Windward Fishing Charters 

4.9/5 (173 reviews)
 
State licensed
 946 Siesta Drive, Sarasota, FL 34242, United States

Windward Fishing Charters 

 
State licensed
4.9/5 (173 reviews)
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946 Siesta Drive
Sarasota, FL, United States
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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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Customer reviews

Rating summary

4.9/5
out of 5 stars from 173 reviews
Boat
4.9/5
Crew
4.9/5
Experience
4.9/5

Photos & videos by reviewers (204)

Fishing with Timothy
A Great tarpon Fishing Experience
If you want to catch fish - Timmy will put you on them!
+201

Angler rating

160
8
2
0
0

Anglers claimed

Good experience

98%

Appropriate for children

98%

Friendly captain

98%

Satisfied with the boat

98%

Recommend this charter

97%

Caught fish

95%

Showing 1 - 5 of 173 reviews
Showing: 5 of 173 reviews
Franke Donlon
Franke Donlon
5.0
Verified
If you want to catch fish - Timmy will put you on them!
4 Hour Trip (PM) on April 20, 20252 adults1 child
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!
Review media 0
Review media 1
Review media 2
Review media 3
Review media 4
Reported catch:
Snook
Redfish
Spotted Seatrout
Response from Captain
April 21, 2025
Thanks Franke I had a great time with you guys!
0
Albert Granger
Albert Granger
5.0
Verified
New
A great time was had by all!
4 Hour Trip (AM) on November 24, 20254 adults
Jack had a beautiful to boat and he was very attentive to ours needs. We had a wonderful day and look forward to fushing with him again.
Reported catch:
Spotted Seatrout
0
Ross Harrison
Ross Harrison
5.0
Verified
Capt Tim was great!
6 Hour Trip on July 2, 20255 adults
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!
Reported catch:
Snook
Redfish
Spotted Seatrout
0
Paul Critchlow
Paul Critchlow
5.0
Verified
Best Fishing Trip Ever
6 Hour Trip on March 1, 20254 adults
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.
Response from Captain
March 2, 2025
Thanks Paul, I had a great time with you guys!
0
David Listman
David Listman
5.0
Verified
A Great tarpon Fishing Experience
6 Hour Trip – Tarpon on June 9, 20251 adult1 child
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.
Review media 0
Reported catch:
Tarpon
0

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
December 2025
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
4 Hour Trip (AM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 8:00 AM
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US $600 
Entire boat: up to 5 people
4 Hour Trip (PM)
FREE Cancellation 3 days notice
4 Hour Trip, starts at 1:00 PM
Seasonal trip Oct 1 - Jul 1
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US $600 
Entire boat: up to 5 people
6 Hour Trip
FREE Cancellation 3 days notice
6 Hour Trip, starts at 8:00 AM
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US $900 
Entire boat: up to 5 people
6 Hour Trip – Tarpon
FREE Cancellation 3 days notice
6 Hour Trip, starts at 8:00 AM
Seasonal trip May 1 - Jul 24
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US $1,000 
Entire boat: up to 5 people
There is 1 person looking at this charter.

Customer reviews

Rating summary

4.9/5
out of 5 stars from 173 reviews
Boat
4.9/5
Crew
4.9/5
Experience
4.9/5

Photos & videos by reviewers (204)

Fishing with Timothy
A Great tarpon Fishing Experience
If you want to catch fish - Timmy will put you on them!
+201

Angler rating

160
8
2
0
0

Anglers claimed

Good experience

98%

Appropriate for children

98%

Friendly captain

98%

Satisfied with the boat

98%

Recommend this charter

97%

Caught fish

95%

Showing 1 - 5 of 173 reviews
Showing: 5 of 173 reviews
Franke Donlon
Franke Donlon
5.0
Verified
If you want to catch fish - Timmy will put you on them!
4 Hour Trip (PM) on April 20, 20252 adults1 child
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!
Review media 0
Review media 1
Review media 2
Review media 3
Review media 4
Reported catch:
Snook
Redfish
Spotted Seatrout
Response from Captain
April 21, 2025
Thanks Franke I had a great time with you guys!
0
Albert Granger
Albert Granger
5.0
Verified
New
A great time was had by all!
4 Hour Trip (AM) on November 24, 20254 adults
Jack had a beautiful to boat and he was very attentive to ours needs. We had a wonderful day and look forward to fushing with him again.
Reported catch:
Spotted Seatrout
0
Ross Harrison
Ross Harrison
5.0
Verified
Capt Tim was great!
6 Hour Trip on July 2, 20255 adults
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!
Reported catch:
Snook
Redfish
Spotted Seatrout
0
Paul Critchlow
Paul Critchlow
5.0
Verified
Best Fishing Trip Ever
6 Hour Trip on March 1, 20254 adults
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.
Response from Captain
March 2, 2025
Thanks Paul, I had a great time with you guys!
0
David Listman
David Listman
5.0
Verified
A Great tarpon Fishing Experience
6 Hour Trip – Tarpon on June 9, 20251 adult1 child
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.
Review media 0
Reported catch:
Tarpon
0

FAQs about Windward Fishing Charters

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The fish you can target

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What is the boat like?

Boat Image
Boat category
Center console boats
Capacity
5 persons
Boat length
22 ft
Year built
2000
Restored in
2022
Boat manufacturer
Pathfinder
Boat type
Center console

Engine model
Yamaha
Powered by
1 x 175HP
Max cruising speed
43 knots
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