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!

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Select date to see availability

Trip date:
Group Size:
November 2026
SuMoTuWeThFrSa
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Group Size
2 adults • 0 children
Change
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

Customer reviews

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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

Reviews (40)

  • Kyla Morris
    Kyla Morris
    us
    Minnesota, US
    Member since 2026
    5.0
    Verified

    What a great trip!

    6 hr Inshore Trip on April 13, 2026 • 3 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!!

  • Jodi Raisl
    Jodi Raisl
    us
    North Dakota, US
    Member since 2026
    5.0
    Verified

    shark bigger than me!

    8 Hr. Nearshore Fishing on August 13, 2026 • 2 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!

  • Sean Magee
    Sean Magee
    us
    New York, US
    Member since 2025
    5.0
    Verified

    Great Trip!

    6 Hr. Nearshore Fishing on April 4, 2026 • 4 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.

  • Drew Spurrier
    Drew Spurrier
    us
    Kentucky, US
    Member since 2026
    5.0
    Verified

    Fishing with Stephen

    4 hr Inshore Trip on August 29, 2026 • 2 adults
  • Teremarie Berrios
    Teremarie Berrios
    us
    Missouri, US
    Member since 2026
    5.0
    Verified

    Fishing with Stephen

    4 hr Inshore Trip on June 22, 2026 • 2 adults
  • Christopher Nielson
    Christopher Nielson
    us
    Utah, US
    Member since 2026
    5.0
    Verified

    Awesome Trip!

    6 hr Inshore Trip on April 11, 2026 • 3 adults

    The three of us had a great time, he kept us on the fish. we will definitely use him again when back in town.

  • Edward Collins
    Edward Collins
    Repeat angler
    us
    Pennsylvania, US
    Member since 2026
    2 trips
    5.0
    Verified

    had a great time caught a ton of fish. 100% booking again

    4 hr Inshore Trip on March 4, 2026 • 2 adults

    had a great time caight a 22 inch mangrove snapper and a ton of other fish. had a blast 100% booking again.

  • Bryson Eldridge
    Bryson Eldridge
    Repeat angler
    us
    Colorado, US
    Member since 2026
    2 trips
    5.0
    Verified

    Talented and Patient Captain

    6 Hr. Nearshore Fishing on March 21, 2026 • 4 adults

    Bailey’s communicated well and the experience was great!

  • Robert Portell
    Robert Portell
    us
    Florida, US
    Member since 2025
    5.0
    Verified

    Wow what a spectacular trip!

    6 Hr. Nearshore Fishing on June 20, 2025 • 4 adults

    Unforgettable Offshore Fishing Trip with Bailey’s Charters I booked an offshore charter with Bailey’s Charters for my son’s 16th birthday, and it was hands-down one of the best experiences we’ve ever had on the water. Captain Stephen Bailey was incredible from start to finish—professional, personable, and incredibly knowledgeable about the area. We did an 8-hour offshore trip, and let me tell you, we filled the cooler! We caught all kinds of fish—Bee-Liners, Amberjack, Rainbow Runner—and every single person on board caught a Red Snapper (which we had to release due to it being out of season, but the pictures we got were worth it!). Some of them were pushing 20 pounds—absolute monsters! Captain Bailey knew all the honey holes and kept us on the fish all day long. His boat was clean, comfortable, and well-equipped for a trip like this, and his gear was top-notch. He made sure the boys had a blast and created memories that will last a lifetime. I truly can’t recommend Bailey’s Charters enough. If you’re looking for a top-tier offshore fishing experience with a captain who knows his stuff and goes the extra mile, this is the one. We’ll absolutely be back! Thanks for a great trip! -Rob Portell

  • Kristin Perkins
    Kristin Perkins
    us
    Connecticut, US
    Member since 2025
    5.0
    Verified

    Awesome Trip!

    4 hr Inshore Trip on May 22, 2025 • 1 adult

    My wife and I booked this trip as part of our vacation! We are from Ct and had never fished in Florida. Captain Steve was a true professional! He was very patient, courteous and a wealth of knowledge! We caught 2 red fish, 1 sheep’s head, 2 sting ray & 1bonnet head adult shark! We had fun and I learned allot… At the end of our trip we took our catch ( just the red 2 red fish & the sheep’s head) to a local hole in the wall restaurant called Singleton’s Seafood Shack ( very close to marina) and they cheffed it up for us! This fishing trip made some great memories and was one of the highlights of our vacation! If you’re having any hesitation Just Pull The Trigger!!! You won’t regret it!!! Thanks Captain Steve!

FAQs about Bailey's Charters

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The fish you can target

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Real catches by this captain

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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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