Bailey's Fishing & Island Charters

Bailey's Fishing & Island Charters Thankful and blessed to fish theses beautiful waters and God’s creatures. Let’s go catching!

Water temps are slightly cooler and the “Fall” redfish schools are back! The fishing will just improve as the weeks cont...
08/30/2026

Water temps are slightly cooler and the “Fall” redfish schools are back! The fishing will just improve as the weeks continue and I’m very excited about my favorite time of year to fish these next few months coming up! The weather will be outstanding, so get your calendar out and book your day fishing with me at Bailey’s Charters soon!

Great day out in the Gulf with this young man who is from Minnesota with dreams of becoming a Marine Biologist. I put hi...
08/18/2026

Great day out in the Gulf with this young man who is from Minnesota with dreams of becoming a Marine Biologist. I put him face to face with some of our finest species to study first hand! lol. Don’t forget that after September 1st, Gag Grouper like the one you see here will be legal to invite to dinner! Just saying if you are into amazing tasting fish. Call or text to see what dates I have available. (727) 431-2050 www.baileyscharters.com

And that’s a wrap for Captain Stephen, third day with these great kids from the FIRST MATE ACADEMY.!! The sharks didn’t ...
07/09/2026

And that’s a wrap for Captain Stephen, third day with these great kids from the FIRST MATE ACADEMY.!! The sharks didn’t seem too hungry today, but my butterflied grunts seemed to do the trick and they couldn’t resist!

It makes my heart so happy to see these smiles, to hear their laughter, all their questions, their endless energy and excitement, all of which I’m very grateful to be able to share and give them memories they will talk about for a lifetime. This is a great program and if it’s ever in your area., I highly suggest you sign them up!

Day 2 for FIRST MATE ACADEMY with these incredible young men I am having the privilege to take out on my boat to continu...
07/08/2026

Day 2 for FIRST MATE ACADEMY with these incredible young men I am having the privilege to take out on my boat to continue their learning of boating safety, fishing, working together and all the aspects of what I do as a charter captain. Today we caught 4 nice sharks, one of which was a nice large nurse shark and all the boys took turns reeling them in.

It was day 1 of 3 for my  Captain’s adventures helping this great organization , First Mate Academy, which is  right her...
07/08/2026

It was day 1 of 3 for my Captain’s adventures helping this great organization , First Mate Academy, which is right here in Ozona, 2 blocks from my home. Such an amazing program that my friend Captain Andy Benedict runs , which is a camp that teaches young men and women ALL aspects of being a first mate on a charter boat. “It’s a learning camp, not a fishing camp”, Andy instructed everyone, and he emphasizes to the children the importance of good character, manners, respect, good behavior, and being kind to one another. I’m very honored and proud that I can help these great kids and this local organization that is one of a kind here in the great state of Florida. Another one of God’s blessings I am so grateful to have.

I don’t often get to go fishing three days in a row, especially with a good friend that I’ve known for over 30 years. Ma...
06/20/2026

I don’t often get to go fishing three days in a row, especially with a good friend that I’ve known for over 30 years. Marc is also one of my oldest art clients who I’ve designed many shirts and fabrics for his business in San Jose, California. It’s nice to have these treasured old friendships, and get to share some fun times together. The winds have been brutal, the fishing tough, but we certainly have had a great time on the water. Anytime for me being on the water, the salt air, and the ocean breeze is always a pure pleasure and grateful for every minute.

Let your actions really show your words, and that’s exactly what happened today on my charter. I literally was just sayi...
06/13/2026

Let your actions really show your words, and that’s exactly what happened today on my charter. I literally was just saying last night at dinner with a sweet good friend, that I’m excited to wake up to go on a Fishing charter because you never know what the day will bring, and no matter what happens, you have to keep your head on, don’t overreact and deal with it, roll with whatever life gives you to the best of your ability…. And that’s exactly what happened! It started as usual at 5 AM out to catch bait for the day when I noticed my live well wasn’t draining and was pouring water into the boat, potentially causing a serious issue. I kept throwing the cast net, but in the back of my mind, wondering what to do. A boat pulls up to me and it’s none other than my good friend Thomas. His power pole broke so he was unable to catch bait, so I took the opportunity since I had enough for my day, to give him some of my bait. Thomas is also an amazing fixer guy so he quickly told me what to do to fix my live well and it worked! You are awesome buddy!The sunrise was beautiful and I continued on my day to pick up my clients. My crew from Puerto Rico and the Dominican Republic were very excited to go fishing, and they ended up getting some nice quality fish and made some lifelong memories. I started up the engine to move to a different spot to target mangrove snapper but I heard a terrible sound coming from the engine. Hobbling back to Clearwater Beach 12 miles out. The engine finally shut down, so I called Sea Tow to rescue us. Through it all I entertained my clients with some of my silly stories, and by putting on some of their favorite Spanish/Latin music and we are all singing and dancing, waiting for our tow boat to arrive . They graciously paid me in full, with a very nice tip. Thank you my friends! God bless. I wonder if God was testing me to see what my reactions would be to certain situations as they were quite a few today. Maybe, but I do know that I’m proud of how I handled things, and the decisions and choices I made. We all ended up ending the day with smiles on our faces and thankful for the new friendships we have made, safe back at home relaxing.

Sometimes in life you have to go to plan B, and that’s what I had to do this morning with my great crew visiting from Ma...
06/01/2026

Sometimes in life you have to go to plan B, and that’s what I had to do this morning with my great crew visiting from Main and local young man from the Brandon area. Seas were a bit rough to head where I wanted to, so I took them to a rock pile and ledge closer to shore. It’s been an incredible weekend., from Friday night to now Sunday evening relaxing here at home. So much gratitude for everything, to the simplicity of nature to the people in my life. God painted a beautiful sunset to enjoy after catching the day’s bait. Wishing everyone a wonderful week ahead.
Captain Stephen Bailey
www.baileyscharters.com

Address

312 Lagoon Drive
Palm Harbor, FL
34683

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