Bailey's Charters 

5.0
(40 reviews)
 
Federally permitted
 Seminole Street 201, Clearwater, FL 33755, United States

Bailey's Charters 

Clearwater, FL, United States
25 ft
4
5.0
(40 reviews)

There's not a better way to enjoy your time in Florida than being on the water. This way of living is in the heart of Bailey's Charters and Captain Stephen. Whether you're here to catch some fish, find a new waterfront restaurant, or simply relax with your loved ones, you'll find all of that here. With a year round fishing season, any time is a good time for fishing.

Capt. Stephen welcomes you aboard his 25' Sea Born boat that accommodates up to 4 guests. Powered by a 300 HP Mercury Verado engine, this center console will take you where the fish are with speed and ease. She's always ready for catching fish, as she's equipped with a live bait tank, a cooler, a wireless trolling motor, and navigational electronics.

Most of the fishing will be just off the beaches, mangrove shorelines, nearshore ledges and reefs, and out to 25 miles to offshore wrecks and live bottom/reefs where we will be fishing in 75' of water. You'll use high quality Daiwa Saltist and Shimano spin reels, spooled with the industry's best braid and topped off with 100% fluorocarbon leader. Free lining live bait, bottom fishing, float rigs with shrimp, and jigging are the most reliable way to get hooked up on out local fish.

Your fishing equipment and licenses are included in the price. As an extra treat, the captain cleans and fillets your catch after the trip, free of charge. Ask him to recommend a great dockside restaurant and head there for a feast! You only need to bring food, drinks, and sunscreen for your trip.

Get in touch with Bailey's Charters for an amazing day out on Florida's South West Coast!

There's not a better way to enjoy your time in Florida than being on the water. This way of living is in the heart of Bailey's Charters and Captain Stephen. Whether you're here to catch some fish, find a new waterfront restaurant, or simply relax with your loved ones, you'll find all of that here. With a year round fishing season, any time is a good time for fishing.

Capt. Stephen welcomes you aboard his 25' Sea Born boat that accommodates up to 4 guests. Powered by a 300 HP Mercury Verado engine, this center console will take you where the fish are with speed and ease. She's always ready for catching fish, as she's equipped with a live bait tank, a cooler, a wireless trolling motor, and navigational electronics.

Most of the fishing will be just off the beaches, mangrove shorelines, nearshore ledges and reefs, and out to 25 miles to offshore wrecks and live bottom/reefs where we will be fishing in 75' of water. You'll use high quality Daiwa Saltist and Shimano spin reels, spooled with the industry's best braid and topped off with 100% fluorocarbon leader. Free lining live bait, bottom fishing, float rigs with shrimp, and jigging are the most reliable way to get hooked up on out local fish.

Your fishing equipment and licenses are included in the price. As an extra treat, the captain cleans and fillets your catch after the trip, free of charge. Ask him to recommend a great dockside restaurant and head there for a feast! You only need to bring food, drinks, and sunscreen for your trip.

Get in touch with Bailey's Charters for an amazing day out on Florida's South West Coast!

Stephen Bailey
Captain
Stephen Bailey
10 years of experience
ID & credentials verified

Select date to see availability

Trip availability and prices

Trip date:
Group Size:
September 2026
SuMoTuWeThFrSa
Loading...
Group Size
2 adults • 0 children
Change
Almost there...
Island Adventure
FREE Cancellation 7 days notice
4 hour trip starts at 10:00 AM
US $350
Entire boat: up to 4 people
4 hr Inshore Trip
FREE Cancellation 7 days notice
4 hour trip starts at 7:00 AM
Jack Crevalle
Snook
Redfish
Pompano
+1
US $550
Entire boat: 2 people
6 hr Inshore Trip
FREE Cancellation 7 days notice
6 hour trip starts at 7:30 AM
Snook
Tarpon
Redfish
Pompano
+2
US $700
Entire boat: 2 people
6 Hr. Nearshore Fishing
FREE Cancellation 7 days notice
6 hour trip starts at 8:00 AM
Amberjack
Cobia
King Mackerel (Kingfish)
Snapper (Mangrove)
+6
US $850
Entire boat: 2 people
8 Hr. Nearshore Fishing
FREE Cancellation 7 days notice
8 hour trip starts at 8:00 AM
Amberjack
Cobia
King Mackerel (Kingfish)
Snapper (Mangrove)
+6
US $1,000
Entire boat: 2 people
There are 4 people looking at this charter.

Customer reviews

Loading...

Rating

5.0
40 reviews
5.0
Boat & equipment
5.0
Captain & crew
5.0
Fishing Experience

Anglers' gallery (125)

What anglers say

100%
Recommended
100%
Caught fish

All reviews (40)

Frequently mentioned
Showing 15 of 40 reviews
Kyla Morris
Kyla Morris
us
Minnesota, US
Member since 2026
5.0
Verified
What a great trip!
6 hr Inshore Trip on April 13, 20263 adults

Captain Steve gave us a fantastic fishing experience! He taught us a lot about fishing for sea trout, snook, and redfish. And he was fun! He didn’t yell or cuss at us if we lost a fish, which I have experienced before. He also cleaned our fish when we got back to the docks. We had an incredible six hour adventure! Can’t wait to call Captain Steve again!!

Reported catch:
Snook
Speckled Trout
Stephen Bailey
Response from Captain

Thank you Kyla for the great review, I appreciate it! Yes, NO. swearing ir getting mad at the customers trying to fish and learn hiw to catch our fiah here! That is just not excusable. Had such a great time with you and your Mom and boyfriend. Hope to take you all out again. Captain Stephen Bailey

Jodi Raisl
Jodi Raisl
us
North Dakota, US
Member since 2026
5.0
Verified
New
shark bigger than me!
8 Hr. Nearshore Fishing on August 13, 20262 adults

the captain was responsive and accomadating. we caught shark, grouper and tried for a lot of other fish too. it was exciting and fun! would do it again and recommend it to others!

Reported catch:
Gag Grouper
Red Grouper
Stephen Bailey
Response from Captain

Thank you very much Jodi for the review and the charter with you and your son! It was a beautiful day to spend out in the Florida waters and catch some fish, and glad we were able to catch a fish larger than him! LOL. The grouper was pretty great too, and look forward to taking you all out again someday if you are back in the area. Thank you, Captain Stephen Bailey

Sean Magee
Sean Magee
us
New York, US
Member since 2025
5.0
Verified
Great Trip!
6 Hr. Nearshore Fishing on April 4, 20264 adults

My 3 brothers and I went out for a 6 hour near shore trip with Captain Stephen. Stephen was an excellent captain. He gathered plenty of bait at early as 4:30 in the morning to fill his live well with bait for our 8 am trip. We caught our limit of mangrove snapper and captain spent an hour filleting our fish at the end of a long day.

Reported catch:
Mangrove Snapper
Stephen Bailey
Response from Captain

Great day, and thank you very much for booking a charter with me! lots of delicious Mangrove Snapper, fun to catch and even better to eat. Glad you and your brothers had a great time. Capt. Stephen Bailey

Eric Delgado
Eric Delgado
us
Florida, US
Member since 2026
5.0
Verified
Best West Coast Trip I could have asked for
6 Hr. Nearshore Fishing on June 27, 20262 adults1 child

The captain was extremely friendly knowledgeable put us right on the fish and was very helpful with my son. Definitely would recommend this trip for anybody looking to have a good time and catch fish

James Hannon
James Hannon
us
Massachusetts, US
Member since 2026
5.0
Verified
awesome time
6 hr Inshore Trip on June 26, 20262 adults

the captain worked hard to get us on the fish. was very hot this day but he found the fish. tha captain was very laid back and nice guy..would recommend to otbers . needed plenty of water and sunscreen

FAQs about Bailey's Charters

Bailey's Charters offers the following trips to customers:
  • US $350 per group - Island Adventure (4 hours)
  • US $550 per group, additional US $50 per person after 2 guests - 4 hr Inshore Trip (4 hours)
  • US $700 per group, additional US $50 per person after 2 guests - 6 hr Inshore Trip (6 hours)
  • US $850 per group, additional US $100 per person after 2 guests - 6 Hr. Nearshore Fishing (6 hours)
  • US $1,000 per group, additional US $100 per person after 2 guests - 8 Hr. Nearshore Fishing (8 hours)
When you book a trip with Bailey's Charters, you can expect the following amenities onboard:
  • Toilet Full flush toilet inside center compartment in helm area. Marine toilet grade paper supplied, a light inside area as well as a door for privacy.
  • GPS
  • Fishfinder
  • Live bait well
  • Wireless trolling motor
  • Ice box
Trips booked with Bailey's Charters include:
  • Rods, reels & tackle
  • Live bait (I typically don't include catching live bait on the trip if it takes more than 30 minutes to gather. I will extend the actual trip if possible with client to give them more actual fishing time. 8 hr offshore trips include this extra time to harvest qualit)
  • Lures
  • Catch cleaning & filleting (I clean fish at the Mayport fish cleaning station after loading the boat on it's trailer. Fish are filleted and put on fresh ice in clean zip loc bags. I also share cooking and recipes for the fish caught.)
  • Drinks (bottled water)
  • Fishing license (Fishing licenses are included except if parties over 4. The extra people will need to get a one day fishing license if they do not already have a Florida Saltwater fishing License.)
Bailey's Charters offers the following types of fishing:
  • Inshore fishing (St. Joseph Sound, Caladesi, spoil islands, Honeymo)
  • Nearshore fishing (out to 5miles, along beaches- Clearwater to Anaclo)
  • Offshore fishing (Up to 25 miles out, weather/seas permitting)
  • Reef fishing (natural bottom with live coral out to 25 miles )
  • Wreck fishing
Bailey's Charters offers the following fishing techniques:
  • Light tackle
  • Bottom fishing
  • Spinning
  • Deep sea fishing
Top targeted fish species with Bailey's Charters include:
  • Amberjack
  • Cobia
  • Grouper (Gag)
  • Grouper (Red)
  • King Mackerel (Kingfish)
  • Redfish
  • Sheepshead
  • Snapper (Mangrove)
  • Snook
  • Spanish Mackerel
  • Speckled Trout

Your captain

Stephen Bailey
Stephen Bailey

Clearwater, Florida, United States

ID & license verified
40 Customer reviews
Typical response within 1 hour
Member since May 2020
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.

I believe it's not only about the fish you hook up on, or the great photos and memories of fish caught, but getting to enjoy life on the water as we Floridians proudly call it. Welcome to my backyard! I have fished all my life, and passionate about seeing people catch fish, even more than I love to. Creating lasting memories and a day out on the water catching fish is my goal.

Stephen Bailey
Stephen Bailey
Fully verified
Angler's Choice
40
reviews
2020
member since
~2h
response
I believe it's not only about the fish you hook up on, or the great photos and memories of fish caught, but getting to enjoy life on the water as we Floridians proudly call it. Welcome to my backyard! I have fished all my life, and passionate about seeing people catch fish, even more than I love to. Creating lasting memories and a day out on the water catching fish is my goal.

The fish you can target

Amberjack
Amberjack
Cobia
Cobia
Gag Grouper
Gag Grouper
Red Grouper
Red Grouper
King Mackerel (Kingfish)
King Mackerel (Kingfish)
Redfish
Redfish
Sheepshead
Sheepshead
Mangrove Snapper
Mangrove Snapper
Snook
Snook
Spanish Mackerel
Spanish Mackerel
Speckled Trout
Speckled Trout
Amberjack
Amberjack
Cobia
Cobia
Gag Grouper
Gag Grouper
Red Grouper
Red Grouper
King Mackerel (Kingfish)
King Mackerel (Kingfish)

Real catches by this captain

  • Fishing with Stephen
    Drew S.
    Drew S.
  • shark bigger than me!
    Jodi R.
    Jodi R.
  • Fishing with Stephen
    Teremarie B.
    Teremarie B.
  • Great Time
    Michael N.
    Michael N.
  • What a great trip!
    Kyla M.
    Kyla M.
  • Great Trip!
    Sean M.
    Sean M.
  • Very good trip! First time here in Florida had a blast with Baileys! Highly recommend it!
    Luke B.
    Luke B.
  • Talented and Patient Captain
    Bryson E.
    Bryson E.
  • had a great time caught a ton of fish. 100% booking again
    Edward C.
    Edward C.
  • Fishing with Stephen
    Michael T.
    Michael T.

What is the boat like?

Boat image
Boat category
Center console boats
Capacity
4 persons
Boat length
25 ft
Year built
2018
Boat manufacturer
Sea Born
Boat type
Center console
Engine model
Mercury Verado
Powered by
1 x 300HP
Max cruising speed
40 knots

What kind of fishing will you do?

Inshore Fishing
St. Joseph Sound, Caladesi, spoil islands, Honeymo
Nearshore Fishing
out to 5miles, along beaches- Clearwater to Anaclo
Offshore Fishing
Up to 25 miles out, weather/seas permitting
Reef Fishing
natural bottom with live coral out to 25 miles
Wreck Fishing

Which fishing techniques you can try

Light Tackle
Bottom Fishing
Spinning
Deep Sea Fishing

Which amenities are available onboard

Toilet
Full flush toilet inside center compartment in helm area. Marine toilet grade paper supplied, a light inside area as well as a door for privacy.
GPS
Fishfinder
Live bait well
Wireless trolling motor
Ice box
What's included in the trip price
Rods, reels & tackle
Live bait
I typically don't include catching live bait on the trip if it takes more than 30 minutes to gather. I will extend the actual trip if possible with client to give them more actual fishing time. 8 hr offshore trips include this extra time to harvest qualit
Lures
Catch cleaning & filleting
I clean fish at the Mayport fish cleaning station after loading the boat on it's trailer. Fish are filleted and put on fresh ice in clean zip loc bags. I also share cooking and recipes for the fish caught.
Drinks
bottled water
Fishing license
Fishing licenses are included except if parties over 4. The extra people will need to get a one day fishing license if they do not already have a Florida Saltwater fishing License.

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
I love children and have more patience than most, and have been referred to as having the patience of Job. I love to teach and see children catch their first fish on Bailey's Charters! There is no age group, just what the parents feel their child is capab
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

 PayPal

 Bank transfer

What’s biting in Clearwater right now

AmberjackAmberjack
CobiaCobia
Grouper (Gag)Grouper (Gag)
Grouper (Red)Grouper (Red)
King Mackerel (Kingfish)King Mackerel (Kingfish)
RedfishRedfish
SheepsheadSheepshead
Snapper (Mangrove)Snapper (Mangrove)
SnookSnook
Spanish MackerelSpanish Mackerel
Speckled TroutSpeckled Trout

Compare similar fishing charters

Current
Bailey's Charters
Bailey's Charters
Federally permitted
5.0
(40)
25 ft
Group size 1 - 4
1 - 4
Fish 1
Fish 2
+9
4 hour trip • 2 persons
US $550
  • Fresh N Salty Charters
    State licensed
    New
    22 ft
    Group size 1 - 6
    1 - 6
    Fish 1
    Fish 2
    +6
    4 hour trip • 4 persons
    US $550
  • Sportsman Charters
    State licensed
    5.0
    (5)
    23 ft
    Group size 1 - 4
    1 - 4
    Fish 1
    Fish 2
    +8
    4 hour trip • 4 persons
    US $500
  • New Gen Fishing Charters
    State licensed
    5.0
    (15)
    22 ft
    Group size 1 - 4
    1 - 4
    Fish 1
    Fish 2
    +2
    4 hour trip • 2 persons
    US $600
  • The Reel Fisher
    State licensed
    5.0
    (51)
    25 ft
    Group size 1 - 5
    1 - 5
    Fish 1
    Fish 2
    +9
    4 hour trip • 1 person
    US $550