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!
Customer reviews
Rating summary
Photos & videos by reviewers (204)
+201Angler rating
Anglers claimed
Good experience
98%
Appropriate for children
98%
Friendly captain
98%
Satisfied with the boat
97%
Recommend this charter
97%
Caught fish
95%
Apr 20, 2025
4 Hour Trip (PM)
If you want to catch fish - Timmy will put you on them!
On 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!
On Easter Sunday, we embarked on an unforgettable fishing adventure and caught an impressive array of fish, including Speckled...
Captain repliedMark review as helpful
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Jun 9, 2025
6 Hour Trip – Tarpon
A Great tarpon Fishing Experience
Captain 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.
Captain 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...
Mark review as helpful
Mark review as helpful
Jul 2, 2025
6 Hour Trip
Capt Tim was great!
Had a blast, Capt Tim was great, got us hooked up with lots of Snook, a big Red, Trout, and some other fish too! Made good memories with big fish in Sarasota bay. Thanks Capt!
Had a blast, Capt Tim was great, got us hooked up with lots of Snook, a big Red, Trout, and some other fish too! Made good memories...
Mark review as helpful
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Mar 1, 2025
6 Hour Trip
Best Fishing Trip Ever
CPT Tim took four of us on an amazing trip along Sarasota and island coastal areas. Caught dozens of fish, including snook, redfish, flounder, and Jack Crevalle. Our 14 year old angler was thrilled with the results, and the older members of the group loved it as well. CPT Tim knew exactly where to go to find the fish.
CPT Tim took four of us on an amazing trip along Sarasota and island coastal areas. Caught dozens of fish, including snook, redfish,...
Captain repliedMark review as helpful
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Dec 24, 2024
4 Hour Trip (AM)
Christmas Eve Fishing trip
Hey may be young but don’t let that fool you. Timothy is well versed in fishing and very knowledgeable. He is very kind and outgoing, and made our fishing trip great. Every spot he took us to, he told us exactly what we needed to do and we executed his plan and caught a good mess of fish. Highly recommend!
Hey may be young but don’t let that fool you. Timothy is well versed in fishing and very knowledgeable. He is very kind and outgoing,...
Mark review as helpful
Mark review as helpful
Trip availability and prices
| Su | Mo | Tu | We | Th | Fr | Sa | |
|---|---|---|---|---|---|---|---|
Customer reviews
Rating summary
Photos & videos by reviewers (204)
+201Angler rating
Anglers claimed
Good experience
98%
Appropriate for children
98%
Friendly captain
98%
Satisfied with the boat
97%
Recommend this charter
97%
Caught fish
95%
Experience:
Boat
Crew
Overall
If you want to catch fish - Timmy will put you on them!
4 Hour Trip (PM) on April 20, 2025
On 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!
On 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...
Mark review as helpful
Experience:
Boat
Crew
Overall
A Great tarpon Fishing Experience
6 Hour Trip – Tarpon on June 9, 2025
Captain 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.
Captain 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.
Mark review as helpful
Experience:
Boat
Crew
Overall
Capt Tim was great!
6 Hour Trip on July 2, 2025
Had a blast, Capt Tim was great, got us hooked up with lots of Snook, a big Red, Trout, and some other fish too! Made good memories with big fish in Sarasota bay. Thanks Capt!
Had a blast, Capt Tim was great, got us hooked up with lots of Snook, a big Red, Trout, and some other fish too! Made good memories with big fish in Sarasota bay. Thanks Capt!
Mark review as helpful
Experience:
Boat
Crew
Overall
Best Fishing Trip Ever
6 Hour Trip on March 1, 2025
CPT Tim took four of us on an amazing trip along Sarasota and island coastal areas. Caught dozens of fish, including snook, redfish, flounder, and Jack Crevalle. Our 14 year old angler was thrilled with the results, and the older members of the group loved it as well. CPT Tim knew exactly where to go to find the fish.
CPT Tim took four of us on an amazing trip along Sarasota and island coastal areas. Caught dozens of fish, including snook, redfish, flounder, and Jack Crevalle. Our 14 year old angler was thrilled with the results, and the older members of the group loved it as well. CPT Tim knew exactly where to go to find the fish.
Mark review as helpful
Experience:
Boat
Crew
Overall
Christmas Eve Fishing trip
4 Hour Trip (AM) on December 24, 2024
Hey may be young but don’t let that fool you. Timothy is well versed in fishing and very knowledgeable. He is very kind and outgoing, and made our fishing trip great. Every spot he took us to, he told us exactly what we needed to do and we executed his plan and caught a good mess of fish. Highly recommend!
Hey may be young but don’t let that fool you. Timothy is well versed in fishing and very knowledgeable. He is very kind and outgoing, and made our fishing trip great. Every spot he took us to, he told us exactly what we needed to do and we executed his plan and caught a good mess of fish. Highly recommend!
Mark review as helpful
FAQs about Windward Fishing Charters
The fish you can target
What is the boat like?
