Are you ready to plunge into the heart-pounding world of deep-sea and inshore fishing in the captivating waters of Islamorada, Florida? Look no further than Size Matters Charters, your gateway to adrenaline-charged fishing expeditions led by the fearless Captain Regina Teixeira. Whether you're an angling enthusiast or a sun-seeking leisure traveler, get ready for an experience that will leave you breathless and exhilarated. At the helm of Size Matters Charters is the remarkable Captain Regina Teixeira, an expert navigator and fishing aficionado. With her at the helm, you're in for an adventure that will satisfy your craving for excitement and exploration. Set foot on the sleek and impeccably maintained 30 ft Hydra Sport, an embodiment of both style and functionality. This vessel, emanating the allure of newness despite its 2017 origins, is the perfect companion for conquering the boundless waters of Islamorada. Powered by a roaring by twin 300 HP Yamaha outboard engines, the boat boasts a top cruising speed of 35 knots, ensuring an electrifying journey to your chosen fishing grounds. Accommodating up to 5 eager companions, the boat's clever design guarantees unrestricted movement, eliminating the hassle of tangled lines and cramped spaces. Captain Teixeira's expertise extends to both deep-sea and inshore fishing, promising an action-packed day whether you're yearning for the vast open sea or the tranquility of coastal waters. Venture up to 30 miles offshore for a chance to battle with prestigious pelagic predators like Mahi Mahi, Wahoo, and Blackfin Tuna. Feel the adrenaline surge through your veins as you utilize onboard outriggers for the thrilling technique of trolling, increasing your chances of a triumphant catch. Worried about equipment? Don't be. Captain Teixeira has you covered with all the essential gear for a successful and safe expedition. To maximize your comfort and enjoyment, remember to pack polarized sunglasses, suitable clothing, sunscreen, and an unquenchable thirst for adventure. In the realm of Islamorada fishing charters, Size Matters Charters stands out as a beacon of excitement and exploration. It's time to embrace the adrenaline, explore the depths, and conquer the waves. Prepare for an unforgettable journey with Captain Regina Teixeira, where deep-sea and inshore fishing dreams become a reality against the backdrop of the enchanting Islamorada waters. Book your adventure now and unleash your inner angler with Size Matters Charters!

Last Week Trip

Morning Fishing

Florida Keys Fishing Report August 2022

Florida Keys Fishing Report

EPSG:4269

Catch of a red grouper fish in Islamorada

11 fish caught while fishing in Islamorada

E-GIFT CARDS

Things To Do in Islamorada Florida

Inshore and Offshore Fishing Charters in Islamorada, FL

Join Captain Regina Teixeira of Size Matters Charters for a fun and action-packed fishing adventure. The crew welcomes guests of all skill sets and they will provide you with a unique inshore &amp; offshore charter. Book a trip now and check out why Islamorada is a paradise for all anglers.

Size Matters Charters, based in the fishing haven of Islamorada, FL, is your gateway to exceptional fishing adventures in the Florida Keys. Under the expert guidance of Captain Regina Teixeira, this premier fishing charter service stands out as one of the best in Islamorada. Captain Regina’s passion for the sea and deep understanding of the local waters make every trip an unforgettable experience. Size Matters Charters caters to all skill levels, offering customized fishing excursions that promise excitement and the opportunity to target some of the most sought after fish species in Islamorada. Whether you're looking for a family-friendly outing or a thrilling deep sea fishing adventure, Captain Regina and her crew ensure a memorable day on the water. Islamorada’s legendary fishing grounds are the perfect backdrop for an unforgettable day on the water with Size Matters Charters. Whether you’re staying close to shore or heading offshore into the blue, there’s no shortage of action. Guests often hook into hard-fighting Blackfin Tuna, prized for both their strength and flavor, or chase the brilliantly colored Mahi-Mahi, known for their dazzling leaps and nonstop energy. The fast and razor-toothed Wahoo and the powerful Great Barracuda also make regular appearances, keeping anglers on their toes from start to finish. No matter what’s biting, every trip with Captain Regina promises excitement, challenge, and the kind of fishing stories you’ll be telling for years. Captain Regina’s expertise also shines when it comes to bottom fishing the reefs and wrecks around Islamorada. Anglers often reel in Gag Grouper, Mangrove Snapper, and Yellowtail Snapper—all prized for their fight and for being some of the best-tasting fish in the Florida Keys. These species offer just the right mix of challenge and reward, making them favorites among both locals and visiting anglers. Outfitted with top-quality gear and a clean, well-equipped vessel, Size Matters Charters ensures every guest enjoys a safe, successful, and memorable day on the water. Whether you’re chasing your first big catch or looking to top your personal record, Captain Regina Teixeira delivers an unforgettable Islamorada fishing experience that’s equal parts excitement, learning, and pure fun. Fishing out of Islamorada, Florida, Size Matters Charters offers a variety of trips targeting some of the Florida Keys’ most exciting gamefish. Depending on the season, guests may encounter Blackfin Tuna, Mahi-Mahi, Wahoo, Gag Grouper, Black Grouper, Amberjack, Yellowtail Snapper, Porgy, Tilefish, and more—whether fishing the Atlantic Ocean or the Florida Bay. Trips depart from Three Waters Resort and Marina, located at 84001 Overseas Hwy, Islamorada, FL 33036. For an unforgettable day with one of the top-rated fishing charters in Islamorada, book your adventure today with Captain Regina and Size Matters Charters.

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Purchase A Size Matters Charters Gift Card Today!

Easily change trip dates, times, or trip type by contacting Size Matters Charters from your receipt or right from our website! We look forward to fishing with you!

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Size Matters Charters The Ultimate Fishing Charter Experience from Islamorada

Captain Regina Teixeira comes from a proud family of fishermen — her grandfather and father were both commercial fishermen, and the ocean has always been a central part of her life. After spending three years fishing recreationally in the Florida Keys, she worked as a mate to hone her skills before earning her captain’s license and launching Size Matters Charters in August 2016. With over 20 years of experience, Captain Regina has built a reputation in Islamorada for her passion, expertise, and determination. Before becoming a full-time captain, she owned a construction company — a venture that taught her grit, precision, and leadership. As someone who has always believed in doing everything a man can do, she brings that same fearless attitude to every charter she runs. Regina’s love of fishing has taken her all over the world, from the deep blue waters of Guatemala to her home in the Florida Keys. While fishing the Pacific Fins Resort Tournament in Guatemala, she experienced an unforgettable moment when a massive blue marlin rose just 15 feet behind the boat and crushed a short line set above the teaser. The fish’s sheer power and beauty, nearly airborne in the clear blue water, left a lasting impression. Back home in Islamorada, one of her favorite memories came when all three lines went off at once — a mahi, a tuna, and a wahoo on at the same time. Moments like these capture everything Regina loves about fishing: the thrill, the chaos, and the pure joy of sharing those experiences with her guests. Today, Captain Regina leads Size Matters Charters with a deep knowledge of the Florida Keys and a commitment to delivering personalized, unforgettable experiences. Whether you’re chasing Mahi Mahi, Wahoo, Blackfin Tuna, Grouper, or Yellowtail Snapper, she’ll make sure your day on the water is one to remember.

Owner & Operator of Size Matters Charters – Islamorada, Florida Keys

Things To Do

Tuna Time

Islamorada Tuna Fishing: Half-Day Charter Trip

Mada Fish Fun

Top Islamorada Fishing: Offshore & Reef Adventure

Wreck Wonders

Expert-Guided Full Day Fishing in Islamorada

Inshore Charters

Top-Rated Fishing Charters in Islamorada, FL Keys

Family Frenzy

Family-Friendly Fishing: Islamorada Wreck Adventure

Expert-Guided Islamorada Fishing: Tuna & Grouper

Your fishing license is covered for the trip.

Fishing License

Common Questions <h3>How much does a fishing charter with Captain Regina in Islamorada cost?</h3>Trips with Captain Regina start at $700 for a 3-hour family-friendly charter and around $850 for half-day trips. Pricing depends on trip length, target species, and number of guests. All trips include licenses, bait, and top-quality gear, so you’re ready to fish as soon as you step aboard. <h3>What’s included in a fishing trip with Captain Regina in Islamorada?</h3>Every trip includes all fishing gear, bait, tackle, ice, and required fishing licenses. Captain Regina also provides expert guidance, local insight, and complimentary cleaning and filleting of your catch at the end of the trip. <h3>What types of fishing trips does Captain Regina offer?</h3>Captain Regina offers wreck, reef, and offshore fishing trips based on season and conditions. You’ll target popular species like Mahi Mahi, Blackfin Tuna, Grouper, Snapper, and Wahoo. Both beginner and experienced anglers are welcome. <h3>Do I need to bring my own fishing gear?</h3>No, all gear is included in your trip. Captain Regina provides high-quality rods, reels, tackle, and bait. Just bring sunscreen, sunglasses, snacks, drinks, and anything you’d like for your comfort on the water. <h3>Is cleaning and filleting included in the trip?</h3>Yes. Cleaning and filleting of your catch are included at no extra cost. You can take your fresh fish home or have it cooked at one of the local Islamorada restaurants after your trip.<h3>Do I need a fishing license to fish with Captain Regina?</h3> No. Fishing licenses are included in every trip. You’re covered under Captain Regina’s charter license, so you can relax and focus on fishing. <h3>When is the best time of year to fish in Islamorada?</h3>Islamorada offers great fishing year-round. Spring through early fall is best for Mahi Mahi, Tuna, and Wahoo, while winter months bring excellent reef and wreck fishing for Snapper and Grouper. <h3>Is Captain Regina’s trip family-friendly?</h3>Yes. Captain Regina welcomes families and kids ages three and up. Her charters are safe, educational, and fun for all experience levels—perfect for introducing young anglers to fishing in the Florida Keys. <h3>Where do trips depart from?</h3>Trips depart from Three Waters Resort and Marina, located at 84001 Overseas Hwy, Islamorada, FL 33036. Guests are encouraged to arrive 10–15 minutes early for check-in and a short briefing before departure. <h3>Why fish with Captain Regina in Islamorada?</h3>Captain Regina combines years of local experience, a passion for fishing, and a welcoming attitude that makes every trip memorable. Whether you’re chasing Mahi offshore or Snapper on the reefs, she ensures a comfortable, fun, and productive day on the water.

Come Fish With Us

Islamorada Fishing Charters Operate Year-Round

DEPOSIT: A deposit is required for all bookings and will be applied at checkout

BALANCE: The remaining balance is due on the trip date as either Credit or Cash.&nbsp;

GUEST CANCELLATION: In the event that you must cancel your booking, you must do so 14 days prior to your trip date to receive a refund on your deposit. Rescheduling is encouraged and dependent on guide availability.

GUIDE CANCELLATION: In the rare event that your guide must cancel due to inclement weather, health, or equipment issues, you will have the option to reschedule your charter for a later date or receive a refund on your deposit. TIPPING: Tips to your guide are greatly appreciated for your quality trip.

Trip Policies

Air Fee

Bait Fee

Divemaster Fee

Mate's Fee

Nitrox Fee

Service Fee

State Taxes

Trimix Fee

Perfect for anglers looking for a quick yet action-packed fishing trip, this adventure takes you to the reefs around Islamorada, just 20 minutes from shore. Target a variety of reef fish, including snapper, grouper, and mackerel, while enjoying the beautiful waters of the Florida Keys. Whether you're a seasoned pro or a first-timer, our experienced crew will guide you every step of the way. All guests who book with us will receive a free Size Matters Charters shirt on the day of the trip—don't miss out on this unforgettable fishing experience! Deposits are non-refundable.

Gag Grouper

Great Barracuda

Grey Snapper

4 hrs 

Half Day Guided Fishing Charter In Islamorada  - Snapper, Mackerel, Barracuda 

This inshore fishing trip is perfect for anglers who love steady action and variety. Spend 4 hours exploring the calm, scenic waters around Islamorada, targeting popular species like Mangrove Snapper, Yellowtail Snapper, Barracuda, and Mackerel. These fish are known for their speed, power, and excitement on light tackle—and many make excellent table fare. Captain Regina provides all the gear you’ll need—just bring your polarized sunglasses, sunscreen, and excitement for a great day on the water. Whether you’re a seasoned angler or new to fishing, this trip offers a fun, relaxing experience filled with plenty of bites and lasting memories. Plus, all guests receive a free Size Matters Charters shirt on the day of the trip! Please note: deposits are non-refundable.

Scup

Size Matters

Half Day Wreck And Reef Fishing Charter In Islamorada  - Snapper, Barracuda, Mackerel 

Join Captain Regina Teixeira for a full-day, 8-hour fishing adventure in Islamorada! Explore offshore waters and vibrant wrecks while chasing Wahoo, Mahi Mahi, Blackfin Tuna, Grouper, and Snapper. This extended trip allows more time for action-packed runs, reef fishing, and multiple species, giving you the ultimate fishing experience. All tackle and equipment are included—just bring sunglasses, sunscreen, and your enthusiasm. Enjoy expert guidance, thrilling battles, and a chance to take home an unforgettable catch. Guests receive a complimentary Size Matters Charters shirt!

Blackfin Tuna

Mahi Mahi or Common Dolphinfish

Wahoo Fish

8 hrs 

Full Day Guided Fishing Trip In Islamorada - Tuna, Wahoo, Mahi-Mahi

Enjoy a fun and safe 3-hour family fishing adventure with Captain Regina Teixeira in beautiful Islamorada! Perfect for guests ages three and up, this trip targets exciting species like Snapper, Barracuda, and Blacktip Sharks. Explore nearby wrecks while learning fishing tips from an experienced captain, making it ideal for both kids and adults. All gear is provided—just bring sunscreen, sunglasses, and a sense of adventure. Reel in memorable catches, enjoy quality time on the water, and create lasting family memories on this action-packed fishing trip.

Barracuda

Blacktip Shark

Red Porgy

3 hrs 

Half Day Family-Friendly Fishing Trip In Islamorada  - Snapper, Sharks, Barracuda, Porgy

Experience the ultimate fishing adventure with Captain Regina Teixeira! Spend 6 hours exploring both offshore waters and nearby wrecks, targeting prized species like Wahoo, Mahi Mahi, Blackfin Tuna, Snapper, and Grouper. Whether you crave high-speed offshore runs or steady reef action, this trip has it all. All gear is provided—just bring your sunglasses, sunscreen, and excitement. Enjoy expert guidance, thrilling battles with hard-fighting fish, and a chance to fill your cooler with memorable catches. Every guest receives a free Size Matters Charters shirt!