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Islamorada Reef and Offshore Fishing Charters

Book your next fishing trip in Islamorada with the one and only Size Matters Charters

Rated #1 by Customers

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Size Matters Charters Available Trips

01 / 5
Half Day Guided Fishing Charter In Islamorada  - Snapper, Mackerel, Barracuda

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

Starting at undefined850.00

4-hour Morning Guided Fishing Adventure with Captain Regina Teixeira

02 / 5
Half Day Wreck And Reef Fishing Charter In Islamorada  - Snapper, Barracuda, Mackerel

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

Starting at undefined850.00

4-hour Wreck Fishing Adventure with Captain Regina Teixeira

03 / 5
Full Day Guided Fishing Trip In Islamorada - Tuna, Wahoo, Mahi-Mahi

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

Starting at undefined1,400.00

8-hour Wreck & Deep Sea Fishing Experience with Captain Regina Teixeira

04 / 5
Half Day Family-Friendly Fishing Trip In Islamorada  - Snapper, Sharks, Barracuda, Porgy

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

Starting at undefined700.00

3-hour Family Fishing Trip with Captain Regina Teixeira - minimum age of guest three years old

05 / 5
Extended Half Day Fishing Charter In Islamorada, FL - Tuna, Grouper, Wahoo, Mahi Mahi

Extended Half Day Fishing Charter In Islamorada, FL - Tuna, Grouper, Wahoo, Mahi Mahi

Starting at undefined1,100.00

6-Hour Wreck Fishing Adventure with Captain Regina Teixeira

Islamorada, FL Fishing with Size Matters Charters

Top Rated Fishing Charter in Islamorada

Meet the Captain

Captain Regina Teixeira

Islamorada, FL Fishing Charter

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.

Size Matters Charters Fishing Photos

Islamorada, FL Catches & Fish Photos

Islamorada, FL Fishing Near Me

5/537 ReviewsIslamorada, FL

Come Fish With Us

Prices range from $700 - $1400

Fishing Charter Locations on Islamorada, FL

Size Matters Charters operates out of the heart of Islamorada, Florida, a world-renowned fishing paradise often called the Village of Islands. This picturesque stretch of the Florida Keys includes Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, Craig Key, and Fiesta Key. With its crystal-blue waters, tropical beauty, and laid-back atmosphere, Islamorada provides the perfect setting for unforgettable fishing adventures.


Known for its incredible variety of fishing opportunities, Islamorada attracts anglers from around the world in pursuit of trophy catches. Captain Regina Teixeira knows just how special these waters are—wherever she travels to fish around the world, she’s often met with admiration (and a bit of envy) from other anglers who can’t believe she gets to fish in Islamorada every day. With Size Matters Charters, guests can experience both inshore and offshore trips, targeting everything from Blackfin Tuna and Mahi-Mahi to Gag Grouper and Great Barracuda. Whether you’re fishing the shallow flats of the Florida Bay or the deep blue waters of the Atlantic, Captain Regina and her experienced crew know exactly where to find the bite, ensuring a fun and productive day on the water.


Beyond its legendary fishing, Islamorada is also a favorite among divers and ocean lovers, thanks to its thriving marine life and vibrant coral reefs. Every trip offers a chance to witness the beauty of the Florida Keys up close—from colorful reef fish to stunning underwater scenery. Size Matters Charters fishes both the Atlantic Ocean and Florida Bay, offering access to some of the best fishing spots in the Florida Keys. Trips depart from Three Waters Resort and Marina, located at 84001 Overseas Hwy, Islamorada, FL 33036.


Discover why Islamorada is known as the Sportfishing Capital of the World and make your next fishing adventure one to remember with Captain Regina Teixeira and Size Matters Charters.

Islamorada, FL Fishing Locations

The map shows where we fish. The red area is our primary fishing area depending on time of year and fishing conditions. The pins represent guest meeting locations.

Our latest news and updates

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19June

E-GIFT CARDS

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Things To Do in Islamorada Florida
19June

Things To Do in Islamorada Florida

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Last Week Trip
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Last Week Trip

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MOST POPULAR TRIPS

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

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

Starting at undefined850.00

4-hour Morning Guided Fishing Adventure with Captain Regina Teixeira

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

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

Starting at undefined850.00

4-hour Wreck Fishing Adventure with Captain Regina Teixeira

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

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

Starting at undefined1,400.00

8-hour Wreck & Deep Sea Fishing Experience with Captain Regina Teixeira

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

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

Starting at undefined700.00

3-hour Family Fishing Trip with Captain Regina Teixeira - minimum age of guest three years old

Extended Half Day Fishing Charter In Islamorada, FL - Tuna, Grouper, Wahoo, Mahi Mahi

Extended Half Day Fishing Charter In Islamorada, FL - Tuna, Grouper, Wahoo, Mahi Mahi

Starting at undefined1,100.00

6-Hour Wreck Fishing Adventure with Captain Regina Teixeira

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Islamorada Fishing Reef /Offshore

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 & offshore charter. Book a trip now and check out why Islamorada is a paradise for all anglers.

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