Bailey's Charters

5.0/5 (35 reviews)

Federally permitted

Seminole Street 201, Clearwater, FL 33755, United States–

Bailey's Charters

Over 9 miles offshore

Clearwater, FL, United States

–

25 ft

5.0/5 (35 reviews)

Meet the Captain

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!

Popular features

Fishing license

Live bait

You keep catch

Catch cleaning & filleting

Drinks

Popular features

Fishing license

Live bait

You keep catch

Catch cleaning & filleting

Drinks

Customer reviews

Rating

5.0

35 reviews

5.0

Boat & equipment

5.0

Captain & crew

5.0

Fishing Experience

Anglers' gallery (121)

What anglers say

100%

Recommended

100%

Caught fish

All reviews (35)

Filter

Sort by: Featured

Frequently mentioned

Showing 1 – 5 of 35 reviews

Robert Portell

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

Reported catch:

Response from Captain

June 23, 2025

Thank you Rob for the time you spent in writing this great review for me, I really appreciate it and know how busy you must be. Thank you! We had a gorgeous day to get offshore and focus on some quality fish. Lots of hands on offshore fishing training and your son was dialed in, aka Snapper King! Great to have you all on board and certainly look forward to taking you out fishing again. Call anytime. Captain Stephen

Seth Hepworth

Georgia, US

•

Member since 2025

5.0

Verified

Captain Bailey

8 Hr. Nearshore Fishing on August 23, 2025 • 3 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:

Kyla Morris

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!!

Reported catch:

Response from Captain

April 18, 2026

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

Andrew Hovanec

Pennsylvania, US

•

Member since 2026

5.0

Verified

New

Great day out!!!

4 hr Inshore Trip on May 21, 2026 • 2 adults • 2 children

A awesome day out on the boat. Captain Steve was great! He worked hard to get us on fish. Was super nice to me and my family. Was enjoyable to talk with and interacted great with my kids.

Sean Magee

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.

Reported catch:

Response from Captain

April 17, 2026

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

Trip availability and prices

Trip Date:

Group Size:

Select date to see availability

June 2026

Su	Mo	Tu	We	Th	Fr	Sa

Number of days

Group Size

2 adults • 0 children

Change

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Island Adventure

4 hour trip starts at 10:00 AM

US $350

Entire boat: up to 4 people

US $350

Entire boat: up to 4 people

4 hr Inshore Trip

4 hour trip starts at 7:00 AM

US $550

Entire boat: 2 people

US $550

Entire boat: 2 people

6 hr Inshore Trip

6 hour trip starts at 7:30 AM

US $700

Entire boat: 2 people

US $700

Entire boat: 2 people

6 Hr. Nearshore Fishing

6 hour trip starts at 8:00 AM

US $850

Entire boat: 2 people

US $850

Entire boat: 2 people

8 Hr. Nearshore Fishing

8 hour trip starts at 8:00 AM

US $1,000

Entire boat: 2 people

US $1,000

Entire boat: 2 people

There are 11 people looking at this charter.

Customer reviews

Rating

5.0

35 reviews

5.0

Boat & equipment

5.0

Captain & crew

5.0

Fishing Experience

Anglers' gallery (121)

What anglers say

100%

Recommended

100%

Caught fish

All reviews (35)

Filter

Sort by: Featured

Frequently mentioned

Showing 1 – 5 of 35 reviews

Robert Portell

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

Reported catch:

Response from Captain

June 23, 2025

Thank you Rob for the time you spent in writing this great review for me, I really appreciate it and know how busy you must be. Thank you! We had a gorgeous day to get offshore and focus on some quality fish. Lots of hands on offshore fishing training and your son was dialed in, aka Snapper King! Great to have you all on board and certainly look forward to taking you out fishing again. Call anytime. Captain Stephen

Seth Hepworth

Georgia, US

Member since 2025

5.0

Verified

Captain Bailey

8 Hr. Nearshore Fishing on August 23, 2025 • 3 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:

Kyla Morris

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!!

Reported catch:

Response from Captain

April 18, 2026

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

Andrew Hovanec

Pennsylvania, US

Member since 2026

5.0

Verified

New

Great day out!!!

4 hr Inshore Trip on May 21, 2026 • 2 adults • 2 children

A awesome day out on the boat. Captain Steve was great! He worked hard to get us on fish. Was super nice to me and my family. Was enjoyable to talk with and interacted great with my kids.

Sean Magee

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.

Reported catch:

Response from Captain

April 17, 2026

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

The fish you can target

What is the boat like?

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

1 x 300HP

Max cruising speed

40 knots

Bailey's Charters

Customer reviews

Rating

Anglers' gallery (121)

What anglers say

All reviews (35)

Trip availability and prices

Customer reviews

Rating

Anglers' gallery (121)

What anglers say

All reviews (35)

FAQs about Bailey's Charters

The fish you can target

What is the boat like?

What’s biting in Clearwater right now

Compare similar fishing charters