Islamorada Attractions

Exciting Adventure & Entertainment Awaits our Guests

Celebrated as the Sport Fishing Capital of the World, Islamorada’s relaxed atmosphere, tropical landscape, and renowned entertainment provide an unmatched year-round destination. Visitors flock here for family vacations, group tours, corporate retreats, romantic escapes and more.

Our Islamorada resort is close to heart-pounding deep-sea fishing trips, ghostly shipwreck dives, and playful snorkeling excursions. You won’t want to miss the exciting shopping, dining, entertainment, and attractions on land as well. The Chesapeake Beach Resort is your connection to limitless fun and adventure in the Florida Keys.

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Theater of the Sea

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

This Marine Mammal Adventure Park offers eco tours; swimming with dolphins, sea lions, and sting rays; educational programs and more in a beautifully landscaped setting. 

info@theaterofthesea.com

Windley Key Fossil Reef Geological State Park

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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.

Sport Fishing

Distance: Onsite
Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

This sophisticated shop offers unique and affordable sportswear, beach or resort wear, bridal options, accessories, and gifts for everyone.

http://www.angelikaclothing.com/

Anthony's

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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. 

http://www.backcountrycowboy.com/

Captain's Imports

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

This large pottery and art shop with gallery is also the home of the World Parrot Mission. You’ll find lots of sale items and great gifts for friends and family.

http://captiansimports.com/

Cover to Cover Books

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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. 

http://www.danicaanne.com/

Whale Harbor Marina

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

Walk right next door to find more than 20 charter boats on hand for ½ or full day fishing in deep-water or backwater. Daily rentals of small boats, skiffs and jet skis are also available.

http://www.whaleharborinn.com/

Robbie's Party Boat

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

Robbie’s Party Boat is always a blast, offering guaranteed fun with two daylight trips and one nighttime trip available daily. http://www.robbies.com/

Tarpon Feeding

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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. 

Anne's Beach

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

This small beach offers a scenic walkway and great views of the shallows surrounding Islamorada. It has bathrooms and picnic tables for your convenience. 

Worldwide Sportsman

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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.

http://www.danicaanne.com/

Founder’s Park and Beach

Location&Lifestyle at The Chesapeake Beach Resort,Islamorada, Fl

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

TopDown at The Chesapeake Beach Resort,Islamorada, Fl

83409 Overseas Highway, Islamorada, Florida Keys, 33036, USA