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Fair Winds Fishing Charters

5.0  (0 Review)

Big Pine Key, Florida

33901 Overseas Highway, Big Pine Key, Florida, 33043

Captain Ben invites you to experience the excitement of sight fishing on the legendary flats of the Florida Keys. Step aboard our well-equipped 17′ Maverick Flats Skiff and get ready for an unforgettable adventure. As Captain Ben expertly navigates the shallow waters, you’ll have the opportunity to spot fish up close and personal. Feel the rush of adrenaline as you cast your line, presenting your bait, lure, or fly with precision. Whether it’s stalking elusive bonefish or engaging in thrilling battles with tarpon and permit, Fair Winds promises an exciting experience for all fishing enthusiasts.

We cater to both novice and experienced anglers, providing personalized trips to pursue the region’s abundant fish species in the shallow, crystal-clear waters. Captain Ben will give his best recommendation depending on the season, weather, and current fishing conditions. Above all our goal is provide a safe, unique, and enjoyable experience for all. Regardless of skill level, Captain Ben is committed to accommodating every angler, offering encouragement and instruction to help you achieve your fishing goals. Our charters can accommodate up to 3 anglers (maximum 2 adults). Don’t forget to bring your sunscreen, sunglasses, snacks/food, additional drinks, and child life jackets if needed. Rest assured, all fishing licenses, bait, and tackle, along with bottled water, will be provided. Join us for an exceptional day of sight fishing amidst the breathtaking beauty of the Florida Keys.

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Ages 13 or above
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Half Day Flats AM (Tarpon and More!)

$500.00 USD

Starts at: 07:00 AM

Duration: 4 hours

Join us for the ultimate half-day flats fishing adventure! Our trips are designed for an unforgettable experience and are perfect for the whole family. On this charter, we will target an array of exciting species, including bonefish, permit, barracuda, jacks, tarpon, sharks, and more. Whether you’re a seasoned angler or a first-timer, Captain Ben ensures a thrilling day! Book your half-day flats fishing trip now and make lasting memories on the water!

This charter is 4 hours and accommodates up to 3 people (2 adults max).

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Half Day Flats PM (Tarpon and More!)

$500.00 USD

Starts at: 12:00 PM

Duration: 4 hours

Experience an afternoon of flats fishing that promises excitement for the entire family! Departing around lunch, our half-day trips provide the perfect opportunity to target an array of species, including bonefish, permit, barracuda, jacks, tarpon, sharks, and more. Captain Ben welcomes both seasoned anglers and beginners alike! Create lasting memories as you cast your line and reel in the catch of the day during a thrilling afternoon on the water. Book your charter now and experience the beauty of the Lower Florida Keys!

This charter is 4 hours and accommodates up to 3 people (2 adults max).

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Full Day Flats (Tarpon and More!)

$700.00 USD

Starts at: 08:00 AM

Duration: 8 hours

Are you ready for a full day of fishing the flats? Whether you’re a seasoned angler seeking a challenge or a family looking to bond over the excitement of the catch, our expert guides ensure a memorable experience for everyone. Having a full day will give you the flexibility to target a variety of species, including bonefish, permit, barracuda, jacks, tarpon, sharks, and more. If you have a fish on your bucket-list, make sure you let Captain Ben know! Book your full-day flats fishing adventure now and enjoy a day filled with excitement, stunning scenery, and the chance to reel in the prized species of the Florida Keys waters!

This charter is 8 hours and accommodates up to 3 people (2 adults max).

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Half Day - Snapper Trip (AM)

$500.00 USD

Starts at: 08:00 AM

Duration: 4 hours

If you’re looking for action and delicious fish you can take home, we invite you to discover the excitement of snapper fishing in the picturesque backcountry of the Florida Keys. Captain Ben’s intimate knowledge of the area will lead you to prime snapper fishing grounds where these delectable fish abound. Feel the anticipation build as you drop your line into a hole or near structure, awaiting the unmistakable tug of a hungry snapper. With Captain Ben’s guidance and expertise, you’ll learn the techniques to hook these feisty fish and reel them in. As you enjoy the tranquility of the backcountry, surrounded by stunning mangroves and abundant wildlife, the thrill of landing a prized snapper will be a memory you won’t soon forget.

This charter is 4 hours and accommodates up to 3 people (2 adults max).

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Half Day - Shark Fishing (PM)

$500.00 USD

Starts at: 12:00 PM

Duration: 4 hours

Embark on an action packed, exhilarating adventure targeting sharks and barracudas on the beautiful flats of the Florida Keys. As Captain Ben guides you to the best locations, get ready to witness the raw power and excitement of these apex predators. Feel the adrenaline surge as you cast your line and tempt these formidable creatures to strike. Whether it’s the thrilling run of a lemon shark or the lightning-fast strike of a barracuda, the battles will test your skills and leave you with lasting memories. Captain Ben’s knowledge of these waters will ensure an unforgettable shark and barracuda fishing experience.

This charter is 4 hours and accommodates up to 3 people (2 adults max).

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Half Day - Sandbar Trip

$500.00 USD

Starts at: 10:00 AM

Duration: 4 hours

If you’re simply looking for a nice time on the water with no hooks involved join us for a memorable sandbar trip or sunset cruise that will leave you in awe.  Relax and unwind as we navigate through the calm turquoise waters, surrounded by breathtaking views of the back country ecosystem of the lower Florida Keys. On our sandbar trip, anchor at a secluded sandbar where you can soak up the sun, swim in the warm waters, and enjoy a refreshing beverage. Alternatively, embark on a romantic sunset cruise, where the golden hues of the sinking sun paint a picture-perfect backdrop for unforgettable moments. Bask in the serenity of the Lower Florida Keys, taking in the beauty of nature and the tranquility of the open water. With Fair Winds Fishing Charters, your sandbar trip or sunset cruise promises to be a delightful and unforgettable experience.

This charter is 4 hours and accommodates up to 3 people (2 adults max).

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Trip Features:

Cleaning & Filleting

Upon arrival from your day on the water, your catch will be filleted and bagged for you and your family/friends to take home and enjoy!

Live Bait Well

Our Captain’s boat is equipped with a live bait well, which may be used to hold bait and other smaller fish you may catch.

Rods, Reels, & Tackle

Our Captains are prepared with all the equipment necessary to catch whatever may swim your way! All the rods, reels, tackle, and bait will be provided to target whatever species you are hoping to catch!

You Keep Catch

Aside from the species required to be released by law and some species that may not be recommended as table fair, whatever fish are landed while out on the water are yours to keep!

What To Bring:

Additional Drinks

Camera

Cash

Hat

Non-Spray Sunscreen

Snacks/Food

Sunglasses

Weather-Appropriate Clothing

Boat Specs:

17' Maverick HPX-V | Flats Skiff
  • Length: 17'
  • Capacity: 3 Persons
  • Hull: Maverick HPX-V

Types of Fish:

  • Barracuda
  • Bonefish
  • Drum (Redfish)
  • Grouper (Goliath)
  • Jack (Crevalle)
  • Permit
  • Pompano
  • Shark
  • Snapper (Dog)
  • Snapper (Lane)
  • Snapper (Mangrove)
  • Snook
  • Tarpon

Listing Policies:

  • Child Friendly
  • Cooler

Boat Reviews:

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