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Your Captain
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Greg Poland
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Ready for an unforgettable day on the water? Captain Greg Poland offers exceptional and custom-tailored Islamorada fishing charters from his brand-new 26ft Contender Bay Boat. Whether you’re an experienced angler hunting for a trophy fish or simply want a relaxing day with the family, we specialize in creating the perfect excursion. We're super flexible and happy to work with you to design a trip that matches your goals, whether it’s a focused angling adventure, a fun stop at the famous Islamorada Sandbar, or a combination of both.
Every trip is a fun-filled adventure on the pristine waters of the Florida Keys. We pride ourselves on offering kid-friendly fishing charters in the Florida Keys, ensuring a comfortable and exciting experience for all ages. Our state-of-the-art boat features a huge sunshade and comfortable seating with backrests for everyone, making it the perfect vessel for families. From shark fishing in the shallow flats to reeling in dinner, Captain Greg Poland guides you through the best spots for a truly memorable fishing experience.
Beyond the excitement of the Keys, we also offer specialized trips with expert Everglades National Park fishing guides. Exploring the calm, magical waters of the backcountry, we navigate through the winding mangrove islands where the fishing is incredible and the scenery is breathtaking. It's a prime location to target species like Snook, Redfish, Tarpon, and Trout. This unique ecosystem offers some of the best fishing in South Florida and an unforgettable encounter with nature.
A fishing charter with us is also a fantastic nature safari. As we travel through the Everglades National Park and the backcountry of the Florida Keys, keep an eye out for incredible wildlife. It's common to get up close and personal with playful Dolphins and gentle Manatees. The area is also a birdwatcher’s paradise, featuring diverse species such as Bald Eagles, Roseate Spoonbills, Egrets, and Peregrine Falcons, adding a layer of natural wonder to your day.
We offer a wide range of options to fit your schedule, from short two-hour trips to all-day adventures. Our brand-new 26ft Contender Bay Boat ensures you ride in style and comfort, featuring a great stereo with Sirius XM and a Yeti cooler full of ice for your drinks. For longer excursions, we can even stop at a local waterfront restaurant for a shore lunch and a bathroom break. Contact Captain Greg Poland today to customize your perfect fishing and exploring charter!
What's Included
Your Guide has some important details about your trip with them.
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When you book your fishing trip, you will need to first put down a deposit to hold the reservation.
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What's Included
Your Guide has some important details about your trip with them.
Show More
When you book your fishing trip, you will need to first put down a deposit to hold the reservation.
Show More
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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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Contender Bay Boat
Boat Type:
Boat Guest Capacity:
6
Boat Length:
26 ft
Manufacturer Name:
Contender
Model Year:
2025
Engine Manufacturer Name:
YAMAHA
# of Engines:
2
Horsepower Per Engine:
300
Maximum Cruising Speed:
35
Features: Downriggers Bait Tank Ice-Box Trolling Motor Fish Finder GPS VHF Radio
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26ft Contender Bay Boat: Features padded seating with backrests, a huge sunshade, and a tanning lounge. Equipped with advanced Garmin electronics, Power-Poles, and a trolling motor. Fully rigged with custom rods, live wells, and Yeti coolers. Perfect for fishing and sandbar trips with a swim ladder!
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Contender Bay Boat
Boat Type:
Boat Guest Capacity:
6
Boat Length:
26 ft
Vehicle Details