Uncle Bear's Charters 

4.8/5 (30 reviews)
 South Belleair Causeway 541S, Belleair Bluffs, FL 33770, United States

Uncle Bear's Charters 

Belleair Bluffs, FL, United States
23 ft
4
4.8/5 (30 reviews)

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Uncle Bear's Charters is ran by Captain Kenny. The name of the business is inspired by his niece who has called him Uncle Bear her whole childhood do to his larger bear like appearance.

Captain Kenny wants to offer a fun and friendly charter for families with young kids but also provide experienced anglers a trip that includes our game fish in the area!

Captain Kenny had worked with other captains in the area for years, as well as fished here his whole life. Born and raised in the area and has never left because of his love for fishing!

If you book with Uncle Bears you can expect a fun trip targeting Snook, Reds, and Trout. We also offer near shore trips where we catch fish like Snapper and Grunts and even other near shore species like Tripletail and King Mackerel.

We cant wait to meet you and even more importantly, can't wait to go fishing together!

Uncle Bear's Charters is ran by Captain Kenny. The name of the business is inspired by his niece who has called him Uncle Bear her whole childhood do to his larger bear like appearance.

Captain Kenny wants to offer a fun and friendly charter for families with young kids but also provide experienced anglers a trip that includes our game fish in the area!

Captain Kenny had worked with other captains in the area for years, as well as fished here his whole life. Born and raised in the area and has never left because of his love for fishing!

If you book with Uncle Bears you can expect a fun trip targeting Snook, Reds, and Trout. We also offer near shore trips where we catch fish like Snapper and Grunts and even other near shore species like Tripletail and King Mackerel.

We cant wait to meet you and even more importantly, can't wait to go fishing together!

Kenny Brush
Captain
Kenny Brush
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...
1hr
Non-refundable
1 hour trip starts at 8:00 AM
Seasonal trip
(Mon, Tue, Wed, Thu, Fri, Sat)
Grouper (Goliath)
King Mackerel (Kingfish)
Snook
Snapper (Mangrove)
+7
US $250
Entire boat: 2 people
1hr pm
Non-refundable
1 hour trip starts at 2:00 PM
Seasonal trip
(Mon, Tue, Wed, Thu, Fri, Sat)
Grouper (Goliath)
King Mackerel (Kingfish)
Snook
Snapper (Mangrove)
+7
US $250
Entire boat: 2 people
2 Hour Trip (AM)
Non-refundable
2 hour trip starts at 8:00 AM
Grouper (Goliath)
King Mackerel (Kingfish)
Snook
Snapper (Mangrove)
+7
US $300
Entire boat: 2 people
2hr PM
Non-refundable
2 hour trip starts at 2:00 PM
Seasonal trip
(Mon, Tue, Wed, Thu, Fri, Sat)
Grouper (Goliath)
King Mackerel (Kingfish)
Snook
Snapper (Mangrove)
+7
US $300
Entire boat: 2 people
3 Hour Trip (AM)
Non-refundable
3 hour trip starts at 8:00 AM
Grouper (Goliath)
King Mackerel (Kingfish)
Snook
Snapper (Mangrove)
+7
US $450
Entire boat: 2 people
4 Hour Trip (AM)
Non-refundable
4 hour trip starts at 8:00 AM
Seasonal trip
(Mon, Tue, Wed, Thu, Fri, Sat)
Grouper (Goliath)
King Mackerel (Kingfish)
Snook
Snapper (Mangrove)
+7
US $600
Entire boat: up to 3 people
4hr PM
Non-refundable
4 hour trip starts at 2:00 PM
Seasonal trip
(Mon, Tue, Wed, Thu, Fri, Sat)
Grouper (Goliath)
King Mackerel (Kingfish)
Snook
Snapper (Mangrove)
+7
US $600
Entire boat: up to 3 people
6 Hour Trip (AM)
Non-refundable
6 hour trip starts at 8:00 AM
Seasonal trip
(Mon, Tue, Wed, Thu, Fri, Sat)
Grouper (Goliath)
King Mackerel (Kingfish)
Snook
Snapper (Mangrove)
+7
US $800
Entire boat: 2 people
There are 8 people looking at this charter.

Customer reviews

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Rating

4.8
30 reviews
4.8
Boat & equipment
5.0
Captain & crew
4.8
Fishing Experience

Anglers' gallery (38)

What anglers say

93%
Recommended

All reviews (30)

Frequently mentioned
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Showing 15 of 30 reviews
Chris Austin
Chris Austin
us
Maine, US
Member since 2026
4.7
Verified
Sometimes you win, sometimes you still win when skunked.
2hr PM on April 2, 20263 adults

We booked a 2-hour charter with Bear, and I’ll be straight with you—we didn’t catch any fish. But here’s the truth…this was still 100% worth it. First off, Bear is just a genuinely good guy. You can tell right away he cares about the experience, not just the catch. He was upfront, worked hard to get us on fish, and kept moving us to different spots trying to make it happen. It just wasn’t our day—sounds like it was slow for everyone out there. That said, we had absolutely perfect weather, saw massive schools of bait fish, and even a dolphin, which made the trip pretty special. More importantly, this turned into something bigger than fishing. I got two solid hours of uninterrupted time with my two sons—one heading into the Army and the other graduating next year. That kind of time is hard to come by, and this trip gave us exactly what we didn’t even realize we needed. There was a small scheduling hiccup beforehand, but it wasn’t on Bear, and he was ready to go the moment it was our time. He was also incredibly apologetic about the fishing, which honestly says a lot about his character. Fishing isn’t what it was back in the day, especially in Florida—but that’s not on the captain. What matters is effort, attitude, and experience… and Bear delivered on all three. If you’re looking for someone who’s going to give it everything he’s got and make sure you have a great time regardless of the outcome, book with Bear. We’ll be back—and next time, we’ll get ‘em.

Kenny Brush
Response from Captain

I’m so happy you guys had a great time. best of wishes to your boy going into the service! I know he will do great things!

Sol Páez
Sol Páez
ar
Santa Fe, Santa Fe, Argentina
Member since 2026
5.0
Verified
Great captain, great vibes!
3 Hour Trip (AM) on May 28, 20263 adults

We had such a great time on our fishing trip! He was extremely nice, patient, and helpful the whole time and made the whole fishing trip really fun and easygoing. The experience was fun, relaxed, and even better than we expected. He even let us stay out a little longer because he really wanted us to leave happy and hopefully catch something. You can tell he genuinely cares about his guests having a good time. Highly recommend booking with him!

Reported catch:
Redfish
Speckled Trout
Kenny Brush
Response from Captain

trips like this are why I do what I do. thanks for booking cant wait till next time!

Tonya Reif
Tonya Reif
us
South Dakota, US
Member since 2026
5.0
Verified
New
Family had a wonderful time!!
2hr PM on July 31, 20264 adults

My husband, boys and I had a great time with Captain Kenny!! We caught a cool catfish and a 22.5" red fish. If we weren't onto the fish he moved us around and he was very personable. We will definitely be fishing with him when we come back to Clearwater!!

Kenny Brush
Response from Captain

had such a great time with yall! cant wait till next time.

Lisa Helget
Lisa Helget
us
Minnesota, US
Member since 2026
5.0
Verified
excellent short trip
1hr on April 25, 20263 adults

we didnt have alot of tiem on our last day . but , it was well worth it next time we will making ar least a 3 hour trip to do this . the captain was great ! great company , great humor curtious kind and determined wirh the little time we had . Thank you !!

Kenny Brush
Response from Captain

happy to have yall

Josh Staggs
Josh Staggs
us
Michigan, US
Member since 2026
5.0
Verified
Great with my 7 year old son.
2hr PM on April 10, 20261 adult1 child

Capt. Kenny was exactly what I was hoping fo in taking my son out on our first salt water fishing trip. He was very patient and extremely helpful with everything. He is willing to move around and find the fish. We will be booking with him again next year without a doubt.

Reported catch:
Speckled Trout
Kenny Brush
Response from Captain

glad you had fun! excited to see yall again next year!

FAQs about Uncle Bear's Charters

Uncle Bear's Charters offers the following trips to customers:
  • US $200 per group, additional US $50 per person after 1 guest - 1hr (1 hour)
  • US $200 per group, additional US $50 per person after 1 guest - 1hr pm (1 hour)
  • US $300 per group, additional US $75 per person after 2 guests - 2 Hour Trip (AM) (2 hours)
  • US $300 per group, additional US $75 per person after 2 guests - 2hr PM (2 hours)
  • US $450 per group, additional US $50 per person after 2 guests - 3 Hour Trip (AM) (3 hours)
  • US $600 per group, additional US $50 per person after 3 guests - 4 Hour Trip (AM) (4 hours)
  • US $600 per group, additional US $50 per person after 3 guests - 4hr PM (4 hours)
  • US $800 per group, additional US $50 per person after 2 guests - 6 Hour Trip (AM) (6 hours)
When you book a trip with Uncle Bear's Charters, you can expect the following amenities onboard:
  • Fighting chair
  • GPS
  • Fishfinder
  • Live bait well
  • Wireless trolling motor
Trips booked with Uncle Bear's Charters include:
  • Rods, reels & tackle
  • Live bait
  • Catch cleaning & filleting
  • Drinks
  • First mate (Not on all trips. )
  • Fishing license
Uncle Bear's Charters offers the following types of fishing:
  • Inshore fishing
  • Nearshore fishing
Uncle Bear's Charters offers the following fishing techniques:
  • Light tackle
  • Heavy tackle
  • Spinning
Top targeted fish species with Uncle Bear's Charters include:
  • Grouper (Goliath)
  • King Mackerel (Kingfish)
  • Redfish
  • Shark (Blacktip)
  • Shark (Bonnethead)
  • Sheepshead
  • Snapper (Mangrove)
  • Snook
  • Spanish Mackerel
  • Speckled Trout
  • Tripletail

Your captain

Kenny Brush
Kenny Brush
Kenny Brush

Belleair Bluffs, Florida, United States

3 Fishing Reports
30 Customer reviews
Typical response within an hour
Member since January 2025

Capt. Kenny runs trips out of Belleair Bluffs aboard 23 ft Nautic star Bay boat. The crew has you covered if you wish to try spinning, or other techniques. The only way to learn is to join them on the water.

3 Fishing Reports
30 Customer reviews
Typical response within an hour
Member since January 2025

Capt. Kenny runs trips out of Belleair Bluffs aboard 23 ft Nautic star Bay boat. The crew has you covered if you wish to try spinning, or other techniques. The only way to learn is to join them on the water.

The fish you can target

Goliath Grouper
Goliath Grouper
King Mackerel (Kingfish)
King Mackerel (Kingfish)
Redfish
Redfish
Blacktip Shark
Blacktip Shark
Bonnethead Shark
Bonnethead Shark
Sheepshead
Sheepshead
Mangrove Snapper
Mangrove Snapper
Snook
Snook
Spanish Mackerel
Spanish Mackerel
Speckled Trout
Speckled Trout
Tripletail
Tripletail
Goliath Grouper
Goliath Grouper
King Mackerel (Kingfish)
King Mackerel (Kingfish)
Redfish
Redfish
Blacktip Shark
Blacktip Shark
Bonnethead Shark
Bonnethead Shark

Real catches by this captain

  • Family had a wonderful time!!
    Tonya R.
    Tonya R.
  • Great captain, great vibes!
    Solci P.
    Solci P.
  • Great with my 7 year old son.
    Josh S.
    Josh S.
  • Great Trip
    David R.
    David R.
  • Father Son Trip Memories with Captain Kenny and Cold Showers!
    Timothy L.
    Timothy L.
  • We caught a nice variety of fish
    Rob K.
    Rob K.
  • Great Time
    Angelo S.
    Angelo S.
  • We caught , trout, red fish and sheephead
    Tate G.
    Tate G.

What is the boat like?

Boat image
Boat category
Center console boats
Capacity
4 persons
Boat length
23 ft
Year built
2017
Boat manufacturer
NauticStar
Boat type
Bay boat
Engine model
Yamaha
Powered by
1 x 250HP
Max cruising speed
55 knots

What kind of fishing will you do?

Inshore Fishing
Nearshore Fishing

Which fishing techniques you can try

Light Tackle
Heavy Tackle
Spinning

Which amenities are available onboard

Fighting chair
GPS
Fishfinder
Live bait well
Wireless trolling motor
What's included in the trip price
Rods, reels & tackle
Live bait
Catch cleaning & filleting
Drinks
First mate
Not on all trips.
Fishing license

How cancellations work

Deposit non-refundable

If it is unsafe to travel, you may still cancel free of charge or change the date(s) of your booking.

More details

What the listing policies are

Pickup agreed upon reservation

Transfer to/from departure site may be available and included in price depending on your location and distance from the dock.

Child friendly
You keep catch
Snook and reds are catch and release year round.
Catch and release allowed

How you can pay

Book with 20% deposit, pay rest to captain

When the captain confirms your trip, FishingBooker charges your credit card a 20% 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

What’s biting in Belleair Bluffs right now

King Mackerel (Kingfish)King Mackerel (Kingfish)
RedfishRedfish
SheepsheadSheepshead
SnookSnook
Spanish MackerelSpanish Mackerel
Speckled TroutSpeckled Trout
TripletailTripletail

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Uncle Bear's Charters
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