Fair Winds Fishing Charters 

5.0/5 (14 reviews)
 
State licensed
 State Road 4a, Little Torch Key, FL 33043, United States
You may qualify for a Loyalty Program discount with Fair Winds Fishing Charters. To check if you can use a Loyalty Program discount for your selected dates, please sign in.

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

Most popular features:

 Fishing License
 Live Bait
 You Keep Catch
 Catch cleaning & filleting
 Drinks
 Child Friendly
 Ice Box
 Rods, reels & tackle

Trip availability and prices

Trip Date:
Days:
Group Size:
Almost there...
Half Day Trip AM – Flats
FREE Cancellation 7 days notice
4 Hour Trip, starts at 8:00 AM
Price for up to 2 people
US $550 
Half Day Trip PM – Flats
FREE Cancellation 7 days notice
4 Hour Trip, starts at 2:00 PM
Price for up to 2 people
US $550 
3/4 Day Trip – Flats
FREE Cancellation 7 days notice
6 Hour Trip, starts at 8:00 AM
Price for up to 2 people
US $650 
Full Day Trip – Flats
FREE Cancellation 7 days notice
8 Hour Trip, starts at 8:00 AM
Price for up to 2 people
US $750 
There are 2 people looking at this charter.

Customer reviews

Rating summary

5.0/5
out of 5 stars from 14 reviews
Boat
5.0/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (14)

Awesome
Awesome
An awesome experience!
+11

Angler rating

14
0
0
0
0

Anglers claimed

Good experience

100%

Appropriate for children

89%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

100%

Caught fish

100%

Showing 1 - 5 of 14 reviews
Giancarlo G.
Giancarlo G.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Captain Ben put us on a ton of fish. Tarpon and Bonefish

VERIFIED
NEW

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.  

 Giancarlo G. recommends Fair Winds Fishing Charters

Craig H.
Craig H.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

An awesome experience!

VERIFIED

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......  

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 Craig H. recommends Fair Winds Fishing Charters

Tim F.
Tim F.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Great day!

VERIFIED

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.  

 Tim F. recommends Fair Winds Fishing Charters

Thomas H.
Thomas H.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

Awesome

VERIFIED

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.  

Review media 0
Review media 1
 Thomas H. recommends Fair Winds Fishing Charters

Reginald H.
Reginald H.
5.0/5

Experience:

5.0/5

Boat

5.0/5

Crew

5.0/5

Overall

May fishing trip

VERIFIED

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!  

 Reginald H. recommends Fair Winds Fishing Charters

FAQs about Fair Winds Fishing Charters

What are the trip rates for Fair Winds Fishing Charters?

Fair Winds Fishing Charters offers the following trips to customers:

  • US $550 per group - Half Day Trip AM – Flats (4 hours)
  • US $550 per group - Half Day Trip PM – Flats (4 hours)
  • US $650 per group - 3/4 Day Trip – Flats (6 hours)
  • US $750 per group - Full Day Trip – Flats (8 hours)
Which amenities are available onboard with Fair Winds Fishing Charters?

When you book a trip with Fair Winds Fishing Charters, you can expect the following amenities onboard:

  • GPS
  • Fishfinder
  • Ice Box
What's included in the trip price with Fair Winds Fishing Charters?

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
What types of fishing does Fair Winds Fishing Charters offer?

Fair Winds Fishing Charters offers the following types of fishing:

  • Inshore Fishing
  • Flats Fishing
  • Backcountry Fishing
What fishing techniques does Fair Winds Fishing Charters offer?

Fair Winds Fishing Charters offers the following fishing techniques:

  • Light Tackle
  • Fly Fishing
Which fish species can I catch with Fair Winds Fishing Charters?

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

Little Torch Key, Florida, United States

1 Fishing Report
ID & license verified
14 Customer reviews
Response time within an hour
Member since October 2023

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

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.

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 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

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
2 people are looking at this charter.