picnic tables for your convenience.
You’ll find a complete line of fishing equipment, clothes, shoes, and more here, along with a large fish tank showcasing major shallow-water sport fish including bonefish, tarpon, snook and others.
Founder’s Park and Beach
Many activities at this well-maintained waterfront park are free to out-of-town guests who bring their hotel room keys. The park is equipped with playgrounds, a sandy beach, fishing pier, and a skate park.
Chesapeake Beach Resort
83409 Overseas Highway
Islamorada, Florida 33036
“Best Labor Day Vacation”Gonzo4OSU
“Our favorite hotel”Madeline P