Trips Available

Windward Fishing Charters offers fishing charters out of Siesta Key and surrounding areas. These charters are for all types of anglers. Whether you are an experienced fisherman or a first timer, Capt. Tim will ensure that everyone has a great time.

  • This trip is a great way to spend the morning. The boat will depart at 8:00 a.m. and will go for a variety of species, also depending on what bite has been hot lately.

  • This trip is a great way to spend the afternoon. The boat will depart at 1:00 pm and will go for a variety of species, depending on what bite has been the best lately.

  • If 4 hours are not enough, this 6-hour charter will give more time to fish longer and run farther. It's recommended to bring a lunch for this trip, or you can stop at a local restaurant on the water per request. You'll target many species and also have time to do different techniques.

  • This trip is for the avid angler looking to target tarpon. From Mid April throughout July we have some of the most exciting fishing that Florida has to offer, catching tarpon. The time of the trip will vary due to tides.

  • Capt. Tim does his best to tailor each charter to be exactly what the guests are looking for. If there is something specific you are looking for, such as sight seeing, sunset tours, or anything else on the water you would like to do, feel free to call and get your perfect trip booked.

  • Do you already have a boat but are looking for a captain to run the boat? Whether your looking to learn about running it, catch fish on your own boat, or just want a captain so you can sit back and enjoy it, Capt. Tim is happy to help make that happen.

Prices based for 3 guests. Additional $50 per additional guest.

Meet The Captain

Captain Tim was raised here locally on Siesta Key and has been fishing these waters since he was a kid here. He takes great pride in his work and does his best to make sure every trip is as successful and enjoyable as he can. Also, he tries to make sure each trip is a good fit for the crew and people of all skill ranges and ages to make sure everyone on the boat has a good time.

What To Expect

When you go fishing with Windward Fishing Charters, you can expect to get to the dock with the boat already having caught live bait, clean, and ready for you to come aboard to go fishing. The boat will have bottled waters and room in an iced down cooler for you to put any drinks or snacks in. Once your on the boat, it is smooth sailing from there, as Captain Tim will take it from there to ensure you and your crew have the best time possible. At the end, any keeper fish will be filleted for you and ready to cook or brought to a local restaurant to be cooked for you.

Captain Timothy was amazing! Did an afternoon charter with him. Very patient and ensured kids were taken care of. Knew spots to go and find fish. We caught probably close to 30 fish throughout the day and although we had to release most secondary to size and/or regulations; the couple we were able to keep, he cleaned and filleted once we got to shore. We highly recommend and will look to do another charter when we come back down to Florida again!!

- Michael O

Two men in sunglasses and caps are swimming in clear green water while holding a large fish.
A couple in swimsuits holding a large fish in clear, light green water near a rocky shoreline with a white building in the background.
A woman on a boat holding a large fish she caught, with the ocean and a small island with trees in the background, under a blue sky.
Two young men on a boat holding a large fish, smiling at the camera, with water and a shoreline with houses and trees in the background, and a cloudy sky overhead.
A person in a boat reaching out to grab a fish that is jumping out of the water.
Three young men stand on a boat holding fish they caught, with clear blue water in the background.
Two young men standing on a boat holding large fish they caught, with the ocean and a partly cloudy sky in the background.
Three people holding a large fish near the boat, in the water.
A sunset over the ocean with a boat near the horizon, calm water reflecting the orange and yellow sky, and some trees along the shoreline.
A variety of freshly caught fish laid out on a wooden dock, with a hide of orange, a camouflage Florida hat, and a large red fish in the background by the water.
Ten fish laid out on a white surface, with some fish overlapping, most of them silver with a yellowish tint, set against a white background with some black equipment visible in the corner.
Man on a boat holding a large fish with a gray body and a black spot near the tail, smiling under a cloudy sky.
Two men on a boat holding a large colorful fish, with a blue ocean and partly cloudy sky in the background.
Two men on a boat holding a large fish they caught, with fishing rods visible in the background.
Man wearing sunglasses and a white long-sleeve shirt holding a large striped fish on a boat in the water with a shoreline and buildings in the background.

Captain Timmy is an outstanding fisherman with local knowledge to put you on the fish you dream of. He does an excellent job of watching and being ready for you. We caught two of these tarpon and they were worth it! I highly recommend Timmy and will 100% go through him again.

- Jack R