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 5 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, the Mayport Jetties, the St. John’s River and out to 10 miles to offshore wrecks and live bottom/reefs, and out to 25 miles into deep sea fishing of 120’. 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, bottom fishing, jigging, and trolling are the most reliable way to get hooked up on Snappers, Grouper, Jacks, Mackerals, Dolphin (Mahi Mahi), Tunas, Sea Bass, Tarpon, and Cobia
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 northeast coast and enjoy the Atlantic’s most exciting fishing!
Customer reviews
Rating summary
Photos & videos by reviewers (80)
+77Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Caught fish
100%
Jun 20, 2025
6 Hr. Offshore Fishing Deep Sea
Wow what a spectacular trip!
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
Unforgettable Offshore Fishing Trip with Bailey’s Charters I booked an offshore charter with Bailey’s Charters for my son’s 16th...
Captain replied
May 22, 2025
4 hr Inshore/Nearshore Trip
Awesome Trip!
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!
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...
Captain replied
Feb 22, 2025
6 hr Inshore/Nearshore Trip
6 hour inshore
Had a great time with Captain Stephen on our 6 hour trip. Started at the Jetties jigging, caught a sheepshead and a black drum. Was a windy day with a little bit of chop. Took a 15-20 minute ride inland and used Carolina rigs and jigging to try and catch more sheepshead around a bridge. Moved one last time to an underwater grass area where we used float rigs to catch 5 reds( kept 2),and 2 bluefish. Overall a great day of fishing. Captain was knowledgeable of the area and was set up to try different types of techniques and teach us how to use them properly. Definitely would recommend and use captain Stephen again!
Had a great time with Captain Stephen on our 6 hour trip. Started at the Jetties jigging, caught a sheepshead and a black drum....
Captain replied
Jul 5, 2025
6 hr Inshore/Nearshore Trip
Slow day turned GREAT day
It took us a while to find the fish and Capt Stephen was trying all his usual spots, but the fish just weren’t bitting, till we got to his last spot and then they were bitting for a solid hour! He’s committed to finding the fish and his efforts paid off, had a great day on the water!
It took us a while to find the fish and Capt Stephen was trying all his usual spots, but the fish just weren’t bitting, till we...
Jun 6, 2025
6 hr Inshore/Nearshore Trip
6 hour inshore trip
We did a 6 hour inshore trip. Captain Bailey brought the gear for all of us and did nearly all the work for the inexperienced fishers. Not only was he a phenomenal guide but an amazing mentor as well. Within the first few minutes we all were reeling in fish. He cheered us on and helped us to success. He truly is a professional at this and we plan on doing another trip with him!!
We did a 6 hour inshore trip. Captain Bailey brought the gear for all of us and did nearly all the work for the inexperienced...
Captain replied
Trip availability and prices
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Customer reviews
Rating summary
Photos & videos by reviewers (80)
+77Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
100%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Caught fish
100%
Experience:
Boat
Crew
Overall
Wow what a spectacular trip!
6 Hr. Offshore Fishing Deep Sea on June 20, 2025
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
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...
Experience:
Boat
Crew
Overall
Awesome Trip!
4 hr Inshore/Nearshore Trip on May 22, 2025
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!
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)...
Experience:
Boat
Crew
Overall
6 hour inshore
6 hr Inshore/Nearshore Trip on February 22, 2025
Had a great time with Captain Stephen on our 6 hour trip. Started at the Jetties jigging, caught a sheepshead and a black drum. Was a windy day with a little bit of chop. Took a 15-20 minute ride inland and used Carolina rigs and jigging to try and catch more sheepshead around a bridge. Moved one last time to an underwater grass area where we used float rigs to catch 5 reds( kept 2),and 2 bluefish. Overall a great day of fishing. Captain was knowledgeable of the area and was set up to try different types of techniques and teach us how to use them properly. Definitely would recommend and use captain Stephen again!
Had a great time with Captain Stephen on our 6 hour trip. Started at the Jetties jigging, caught a sheepshead and a black drum. Was a windy day with a little bit of chop. Took a 15-20 minute ride inland and used Carolina rigs and jigging to try and catch more sheepshead around a bridge. Moved one last time to an underwater grass area where we used float rigs to catch 5 reds( kept 2),and 2 bluefish. Overall a great day of fishing. Captain was knowledgeable of the area and was set up to try different...
Experience:
Boat
Crew
Overall
Slow day turned GREAT day
6 hr Inshore/Nearshore Trip on July 5, 2025
It took us a while to find the fish and Capt Stephen was trying all his usual spots, but the fish just weren’t bitting, till we got to his last spot and then they were bitting for a solid hour! He’s committed to finding the fish and his efforts paid off, had a great day on the water!
It took us a while to find the fish and Capt Stephen was trying all his usual spots, but the fish just weren’t bitting, till we got to his last spot and then they were bitting for a solid hour! He’s committed to finding the fish and his efforts paid off, had a great day on the water!
Experience:
Boat
Crew
Overall
6 hour inshore trip
6 hr Inshore/Nearshore Trip on June 6, 2025
We did a 6 hour inshore trip. Captain Bailey brought the gear for all of us and did nearly all the work for the inexperienced fishers. Not only was he a phenomenal guide but an amazing mentor as well. Within the first few minutes we all were reeling in fish. He cheered us on and helped us to success. He truly is a professional at this and we plan on doing another trip with him!!
We did a 6 hour inshore trip. Captain Bailey brought the gear for all of us and did nearly all the work for the inexperienced fishers. Not only was he a phenomenal guide but an amazing mentor as well. Within the first few minutes we all were reeling in fish. He cheered us on and helped us to success. He truly is a professional at this and we plan on doing another trip with him!!
FAQs about Bailey's Charters
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