Enjoy the beautiful views and sea breeze of the Atlantic Ocean from the spacious pool and pool deck located between the guest room and the ocean. Soak up the sun on a sandy beach and enjoy the sparking waters of the Florida Keys. Grill dinner on the provided barbecues and picnic on the beach. All of the rooms at Caloosa Cove feature kitchens, balconies, and ocean views.

Board the MIDNIGHT RIDER and prepare for the ultimate tournament-styled fishing experience. Our 42’ Yellowfin is fitted with quad 350 Mercury Verado power and our professional crew knows these fishing grounds and will put you on the fish.

Calling the Upper Keys home since 2014, Captain David Wilkerson has spent the last nine years mastering the waters of the Keys from backcountry fishing in Everglades National Park to the deep reefs and wrecks found here. Get In Charters is based on a simple motto from Captain David’s grandad. David would ask him to take him fishing which was always met with a hearty reply of “Get In”, and fishing they would go!

Captain Jon has had a fishing pole in his hand since age 5 and he has not been able to put it down since. He began coming to beautiful Islamorada yearly starting in 2001. Over the course of many years, he experienced all the various types of fishing in the beautiful Florida Keys and grew to love the variety of species available. It has become his passion to help others enjoy sportfishing in the Florida Keys.

Experience an unforgettable adventure on the water in Islamorada with Best Day Ever Charters. Offering personalized boat tours, fishing excursions, and private charters, Best Day Ever Charters ensures a day filled with fun and excitement. Whether you’re looking to explore the beautiful coastal scenery, catch some fish, or just relax on the boat, their experienced crew will make it a memorable trip for you and your family.