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.
Captain
Ben Moloney
Most popular features:
Rating summary
Photos & videos by reviewers (14)
Angler rating
Anglers claimed
Good experience
100%
Appropriate for children
89%
Friendly captain
100%
Satisfied with the boat
100%
Recommend this charter
100%
Caught fish
100%
Experience:
Boat
Crew
Overall
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
Half Day Trip AM – Flats on July 10, 2024
Ben was an awesome guide who worked hard to find and land fish for us. Even with not so great weather and Tarpon that were in hiding, he was still able to get us on other fish. We mainly wanted to catch Tarpon, but also were interested in catching shark, Barracuda, Goliath grouper and snapper... All of which we ended up catching . If you haven't had a chance to fish for shark and the other fish listed above in the flats of the inshore waters, its something definitely worth doing with Ben...
Ben was an awesome guide who worked hard to find and land fish for us. Even with not so great weather and Tarpon that were in hiding, he was still able to get us on other fish. We mainly wanted to catch Tarpon, but also were interested in catching shark, Barracuda, Goliath grouper and snapper... All of which we ended up catching . If you haven't had a chance to fish for shark and the other fish listed above in the flats of the inshore waters, its something definitely worth doing with Ben......
Experience:
Boat
Crew
Overall
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.
Experience:
Boat
Crew
Overall
Half Day Trip AM – Flats on May 7, 2025
Captain Ben was awesome. We caught multiple bucket list fish from barracuda, mangrove snapper, and some monster bonefish. Made for a once in a lifetime opportunity that won’t be forgotten.
Captain Ben was awesome. We caught multiple bucket list fish from barracuda, mangrove snapper, and some monster bonefish. Made for a once in a lifetime opportunity that won’t be forgotten.
Experience:
Boat
Crew
Overall
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!
Fair Winds Fishing Charters offers the following trips to customers:
When you book a trip with Fair Winds Fishing Charters, you can expect the following amenities onboard:
Trips booked with Fair Winds Fishing Charters include:
Fair Winds Fishing Charters offers the following types of fishing:
Fair Winds Fishing Charters offers the following fishing techniques:
Top targeted fish species with Fair Winds Fishing Charters include:
Little Torch Key, Florida, United States
Meet Captain Ben Moloney, your guide for thrilling flats fishing in the beautiful Lower Florida Keys. Captain Ben's fishing journey began at just 13, side by side with his older brother, exploring the Keys' pristine waters. Little did he know that these early adventures would shape his entire life. In 2019, Captain Ben faced a tragic loss when his brother, and greatest fishing mentor, passed away. To honor his brother's legacy and continue their shared passion, Ben embarked on a mission that blended his love for the ocean with his dedication to his brother's memory. Before guiding anglers through the flats, Ben served his country as a Reconnaissance Marine for an impressive five years. During his military service, he honed skills like navigation, adaptability, and resilience. These traits would later serve him well as a fishing guide.
Inshore Fishing
Flats Fishing
Backcountry Fishing
Light Tackle
Fly Fishing
GPS
Fishfinder
Ice Box
Rods, reels & tackle
Live Bait
During winter months fishing for live bait is sometimes necessary and is included in overall price.
Lures
Catch cleaning & filleting
Cleaning fish is included in the price of the trip
Drinks
Bottled Water will be available.
Fishing License
Fishing license is covered and included with the charter.
Fly Fishing Equipment
Free cancellation up to 7 days prior to trip
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.
Pickup not included
Transfer to/from departure site is not included in trip rates.
Child Friendly
Children of all ages are welcome.
You Keep Catch
Catch and Release Allowed
Pay online in full
Pay online in full through FishingBooker and save on credit card fees at the dock.
No additional fees.
Book with 25% deposit, pay rest to captain
When the captain confirms your trip, FishingBooker charges your credit card a 25% 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
Checks
Bank Transfer
Fair Winds Fishing Charters - Updated 2025 Prices