Windward Fishing Charters
Windward Fishing Charters
Windward Fishing Charters is located in Sarasota and offers to show you a memorable time out of Siesta Key and the surrounding areas. Whether you are an experienced fisherman or a first-timer, Capt. Timothy will ensure that everyone has a great time. Also, kids are more than welcome to come aboard, just make sure to let the captain know ahead of time to make sure he has child life jackets on board.
Capt. Timothy will do his best to make sure you have a fun day full of fishing. This involves many different trip options. On these trips, you can expect to use techniques such as light tackle, heavy tackle, bottom fishing, and trolling.
Your fishing adventure starts on a 22' Pathfinder boat fully restored in 2022. It's equipped with a tower for shade and sighting fish, power pole, GPS/sonar, coolers for drinks and fish, and a wireless trolling motor. She can safely take up to 5 anglers and also comes with an ice box to put the keeper fish in.
All rods, reels, terminal tackle, live bait, lures, bottled water, and ice are included in the price so you can focus on what really matters, fishing. Your trip will include all the necessary fishing licenses for the day. At the end of the trip, Capt. Tim will clean and bag the keepers that you want to take home.
Book your trip now and hit the water with Windward Fishing Charters!
Windward Fishing Charters is located in Sarasota and offers to show you a memorable time out of Siesta Key and the surrounding areas. Whether you are an experienced fisherman or a first-timer, Capt. Timothy will ensure that everyone has a great time. Also, kids are more than welcome to come aboard, just make sure to let the captain know ahead of time to make sure he has child life jackets on board.
Capt. Timothy will do his best to make sure you have a fun day full of fishing. This involves many different trip options. On these trips, you can expect to use techniques such as light tackle, heavy tackle, bottom fishing, and trolling.
Your fishing adventure starts on a 22' Pathfinder boat fully restored in 2022. It's equipped with a tower for shade and sighting fish, power pole, GPS/sonar, coolers for drinks and fish, and a wireless trolling motor. She can safely take up to 5 anglers and also comes with an ice box to put the keeper fish in.
All rods, reels, terminal tackle, live bait, lures, bottled water, and ice are included in the price so you can focus on what really matters, fishing. Your trip will include all the necessary fishing licenses for the day. At the end of the trip, Capt. Tim will clean and bag the keepers that you want to take home.
Book your trip now and hit the water with Windward Fishing Charters!
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Trip availability and prices
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Customer reviews
Rating
Anglers' gallery (216)
What anglers say
Reviews (191)
Barbara Ekker•
Wisconsin, USMember since 20265.0VerifiedAbsolute amazing time
4 Hour Trip (PM) on March 11, 2026 • 3 adultsWe had an absolutely fantastic time fishing! Our captain was a blast to be around and worked hard the entire trip to make sure we had the best experience possible. We caught a ton of fish and had so much fun doing it. You can really tell he puts in the effort to make sure everyone has a great time. Highly recommend!
David CristRepeat angler•Illinois, US•Member since 20234 trips5.0VerifiedCaptain Tim works for you!
4 Hour Trip (PM) on March 18, 2026 • 4 adults • 2 childrenwe had a cold front come through so I knew tge fishing would be marginal at beet. Capt. Tim made multiple stops trying to grt us onto fish. we caught several Snook but the hits were tough to get. i woukd definitely recommend this boat and captain if you want someone to work hard to get on the fish!!
Timothy HughesRepeat angler•North Carolina, US•Member since 20223 trips5.0VerifiedFishing with Timothy
4 Hour Trip (AM) on June 9, 2026 • 3 adults
Bill Argue•Florida, USMember since 20265.0VerifiedApril fishing trip
4 Hour Trip (AM) on April 10, 2026 • 2 adults
Joel SingerRepeat angler•Ohio, US•Member since 20225 trips5.0VerifiedThe Best!
4 Hour Trip (PM) on December 18, 2025 • 2 adultsOur 4th year in a row booking with Captain Tim. Went twice this week. Always a great time and lost count of how many we caught. Looking forward to next year.
Bobby CarriganRepeat angler•Gainesville, FL, US•Member since 20242 trips5.0Verifiedgreat time
4 Hour Trip (PM) on January 2, 2026 • 5 adults • 3 childrenwe had a great time
Franke Donlon•New York, USMember since 20255.0VerifiedIf you want to catch fish - Timmy will put you on them!
4 Hour Trip (PM) on April 20, 2025 • 3 adults • 1 childOn Easter Sunday, we embarked on an unforgettable fishing adventure and caught an impressive array of fish, including Speckled Trout, Redfish, Snook, and Jack Crevalle. Captain Timmy was exceptional—easygoing, friendly, and incredibly knowledgeable. His demeanor, dedication and hard work made the experience truly enjoyable. He tailored the fishing trip to suit our preferences - and 12-year-old fishing enthusiast, ensuring that we had a memorable time on the water. We highly recommend Windward Fishing Charters—definitely a 5-star experience all around!
David ListmanRepeat angler•Pennsylvania, US•Member since 20255 trips5.0VerifiedA Great tarpon Fishing Experience
6 Hour Trip – Tarpon on June 9, 2025 • 2 adults • 1 childCaptain Timmy was great. He's a veteran in the area with a fine boat and equipment. He's been fishing these water since he was a kid and he knew all the right spots. He called in advance to change the start time so that we could take advantage of the tides. We hook 3 and reeled in a 60 pounder.
Regina Murphy•New York, USMember since 20235.0VerifiedFishing trip in May
4 Hour Trip (AM) on May 1, 2023 • 4 adults
Frank Kish•Pennsylvania, USMember since 20245.0VerifiedAwesome! We want to go again!
4 Hour Trip (AM) on May 18, 2024 • 5 adults • 1 childCaptain Tim and his deckhand Jack were a knowledgeable and friendly crew leading our group of 4. My 10 year old provided the review headline since we had a great time catching a bunch of snook, 1 big blue bluefish and few saltwater catfish to keep things interesting. Captain Tim kept us on the fish and explored 5 different spots. Highly recommend for a fun inshore 4 hour morning trip.
Rating
Anglers' gallery (216)
What anglers say
All reviews (191)
My son & I have chartered w/ Captain Tim multiple times as this point. We never get skunked. He knows where to find fish. Always polite, professional having all the gear you’ll need. Highly recommend booking with him.
Conditions weren’t the best. We targeted snook and Captain Timmy delivered. Not just snook. we caught grouper, snapper, and speckle trout. Even one hardhead. Truly, I enjoyed fishing and sharing information with Captain Timmy. 👍
My son & I have chartered Captain Tim for multiple trips for multiple years now. And we always catch fish! He is very knowledgeable of the area, kind & friendly. We will return and recommend others to book his charter.
the conditions were not great but Tim worked hard to get us on fish. He moved us to every location that should produce fish. We caught several but some were not in season. We did catch some keepers. We had fun even though we didn’t catch alot. I would do it again.
We had an absolutely fantastic time fishing! Our captain was a blast to be around and worked hard the entire trip to make sure we had the best experience possible. We caught a ton of fish and had so much fun doing it. You can really tell he puts in the effort to make sure everyone has a great time. Highly recommend!
FAQs about Windward Fishing Charters
- US $650 per group, additional US $50 per person after 3 guests - 4 Hour Trip (AM) (4 hours)
- US $650 per group, additional US $50 per person after 3 guests - 4 Hour Trip (PM) (4 hours)
- US $900 per group, additional US $950 per person after 3 guests - 6 Hour Trip (6 hours)
- US $1,000 per group, additional US $50 per person after 3 guests - 6 Hour Trip – Tarpon (6 hours)
- GPS
- Fishfinder
- Live bait well
- Wireless trolling motor
- Ice box
- Rods, reels & tackle
- Live bait (Bait is on the boat ready to go before the trip starts and is included in the price. )
- Lures
- Catch cleaning & filleting (yes)
- Drinks (bottled waters are on the boat, and alcohol is allowed)
- Fishing license (Fishing licenses are included and cover all guests. )
- Inshore fishing
- Nearshore fishing
- Flats fishing
- Backcountry fishing
- Light tackle
- Heavy tackle
- Bottom fishing
- Trolling
- Jigging
- Black Drum
- Cobia
- King Mackerel (Kingfish)
- Pompano
- Redfish
- Sheepshead
- Snapper (Mangrove)
- Snook
- Speckled Trout
- Tripletail
Your captain
Sarasota, Florida, United States
Captain Tim grew up fishing these waters that he will take you fishing on. He dreamed of becoming a fishing charter captain since he was a child, and will always go the extra mile to make sure everyone on the boat has a great time. Captain Tim also loves to be able to teach his guests new fishing techniques and takes great pride in his work.
Real catches by this captain
What is the boat like?
What kind of fishing will you do?
Which fishing techniques you can try
Which amenities are available onboard
How cancellations work
You can cancel or modify your booking up to 3 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
How you can pay
When the captain confirms your trip, FishingBooker charges your credit card a 10% 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
When paying the remaining balance with a credit card, an additional 3% charge will apply.
What’s biting in Sarasota right now
Black Drum
Cobia
King Mackerel (Kingfish)
Redfish
Sheepshead
Snook
Speckled Trout
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