Bailey's Charters 

5.0/5 (38 reviews)
 
Federally permitted
 Seminole Street 201, Clearwater, FL 33755, United States

Bailey's Charters 

Over 9 miles offshore
Clearwater, FL, United States
25 ft
4
5.0/5 (38 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!

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Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
July 2026
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Number of days
1
Group Size
2 adults • 0 children
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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
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US $550
Entire boat: 2 people
6 hr Inshore Trip
FREE Cancellation 7 days notice
6 hour trip starts at 7:30 AM
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US $700
Entire boat: 2 people
6 Hr. Nearshore Fishing
FREE Cancellation 7 days notice
6 hour trip starts at 8:00 AM
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US $850
Entire boat: 2 people
8 Hr. Nearshore Fishing
FREE Cancellation 7 days notice
8 hour trip starts at 8:00 AM
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US $1,000
Entire boat: 2 people
There are 16 people looking at this charter.

Customer reviews

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Rating

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

Anglers' gallery (122)

What anglers say

100%
Recommended
100%
Caught fish

All reviews (38)

Frequently mentioned
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Showing 15 of 38 reviews
Seth Hepworth
Seth Hepworth
us
Georgia, US
Member since 2025
5.0
Verified
Captain Bailey
8 Hr. Nearshore Fishing on August 23, 20253 adults

We had an amazing time on our private charter out of Jacksonville! Captain Bailey was an incredible captain — professional, knowledgeable, and made sure we were comfortable the entire trip. He knew exactly where to take us, and his experience on the water really showed. The boat was clean and well-kept, and the whole experience felt safe and fun from start to finish. If you’re looking for a private charter with someone who truly knows the area and makes the trip enjoyable, I highly recommend booking with Captain Bailey. We’ll definitely be going out with him again!

Reported catch:
Cobia
Red Snapper
Vermilion Snapper
Amberjack
Eric Delgado
Eric Delgado
us
Florida, US
Member since 2026
5.0
Verified
New
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
New
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

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
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

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
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

FAQs about Bailey's Charters

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The fish you can target

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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
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