Fair Winds Fishing Charters 

5.0
(35 reviews)
 
State licensed
vob.svg 
Veteran Owned
 183 Barry Avenue, Little Torch Key, FL 33042, United States

Fair Winds Fishing Charters 

Little Torch Key, FL, United States
17 ft
2
5.0
(35 reviews)

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.

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.

Ben Moloney
Captain
Ben Moloney
ID & credentials verified
responds within an hour

Select date to see availability

Trip availability and prices

Trip date:
Group Size:
September 2026
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Group Size
2 adults • 0 children
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Half Day Trip – Flats
FREE Cancellation 7 days notice
4 hour trip multiple starting times (8:00 AM, 1:00 PM)
Barracuda (Great)
Bonefish
Permit
Tarpon
+1
US $600
Entire boat: 2 people
3/4 Day Trip – Flats
FREE Cancellation 7 days notice
6 hour trip starts at 8:00 AM
Barracuda (Great)
Bonefish
Permit
Tarpon
+1
US $750
Entire boat: 2 people
Full Day Trip – Flats
FREE Cancellation 7 days notice
8 hour trip starts at 8:00 AM
Barracuda (Great)
Bonefish
Permit
Tarpon
+1
US $850
Entire boat: 2 people
There are 2 people looking at this charter.

Customer reviews

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Rating

5.0
35 reviews
5.0
Boat & equipment
5.0
Captain & crew
5.0
Fishing Experience

Anglers' gallery (38)

What anglers say

100%
Recommended
97%
Caught fish

All reviews (35)

Frequently mentioned
Showing 15 of 35 reviews
Isbel Muniz
Isbel Muniz
us
Florida, US
Member since 2026
5.0
Verified
Best charter ever!
Half Day Trip – Flats - 1:00 PM on July 17, 20262 adults

An unforgettable day on the water! Captain Ben was incredibly patient, knowledgeable, and truly an expert. He helped make my 13-year old sons dream come true by putting him on not one, but two tarpon! We also saw lots of dolphins, sharks, bonefish, barracudas, and stingrays, making the experience even more incredible. I couldn’t have asked for a better charter—highly recommend! We will definitely be back on the water with Ben!

Reported catch:
Great Barracuda
Ben Moloney
Response from Captain

Thanks for coming out Isbel!

Eric Nee
Eric Nee
us
Maryland, US
Member since 2026
5.0
Verified
Outstanding day fishing!
Half Day Trip – Flats - 2:00 PM on April 2, 20262 adults

I told Captain Ben I wanted to catch barracuda to again relive the memories when I came down to the Keys decades ago during a college road trip. Scooting around the beautiful Florida Keys’ flats pursuing Cuda,” and then catching the toothy critters was a fantastic thill. Outstanding trip! Thanks Captain Ben!

Reported catch:
Great Barracuda
Ben Moloney
Response from Captain

Thanks for coming out Eric!

Steve Sparks
Steve Sparks
us
Ohio, US
Member since 2026
5.0
Verified
New
Great Experience!
3 Hour Trip Shark Trip on August 4, 20262 adults

Me and my son had an exellent time! Would highly recommend to anyone and we will be going again when we return to the Keys.

Reported catch:
Lemon Shark
Ben Moloney
Response from Captain

thanks Steve!

Joe Badham
Joe Badham
Repeat angler
us
Michigan, US
Member since 2020
2 trips
5.0
Verified
Exactly the trip I wanted!
3 Hour Trip Shark Trip on April 20, 20261 adult

Capt. Ben is the guy I would want to fish with all the time! Caught countless snappers, a couple of barracuda, and rounded off the morning with a beautiful lemon shark! A fight of a lifetime! What a great day!

Reported catch:
Lemon Shark
Ben Moloney
Response from Captain

Thanks Joe!

Jay Iverson
Jay Iverson
Repeat angler
us
Iowa, US
Member since 2021
5 trips
5.0
Verified
Lots of unique action
Half Day Trip – Flats on March 10, 20262 adults

Ben worked hard trying to create opportunities. From an airborne large baracuda launching out of the water to a beautiful big cobia being eaten by a huge bull shark boats idea, to the mess of snappers for lunch. Good times.

Ben Moloney
Response from Captain

Thankyou for coming out Jay!

FAQs about Fair Winds Fishing Charters

Fair Winds Fishing Charters offers the following trips to customers:
  • US $600 per group - Half Day Trip – Flats (4 hours)
  • US $600 per group - Half Day Trip – Flats - 1:00 PM (4 hours)
  • US $750 per group - 3/4 Day Trip – Flats (6 hours)
  • US $850 per group - Full Day Trip – Flats (8 hours)
When you book a trip with Fair Winds Fishing Charters, you can expect the following amenities onboard:
  • GPS
  • Fishfinder
  • Ice box
Trips booked with Fair Winds Fishing Charters include:
  • 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
Fair Winds Fishing Charters offers the following types of fishing:
  • Inshore fishing
  • Flats fishing
  • Backcountry fishing
Fair Winds Fishing Charters offers the following fishing techniques:
  • Light tackle
  • Fly fishing
Top targeted fish species with Fair Winds Fishing Charters include:
  • Bonefish
  • Jack Crevalle
  • Permit
  • Redfish
  • Shark (Bonnethead)
  • Shark (Lemon)
  • Snapper (Mangrove)
  • Snapper (Mutton)
  • Snook
  • Tarpon

Your captain

Ben Moloney
Ben Moloney

Little Torch Key, Florida, United States

1 Fishing Report
ID & license verified
35 Customer reviews
Typical response within an hour
Member since October 2023
Angler's Choice

The Angler's Choice Award is given to listings that consistently deliver a high-quality service and earn great reviews from customers.

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.

Ben Moloney
Ben Moloney
Fully verified
US veteran
Angler's Choice
1
reports
35
reviews
2023
member since
~1h
response
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.

The fish you can target

Bonefish
Bonefish
Jack Crevalle
Jack Crevalle
Permit
Permit
Redfish
Redfish
Bonnethead Shark
Bonnethead Shark
Lemon Shark
Lemon Shark
Mangrove Snapper
Mangrove Snapper
Mutton Snapper
Mutton Snapper
Snook
Snook
Tarpon
Tarpon
Bonefish
Bonefish
Jack Crevalle
Jack Crevalle
Permit
Permit
Redfish
Redfish
Bonnethead Shark
Bonnethead Shark

Real catches by this captain

  • Bucket List Fish!
    Rob M.
    Rob M.
  • Epic Adventure
    Lucinda O.
    Lucinda O.
  • Great trip!
    Sunny S.
    Sunny S.
  • Lots of unique action
    Jay I.
    Jay I.
  • Beautiful day on the flats.
    Bill V.
    Bill V.
  • Awesome
    Thomas H.
    Thomas H.
  • An awesome experience!
    Craig H.
    Craig H.
  • Very cool trip
    Daniel L.
    Daniel L.
  • Great day of fishing
    Kevin D.
    Kevin D.

What is the boat like?

Boat image
Boat category
Skiffs and flats boats
Capacity
2 persons
Boat length
17 ft
Year built
2003
Boat manufacturer
Maverick
Boat type
Flats boat
Engine model
Yamaha
Powered by
1 x 70HP
Max cruising speed
35 knots

What kind of fishing will you do?

Inshore Fishing
Flats Fishing
Backcountry Fishing

Which fishing techniques you can try

Light Tackle
Fly Fishing

Which amenities are available onboard

GPS
Fishfinder
Ice box
What's included in the trip price
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

How cancellations work

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.

More details

What the listing policies are

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

How you can pay

Pay online in full

Pay online in full through FishingBooker and save on credit card fees at the dock.

No additional fees.

Book with 15% deposit, pay rest to captain

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

 Visa

 Mastercard

 American Express

 PayPal

 Checks

 Bank transfer

When paying the remaining balance with a credit card, an additional 3% charge will apply.

What’s biting in Little Torch Key right now

BonefishBonefish
Jack CrevalleJack Crevalle
PermitPermit
RedfishRedfish
Snapper (Mangrove)Snapper (Mangrove)
Snapper (Mutton)Snapper (Mutton)
SnookSnook
TarponTarpon

Compare similar fishing charters

Current
Fair Winds Fishing Charters
Fair Winds Fishing Charters
State licensed
5.0
(35)
17 ft
Group size 1 - 2
1 - 2
Fish 1
Fish 2
+8
4 hour trip • 2 persons
US $600