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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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!
Capt Tim was great with the kids and knew all the best spots to catch a wide variety of fish. 100% would definitely go again when we are back in Sarasota.
we 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!!
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.
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.
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.
Free cancellation up to 3 days prior to trip
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.
Pickup included in price
Book with 10% deposit, pay rest to captain
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.
