Size Matters Charters 

5.0/5 (120 reviews)
 
Federally permitted
 Overseas Highway 84001, Islamorada, FL 33036, United States

Size Matters Charters 

Federally permitted
Islamorada, FL, United States
30 ft
6
5.0/5 (120 reviews)

If you're in the market for a day to remember, look no further than Size Matters Charters. With Captain Regina at the helm, you'll benefit from years of knowledge and experience.

These waters are known for Great Barracuda, Dolphin (Mahi Mahi), Wahoo, Mangrove Snapper, Gag Grouper, Blackfin Tuna, Yellowtail Snapper, Cero Mackerel, Sailfish, Mutton Snapper, Skipjack, Nurse Shark, and more – with any luck, it won't take long to hook into some.

For these species, you're likely to troll and bottom fish using light or heavy tackle.

Looking to get the whole family outdoors? Kids are absolutely welcome! If you don't have a child-sized life vest of your own, be sure to ask if there's one on board. Also remember to bring snacks for a boost of energy when needed!

Your boat for the day is a 30' Center console that holds up to 6 passengers. It comes with outriggers, everything you need for a productive day on the water. There's a toilet on board for your convenience.

Capt. Regina has rods and reels for you, along with lures.

A First Mate will be there to make sure everything is running smoothly. A 10–20% tip is customary to show your appreciation for their hard work.

There's no need to buy a fishing license, so all you have to do is look forward to your trip! Be mindful that some species may have special rules or limited seasons. Your captain will help you follow regulations while you fish.

It's always wise to bring a hat, sunglasses, bottled water, and sunblock (non-spray). If you'd like to bring other drinks, just ask. Alcohol is allowed in moderation, so long as you avoid hard liquor as well as glass bottles.

Now's the time to experience fishing in Islamorada for yourself, with Size Matters Charters!

If you're in the market for a day to remember, look no further than Size Matters Charters. With Captain Regina at the helm, you'll benefit from years of knowledge and experience.

These waters are known for Great Barracuda, Dolphin (Mahi Mahi), Wahoo, Mangrove Snapper, Gag Grouper, Blackfin Tuna, Yellowtail Snapper, Cero Mackerel, Sailfish, Mutton Snapper, Skipjack, Nurse Shark, and more – with any luck, it won't take long to hook into some.

For these species, you're likely to troll and bottom fish using light or heavy tackle.

Looking to get the whole family outdoors? Kids are absolutely welcome! If you don't have a child-sized life vest of your own, be sure to ask if there's one on board. Also remember to bring snacks for a boost of energy when needed!

Your boat for the day is a 30' Center console that holds up to 6 passengers. It comes with outriggers, everything you need for a productive day on the water. There's a toilet on board for your convenience.

Capt. Regina has rods and reels for you, along with lures.

A First Mate will be there to make sure everything is running smoothly. A 10–20% tip is customary to show your appreciation for their hard work.

There's no need to buy a fishing license, so all you have to do is look forward to your trip! Be mindful that some species may have special rules or limited seasons. Your captain will help you follow regulations while you fish.

It's always wise to bring a hat, sunglasses, bottled water, and sunblock (non-spray). If you'd like to bring other drinks, just ask. Alcohol is allowed in moderation, so long as you avoid hard liquor as well as glass bottles.

Now's the time to experience fishing in Islamorada for yourself, with Size Matters Charters!

Regina Teixeira
Captain
Regina Teixeira
10 years of experience
ID & credentials verified
responds within an hour

Select date to see availability

Trip availability and prices

Trip Date:
Group Size:
August 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
Change
Almost there...
3 Hour Family Trip
FREE Cancellation 7 days notice
3 hour trip starts at 7:30 AM
Barracuda (Great)
Snapper (Mangrove)
Snapper (Mutton)
Snapper (Yellowtail)
+2
US $700
Entire boat: up to 6 people
Half Day Trip
In high demand Last booked: 1 day ago
FREE Cancellation 7 days notice
4 hour trip starts at 7:00 AM
Barracuda (Great)
Snapper (Mangrove)
Grouper (Gag)
Snapper (Mutton)
+1
US $850
Entire boat: up to 6 people
3/4 Day Trip
FREE Cancellation 7 days notice
6 hour trip starts at 7:00 AM
Barracuda (Great)
Dolphin (Mahi Mahi)
Sailfish
Wahoo
+7
US $1,100
Entire boat: up to 6 people
Full day trip
FREE Cancellation 7 days notice
8 hour trip starts at 7:00 AM
Barracuda (Great)
Dolphin (Mahi Mahi)
Sailfish
Wahoo
+8
US $1,400
Entire boat: up to 6 people
There are 14 people looking at this charter.

Customer reviews

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Rating

5.0
120 reviews
4.9
Boat & equipment
5.0
Captain & crew
4.9
Fishing Experience

Anglers' gallery (206)

What anglers say

99%
Great experience
99%
Family friendly
100%
Friendly captain
100%
Good boat
99%
Recommended
94%
Caught fish

All reviews (120)

Frequently mentioned
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Showing 15 of 120 reviews
Ting Liang
Ting Liang
us
Florida, US
Member since 2026
5.0
Verified
captain Regina is the best captain ever!
3/4 Day Trip on June 20, 20262 adults

We had an amazing experience with Size Matters Fishing Charter! Captain Regina and crew were incredibly knowledgeable, professional, and friendly from start to finish. They took the time to explain everything, shared their expertise, and made sure everyone on board had a great time. The fishing was fantastic—we caught tuna and yellowtail snapper, and the crew worked hard to keep us on the fish all day. We even had a couple of mahis on the line that got away due to user error on my part, but instead of making me feel bad, the crew was so supportive and encouraging. They kept the experience fun and positive, which made it even more memorable. If you’re looking for a charter with an experienced crew, great fishing, and an all-around enjoyable atmosphere, I highly recommend Size Matters Fishing Charter. We made great memories, caught some incredible fish, and can’t wait to book another trip!

Reported catch:
Dolphin (Mahi Mahi)
Yellowtail Snapper
Blackfin Tuna
Great Barracuda
Regina Teixeira
Response from Captain

You guys were awesome! Thanks for fishing with us!

Chandalyn Pulmano
Chandalyn Pulmano
Repeat angler
us
Georgia, US
Member since 2024
2 trips
5.0
Verified
Dinner for two (plus a few more)
Half Day Trip on May 15, 20262 adults

Had an awesome fishing trip on the Size Matters charter in Islamorada! We caught yellowtail, saw a huge bull shark, and had a great time from start to finish. Captain Regina and first mate Tony were both fantastic—super knowledgeable, friendly, and made the whole trip fun and easy. Highly recommend this charter if you’re in the Keys. We’ll definitely be booking with them again next time we’re in Islamorada!

Reported catch:
Yellowtail Snapper
Regina Teixeira
Response from Captain

Thank you so much, it was a fun day today!

Jennifer Nolan
Jennifer Nolan
us
Tampa, FL, US
Member since 2026
5.0
Verified
New
Beautiful day on the water!
3/4 Day Trip on August 5, 20262 adults

Captain Regina and Tony are amazing! Gorgeous boat and Regina knows her fishing! Any day of fishing on the Islamorada Hump or offshore in the Gulf Stream is amazing but they truly made it even better 🎣😎☀️

Joseph Mills
Joseph Mills
us
Florida, US
Member since 2026
5.0
Verified
New
Met all our request! Caught lots of fish!
3/4 Day Trip on July 31, 20266 adults

Took my grandboys on their first charter fishing trip. It will be a memory to last a lifetime. They caught Yellowtail snapper, and a ton of Mahi!. The Captain was very skilled and personable. A great trip!

Reported catch:
Dolphin (Mahi Mahi)
Yellowtail Snapper
Regina Teixeira
Response from Captain

Enjoyed every minute with you guys! Even through the chaos of mahi fishing! Thanks for choosing Size Matters ❤️

Rick Botoff
Rick Botoff
us
New Jersey, US
Member since 2026
5.0
Verified
Great day for All of us!
Full day trip on March 26, 20264 adults

The trip was fun for my grandsons and me. We all caught fish. Unfortunately, the wind picked up and the waves made it difficult to troll for certain species of fish. But the captain, kept moving until we ran into fish to catch. We are looking forward to fishing wth the boat, SIZE MATTers again in a few months!

Regina Teixeira
Response from Captain

it was a great day! Made new friends! Fishing did get a lil sporty out there. See you next time

FAQs about Size Matters Charters

Size Matters Charters offers the following trips to customers:
  • US $700 per group - 3 Hour Family Trip (3 hours)
  • US $850 per group - Half Day Trip (4 hours)
  • US $1,100 per group - 3/4 Day Trip (6 hours)
  • US $1,400 per group - Full day trip (8 hours)
When you book a trip with Size Matters Charters, you can expect the following amenities onboard:
  • Toilet Enclosed bathroom
  • GPS
  • Fishfinder
  • Live bait well
  • Outriggers Sea conditions permitting
  • Ice box
  • Radar
Trips booked with Size Matters Charters include:
  • Rods, reels & tackle
  • Lures
  • Catch cleaning & filleting (No charge for cleaning or filleting your catch)
  • First mate (Customary tip is 15-20%. Mates work hard, loading the boat, getting rods and tackle ready for whatever fish may swim by! They also have to offload the boat and deep clean it)
  • Fishing license (all fishing licenses and federal permits onboard )
Size Matters Charters offers the following types of fishing:
  • Inshore fishing
  • Offshore fishing (Up to 25 miles offshore chasing fish!)
  • Reef fishing
Size Matters Charters offers the following fishing techniques:
  • Light tackle
  • Heavy tackle
  • Bottom fishing
  • Trolling
  • Spinning
Top targeted fish species with Size Matters Charters include:
  • Barracuda (Great)
  • Bonito
  • Cero Mackerel
  • Dolphin (Mahi Mahi)
  • Grouper (Gag)
  • Sailfish
  • Shark (Nurse)
  • Snapper (Mangrove)
  • Snapper (Mutton)
  • Snapper (Yellowtail)
  • Tuna (Blackfin)
  • Wahoo

Your captain

Regina Teixeira
Regina Teixeira
Regina Teixeira

Islamorada, Florida, United States

6 Fishing Reports
ID & license verified
120 Customer reviews
Typical response within an hour
Member since May 2018
Angler's Choice

The Angler's Choice Award is given to listings that consistently deliver a high-quality service and earn great reviews from customers.

Captain Regina Teixeira comes from a family of fishermen. Her father and grandfather were both men of the sea and she continues the family tradition. Capt. Regina has been fishing the Keys for the past 8 years, learning the tricks of the local fish and where the hottest fishing spots are. For the past 2 years she has been operating her own charter business, putting customers on the hottest bite around while providing a world-class customer service experience.

Our Team
Tony D.

Tony D.

First mate

6 Fishing Reports
ID & license verified
120 Customer reviews
Typical response within an hour
Member since May 2018
Angler's Choice

The Angler's Choice Award is given to listings that consistently deliver a high-quality service and earn great reviews from customers.

Captain Regina Teixeira comes from a family of fishermen. Her father and grandfather were both men of the sea and she continues the family tradition. Capt. Regina has been fishing the Keys for the past 8 years, learning the tricks of the local fish and where the hottest fishing spots are. For the past 2 years she has been operating her own charter business, putting customers on the hottest bite around while providing a world-class customer service experience.

Our Team
Tony D.

Tony D.

First mate

The fish you can target

Great Barracuda
Great Barracuda
Skipjack
Skipjack
Cero Mackerel
Cero Mackerel
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Gag Grouper
Gag Grouper
Sailfish
Sailfish
Nurse Shark
Nurse Shark
Mangrove Snapper
Mangrove Snapper
Mutton Snapper
Mutton Snapper
Yellowtail Snapper
Yellowtail Snapper
Blackfin Tuna
Blackfin Tuna
Wahoo
Wahoo
Great Barracuda
Great Barracuda
Skipjack
Skipjack
Cero Mackerel
Cero Mackerel
Dolphin (Mahi Mahi)
Dolphin (Mahi Mahi)
Gag Grouper
Gag Grouper

Real catches by this captain

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What is the boat like?

Boat image
Boat category
Center console boats
Capacity
6 persons
Boat length
30 ft
Year built
2017
Boat manufacturer
Hydra Sport
Boat type
Center console
Engine model
Yamaha
Powered by
2 x 300HP
Max cruising speed
30 knots

What kind of fishing will you do?

Inshore Fishing
Offshore Fishing
Up to 25 miles offshore chasing fish!
Reef Fishing

Which fishing techniques you can try

Light Tackle
Heavy Tackle
Bottom Fishing
Trolling
Spinning

Which amenities are available onboard

Toilet
Enclosed bathroom
GPS
Fishfinder
Live bait well
Outriggers
Sea conditions permitting
Ice box
Radar
What's included in the trip price
Rods, reels & tackle
Lures
Catch cleaning & filleting
No charge for cleaning or filleting your catch
First mate
Customary tip is 15-20%. Mates work hard, loading the boat, getting rods and tackle ready for whatever fish may swim by! They also have to offload the boat and deep clean it
Fishing license
all fishing licenses and federal permits onboard

How cancellations work

Free cancellation up to 7 days prior to trip

You can cancel or modify your booking up to 7 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

More details

What the listing policies are

Pickup not included

Transfer to/from departure site is not included in trip rates.

Child friendly
3 years old and up, must wear life jacket up to age 6
You keep catch
Catch and release allowed

How you can pay

Book with 15% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 15% deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

 Cash

 Visa

 Mastercard

 American Express

When paying the remaining balance with a credit card, an additional 3% charge will apply.

What’s biting in Islamorada right now

Barracuda (Great)Barracuda (Great)
BonitoBonito
Dolphin (Mahi Mahi)Dolphin (Mahi Mahi)
SailfishSailfish
Snapper (Mangrove)Snapper (Mangrove)
Snapper (Mutton)Snapper (Mutton)
Snapper (Yellowtail)Snapper (Yellowtail)
Tuna (Blackfin)Tuna (Blackfin)
WahooWahoo

Compare similar fishing charters

Current
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5.0
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30 ft
Group size 1 - 6
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+10
4 hour trip • 6 persons
US $850