Chesapeake Beach Resort

Relax and let go in an island paradise...

Area Attractions

Experience A Myriad of Things to Do in Islamorada

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

Our Islamorada fishing resort is home to heart-pounding deep-sea fishing trips, ghostly shipwreck dives, playful snorkeling excursions and more below the waves. Plus, don’t miss exciting shopping, dining, entertainment and attractions on land. No matter your preference, the Chesapeake Beach Resort is your connection to limitless fun and adventure in the Keys.


Theater of the Sea
Phone: 305-664-2431 * 
84.5 Oceanside
Islamorada, FL 33036

Marine Mammal Adventure Park. Eco tours, swim with Dolphins, Sea Lions, and Sting Rays, plus other programs in beautifully landscaped setting. Reservations required for swims.

Windley Key Fossil Reef Geological State Park
Phone: (305) 664-2540 
Mile Marker 85.5, Bayside 
Islamorada, FL 33036

History of Diving Museum
Phone: 305-664-9737 
Mile Marker 83, Bayside
Overseas Highway
Islamorada, FL 33036

Islamorada Tennis Club
Phone: (305) 664-5341 
Mile Marker 77, Bayside
Overseas Highway 
Islamorada, FL 33036

Lignumvitae Key Botanical State Park
Phone: (305) 664-2540 
Mile Marker 78.5
Overseas Highway 
Islamorada, FL 33036

Long Key State Park
Phone: (305) 664-4815 
Mile Marker 67.5
Overseas Highway 
Islamorada, FL 33036

Easy Adventures Boat Tours
Phone: (305) 852-4553
P.O. Box 1001
Islamorada, FL 33036

Sport Fishing

Wade out from our shore and reel in a tarpon, or search for a marlin, the Big King. Our on-site fishing charters provide both deepwater game and backwater sport fishing. Islamorada enjoys some of the richest waters ever found in the Sport Fishing Capital of the World.

  • Mahi Mahi
  • Marlin
  • Sailfish
  • Fighting Tuna
  • Bonefish
  • Snook
  • Black Drum
  • Redfish
  • Tarpon
  • Wahoo

Key Ingredient Charters:

Capt. Marc Bellefleur a specialist in Fly and Light tackle.

Call for information and advance booking call 305-852-7366.

Enjoy the backwater and flats fishing experiences with one of the best teaching captains in the area. Ideal for the new angler or seasoned pro Marc provided the expertise making your fishing adventure enjoyable.

Chesapeake Blue Water Charters: 

Capt. Wayne Parker

The Danica Anne, a 42 ft post for offshore fishing,

So whether you want to go for the monster Marlin or Dolphin, or you prefer to fish for the smaller Yellowtail Snapper the choice is yours.

Please mention the Deep Sea Fishing Savings in advance of making reservations at Chesapeake Beach Resort!

Some Area Charter Recommendations:

Whale Harbor Marina: 
Right next door, you can simply walk over and it is so convenient. Over 20 Charter Boats on hand for ½ or full day fishing in Deep Water or Back Water fishing excitement. Including Capt. Skip Bradeen and the Blue Chip Too.

Robbie's Party Boat:
Two daylight trips and one nighttime trips daily.
For information on party boat fishing call 305-664-8070 or visit their website at:

World Wide Sportsman
305-664-4615 · Fax: 305-517-2618 · 
81576 Overseas Highway Islamorada, FL 33036
Complete line of fishing equipment, clothes, shoes, etc.

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. Learn More.

  • 70 Nautical Sq. Miles
  • Spirit of Pennekamp Glass Bottom Boat Rides
  • Diving & Snorkeling
  • Visitor Center
  • 30,000 Gallon Saltwater Aquarium
  • Nature Trails
  • Canoe & Kayak Trail
  • Beaches on Largo Sound
  • Campground
  • Group Pavilions


Angelika Clothing Company
305-664-9008 · Fax: 305-664-4731 · Email:
81917 Overseas Highway Islamorada, FL 33036
*Sophisticated Sportswear *Beach/Resort Bridal *Unique and Affordable Clothing *Accessories and Gifts

98200 Overseas Hwy Key Largo, FL 33037
The Key's largest and most complete women's clothing store. Full Line of Liz Claiborne Women's Wear.

Backcountry Cowboy Outfitters
305-517-4177 · Fax: 305-517-4155 · Email:
82240 Overseas Hwy. Islamorada, FL 33036
Kayak rentals (delivery available) and Guided Tours Outdoor retailer located in the heart of Islamorada offering kayak sales, rentals and guided educational tours representing kayaks from EDDYLINE, LIQUIDLOGIC, PERCEPTION and DAGGER. BCO also offers an impressive selection of outdoor wear from THE NORTH FACE, EXOFFICIO, MOUNTAIN HARDWEAR, HORNY TOAD among others and footwear from KEEN, CHACO & MION among many others. Call or email to inquire about kayak rentals or reserve your place on a guided tour. Open 7 days a week.

Captain's Imports
305-453-1800 · Fax: 305-453-0120 · Email:
99150 Overseas Highway Key Largo, FL 33037
This is a large pottery and art shop with gallery at MM 99, where the blinking light is in Key Largo on the bayside. This is also the home of the World Parrot Mission. Offering exotic and unique items for your walls, painted Talavera pottery, clay pottery, and metal art for pool or patio or in your house! They are now also carrying bronze statues over 6ft tall. Always a lot of sale items; and great gifts for friends and family. Fun and Friendly Staff!

Ciao Bella Hair and Day Spa
305-664-4558 · Fax: 305-664-4571 · Email:
82913 Overseas Highway Islamorada, FL 33036
Salon and Day Spa. We do hair, nails, skin care, pedicures, make-up, waxing, massages and all bridal needs.

Cover to Cover Books
305-853-2464 · Fax: 305-664-2465 · Email:
91272 Overseas Hwy Tavernier, FL 33036
Unique bookstore offering internet, coffee bar, tutoring, books and gifts. Be sure to stop in and meet the Book Babes!

Earth Naturals of The Florida Keys
305-664-4252 · Fax: 305-664-4252 
82661 Overseas Hwy Islamorada, Florida 33036
Semi precious stones, jewelry, fossils, make your own beaded jewelry

Fish Lips Island Cargo 2
82245 Overseas Hwy. Islamorada, FL 33036
Fun, funky gift store, unique gifts, tropical décor, pet products, kid's items, greeting cards, and much more. Always something new. We are pet friendly. Your pets are always welcome.

Floral Fantasy & Gifts
81905 Overseas Highway Islamorada, FL 33036
Unique florist offering fresh flower arrangements and gifts. Also specializing in weddings.

Hooked On Books
305-517-2602 · Fax: 305-517-2665 · Email:
81909 Overseas Hwy. Islamorada, FL 33036
New and used books, Children's Books, Florida Authors, Audio Books, Cards and more. Huge Selection.

Islamorada Fish Company
305-664-9271 · Fax: 305-664-5071 · Email:
81532 Overseas Highway Islamorada, FL 33036
Picture perfect sunsets while enjoying the freshest seafood. Family friendly, casual, waterside dining. Retail seafood market. We'll cook your catch. Weekend entertainment. Open for lunch and dinner. Taste of Islamorada Winner.

Island Body and Sol
305-664-3264 · 800-475-2765 · Fax: 305-664-3260 · Email:
123 Beach Road (At the Moorings) Islamorada, FL 33036
Day spa at The Moorings, a beautiful serene resort in Islamorada. Island Body and Sol offers massage therapy, facials, reflexology, body treatments, manicures, pedicures, all natural botanical bath and skincare products from around the world. Beach Yoga on Mondays, Wednesdays and Fridays at 8:30 AM and Sundays at 9:30 AM.

Joan Purcell Gallery
80925 Overseas Highway Islamorada, FL 33036
All types of Fine Art - specializing in Mermaids! You can have your portrait done as a mermaid. Just bring in your best photograph of you at any age. Located in the Galleria at mile marker 81 Oceanside in Beautiful Islamorada!

Lion's Lair Swimwear
305-664-9922 · 800-220-1691 · Fax: 306-664-9972 · Email:
82185 Overseas Highway Islamorada, FL 33036
Retail Swimwear, Jewelry and Gifts. the Hottest bathing suits in town. Come in and see Kim or one of her helpful sales associates for the PERFECT fitting bikini or one piece suit to flatter ANY figure.

Ocean Gifts & Hammocks
305-664-2222 · Fax: 305-664-0005 · Email:
82700 Overseas Highway Islamorada, FL 33036
Manatee mailboxes, unique tropical gifts from around the world, rope furniture and hammocks from Nags Head Hammocks. Open seven days a week 9am - 6pm.

Paradise Yoga
305-517-9642 · Fax: 305-517-9642 · Email:
81927 Overseas Highway Islamorada, FL 33036
Yoga instruction, sales of yoga products, clothes and accessories.

Petals with Pizzazz
305-852-8771 · 800-413-7843 · Email:
90290 Overseas Hwy. Tavernier, FL 33070
Floral boutique located in Tavernier for over 42 years; Four designers on staff; Delivery from Ocean Reef to Marathon and all over the World; Family owned and operated with specialty in Tropicals, Exotics and Ikebana, which is a Japanese Art form, as well as unique gifts including personalized gift baskets for men, women and children including their ever popular Offshore and Backcountry fishing gift baskets; Petals with Pizzazz is also your one stop wedding design florist.

Rain Barrel Gallery LLC
305-852-3084 · Email:
86700 Overseas Hwy. Islamorada, Florida 33036
A Working Artisan Village featuring numerous local artists specializing in a variety of mediums set in a peaceful natural hammock.

Redbone Inc.
305-664-2002 · Fax: 305-664-9036 · Email:
PO Box 273 Islamorada, FL 33036
Non-profit organization raising funds with fishing tournaments, art gallery.

Rudy's for Kids
305-664-5515 · Fax: 305-664-5517 · Email:
86707 Overseas Hwy Islamorada, Florida 33036
A unique, award winning shop with a tropical, marine life theme...Exclusively for kids! Gifts, books, toys and children's apparel in infant to teen sizes. We are also the Upper Key's only complete skateboard supply and repair shop offering a full line of name brand components and protective gear. Now next door to Chili Willi's.

Sandal Factory Outlet/T-Shirt City
305-453-9144 · Fax: 305-453-9604 · Email:
PO Box 1101 Islamorada, FL 33036
T-shirts and huge selection of shoes and much more! Great Prices!

Sea Dragon Exotic Island Decor
305-664-0048 · Fax: 305-664-0052 · Email:
82239 Overseas Highway Islamorada, FL 33036
Specializing in Teak furniture, lighting, exotic silks, waterscapes, wall art, pillows, candles and more. Home décor with a tropical Asian flair.

Spanish Gardens Cafe
305-664-3999 · Fax: 305-664-3969 · Email:
80925 Overseas Highway Islamorada, FL 33036
Café, Market and Gallery with Spanish & Mediterranean style Cuisine, Homemade Soups, Freshest Salads and sandwiches, hot and cold tapas and our Featured Paella on Fridays and Saturdays! Plus we offer the finest cheeses and meats sliced to sell.

Stacie Krupa Studio Gallery of Art
305-942-0614 · Fax: 305-664-0603 · Email:
82935 Overseas Hwy., Suite 1 Islamorada, Florida 33036

Distinguished fine original paintings and drawings from world famous master artist, Stacie Krupa - Fine Art for the Art Collector - Large in your face depictions of local wild life and sea life.

Theater of the Sea
305-664-2431 · Fax: 305-664-8162 · Email:
84721 Overseas Hwy Islamorada, FL 33036

Marine park, eco tours, and swim with dolphins plus other programs in beautifully landscaped setting. Reservations required for swims. Stop in and visit our amazing Gift Shop!

Waves by the Sea Salon

82685 Overseas Highway #2 Islamorada, FL 33036
Salon and Day Spa: Hair, Nails, Facials, Pedicures; All bridal needs.
*Shampoo service is complimentary.

World Wide Sportsman
305-664-4615 · Fax: 305-517-2618 · Email:
81576 Overseas Highway Islamorada, FL 33036
Complete line of fishing equipment, clothes, shoes, etc.


The Chesapeake Beach Resort is next door to or very close to some of the best dining in all of the Keys. Below are some of the recommended Places to dine and relax.

Whale Harbor Restaurants
Savor the seafood at Wahoo Bar and Grill located adjacent to the Chesapeake Beach Resort at Mile Marker 83.5.  Please let them know you are our guest! Packages for wedding and reunions are available.
Dinner reservations: (305) 664-4959

Ziggie & Mad Dog's
Fine dining restaurant and lounge. Featuring the best in steaks and chops seafood. Located a half-mile from the resort at Mile Marker 82. Reservations recommended. Please let them know you are our guest!
Dinner reservations: (305) 664-3391

Lazy Days Oceanfront Bar and Grill
You hook ‘em and we cook ‘em! Located at Mile Marker 79.
Dinner reservations: (305) 664-5256

Kaiyo Grill & Sushi
Located at Mile Marker 82.
Dinner reservations: (305) 664-5556


Islamorada, the Sport Fishing Capital of the World, will enchant you with its fine dining, boutiques and natural wonders. Come spend a day, and revel in everything the Florida Keys has to offer.

Whale Harbor Marina

Right nextdoor and so convenient. -Daily rentals of small boats and skiffs along with Jet skis. Visit to learn more.

World Wide Sportsman
305-664-4615 · Fax: 305-517-2618
81576 Overseas Highway Islamorada, FL 33036

Complete line of fishing equipment, clothes, shoes, etc. Visit to learn more.

Children’s Activities

Your children can enjoy a full schedule of eco-toursfishing tripsdive-snorkel outings and visits to attractions. In Islamorada, you'll also find free activities to entertain your children between excursions. The leaders of the Village of Islamorada have turned their stretch of U.S. 1 into a beautifully landscaped scenic roadway. Families are welcome to park and take in the view, or go fishing from one of the old railroad bridges. Here are other suggestions for free, or low-cost, activities for children:

Tarpon Feeding

For a small fee, your child can feed tarpon at Robbie's Marina, Mile Marker 77. Tarpon and sharks also hang out at many waterfront restaurants, such as the Islamorada Fish Company at Mile Marker 81.5, bayside, where they sometimes put on free shows.

Anne's Beach
Mile Marker 70, Oceanside

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

Sport Fish Tank
Worldwide Sportsman
Mile Marker 81.5, bayside

A large fish tank in the center of this sporting-goods store and restaurant complex houses live samples of the major shallow-water sport fish of the Keys including bonefish, tarpon, snook and others.

Founder’s Park and Beach
U.S 1, Mile Marker 86.5, Bayside

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 for older children.