Fair Winds Fishing Charters
Fair Winds Fishing Charters
Ready to catch some fish in Summerland Key? Make it happen, with Fair Winds Fishing Charters!
Depending on conditions, you might hook into Tarpon, Bonefish, Permit, Snapper, Snook, Lemon Shark, Bonnethead Shark, Jack Crevalle, Redfish, and anything else that bites. Depending on the species you’re after, you may find yourself light tackle fishing, or maybe something more specialized in this area. Capt. Ben also offers fly fishing and provides all the gear you will need.
Your vessel for the day is a 17’ Flats boat that can carry up to 2 passengers. It has all the essentials. Capt. Ben will supply rods and reels for you, along with lures. Live bait is available, but be sure to ask about it so you know if you’ll be catching it yourself.
Your fishing license for the day is covered by the charter boat, so all you have to do is look forward to your trip! Some fish have special regulations, including when you can keep them. Your captain will help you follow regulations while you fish.
Families who love fishing together will be glad to know that kids are welcome aboard! It’s recommended to bring polarized sunglasses, snacks, sunscreen (non-spray), and a hat. Bottled water is included, free of charge. Alcohol is allowed in moderation, so long as you avoid hard liquor as well as glass bottles.
For more information about fishing with Fair Winds Fishing Charters, feel free to send Capt. Ben a message down below.
Customer reviews
Rating summary
Photos & videos by reviewers (15)
+12Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
90%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Caught fish
100%
Jul 2, 2025
Half Day Trip AM – Flats
Captain Ben put us on a ton of fish. Tarpon and Bonefish
Ben has a ton of experience and positions you on the fish to give you the best chance to land your bait right in front of the fish. From there it’s all up to you to try and hook the fish of your dreams. Captain worked all trip in tough conditions and still found fish. My dad and I highly recommend Captain Ben and plan on going out with Ben next time we are in the keys.
Ben has a ton of experience and positions you on the fish to give you the best chance to land your bait right in front of the...
Aug 28, 2025
Half Day Trip AM – Flats
Great caption never gave up on us.
Our captain was awesome, he did everything right to make sure we got fish to the Boat. I’ve been on many guided trips where I caught nothing but still had a good time. Our captain was the best I highly recommend him. He never stop looking for fish he used ever tool he had. Great job captain thank you.
Our captain was awesome, he did everything right to make sure we got fish to the Boat. I’ve been on many guided trips where I...
Captain replied
Aug 31, 2025
3/4 Day Trip – Flats
Great time! Great trip! Lots of fish!
Captain Ben worked hard both mornings I had booked. He was knowledgeable and willing to hit the spots necessary to get into the fish.
Captain Ben worked hard both mornings I had booked. He was knowledgeable and willing to hit the spots necessary to get into the...
Captain replied
May 14, 2025
3/4 Day Trip – Flats
May fishing trip
Capt Ben was the best, very knowledgeable and worked tirelessly to put me on fish! and boy did we catch fish!great Capt and guy!
Capt Ben was the best, very knowledgeable and worked tirelessly to put me on fish! and boy did we catch fish!great Capt and guy!
Jan 13, 2025
3/4 Day Trip – Flats
Great day!
Captain Ben was great. Put me on to fish most of the day. Spent the afternoon stalking the big ‘cuda! Managed a bonefish, bucket list fish for me, when we didn’t really expect to see many or any. Very knowledgeable and friendly. Would highly recommend Ben.
Captain Ben was great. Put me on to fish most of the day. Spent the afternoon stalking the big ‘cuda! Managed a bonefish, bucket...
Trip availability and prices
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Customer reviews
Rating summary
Photos & videos by reviewers (15)
+12Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
90%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Caught fish
100%
Experience:
Boat
Crew
Overall
Captain Ben put us on a ton of fish. Tarpon and Bonefish
Half Day Trip AM – Flats on July 2, 2025
Ben has a ton of experience and positions you on the fish to give you the best chance to land your bait right in front of the fish. From there it’s all up to you to try and hook the fish of your dreams. Captain worked all trip in tough conditions and still found fish. My dad and I highly recommend Captain Ben and plan on going out with Ben next time we are in the keys.
Ben has a ton of experience and positions you on the fish to give you the best chance to land your bait right in front of the fish. From there it’s all up to you to try and hook the fish of your dreams. Captain worked all trip in tough conditions and still found fish. My dad and I highly recommend Captain Ben and plan on going out with Ben next time we are in the keys.
Experience:
Boat
Crew
Overall
Great caption never gave up on us.
Half Day Trip AM – Flats on August 28, 2025
Our captain was awesome, he did everything right to make sure we got fish to the Boat. I’ve been on many guided trips where I caught nothing but still had a good time. Our captain was the best I highly recommend him. He never stop looking for fish he used ever tool he had. Great job captain thank you.
Our captain was awesome, he did everything right to make sure we got fish to the Boat. I’ve been on many guided trips where I caught nothing but still had a good time. Our captain was the best I highly recommend him. He never stop looking for fish he used ever tool he had. Great job captain thank you.
Experience:
Boat
Crew
Overall
Great time! Great trip! Lots of fish!
3/4 Day Trip – Flats on August 31, 2025
Captain Ben worked hard both mornings I had booked. He was knowledgeable and willing to hit the spots necessary to get into the fish.
Captain Ben worked hard both mornings I had booked. He was knowledgeable and willing to hit the spots necessary to get into the fish.
Experience:
Boat
Crew
Overall
May fishing trip
3/4 Day Trip – Flats on May 14, 2025
Capt Ben was the best, very knowledgeable and worked tirelessly to put me on fish! and boy did we catch fish!great Capt and guy!
Capt Ben was the best, very knowledgeable and worked tirelessly to put me on fish! and boy did we catch fish!great Capt and guy!
Experience:
Boat
Crew
Overall
Great day!
3/4 Day Trip – Flats on January 13, 2025
Captain Ben was great. Put me on to fish most of the day. Spent the afternoon stalking the big ‘cuda! Managed a bonefish, bucket list fish for me, when we didn’t really expect to see many or any. Very knowledgeable and friendly. Would highly recommend Ben.
Captain Ben was great. Put me on to fish most of the day. Spent the afternoon stalking the big ‘cuda! Managed a bonefish, bucket list fish for me, when we didn’t really expect to see many or any. Very knowledgeable and friendly. Would highly recommend Ben.
FAQs about Fair Winds Fishing Charters
The fish you can target
What is the boat like?
