Fair Winds Fishing Charters
5.0/5 (17 reviews)
State licensed
State Road 4a, Little Torch Key, FL 33043, United States–
Fair Winds Fishing Charters
State licensed
5.0/5 (17 reviews)
State Road 4a
Little Torch Key, FL, United States
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.
Rating
5.0
17 reviews
5
17
4
0
3
0
2
0
1
0
5.0
Boat & equipment
5.0
Captain & crew
5.0
Fishing Experience
Anglers' gallery (16)
+10
All reviews (17)
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Showing 1 – 5 of 17 reviews
Clark Forster
5.0
Verified
Capt Ben is the best
Half Day Trip – Flats - 2:00 PM on January 2, 2026 • 1 adult
Couldnt recommend Captain Ben more. Not only did he put me on all sorts of fish, he catered to my every need. We went
to a variety of different spots and he was super flexible with his gameplan based on conditions and my perosnal preferences. My only regret is that I booked a half-day instead of a full-day. I will be back again to fish with Capt Ben!
Reported catch:
Response from Captain
January 3, 2026
Thank you very much for the kind words Clark. Hope we can do it again!
0
Johnny Vasquez
5.0
Verified
Great caption never gave up on us.
Half Day Trip – Flats on August 28, 2025 • 2 adults
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.
Response from Captain
August 29, 2025
Thanks a lot Johnny, glad you could come out👍🏼
0
Giancarlo Generosi
5.0
Verified
Captain Ben put us on a ton of fish. Tarpon and Bonefish
Half Day Trip – Flats on July 2, 2025 • 2 adults
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.
Reported catch:
0
Peter Karl
5.0
Verified
Great time! Great trip! Lots of fish!
3/4 Day Trip – Flats on August 31, 2025 • 1 adult
Captain Ben worked hard both mornings I had booked. He was knowledgeable and willing to hit the spots necessary to get into the fish.
Reported catch:
Response from Captain
September 5, 2025
Thanks Pete!
0
Thomas Henry
5.0
Verified
Awesome
Half Day Trip – Flats on May 7, 2025 • 2 adults
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.
Reported catch:
0
Trip availability and prices
Trip Date:
Days:
Group Size:
Select date to see availability
February 2026
| Su | Mo | Tu | We | Th | Fr | Sa | |
|---|---|---|---|---|---|---|---|
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Number of days
1
Group Size
2 adults • 0 children
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3 Hour Trip Shark Trip
FREE Cancellation 7 days notice
3 Hour Trip
starts at 8:00 AM
US $350
Entire boat: 2 people
US $350
Entire boat: 2 people
3 Hour Trip Shark Trip - 2:00 PM
FREE Cancellation 7 days notice
3 Hour Trip
starts at 2:00 PM
US $350
Entire boat: 2 people
US $350
Entire boat: 2 people
Half Day Trip – Flats
FREE Cancellation 7 days notice
4 Hour Trip
starts at 8:00 AM
US $550
Entire boat: 2 people
US $550
Entire boat: 2 people
Half Day Trip – Flats - 2:00 PM
FREE Cancellation 7 days notice
4 Hour Trip
starts at 2:00 PM
US $550
Entire boat: 2 people
US $550
Entire boat: 2 people
3/4 Day Trip – Flats
FREE Cancellation 7 days notice
6 Hour Trip
starts at 8:00 AM
US $700
Entire boat: 2 people
US $700
Entire boat: 2 people
Full Day Trip – Flats
FREE Cancellation 7 days notice
8 Hour Trip
starts at 8:00 AM
US $800
Entire boat: 2 people
US $800
Entire boat: 2 people
There are 4 people looking at this charter.
Rating
5.0
17 reviews
5
17
4
0
3
0
2
0
1
0
5.0
Boat & equipment
5.0
Captain & crew
5.0
Fishing Experience
Anglers' gallery (16)
+10
All reviews (17)
Filter
Filter
Sort by: Featured
Featured
Showing 1 – 5 of 17 reviews
Clark Forster
5.0
Verified
Capt Ben is the best
Half Day Trip – Flats - 2:00 PM on January 2, 2026 • 1 adult
Couldnt recommend Captain Ben more. Not only did he put me on all sorts of fish, he catered to my every need. We went
to a variety of different spots and he was super flexible with his gameplan based on conditions and my perosnal preferences. My only regret is that I booked a half-day instead of a full-day. I will be back again to fish with Capt Ben!
Reported catch:
Response from Captain
January 3, 2026
Thank you very much for the kind words Clark. Hope we can do it again!
0
Johnny Vasquez
5.0
Verified
Great caption never gave up on us.
Half Day Trip – Flats on August 28, 2025 • 2 adults
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.
Response from Captain
August 29, 2025
Thanks a lot Johnny, glad you could come out👍🏼
0
Giancarlo Generosi
5.0
Verified
Captain Ben put us on a ton of fish. Tarpon and Bonefish
Half Day Trip – Flats on July 2, 2025 • 2 adults
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.
Reported catch:
0
Peter Karl
5.0
Verified
Great time! Great trip! Lots of fish!
3/4 Day Trip – Flats on August 31, 2025 • 1 adult
Captain Ben worked hard both mornings I had booked. He was knowledgeable and willing to hit the spots necessary to get into the fish.
Reported catch:
Response from Captain
September 5, 2025
Thanks Pete!
0
Thomas Henry
5.0
Verified
Awesome
Half Day Trip – Flats on May 7, 2025 • 2 adults
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.
Reported catch:
0
FAQs about Fair Winds Fishing Charters
The fish you can target
What is the boat like?
Boat category
Skiffs and flats boatsCapacity
2 personsBoat length
17 ftYear built
2003Boat manufacturer
MaverickBoat type
Flats boatEngine model
YamahaPowered by
1 x 70HPMax cruising speed
35 knots