Bailey's Charters
Bailey's Charters
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!
Select date to see availability
Trip availability and prices
| Su | Mo | Tu | We | Th | Fr | Sa | |
|---|---|---|---|---|---|---|---|
Customer reviews
Rating
Anglers' gallery (125)
What anglers say
Reviews (40)
Kyla Morris5.0VerifiedWhat a great trip!
6 hr Inshore Trip on April 13, 2026 • 3 adultsCaptain 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 Raisl5.0Verifiedshark bigger than me!
8 Hr. Nearshore Fishing on August 13, 2026 • 2 adultsthe 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 Magee5.0VerifiedGreat Trip!
6 Hr. Nearshore Fishing on April 4, 2026 • 4 adultsMy 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.
Christopher Nielson5.0VerifiedAwesome Trip!
6 hr Inshore Trip on April 11, 2026 • 3 adultsThe three of us had a great time, he kept us on the fish. we will definitely use him again when back in town.
Drew Spurrier5.0VerifiedFishing with Stephen
4 hr Inshore Trip on August 29, 2026 • 2 adults
Teremarie Berrios5.0VerifiedFishing with Stephen
4 hr Inshore Trip on June 22, 2026 • 2 adults
Edward Collins5.0Verifiedhad a great time caught a ton of fish. 100% booking again
4 hr Inshore Trip on March 4, 2026 • 2 adultshad a great time caight a 22 inch mangrove snapper and a ton of other fish. had a blast 100% booking again.
Bryson EldridgeRepeat angler5.0VerifiedTalented and Patient Captain
6 Hr. Nearshore Fishing on March 21, 2026 • 4 adultsBailey’s communicated well and the experience was great!
Robert Portell5.0VerifiedWow what a spectacular trip!
6 Hr. Nearshore Fishing on June 20, 2025 • 4 adultsUnforgettable 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 Perkins5.0VerifiedAwesome Trip!
4 hr Inshore Trip on May 22, 2025 • 1 adultMy 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!
Rating
Anglers' gallery (125)
What anglers say
All reviews (40)
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!!
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
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
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
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!
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
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.
FAQs about Bailey's Charters
- 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)
- 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
- 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.)
- 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
- Light tackle
- Bottom fishing
- Spinning
- Deep sea fishing
- Amberjack
- Cobia
- Grouper (Gag)
- Grouper (Red)
- King Mackerel (Kingfish)
- Redfish
- Sheepshead
- Snapper (Mangrove)
- Snook
- Spanish Mackerel
- Speckled Trout
Your captain
Clearwater, Florida, United States
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.
Real catches by this captain
What is the boat like?
What kind of fishing will you do?
Which fishing techniques you can try
Which amenities are available onboard
How cancellations work
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.
What the listing policies are
Pickup not included
Transfer to/from departure site is not included in trip rates.
How you can pay
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
Amberjack
Cobia
Grouper (Gag)
Grouper (Red)
King Mackerel (Kingfish)
Redfish
Sheepshead
Snapper (Mangrove)
Snook
Spanish Mackerel
Speckled TroutCompare similar fishing charters
State licensed5.0(2)22 ftGroup size 1 - 61 - 6
+64 hour trip • 6 personsUS $550
State licensed5.0(16)22 ftGroup size 1 - 41 - 4
+24 hour trip • 4 personsUS $600
