If you like Jaws as much as captain greg does you are going to love this trip! These waters are home to some of the most powerful and exciting shark species in the Florida Keys, including blacktips, bull sharks, lemons, nurse sharks, and the occasional hammerhead. We fish the shallow flats, bridge channels, and nearshore edges where sharks hunt, giving you up-close action and unforgettable battles. Whether you're looking for a family-friendly thrill or a hardcore fight with a true apex predator, this charter delivers nonstop excitement. Trips are available in 4-hour, 6-hour, and 8-hour options, making it easy to fit a shark adventure into any schedule. This is one of the most exhilarating experiences Islamorada has to offer—and a must-do for anglers looking for something unforgettable.

Enjoy sun, shallow waters, and family fun on Captain Greg Poland’s Sandbar Trips in Islamorada. Perfect for families and groups, these trips combine swimming, wading, and light fishing in crystal-clear waters. Choose from 2-hour, half-day, 3/4-day, or full-day trips for up to 6 passengers. Captain Greg guides you to the best sandbar locations, ensuring safety, comfort, and fun for guests of all ages. Whether splashing in the shallow waters, relaxing, or fishing, this experience offers an unforgettable day on the water, complete with expert guidance and a chance to explore some of the Florida Keys’ most beautiful spots.

A $200 deposit is required to reserve a booking per day.

Experience the heart of inshore fishing in the Florida Keys with our Islamorada Flats and Bridge Fishing Charters. These trips take you across shallow flats, hidden channels, and the legendary Islamorada bridge systems—prime territory for some of the most sought-after gamefish on the planet. We target tarpon, bonefish, permit, and goliath grouper, giving anglers the opportunity to chase true Florida Keys icons in calm, scenic waters. Whether you’re stalking tailing bonefish on the flats, drifting live baits for tarpon under the bridges, or battling a powerhouse goliath grouper, every trip delivers a memorable fishing experience. Choose from 4-hour, 6-hour, or 8-hour charters tailored to your schedule. From quick action-packed outings to full-day pursuits, our Islamorada Flats and Bridge Fishing Charters are designed for anglers of all experience levels.

This Half-Day Islamorada fishing charter is four hours, providing an ideal timeframe for serious anglers and families alike during peak seasons. Focusing on the renowned backcountry flats and mangrove networks of the Florida Keys, the trip targets premier game fish, including Tarpon, Snook, and Redfish.

Offered on a high-end 26ft Contender Bay Boat, the charter ensures a comfortable experience. During the busy Spring Break and Tarpon Season (March through June), flexible scheduling allows for earlier or later departures to suit your vacation plans. The guided trip welcomes all skill levels, from novice to expert. The trip fee includes all fishing necessities: custom rods, tackle, bait, and the required fishing license. This efficient charter is designed to deliver a high-quality fishing experience with maximum opportunity for the target species.

Head offshore into the rich blue waters of Islamorada for an unforgettable deep-sea adventure. Our offshore fishing charters focus on the productive waters just beyond the reef, where migrating pelagics and hard-fighting sportfish gather. These trips offer fast-paced action and a chance at some of the most iconic species in the Atlantic. We target Atlantic sailfish, blackfin tuna, mahi mahi (common dolphinfish), mutton snapper, and wahoo. Depending on the season and conditions, we may troll, live bait, or run-and-gun to stay on the fish and keep the rods bending. Islamorada’s offshore fishery is known for its steady action, colorful species, and memorable fights. Charters are available in 4-hour, 6-hour, and 8-hour trips, giving anglers the flexibility to choose the experience that fits their goals. Whether you're chasing your first sailfish or looking to fill the cooler with mahi and tuna, our Islamorada Offshore Fishing Charters deliver a classic Florida Keys adventure.

This Islamorada fishing charter offers a perfect two-hour introduction to the legendary Florida Keys waters, ideal for beginners, families with young children, or those with limited time. We specialize in light-tackle fishing across the backcountry flats and near the mangrove islands, targeting highly sought-after species including Tarpon, Snook, and Redfish.

Operating from a modern 26ft Contender Bay Boat, the trip ensures comfort and safety. All necessary equipment is provided, including custom rods, tackle, bait, and a fishing license. Your expert guided trip is structured to maximize action and accommodate all skill levels. This concise charter is designed for quick, high-intent angling, focusing on the quality of the catch and the experience on the water.

Experience the magic of the Florida Keys on a guided fly fishing trip designed for anglers of all levels, from beginner to expert. This two-hour adventure is a perfect introduction to the world-famous Islamorada backcountry—ideal for beginners, families, or anyone looking to enjoy a focused, action-packed session on the water. Led by a certified casting instructor, this trip offers personalized coaching and expert guidance tailored to your skill level and goals. We’ll explore pristine flats and mangrove islands, sight casting to some of the most exciting game fish in the world, including Tarpon, Snook, Redfish, Bonefish, and more. Whether you’re new to fly fishing or looking to refine your technique and presentation, you’ll receive hands-on instruction to elevate your skills. You’ll fish from a comfortable technical skiff, perfectly suited for shallow-water fly fishing. All high-quality equipment is provided, including premium fly rods, reels, custom-tied flies, and a fishing license, so you can focus entirely on the experience. This concise charter emphasizes quality over quantity, blending professional instruction, thrilling sight-fishing opportunities, and the unforgettable beauty of the Florida Keys.

This 3/4 Day Islamorada fishing charter runs for six hours, offering ample time to explore the vast backcountry flats and mangrove islands of the Florida Keys. The extended duration is perfectly suited for both serious anglers seeking multiple target species and families looking for a comprehensive experience. We primarily focus on premier game fish, including Tarpon, Snook, and Redfish.

The trip is conducted aboard a high-end 26ft Contender Bay Boat, providing superior comfort and stability. This guided trip is designed to maximize fishing time and is suitable for all skill levels, from novices to experts. The $1,100.00 fee is all-inclusive, covering your mandatory fishing license, custom rods, high-quality tackle, and bait. During peak seasons, the flexible schedule allows for customized departure times. Book this charter for a deep, high-quality angling experience with maximum opportunity for memorable catches.

This Full-Day Islamorada fishing charter provides an immersive eight-hour experience for anglers seeking comprehensive coverage of the Florida Keys best spots. This extended guided trip allows ample time to explore both the expansive backcountry flats and the nearby Atlantic reef systems, increasing opportunities for multiple trophy catches. Primary targets include the inshore giants Tarpon, Snook, and Redfish, with options to pursue Shark or other seasonal species based on angler preference and conditions.

The trip is conducted aboard a fully equipped 26ft Contender Bay Boat, ensuring comfort throughout the day. This charter is suitable for all skill levels, from families to serious experts. The $1,500.00 rate is all-inclusive, covering your mandatory fishing license, premium tackle, custom rods, and bait. Book this full-day experience to maximize your time on the water and access the most remote, high-yield fishing grounds.

Experience the thrill of spotting playful dolphins in their natural habitat with Captain Greg Poland’s Dolphin Watching Tours. Ideal for families and first-time visitors, this trip combines relaxation and excitement as you cruise the waters of Islamorada. Learn about dolphin behavior and the local ecosystem from an expert guide. Trips range from 2-hour adventures to full-day explorations for up to 6 guests. Perfect for creating lasting memories, this tour offers photo opportunities, expert guidance, and a safe, family-friendly experience on the beautiful waters of the Florida Keys.

A $200 deposit is required to reserve a booking per day.

Discover the beauty of Islamorada with Captain Greg Poland’s private Eco Tours. Perfect for families, nature enthusiasts, and curious travelers, these trips showcase the local ecosystem, mangroves, and abundant wildlife. Glide through crystal-clear waters while learning about Florida’s marine habitats from an expert guide. Choose from 2-hour, half-day, 3/4-day, or full-day trips with up to 6 passengers. Captain Greg ensures a safe, educational, and memorable adventure on the water, giving guests a true up-close experience with the natural wonders of the Florida Keys.

A $200 deposit is required to reserve a booking per day.

Relax and take in the breathtaking Florida Keys sunset on a private Sunset Cruise with Captain Greg Poland. Perfect for couples, families, and friends, this 2-hour trip offers stunning views, calm waters, and a peaceful atmosphere. Guests enjoy the expertise of a seasoned captain who guides you through the best viewing spots while ensuring comfort and safety. Ideal for photography, celebration, or simply unwinding on the water, this cruise accommodates up to 6 passengers and creates unforgettable memories as the sun dips below the horizon in beautiful Islamorada.

A $200 deposit is required to reserve a booking per day.

Experience Islamorada through the eyes of a local with Captain Greg Poland’s A Day With a Local trip. This fully customizable adventure allows guests to explore the best local spots, including restaurants, scenic areas, and hidden gems accessible by boat. Ideal for families, couples, or friends, this flexible tour combines sightseeing, fun on the water, and expert local insights. Choose from 2-hour, half-day, 3/4-day, or full-day options with up to 6 passengers. Captain Greg ensures a safe, educational, and unforgettable experience, making your visit to the Florida Keys truly unique.

A $200 deposit is required to reserve a booking per day.